11 Ways CEOs can use one-on-ones to scale excellence in their leadership teams

Founders often want to stay involved in many or even most aspects of their businesses (see the conversations over “founder mode”). However, most soon realize that if they ever want a vacation, a sustainable romantic relationship, or a sustainable, scalable business, they need to scale the capacity of the people on their leadership team to lead the organization without them.

Instead, CEOs are using this precious time to manage projects and run through a to-do list with their most senior leaders.

One-on-ones are an extraordinary opportunity to unlock the potential of your team to think more clearly, lead more effectively and to unlock growth for your company. 1:1s are an opportunity for a creative conversation (see item 10)

I know you’re busy, so here are the 11 ways you can use one-on-ones to scale excellence in your leadership teams:

1. Have them regularly. (read why below)

2. Limit the number of agenda items.

3. Get more feedback than you give.

4. Start with wins and increase your positive to negative feedback ratio.

5. Use 1:1s to coach your team to solve their own problems, not to solve problems for them.

6. Align on a time horizon to focus each conversation on.

7. Listen actively and deeply before responding.

8. Follow up on past conversations.

9. Flip who runs the show

10. Create a standard agenda with each direct report.

11. Get feedback on the meeting format.

I just saved you a few minutes!

The first four easy pieces are crucial to making your 1:1s better. If you want to know the reasons why and some research that proves the point, read on.

The real, outsized impact is in items 5, 6, and 7. These are deeper mindset shifts backed by powerful frameworks. Putting them into practice will take time, effort, and feedback to realize the real value and potential, but the possible gains are enormous.

Items 8-11 are ways to lock in the gains from items 1-7. Use these moves to make sure your 1:1s are continuously improving.

1. Have them!

Many leaders cancel or reschedule 1:1s when more urgent issues come up. But a big part of leadership is about creating stability, and keeping your 1:1s at a steady cadence is one great way to build stability. Plus, it bears fruit: research from Gallup found that employees who have regular one-on-one meetings with their managers are almost three times more likely to be engaged than those who don’t. We can guess why just having them is better than not having them - keeping the meeting as planned sends a signal that the meeting matters and that the employee matters.

Set the example for your direct reports by holding regular 1:1s with them, and ensure they do the same with their teams. 

(For more on why great leadership creates stability in the midst of change, listen to this episode of the Conversation Factory with author Ashley Goodall. He co-wrote the blockbuster Nine Lies About Work, and most recently, The Problem with Change).

2. Limit the number of agenda items so you can make meaningful progress.

If you try to talk about everything, you can’t go into depth about anything. Boil it down to a handful of items to dive into - 3-5 tops. Don’t run through the whole To-Do list!

3.  Get more feedback than you give.

A positive side-effect of asking questions to get feedback is that you’ve demonstrated you seek and can process challenging feedback. Over time, this creates trust and allows you to offer more challenging feedback to your reports.

During your 1:1s, ask questions that help you be a more effective leader for them:

• “Is there anything I can stop/start doing that would make your life easier?” 

This is a good place to start. When you’re ready, ask this varsity-level question:

• “What’s one thing you think would be really hard for me to hear, but that I really need to? I’d like to hear that feedback.”

Set the example of being radically open to feedback and make sure your FQ (Festering Quotient) is low in your relationship. Simply put, the longer you wait to talk about an issue, the more stinky it gets, for everyone involved.

(For more on the FQ and the SBIO model of giving situational feedback, listen to this podcast about The Intentional Conversations That Build Powerful Co-founder Relationships, with Rei Wang and Anita Hossain, co-founders of coaching platform The Grand.)

4. Start with wins and increase your positive-to-negative feedback ratio

Top performing teams maintain a nearly 6:1 ratio of positive to negative comments, according to HBR. It is likely that the abundance of positive comments helps create a deeply felt sense of psychological safety and the connective tissue that allows feedback to be heard as constructive rather than negative…and to be acted on, all while driving performance.

You can leave this ratio to chance, or you can choose, as the leader, to create a culture of celebrating wins. One-on-ones are the perfect opportunity to plant the seeds of that culture. Too often, I see 1:1s getting bogged down in project management and troubleshooting. Start with wins, and start creating a better feedback ratio early.

Also note: the more specific your feedback is, the better. 

Think about feedback as four quadrants, represented by the suits of a deck of cards: Hearts, Diamonds, Clubs and Spades. Feedback can be Warm (positive) or Cool (negative), and Sharp (clear) or Fuzzy (vague). Note this is not my framework! I first learned it from my friend Peter Haasz.

Giving people “Warm and Fuzzy” feedback in your one-on-ones is nice, like the Heart that represents it, but giving pieces of Sharp and Warm feedback, like little Diamonds, makes people feel really seen. An additional positive side-effect is that the more you notice and name their excellence, the more excellence you can evoke in them over time.

For example, compare these two pieces of feedback:

“Great job on that client presentation.”

vs. 

“The way you reframed the client’s objections to the roadmap shift as a natural evolution that would be a win-win took a lot of presence of mind. You really commanded the room in that moment. Great job.” 

Spend more time in the Warm-and-Sharp Quadrant than you do in the Warm-and-Fuzzy Quadrant of The Feedback Matrix, and spend time between your 1:1s collecting diamonds to share with your direct reports.

It’s best practice to give your direct reports cool-and-sharp feedback in the moment or as close as possible to whatever happened to evoke the feedback. Don’t wait for a 1:1. The Feedback Matrix above classifies cool-and-sharp feedback as the playing card suit “spades.” (Spades are what the British call a shovel). Just as a spade is a handy garden tool, think of cool-and-sharp feedback as a tool to help folks get better. Share that feedback with them when you can be cool and calm about giving them the feedback—, i.e., when you can share the feedback in a helpful, non-clubbing- them-over-the-head kind of way

5. Use 1:1s to coach your team to solve their own problems, not to solve their problems for them.

After working with me for a few months, many of the CEOs I coach ask me, “How can I work with my team the way you work with me?” These leaders see how our coaching conversations make space for their own deep thinking and strategic problem solving and they want to do the same for their teams. But these CEOs are all smart and effective problem solvers; it’s easy for them to slip back into their problem-solving habits. But, “what got you here won’t get you there.” 

In order to scale your leadership impact, you need to scale your team’s impact. That scale will happen more rapidly if you slow down and learn to coach their thinking, instead of doing it all for them. 

Slowing down and leveraging a coaching approach can feel frustrating at first. The best way to make progress with anything is to put it on your calendar and stick with it. Developing a coaching habit with your team is no different. Insert a regular coaching conversation agenda item in your standard 1:1 agenda in collaboration with your direct reports.

In short, remove the option to NOT coach by telling them you will be coaching them, not solving problems for them. Ask them to come to the conversation with the key priorities they feel blocked on and what they think their best solution options for each one are. 

Then, to help coach them to think through problems, leverage the SSOON Model of Coaching Conversations.  The SSOON model helps make their implicit thinking explicit in five simple steps so you can understand their thinking process.

1. Situation: What’s the context around the challenge the coachee is facing? A coaching stance here is to just ask more questions to uncover what’s really going on and encourage the coachee to share their thoughts and experiences fully.

2. Success: Here, the focus shifts to envisioning the desired future. The coach helps the coachee articulate what success looks like and explores possibilities that may exceed their initial expectations, often using imaginative questions to clarify their vision. 

3. Obstacles: In this step, the coach encourages the coachee to identify any barriers preventing them from achieving success. By reflecting on these obstacles, the coachee can gain clarity on what stands in their way.

4. Options: Once success is clearly defined and obstacles are acknowledged, the conversation moves to exploring potential actions. The coach facilitates brainstorming and may offer gentle suggestions to help the coachee consider various paths forward that they haven’t considered.

5. Next Steps: Finally, the coach guides the coachee to commit to specific actions they will take moving forward. This involves selecting manageable and impactful steps that can lead to the desired outcome, reinforcing a sense of accountability and momentum.

Together, these five elements help create a structured and reflective coaching dialogue, empowering the coachee to navigate their challenges and achieve their goals through clearer thinking, guided by you.

6. Create a standard agenda together, but follow the structure of creative conversations.

I talk about these phases in more depth here, but you can also read one of my favorite books, Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers, which is the source of the delightful diagram above. 

(See below for 22 questions to use across these three phases to create your own ideal 1:1 agenda with your direct reports.)

7. Listen deeply and actively before responding.

Remember the Talking and Thinking Gap, which captures the fact that while people can think at up to 4,000 words a minute, most of us can only speak at 125 words per minute. So, in every interaction, people always have more to say than they can ever express.

For leaders, this means that in your meetings, you don’t hear everything your direct reports want to say. Plus, you’re often likely thinking a bit about what you might say in response, or something else entirely! Don’t forget this classic quote from the late U.S. ambassador Robert J. McCloskey:

““I know that you believe you understand what you think I said, but I am not sure that you realize that what you heard is not what I meant.” ”

— Robert J. McCloskey

Assume that you did not fully understand everything your teammate meant to convey.

Active listening is usually defined as making sure you heard what you thought you heard by repeating it back and getting confirmation.

To listen more deeply, try leveraging the Listening Triangle to get to the heart of what’s being said.

When you get confirmation that you heard them right (by sharing your active-listening paraphrase), ask another question from a slightly different angle to deeper into their response. The listening triangle helps you get to the heart of what someone is really saying.

Re-asking also helps create the kind of psychological safety essential for an effective leadership relationship, confirming that you really want to understand their perspective.

8. Flip who runs the show.

Share your plan to coach more, and share this article with them so they know the game plan you’ll be sourcing from. Sketch out an agenda together (Item #6!) then hand the agenda over to them and let them take the reins. This eliminates almost entirely the possibility of backsliding on your intentions!

9. Align on a time horizon to focus each conversation on.

Often, 1:1s can get stuck in the now—the immediate challenges of a company’s day-to-day survival and growth—which is natural. 

In fact, most people are encouraged to focus on the most urgent and important items on their to-do list. This is a trap! The idea of focusing on the urgent and important is a mis-application of a speech by former president Dwight Eisenhower in 1954. In the speech, Eisenhower was quoting Dr. J. Roscoe Miller, President of Northwestern University, as saying:

““I have two kinds of problems, the urgent and the important.
The urgent are not important, and the important are never urgent.”
”

— Dr. J. Roscoe Miller

This "Eisenhower Principle" is said to be how he organized his workload and priorities. For years, I was told to focus on the Important/Urgent quadrant (in red, far left) as a first priority and to delegate or ignore the Not Urgent/Not important (in blue, lower right on both matrices below). But the quote is actually pointing us to the upper right yellow-green quadrant - the NOT urgent YET Important quadrant. 

These NOT urgent YET Important items are the ones that easily fall off a to-do list filled with urgency but lacking items that address longer-term or even medium-term strategic impact.

Working with your leadership team to focus weekly or bi-weekly conversations on the non-urgent but important items will slowly create a buffer against the tyranny of urgency. The matrix on the right is the ideal Eisenhower matrix - intentionally making ample time for the non-urgent as the lion’s share of our focus.

Make sure you use periodic conversations to look even further ahead - where does this person want to be in 10 years? In five? Where do you both see the company in three years? Shift the time horizon for each conversation intentionally.

10. Follow up on past conversations.

Make sure topics and issues don’t dangle. Following up on past issues with your direct reports will remind them not only to stay accountable to you, but also to follow up with their direct reports so that they remain accountable too. All of it trickles down to create a culture of accountability organization-wide. I hosted a lovely podcast conversation with the co-founders of Huddle who called this shift "building an Integrity Culture" - a culture where you expect yourself and others to do what they say they will. Listen here.

11. Get feedback on the meeting format.

Regularly check in with your direct reports and ask them: Are you getting what you need from these conversations? What’s working? What could be improved? 

As mentioned above, you will find that the unique needs of each member of your team will shape the 1:1s over time, even though they will all follow the same open-explore-close architecture.

22 questions to try out in your 1:1s

Questions are the rocket fuel of conversations, and 1:1s are no exception. Here are some tried-and-true questions to take for a test drive on your next one-on-one, organized according to the open-explore-close pattern of powerful, creative conversations:

Opening:

1. The “Traffic Light” check in. 🚥 Are you Green (all systems go, full speed ahead), in the Red zone (ie, having some significant challenges you’re managing that are stopping you in your tracks) or yellow (ie, you need to slow down to stay safe)

2. What has your attention right now?

3. What's driving you crazy these days? 

4. What's making you happy to come to work these days? 

5. What is the general mood and morale of the team(s) you're on? 

6. How are things outside of work?

7. How is stress at work?

8. How is your workload at work?

Exploring Key Topics:

1. Progress towards goals:

a. What Victories do we need to celebrate? 

b. What are some important Roadblocks we need to remove?

2. Career development:

a. Where do you want to go? How are we going to get you there?

3. Coaching questions:

a. How can I help (with challenge X)?

b. What does “good” look like? What’s your real goal?

c. What’s the real challenge for you here?

d. If you're saying yes to this, what are you saying no to? (nod to Michael Bungay Stanier for this powerful question)

e. Check out the SSOON model of coaching to make sure you lead a coaching conversation effectively.

4. Feedback for the leader:

a. What’s one thing you think would be really hard for me to hear?

b. Anything I'm doing that I need to stop? 

c. Anything I should be doing that I'm not? 

d. Anything I'm doing that I should keep doing?

e. What should I be doing more of, or less of, to make your experience at ___ the best it can be?

Closing:

1. What's your next step?

2. What was most useful to you?

Leading Teams to Unlock Creative Potential with Design Thinking

There is more intelligence inside our organizations and our teams than we are using.

It’s the job of leaders to unlock the creative power of their teams - not to generate solutions to all problems for them.

Leaders can do this by leading conversations that leverage the power of a creative process - finding new, unexpected and innovative solutions to challenging problems instead of business as usual. 

This creative process has gone by many names, has been studied for decades, and offers leaders powerful, practical tools to drive change and innovation through creative conversations. My book, Good Talk: How to Design Conversations that Matter is just one of many, many books on this topic. In this essay I’ll break down some essential tools of leading creative conversations and share some other books on the topic for your further reading.

At various times, this process has been called Creative Problem Solving (CPS), and more recently known as Design Thinking. Over the decades these approaches have been hailed as practical and functional, or a terribly failed experiment.

While the realities on the ground of how these methods get implemented is nuanced (to say the least!), Creative Problem Solving and Design Thinking work because they leverage some fundamental forces of creative gravity. In my days as a physicist, we liked to joke that gravity isn’t just a good idea, it’s the law. 

You try to get a plane in the air without understanding aerodynamics and the fundamentals of gravity! Working with a basic understanding of the laws of creativity means leaders can make meetings soar, instead of feeling like a drag. And yet most leaders are flying blind or working with outmoded theories.

These methods are best learned in action, so…Let’s do an experiment, shall we? After the game, I’ll unpack the five keys to leading more impactful creative problem solving meetings with your team.

I’ve been playing improv games to help teams learn design thinking in action for years. And I remember the first time I saw a colleague lead a group through this particular game more than 10 years ago. At the time, I had taken some improv classes and had already been teaching design thinking for awhile, but had never thought to put them together. It lit a spark in me that still burns to this day. There are many ways to lead this game and to help teams unpack their experience and make meaning of it. This is my approach.

Setting the Scene

I set the scene by asking the group if anyone has done any improv.

Some have, some haven’t.

I remind those that have done improv that we will be “breaking” some of the rules of improv. This will create some discomfort, and I ask for their patience and curiosity with the discomfort. 

For those who haven’t done improv, I *also* ask them for their patience and curiosity with the exercise ahead.

Yes, But

“Grab a partner and plan a party together for the next 2 minutes. One person will suggest a party idea. The other will respond with yes, but….

And you’ll continue to offer suggestions, back and forth, always starting with yes, but…”

It’s a simple instruction. If you do this exercise in person, you’ll hear the noise in the room rise as people dutifully try to follow your instructions and have a “Yes, But..” conversation. And one minute later, you’ll hear the chatter in the room die down as people struggle to keep the conversation going.

At two minutes I rescue the room from the pain of continuing. 

“What was that like?” I ask

“Painful”

“Hard”

“Slow”

“Argumentative”

…come the replies.

“Did anyone actually get to plan the party?” I probe

Most teams admit that they got bogged down pretty early - where to get the ice became an intractable problem. They got lost in the details.

I draw the axes of Energy over Time and ask the teams - did your energy go up or down during the conversation? The chart below summarizes the overall experience - Energy in the groups drops, fast.

Now, there will be one or two pairs who had a BLAST during this conversation. In some organizations the proportions of “Yes, but” enjoyers are even higher.

“I loved how they kept poking holes in my ideas and I had to find solutions!”

But the room as a whole admits that such conversations create a one-sided effort that does wear thin over time since poking holes is a lot easier than plugging them.

The main points I want teams to notice is that:

Many people do not enjoy “Yes, But” Conversations.

Some people like “Yes, But” Conversations

Overall, “Yes, But” conversations drain energy

Yes, And

“Grab the same partner. The other partner now gets to suggest a party idea. You’ll continue to offer responses, back and forth, always starting with yes, and…for the next 2 minutes”

Again, if you do this exercise in person, you’ll hear the noise in the room rise as people dutifully try to follow your instructions and have a “Yes, And..” conversation. And one minute later, you’ll hear the chatter in the room continue to rise as people really get into the party ideas

At two minutes I have to shout to be heard and get the room to settle down.

“What was that like?” I ask

“Fun”

“Energizing”

“Collaborative”

“Flow”

…come the replies.

“Did anyone actually get to plan the party?” I probe

The room usually explodes with people ready to launch their party ideas into the stratosphere.

Returning to the Energy X Time Chart, I ask the room how the arc of their energy was for this conversation. 

“Was it going up and to the right?”

Most of the room agrees.

“Or was it starting to level off?” I enquire

Now, in a mirror to the “yes, But” portion, there were several  pairs who felt like the “Yes, And” energy was getting to be a bit much towards the end of the conversation. Could they really afford Jay-Z and Beyonce for this intergalactic unicorn party on the moon? Who was going to fund the rocket flight - Bezos or Musk?! Things were starting to feel a bit out of hand for some.

At this point, I want the group to understand:

“Yes, And” Conversations are energy producing

Some people run out of steam with “Yes, And” Conversations

Different people run out of creative energy at different rates.

It is the job of a leader to make space for these modes of creative thinking. We need “Yes, And” thinking to make sure we have MORE creative ideas on the table. And we need “Yes, But” thinking to make sure the ideas actually hold water.

Opening and Closing at the same time sucks

At this point, I can point out the fundamental problem:

There are people who LOVE poking holes in ideas.

There are even folks who love having their ideas being poked.

But generally speaking, it’s more energizing to build on ideas.

So why are our creative meetings so broken?

The problem is that teams are generally playing BOTH games at the same time. We have all been in meetings where people are simultaneously generating and destroying ideas.

“What if we try___________?”

We did that last year… it didn’t work.”

“What if we try___________?”

“We can’t get that past legal.”

“What if we try___________?”

“That sounds expensive”

Like a quantum foam of particles being born of the vacuum and disappearing from existence in an instant, almost nothing escapes this kind of meeting, where “Yes, And” people are cut off by “Yes, But” people before ideas even get to develop or mature.

The leader who understands the physics of creative conversations makes sure we play both the “Yes, And” and the “Yes, But” games ONE AT A TIME. 

Yes, And is Opening. Divergent or Generative Energy.

Yes, But is Closing, Convergent or Subtractive Energy.

Electrons and protons are negatively and positively charged, respectively…but we need both in balance to make up the universe we live in.

So, too, do leaders need to balance positive and negative energy to drive creative thinking.

Creative Culture is limited by classic Cognitive Biases

At least two common cognitive pathways keep us from pushing through “Yes, But” thinking into new and innovative solutions: The Loss-Aversion Bias and the Negativity Bias.

The Negativity bias is thought to be an adaptive evolutionary function (Cacioppo & Berntson, 1999; Vaish et al., 2008; Norman et al., 2011). Our prehistoric ancestors were exposed to environmental threats that were truly threatening - the sound of snapping branches in the woods could actually be a tiger or worse. Being highly attentive to potentially negative stimuli played a useful role in survival. Seeing gaps and challenges in ideas as fatal flaws to be avoided at all costs makes us flee from new ideas.

The Loss-Aversion Bias is summed up by the old saying “A bird in the hand is worth two in the bush”. Loss aversion was first proposed back in 1979 by Amos Tversky and Daniel Kahneman as an important framework for prospect theory – an analysis of decision under risk. We feel the possible loss of, say $10, much much more sharply than the gain of $10. Investopedia suggests that “human beings experience losses asymmetrically more severely than equivalent gains. This overwhelming fear of loss can cause investors to behave irrationally and make bad decisions, such as holding onto a stock for too long or too little time.”

Samuelson and Zeckhauser, in their 1988 paper “Status quo in decision making” pointed out that incumbents do much better than they would in a neutral election.

These cognitive biases keep us rooted in protecting what we have instead of exploring new possibilities - because doing so costs time and energy.

Creative leaders make space for Opening, Exploring and Closing.

In 2010 I read Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers. Gamestorming brought together decades of practical wisdom and research into how groups can work together, better by thinking of work through the lens of game theory.

Yes, And is a Game. The rules create an additive thinking space.

Yes, But is a Game. The rules create a thinking space of subtraction.

It’s easy to get frustrated when you are playing a different game than everyone else on the field. Can you imagine trying to play soccer while everyone else is playing rugby? Or playing chess while your partner is playing backgammon?

It’s impossible to make any progress this way.

Gamestorming opened my eyes to the importance of balancing these three games, in sequence, as in the diagram of a creative process below. The authors also  opened my eyes to a third energy: Emergence, or exploring.

Opening: Divergent (positive)

Exploring: Emergent (neutral)

Closing: Convergent (negative)

In the universe, we have electrons and protons, but it’s actually neutrons that help hold atoms together. And just so, a culture of innovation is found in making space for creative emergence - a kind of “neutral” space, where we are not generating or eliminating ideas, but holding space for them to be heard and to combine and recombine.

Openers love opening and may resist closing.

Closers love closing and may drag their heels in opening.

Almost everyone finds exploring a bit challenging, which is why Sam Kaner’s Facilitator's Guide to Participatory Decision-Making describes this middle part of the creative process as the “Groan Zone”.

We all need to become switch hitters in the creative process if we’re going to work together.

Openers need to learn to close - to choose and launch

Closers need to learn to lean into opening, to get curious about ideas before poking holes in them.

Leaders can create the guardrails for conversations that make this possible. 

Creative Leaders are Multipliers

Leaders have an outsized influence on how teams solve problems. They can intentionally set up a space where these three modes of creative conversation can flow. If they know where the rough air is going to be in the process, they can plan for it.

For example, in her bestselling book Multipliers: How the best leaders make everyone smarter, Liz Wiseman posits that there are at least two types of leaders 

- Multipliers, who expect great results from their teams AND create the conditions for genius to emerge 

and …

- Diminishers, who micromanage, take credit and waste the genius in their teams and organizations.

Multiplier leaders provide the support and forward movement for teams to navigate the perilous middle of the creative process with grace. They expect great results and know that setting time aside for thinking through options and opportunities creates the best results - what Daniel Kahneman calls “Thinking Slow” in his book “Thinking: Fast and Slow”.

How might we create the conditions for effective creative thinking for our teams?

At this point, the hour is coming to a close and there’s precious little time for much more than reflection and projection - getting people who’ve gone through this improv game to think about what it was like, and how they might lead differently in the future. And for them to share what they might already be doing that looks and feels like what we’ve been talking about for the last 45 minutes or so.

Five Steps for Leading Creative Conversations

Make space for Opening, Exploring and Closing. Doing all three in one short meeting may not be possible or feasible at first.

1. Open with a clear challenge statement. What problem are we here to solve? Defining the problem well is a powerful form of creative leadership. More on that here.

2. Open Pt 1: Think alone, then think together. Get everyone to write down their ideas in silence. For more on why, check out “Your next meeting should be silent”

3. Open Pt 2: Get people to share their ideas. No “Yes, But” energy allowed…yet!

4. Explore: Share ideas and remix them. Combine the best parts of ideas together. While some people criticize collective creativity with the saying “A camel is a horse designed by committee” I challenge you to cross the Sahara desert on a horse!

5. Close: Decide on one or more ideas to prototype, test or evolve.

Step Zero should usually be “Decide how you’re going to decide”.

Leaders need to set groups up for success by letting them know if this is a democracy or an advisory committee. Leaving things vague just causes a mess.

Step Six should usually be “Let’s talk to real people facing the challenge we described in step one without showing them our ideas yet” so that we reduce the chances of a third dangerous and common cognitive bias - the Confirmation Bias, ie “the tendency to search for, interpret, favor, and recall information in a way that confirms or supports one's prior beliefs or values”.

In the Toyota System of continuous Improvement, this is called Genba, or Genba Walks - “going to the real place where the actual work is done”

Leadership is Designing and Facilitating the conditions for Transformative conversations.

Left to our own devices, conversations will be an unstructured mix of “Yes, And” and “Yes, But” modes of working. Leaders have the opportunity to set up conversations to run on a different operating system - one where teams cycle through “yes, and” and “yes, but” thinking in ways that create respect, psychological safety and forward movement.

This mode of leadership isn’t directive or authoritative, but is more akin to the style of leadership Daniel Goleman described in HBR in 2000 as a Leadership That Gets Results - a coaching mode of leadership. Coaching and Facilitation are two sides of one coin - leadership based in empathy and an understanding of how humans are built - but that’s a conversation for another time.

The Support Matrix

In early May of 2023, the surgeon general of the US released an advisory report calling attention to the loneliness epidemic.

If you’re new to this topic, in short, people today have fewer friends and fewer systems of support than ever before.

Why is this important?

At a societal level, if a population is lonely and disconnected, you’re going to see the impacts in an uptick of negative health outcomes from an increased incidence of heart disease to increases in suicides - that’s why it’s so powerful that the surgeon general is weighing in on this.

Why is this important to you, the reader, in your life?

How much support does a person need?

Some ages back, I wrote about how founders can’t emotionally bootstrap their companies.

Since I wrote that essay, that perspective has been reinforced and expanded through many, many conversations I’ve had with founders and leaders who tell me that they need a whole spectrum of support to sustain themselves, their companies and their relationships.

For example, my podcast conversation with the co-founders of the next-gen gaming platform Artie confirmed that having a coach and a therapist is totally a thing, and nothing to be ashamed about!

What kind of systems of support?

For me, I have a five-legged stool of support systems, regular conversations and gatherings that are blocked in my calendar.

My Therapist (one hour weekly, on and off for 15+ years)

My Men’s Group (two hours weekly, four years strong)

My Coaching Forum (five hours monthly, currently entering our third year)

My Sunday Dinner + Drinks (2-3 hours weekly…this dinner with friends has been going strong for over 10 years).

My journaling and sketching habit - sometimes daily, sometimes less. I have notebooks for my mental health and for my coaching practice.

But we could bucket these into a basic spectrum of support, sized like t-shirts: Large, Medium and Small. The three key conversational buckets, or legs of support are:

• Groups,

• One-on-one conversations, and

• Conversations with myself

Now, I love sorting conversations by size, ie, amount of people, as the Spectrum of Support stool diagram does above, but we could just as easily sort these spectrums of support with many other lenses.

For example:

Self/peer facilitated vs expertly facilitated. My therapist is accredited and expert in their field, while my men’s group and coaching forum are peer-facilitated. It’s great to have self/peer facilitated spaces because guiding conversations is such a critical leadership skill, and these spaces can create opportunities to hone your own approach. Experts, on the other hand, bring safety, clarity and assurance to their approach, and I always learn something new I can steal!

Self-growth focus vs Life Focus: My Sunday dinner conversations are sometimes about life, the universe and everything, but often we talk about media, politics, and other tomfoolery. On the other hand, my men’s group is only focused on personal growth and self-transformation. We don’t talk about stories, we process emotions. I find safety and security in knowing that I have a space like my men’s group that will always be laser focused, vs a space that is flexible and loose.

Self/Others/Nature/Transcendence: My friend and podcast guest Casper ter Kuile uses four very different categories, when he describes rituals that foster connection. Ritual can simply mean “a way to create space and time for something that matters.” He thinks about:

• rituals for connecting with yourself,

• rituals that connect you to others

• rituals for fostering connection to nature

• rituals that create time to connect with something transcendent, which for some might be a sense of “god”, oneness, or something else.

Since he’s largely inspired by what I like to call “Biomimicry but using religion” it’s not surprising that he includes time for focusing on something larger than what we can see with our eyes - connection with the transcendent is a feature of all religions. Connecting with something bigger than ourselves helps inspire awe and wonder, both surprisingly helpful experiences. His company, The Sacred Design Lab explores what we can learn from religion to inspire leadership, gathering and transformation and he wrote a wonderful book on the power of ritual. You can check out our conversation here!

Why is regular, even structured, self-talk so important? Check out my essay here on how impactful self-talk can be on your quality of life. In short, how you talk to and with yourself is the fundamental rate-limiter of your overall success and happiness.

The Commitment-Intimacy Support Matrix

The spectrum that has been on my mind is at the intersection of commitment and intimacy - what I am currently focusing on as the essential factors in any Support Matrix.

I began to realize that the systems of support, the spaces and places that had delivered the most impact to me were all high-commitment and high-intimacy spaces.

For example: My men’s group is a high-commitment space - we commit to coming together each week. If we need to miss a session, we have to reach out to other members and have a 1-1 check in with someone to share what we’re making more important than the meeting.

(Note - it’s 100% okay to say - “I am prioritizing going to a party with my partner” - and committing to being 100% present to having a great time at said party and coming back and sharing that joy with the group!)

Since we’re a high-commitment space, you can’t just flake out. If you do, we’ll call you out on breaking your commitments. We’re also high-intimacy, in the sense that we can bring anything to the group to talk about - it’s one of the few spaces where we can say whatever we need to.

My coaching forum is also a high-intimacy space. Even though we focus on helping each other grow our coaching practice (both in professional excellence and revenue) we also focus on sharing what is really going on in our lives - losses of family members, parenting, fertility journeys, self-doubt, and so on.

Often I see people trying to learn, develop and grow using low-commitment and low-intimacy spaces: Webinars, reading, social media.

These are like snacks. They can keep you alive and moving forward, but they are just not enough.

Deeper commitment is more deeply nourishing.

Deeper intimacy, allowing yourself to really be seen and to see others, is powerful.

The Holy Trinity of Professional Development: Coaching, Mentoring and Peer Forum

With my executive coaching clients, I find there is a powerful trinity of support systems they need to thrive in their roles: Coaching, Mentoring, and Peer Forums.

Sometimes these support systems are more ad-hoc and casual, but I’ve found that they are all like 401ks - the value of commitment and intimacy compounds over time as you reinvest.

Coaching is powerful because it focuses on the belief that the coachee has the answer within, that they can and should find their own way. It creates the space and time for them to think deeply, with a caring and committed thought partner (like me! - learn more about my coaching here).

Coaching is less directive, which means the coachee can tap into their own reserves in a powerful way.

Mentoring is powerful because it helps a leader get vital feedback and information about their unique context. No matter how much confidence and clarity a person can get from coaching, it is incredibly helpful to connect with someone who’s “been there/done that” in some relevant way. Finding great mentors (plural - the more the better) is hard, but worthwhile.

Peer Forums can go by lots of different names: Peer Coaching, Peer Exchange Groups, Masterminds. Organizations like EO, YPO, Starting Bloc, and Vistage host peer groups that are powerful in five ways:

1. They are long (in duration - for example, YPO-style groups meet monthly for a full day in person, while my coaching peer group meets monthly for five hours online.

2. They are ongoing - they usually continue to meet with no end date in sight.

3. They are small - often capped at 10 people - which feeds intimacy.

4. They are highly structured. Either they are expertly facilitated or the people in the group are expertly trained to self-facilitate.

5. They are normalizing. When the group is more similar than different in essential ways, they can provide deeply nourishing feedback that, yes, the challenge you are facing is face-able, since others have also faced it in some manner.

Balancing Diversity with Similarity in Support Systems

Balancing variety and diversity with similarity and familiarity is essential, and also a fundamental challenge of peer groups, coaching and mentoring.

For example - in my men’s group, it's very powerful that some of us are dads, some of us are trying to become dads, and some of us never want kids. It provides richness to the conversation.

On the other hand, when someone is struggling with parenting, it’s incredibly helpful for someone else in the group to be able to say, “I see you,” from having had a similar experience.

On the other hand, there are men’s groups only for dads - having someone who never wants kids in such a group just makes no sense!

Similarly, it can be helpful for a CEO group to only have CEOs or for a CTO group to just have CTOs, but it can be very helpful for them to be in different industries and stages of growth. On the other hand, the peer groups in EO, YPO and others often work to create groups that are in similar stages of development.

Filtering in this way can have advantages …but also drawbacks: too much sameness sucks the richness from the conversation.

How can we find the sweet spot between diversity and similarity?

The Q of a gathering

In 2012, Jonah Lehrer wrote a wonderful article in the New Yorker about Groupthink. In the later half of the article, he discussed the work of Brian Uzzi, a sociologist at Northwestern, who dedicated his career to uncovering the ideal team composition. He focused on Broadway musicals as an ideal way to study the complex ways team creativity can impact success, with easy to measure inputs (people) and outputs (box office numbers!).

Musicals, to Uzzi, epitomize group creativity. Collaboration is paramount – composers work with lyricists, choreographers with directors, etc. - to create a successful show. Uzzi studied all 474 Broadway musicals from 1945 to 1989, tracking relationships and using a value he called "Q" to measure the amount of social connectivity and familiarity a team had.

Often musicals are developed by teams of artists that have worked together several times before—a common practice to reduce risk with “known quantities." We still see this today in marketing “from the team that brought you X.” Such musical productions would have a relatively high Q. A musical created by a team of strangers would have a low Q.

Uzzi, in essence, compared familiarity with success and reported:

“Frankly, I was surprised by how big the effect was…I expected Q to matter, but I had no idea it would matter this much.”

A low Q (low familiarity, or an overly-fresh team) correlated with low success, which Uzzi expected - it may take time to develop a successful collaboration. What was surprising was that a very high Q was also correlated with low success!

It was possible to be too familiar.

Lehrer summarized Uzzi’s insight:

“The artists all thought in similar ways, which crushed innovation.”

I love this idea of balancing freshness and familiarity in all our gatherings, not just in the success of musicals or the general creativity of teams.

I have seen this play out in my own life - I have an annual eggnog party where I make a quadruple batch of the New York Times classic Nog. It’s been going for about ten years, with a small break for the pandemic. In the before-times, the gathering was often a familiar group of groups from my life - grad school, work, other friends, who knew each other a bit, and more and more over the years. It was always a large and raucous group, but our Q was increasing too much, as it turned out. I had created a guest list that was more regulars than new additions. (although the addition of my wife about five years ago did provide a solid Q-infusion since she has fun friends!)

Last year, I started hosting a series of smaller salon-like gatherings dedicated to serendipity. My wife and I split the invite list and started reconnecting to old acquaintances and new folks we were meeting as we ventured out in the post-pandemic re-socializing of New York. Some folks would get re-invited, others were one-offs. After hosting just 2-3 of these gatherings, the dates of the Egg Nog party approached. We decided to invite everyone who had been to a salon and the whole old timers Nog list.

The group that wound up coming to Nog Fest 2022 had a really great Q-value. A solid balance of freshness and familiarity that everyone commented on.

Similarly, in peer groups, we can be tempted to find a group that all narrowly meet a certain criteria or be a certain type to create a maximal Q-value. But Uzzi’s Q research shows us that variety is the spice of life, and that cultivating diversity of many types can have outsized rewards.

We are social animals and we require varied social nourishment

As a professional, I focus a lot on my own professional development and on helping my clients develop themselves. But, of course, we’re more than just our work.

This is where the conversation moves into the ideas of third places, long-term conversations, and, the importance of clubs in helping us stay connected to each other (which is what the film by my friend Rebecca Davis, Join or Die is all about — Robert Putnam’s groundbreaking work on why you should join a club, and why the fate of America depends on it. If you are dubious, check out the trailer!)

Lower commitment spaces with medium intimacy, like communities and third places, can be extremely helpful for overall mental health and personal flourishing.

Each of us has our own loneliness epidemic that we need to attend to with a spectrum of support tailored to our needs and goals.

My friend and podcast guest Kat Vellos wrote a whole book called We Should Get Together on how challenging it is to build adult friendships due to many, many structural factors, and she shares tons of suggestions on how to build deeper connections. You can check out our podcast conversation here and find links to her work.

My podcast guest Nick Gray says to host more parties, and his work is around helping people do just that. If you haven’t listened to our conversation, you should! And he’s right…if more people held more parties more often, that would be great. But 2-hour, mid-week cocktail parties, while surprisingly powerful, only scratch certain itches and can only provide certain types of support. That said, being the host and creating the support you most want to have is incredibly powerful. In fact, that advice is the advice my coach Robert Ellis gives!

I’d love to hear how many legs your support stool has, and what your key legs of support are!

The Four Quadrants of Employee Performance

Hiring, retaining and developing talent is a key leadership skill. Without great talent it’s impossible to have a great team. And without a great team, it’s impossible to build a great organization.

Hiring, retaining and developing talent is also time consuming, both in amount of time daily and weekly and length of time, over months. 

How much time? 

The HBR classic The First 90 Days (summarized here) has a diagram that explains that a new hire can actually take 3 months to start delivering value and another 3 months to start to see a breakeven return on your investment. 

The space under the line to the lower left is “value consumed” as a hire learns about the organization and the job. There’s no net contribution to be expected until three months in (90 days) -  that’s one of the main reasons that new hires should read The First 90 Days, and use it to develop a plan to manage expectations of their employers - which are always high!

You, as a Leader, are understandably itchy to hire employees that can “hit the ground running” on day one…but that’s rarely a realistic expectation.

Does that mean you have to wait for 3-6 months to find out if you’ve made a good hire?

The Four Quadrants of Employee Performance

Danny Meyer is one of my favorite business thinkers. He’s the pioneering restaurateur behind such acclaimed establishments as Gramercy Tavern, Blue Smoke, and the amazing and ubiquitous Shake Shack.  He’s also renowned for his focus on genuine hospitality and employee-first business thinking through his consulting firm, Union Square Hospitality Group. 

He wrote one of my favorite business books, Setting the Table. Read it!

Danny recently shared one of his most impactful leadership frameworks with Tim Ferris and summarized it here. The core idea is that there are four essential types of employees with four different attitudes towards performance. For each, you can have an action point and a time frame when you start to discover what kind of employee they are.

Flowers and Gems, Puzzles and Candles

Meyer breaks down the four quadrants of employee performance this way: Can and Can’t, Will and Won’t.

“If you've got somebody who can and will, I want to celebrate that person. Those are my flowers. I really want to water them.”

It's easy for leaders to take the Can/Will employees for granted. But it's important to "water these flowers" with praise and recognition. This helps with retention, sure, but it also makes it clear what kind of culture you want to cultivate. More on that later.

“If you have someone who can't but will, I'm gonna coach them. The wick on my candle is pretty long for someone who will…If you can teach them how to do the thing, they've got the right hospitality attitude. Once they learn …you're going to have a loyal employee for life.”

What’s amazing here is that Meyer goes on to say that he has a “six month wick” for these folks (just like HBR suggests!) …and refers to these employees as gems.

Employees that have the right mindset but not the skillset are diamonds in the rough. Many things are teachable. Hospitality, in Meyer’s view, is something that is easier to hire for than to coach.

Coaching is a crucial skill for leaders, and one that is rarely taught. Cultivating a coaching leadership style is one of the key pillars of conversational leadership. You can check out a summary of my core coaching frameworks for leaders here.

Can’t and Won’t: Light a Candle under them

Unmotivated and underperforming team members affect the whole team’s morale and productivity. Meyer says:

“Someone who can't and won't, I'm going to put the candle underneath their rear end, and they're going to have to learn that this isn't working, because the longer that person stays…everyone else on the team says, “why should I try?”

I’ve seen this play out firsthand in my executive coaching practice. A client of mine made a significant hire and found that this person lacked some crucial skills and essential attitudes that got missed in the hiring process. At the two month mark, we agreed that they would light a candle under that hire. That conversation cleared a pathway to letting the hire go at the three month mark if there wasn’t radical improvement. The frustration and disappointment my client worked through in the first two months was alleviated by clear communication of expectations and goals, and it made the process of letting the hire go a month later much more smooth and regret-free.

Can and Won’t: The Toughest Puzzle

It’s like trying to make a puzzle piece fit into the wrong slot, over and over again - but no matter how much the edges fray, it’s just not a perfect fit.

“The hardest one I find is the can but won't, that's the person that you can say to them “You're way better than this, but for some reason, you're just choosing not to bring it here.”

He describes the process of letting these Can't/Won't employees go as saying “you’re a great player, but I think you are part of a different puzzle”.

Meyer’s four quadrants, key action points and time windows are summed up here:

The Culture Equation (or, how to Scale Culture)

Meyer suggests, later in his interview with Tim Ferris, that the culture you have is, in essence, the sum of all the ideal behaviors you reward and celebrate minus all of the unwanted behaviors you tolerate.

Meyers believes that employees will notice when you, as a leader, tolerate the Can/Won’t and the Can’t/Won’t folks, thinking to themselves:

“Why do they keep batting that person in the lineup instead of benching them or sending them to the minor leagues!?”

The way to scale culture is, in short, watering your flowers assiduously and lighting candles intentionally under your potential puzzle pieces.

Easy, right?!

In practice, this is hard. Having so-called difficult conversations are, by definition, difficult. Leaders avoid these uncomfortable conversations and let them simmer, hoping they’ll resolve themselves, somehow.

Meyer’s culture equation points out the cost of doing nothing - it’s impossible to scale the culture you want to create if you let your underperforming employees sap the energy of your flowers and gems.

Leaning into the Coaching Conversation: Conversational Leadership

Watering Flowers and letting Puzzle pieces go isn’t quite enough. Your highest ROI employees are actually the gems - Can’t/Will folks who need more support and coaching to unlock their potential. 

In fact, if you’re working in a high complexity and high volatility environment, eventually everyone, you included, will be faced with an uncertain situation for which there is no easy solution. At some point, we’re all going to be in a Can’t moment. If we’re going to step into the Can’t/Will attitude, and help our teams to do the same, coaching is going to be a perennially crucial skill.

If we can foster a coaching mindset for ourselves and our teams, we can always turn Can’t into Can with a calm, consistent Will.

If you want to hone your skills as a coaching leader, check out my essay here. If you want a coach for yourself, check out my coaching page here and see if I might be a good fit for your needs.

The 9+P Model of Gathering Design

How do you lead a powerful gathering?

START WITH A POWERFUL PLAN USING THE 9P MODEL OF PLANNING.

Learn more for free: Download the 9P worksheet or Check out the 9P Mural Template.

There are more than the 9Ps in this model that can help you plan better gatherings, like:

More and more elegant Patterns of Conversation (explained in the Mural board)

More intentional Positionality to the people and purpose of the gathering (best explained in my podcast conversation with Dr. Lesley-Ann Noel, who introduced me to this concept) and what

Intentional modes of Presence that can help you lead the conversation. To master presence, sign up for my free course on Facilitation, which focuses on how you most want to show up as a leader in the moment to foster the impactful conversations you most want to lead.

Learn and master the essentials. Go beyond the basics.

It can take as little as 10 minutes of reflection to make a gathering plan that serves as a powerful backbone to an impactful gathering.

Check out this self-paced course, where I share tools, templates and patterns to make session planning and design impactful and low-effort.

You'll master a simple framework that will help you craft a clear plan to make your next important gathering as powerful as you need it to be.

45 minutes of video learning and 4 essential frameworks for planning sessions that deliver impact.

Design Powerful Agendas

Start for Free with Mastering Presence

I call this model the 9+ P model of planning because there are way more than the 9Ps in this course.

Again, one of my favorite Ps that isn’t in the nine is Presence - knowing how you need to show up to move the conversation forward.

Mastering how you want to show up is such an important skill. I made this free course with facilitators and leaders with a facilitative approach in mind.

The tools, short Videos and self-guided exercises can help you reimagine and develop a purposeful approach to your leadership.

Sign up for the course, and get 42 essays on modes of leadership, facilitation and presence sent to your inbox for 42 days!

These resources will help you understand what value you bring as a facilitator and a leader…and to increase the range and breadth of what you feel comfortable bringing into the room.

The course uses the metaphor of “hats” to get you to visualize and clarify how you want to show up as a facilitator and leader.

Get the Free Facilitation Course!

Where do you want to lead the conversation?

Conversational Leadership Essentials: Do you Consult or Coach?

Questions evoke answers that are in their likeness. Broad questions usually get broad answers. Generous or thoughtful questions often evoke more generous and thoughtful answers.

Conversations are the fundamental unit of change in any context, and questions are what drive conversations. So if you want to lead powerful change, then you need to master powerful questions. And you may also need to revise your theory of change. It’s common to believe that people will change when told that there’s a better way. But the most powerful changes are self-motivated. Consulting can produce powerful change…but coaching can produce longer-lasting change.

Are you Asking or Telling?

When a waiter comes by your table and asks you and your companions mid-meal “Is Everything Good?” it’s not really a question.

It’s more of a statement, an assumption or presumption….and the generally polite response is a nod or a smile.

“How is everything?” is a question that doesn’t assume that everything is good, but it's SO broad. EVERYTHING? I can’t begin to form an answer. When someone asks me that question, I literally start to scan my entire life.

Similarly, when a leader sits down with a direct report, asking “How is everything?” can be an overbroad question that people can find hard to answer. Breaking “everything” into key components like work-life balance, workload overall, and personal development goals can make it much easier to answer.

A question like “everything good?” sits somewhere between a “pure ask” and a “pure tell” - A pure tell in this situation would be like a waiter coming by and telling you “You’re good. Here’s the check.”

Yikes.

Telling is clearly not the right conversational move in this context.

Questions can lead the conversation toward the past, present or future

“How has your service been?” seeks to understand the past.

“Do you need anything?” seeks to learn if you need anything in the immediate future.

Questions focus the attention of the people hearing it. With our questions, we can draw people’s attention to the past or toward the future. We can focus the conversation on the positives or on the shortcomings of a situation. Each way of forming a question is a way of directing the conversation. Choosing a direction for the conversation is leadership.

One way to see the Past-Present-Future spectrum in action is in project management.

A retrospective asks “How did we do?” at the end of a project, the equivalent of asking a person “How have you been?”

“How are we doing?” is a question that seeks to understand the current situation.

“How will we succeed?” is a question we can ask at the start of a project about the future.

“How did we succeed?” is a question we can ask in the present from the future.

Asking from the future is sometimes called “Backcasting.”

Where do you want to lead the conversation?

Anyone, at any moment, can lead a conversation, just by speaking up. What you say, how you ask, and what you notice, will draw people’s attention to one aspect of the conversation or another.

Where do you want to lead the conversation? What is your compass as you navigate complex challenges?

One fundamental conversational leadership framework I like to use with my coaching clients combines the ASK-TELL spectrum with the PAST-FUTURE spectrum.

I hold these spectrums in mind, together, as I am leading a coaching conversation. And I often draw these spectrums as a 2x2 matrix, below, for my clients when I’m coaching them around *their* coaching skills. Let’s call this the Conversational Leadership Matrix 2.0, since an earlier version can be found in my book, Good Talk.

When to Coach? When to Consult?

When a building is on fire, there’s no time to spare.

If you know where the exits are, just tell people “the building is on fire. The exits are down the hall.”

If you know what a person’s problem is and you can solve it, go ahead and tell them:

“These are the problems you’ve been having. This is the solution that will fix it.”

That’s the “consulting path” in blue, in the diagram below. A Consulting conversation can be a very powerful one.

The “coaching path”, in orange, is different. It creates space and time for someone to decide for themselves what their real challenge is, what they really want to create, and how they will proceed.

Most of the time, challenges that feel like a raging fire are not actual emergencies. It can be worthwhile to slow down and let the person find their own solution.

Framing Powerful Questions IS Leadership

Telling and directing can often feel easier than finding a really powerful question to ask. But telling/directing people has several major downsides:

1. For complex challenges, that aren’t fires (ie, emergencies), simple solutions rarely exist. Complicated challenges can be solved with your past expertise. For complex challenges, your hunch is just a hunch. If you’re new to the complex/complicated distinction, check out the Cynefin framework.

2. Telling places the burden of knowledge, of knowing the "right" solution, on the shoulders of a single person (the leader) in situations that require more nuance or a diverse knowledge set

3. Telling disempowers the people being told/led because it discourages them from finding their own solution.

4. The solutions we find for ourselves are the ones we’re most likely to stick with (The IKEA effect is powerful!)

5. The most Creative and Innovative solutions are most often found by the people who are closest to the challenge. Respecting the knowledge of the person with the challenge means respecting the person. Telling can feel like disrespecting the person.

6. Over time, telling creates a person or team that counts on being told and not listening to their own creativity. It's often triggering for people who have spent time with leaders who rely on telling/directing without justification, so, why bother being creative?!

For these reasons (at least!), coaching, with permission, is one of the most powerful ways to lead and to create change that sticks. Don’t forget the story about the company that replaced all their managers with coaches and achieved 20% more productivity and engagement!

Coaching is a modality that leans into asking over telling, and plays artfully with the past-future spectrum.

Telling people things is a tempting path. It’s a more old-school form of “heroic” leadership. It can offer a sort of short-term high, a dopamine response. Coaching is a slower form of conversational leadership, and the satisfaction from these conversations takes a bit more time.

Hacking Coaching Conversations with the SOON Model

If you want to add coaching to your leadership utility belt, one of my favorite simple models of coaching is the SOON model. It can be a helpful compass for you to find your way in a complex coaching conversation and optimize the flow of the conversation for maximum impact. Let’s break the model down, and as you read along, lets map these key coaching questions to the Conversational Leadership Matrix above.

If you crave a practical roadmap of coaching and want to build your coaching habit as a leader, I highly recommend "The Coaching Habit" from Michael Bungay Stanier! A deeper dive into *why* coaching can be such a powerful conversational “technology” can be found in Timothy Gallwey's "Inner Game of Tennis." If you want to learn from *my* coach, check out my conversation with Robert Ellis, the author of “Coaching from Essence” here.

The SOON model traditionally starts with “success” but I’ve found that people start with where they are - the Situation, and the best coaches let the coachee unwind what the current state is, and how they got there. So I’ve added an extra S!

SSOON stands for Situation, Success, Obstacles, Options and Next Steps.

1. Situation

The Situation is what people come to the coaching conversation with. It’s the answer to the question “What’s going on?” or “How can I help?” These kind of questions are directed to the present, from the present. The coachee might tell you about the past or the challenge, or how things came to be the way they are. It’s your job to probe, inquire and hold space for the full story.

Given that there’s a huge gap between how fast we can talk and how fast we can think (4000 wpm vs 125 wpm) there’s no way that someone can possibly tell you all they could about what they are thinking about a certain issue or challenge. So, it’s worth slowing down and making sure you really understand the situation. Learn more about the thinking/talking gap here.

A transformational coaching stance is to draw the coachee’s attention towards the future, from the past or present challenges.

2. Success

What is Success? This is a question about the future, from the present. The clearer we can help the coachee to think and talk about “what does good look like?” the more helpful we can be as the conversation continues. What is the Ideal Future we’re trying to create?

Asking from the present, to the future, to clarify success and “keep our eye on the prize”, is powerful. But a transformational coaching stance can amp up a vision of success in two ways. One approach is to ask “What’s better than you can imagine?” (a favorite question of *my* coach Robert Ellis). Another conversational tool is to stand in that Ideal Future and ask questions as if that future was now. Sometimes this is called “the Magic Wand” question. “You have the goal we’re defining as Success…now what?” That can help us understand what REAL success looks like. Slow the conversation down. Leverage the Listening Triangle to really expand and clarify that Ideal Future.

3. Obstacles

What are the Obstacles? The Success questions look to amplify the positive aspects of what we’re trying to accomplish. But we need to be open and honest with ourselves about what’s in the way after we’ve clearly defined where we really want to go. List all of the obstacles!

The simplest way is a question that points towards the past “Why don’t you have it (the success state outlined earlier)?”

4. Options

Once we’re clear on the goal and what’s in the way, we need to get clear on the Options ahead of us - the near future. Some say that “the obstacle is the way”. Others say that the best way to eat an elephant is one bite at a time…and that starting with the tusks is the hardest way ahead!

Laying out all the options that can create forward movement toward success is a brainstorming exercise that the coachee needs time and space to think through. What are all the ways they can answer the question “What could you do?”

Once they’ve hit a wall, it’s possible to move into “tell” territory, gently, with questions like “Have you considered something like…?” if you have relevant information, knowledge or experience.

Telling in small doses can be impactful once we’ve asked deeper questions. This is when I find that offering a framework can be extremely helpful - not to give a solution to the coachee, but to help them see their choices in relationship to each other. Mapping options to some timeless frameworks like the Systems Thinking Iceberg, the Ladder of Intervention or my other all-time favorite ladder, the Abstraction Ladder, can help summarize and concretize the work so far, and set you and the coachee up for…

5. Next Steps

At this point, we might be getting close to the time when the conversation needs to end. Once the Zoom room closes, what will happen? What can the coachee commit to doing? If you’ve slowed down the conversation in the Options phase, there will be plenty on the table that they can do…but asking “What will you do?” is a question that points towards commitment.

One framework that my coach Robert loves to use is the idea of the Domino Effect. It’s a wonderful fact of physics that a domino can knock over another domino that’s 1.5X larger. It only takes 29 dominos, each just a bit larger than the next, to knock over an Empire State Building-sized domino.

Picking just one thing that is small enough to be easy to commit to and big enough to be edgy can be powerful. Think of this as the “biggest smallest thing.”

Ask the coachee to find that domino that will set them up for the success they defined earlier - a question that points towards the future.

Shifting the Analysis-Action Set point

Everyone has their own habitual, or learned set point between Analysis and Action.

Some people love to jump straight into action…while others would rather stay in Analysis mode forever…or at least until they feel 1000% sure of their path ahead. Amazon Executive Chairman and Founder Jeff Bezos has been famously quoted from a 2016 annual shareholder letter about this challenge. He suggested that while it's always nice to have access to all of the information you'd want before making a choice and moving into action, in the vast majority of cases, waiting until you know everything you should know is impossible…and detrimental.

"Most decisions should probably be made with somewhere around 70 percent of the information you wish you had," Bezos wrote in the letter. "If you wait for 90 percent, in most cases, you're probably being slow."

A SSOON coaching conversation moves a person between Analysis, Insights and Action within a fixed time period, all while keeping our minds fixed on Impact - the reason we want to take action. A SSOON conversation is a balanced conversation - one that puts equal emphasis on Analysis, Insights and Action.

Even outside of an official coaching conversation, we can choose to use the tools of coaching to co-create our approach to problem-solving, and to make sure we’re not putting too much emphasis on one mode of thinking vs another. In the context of group conversations, the coaching mindset looks a lot like facilitation. To learn more about leading groups intentionally, check out this essay on three essential conversations for group transformation and this essay on the nine elements of transformational facilitation.

Finding a Sacred Space is an absolute necessity for Leaders

How do you follow your Bliss?

Joseph Campbell invented the term "Follow your Bliss" and this is the moment when he shared his method for doing just that - finding a place and time, each day, for just you, to connect to what matters most, to you - what he calls “a Sacred Space”

I’ve recently been re-watching The Power of Myth, a PBS series from 1988, where Bill Moyers interviewed Joseph Campbell, then a professor at Sarah Lawrence who wrote several books developing the idea of “The Hero’s Journey” and exploring the connections between the world’s mythologies. Amazingly, you can watch the whole series on YouTube here.

What Does iT Mean to Have a Sacred Place?

Why would someone need a sacred space, especially if you don't believe in a god or gods? Sacred comes from the Proto-Indo-European root root *sak- which meant to "to sanctify”…which just means to set aside or set apart, much like the idea of an “Inner Sanctum”…an inward, protected place. (FYI, Proto-Indo-European is the language that the Sanskrit language group and the Latin languages sprouted from)

Why DO Leaders need a sacred space?

It’s easy to get pulled into the day to day and get lost. Leadership is about holding the vision and helping other people connect with that vision.

Holding space for others takes energy, focus and intention that needs to be replenished, every day. Sleep gives some replenishment for the body and mind…but a sacred space is for your soul!

Below is a transcription of Campbell’s exhortation to each of us to find our “Bliss Station” each day. I can’t really say it any better than him!

This is a term I like to use now as an absolute necessity for anybody today. 

You must have a room or a certain hour a day or so where you do not know what was in the newspapers that morning. 

You don't know who your friends are. You don't know what you owe to anybody. 

You don't know what anybody owes to you.

 But a place where you can simply experience and bring forth what you are and what you might be. This is the place of creative incubation. 

And first you may find that nothing's happening there. But if you have a sacred place and use it.

…most of our action is economically or socially determined and does not come out of our life. I don't know whether you've had the experience I've had but as you get older, the claims of the environment upon you are so great that you hardly know where the hell you are. 

What is it you intended? 

You're always doing something that is required of you. 

This minute, that minute, another minute. 

Where is your bliss station? Try to find it. Get a phonograph and put on the records. The music that you really love, even if it's corny music that nobody else respects. I mean, the one that you like or the book you want to read. 

Get it done and have a place in which to do it

Any Leader who wants to be truly effective needs to find this time, in order to renew themselves, to reorient themselves, to ground themselves.

What do I do in this so-called Sacred Space?

First off, Don’t Underestimate the Power of Self-Reflection (says the Harvard Business Review).

Maybe the simplest and most effective morning practice are Morning Pages. Coined and championed by author Julia Cameron, morning pages ask us to hand-write three pages, long hand, without stopping, first thing each day. It can be transformative if you give it a try.

Not into writing?

Some years ago the wonderful podcast, OnBeing, featured this Tree of Contemplative Practices.

“The branches represent different groupings of practices. For example, Stillness Practices focus on quieting the mind and body in order to develop calmness and focus. Generative Practices may come in many different forms but share the common intent of generating thoughts and feelings, such as thoughts of devotion and compassion, rather than calming and quieting the mind.”

Try walking, singing, sketching…anything that falls under the category of “following your bliss” or stepping back from the day-to-day and giving yourself space to be.

The Tree of Contemplative Practices Image by Carrie Bergman + design by Maia Duerr/The Center for Contemplative Mind in Society..

Your Toughest Conversations Are the Ones You Have with Yourself

For Leaders, Your Inner Voice is a Superpower...until it isn't. Here are four ways to shift it.

As a leader, it's natural to think of strategies to tackle current issues or prepare for future ones - that’s the job. But if you find yourself constantly thinking about your company’s challenges, if your thoughts spiral out of control (or inwards), work can take over your life and have a negative impact on your relationships, your health and eventually, your company.

How you manage your inner talk is as important as how you manage your leadership team or how you recruit investors, advisors and board members. 

There is no silver bullet, but there are simple tools you can apply on your own and ways to seek out the right kind of help to get you moving.

Who sits on your inner board of directors?

The idea of having a host of voices in your head isn’t particularly flattering. It can conjure images of a Hollywood-type of schizophrenia. Yet, it’s a fact: each of us has a crowd between our ears. Some of the voices in our heads cheer us on; others put us down. Some whisper to us as we try to fall asleep.

It’s easy to overlook our internal conversation in the bustle of life’s duties. Our culture’s outward focus can keep us from taking time to look inward, and it’s a shame since our inner conversation is the foundation for all of the other conversations we engage in. And shifting our inner chatter can deliver a tremendous ROI. (that's why I included a whole chapter about inner speech in my book Good Talk, about how to design conversations that matter)

What Inner Speech can help with

Being able to reflect silently, to talk to and with ourselves can help us:

++ Make sense of experiences (like when we journal)

++ Remember things, like repeating your grocery list as you walk through the supermarket (don't forget the eggs!)

++ Visualize, simulate and plan for the future (like when we daydream or strategize)

++ Control yourself (like saying "Don't go there!" to yourself as you walk into a conflict)

When we take time to listen to and engage with the voices in our heads, we can begin to identify patterns and themes. We can become aware of how our inner dialogue either supports or undermines our success. We can start to distinguish the helpful from the unhelpful and make changes accordingly.

We can learn how to talk back to ourselves more kindly, offering ourselves words of encouragement and perspective when life gets tough. We can also recognize when certain thought patterns are leading us down a destructive path, and choose different paths instead.

By becoming conscious of our inner conversation, we gain a powerful tool for self-improvement and self-empowerment. It's like gaining a superpower! In fact, inner speech is much, much faster than outer speech, or writing. We can write at 40 words per minute, speak outwardly at 150 words per minute, but some research has clocked inner speech at 4000 words per minute! 

Harnessing that power is incredible.

But sometimes this superpower can turn on itself. Dr. Ethan Koss, in his book Chatter, points out that inner speech can become chatter: a circular, repeating, enervating inner grind.

When Inner Speech runs off the rails

When our inner speech gets out of control, Dr. Koss suggests that:

++ It can make it hard to perform in the moment, because we're stuck anxiously ruminating on the past or projecting into the future.

++ We can burn out our friends and partners by continuously sharing the same challenges with them over and over again.

++ We can burn ourselves out. Overactive inner speech can affect our sleep, which is essential to a healthy life. Extended stress is similarly toxic.

Four approaches to Managing Inner Chatter On your own

In order to combat hyper-active chatter, Dr. Koss suggests three key types of approaches: Those you can do with yourself, those you can apply with others, and things you can do in your physical space. Here are four approaches you use on your own, either in your head or in your space.

1. Talk to yourself by your first Name

2. Use Temporal Distancing

3. Change your Space

4. Slow down and Get into your body

1. Talk to yourself by Name

Use your name when you talk to yourself. It can make your inner voice kinder and more friendly, instantly. It automatically shifts your perspective into a "coaching" mode...we're great at solving challenges for others, so, when we talk to ourselves in the second person, we leverage this linguistic machinery for our own benefit.

2. Use Temporal Distancing

Inner speech, when it gets stuck, is usually stuck in the past or in the near future. Shifting your temporal frame gets you unstuck.

Ask yourself: "How will you feel about this in six months or a year? How do you want to feel about this in five years?"

3. Change your Space

The easiest way to change conversations is to change the space or place the conversation happens in...that's why the "interface" for a conversation is at the center of my Conversation OS Canvas. You can change the space or interface of your conversations by journalling, recording yourself talking out loud in your house or more powerfully…while going for a walk. 

Dr. Koss also suggests that you can "order your surroundings to order your mind"...ie, tidy up your desk or your house when you're caught in anxious chatter!

4. Slow down and Get into your body

We all have voices in our heads. But it’s important to remember that they are just that: voices. In our heads.

Powerful action comes from our whole selves - our heads, our hearts and our guts. So, listen to the voices in your head, but also take time to slow down and listen to your heart and your body. These parts of you have real voices, too. And a Real Voice can change your life, and help you make sense of the world. 

But we can’t hear these other voices until we can get quiet and take a step back. We need space to tune in and listen to our whole selves, our whole voices. Being in silence, mindfully connecting to your whole self, is always time well spent.

The best way to shift your thinking: Talk to someone who expands your thinking frame

When you’re stuck in an inner chatter rut, it can be hard to break out of it, even with the tools above. Your inner speech becomes a monologue. That’s when you need to find a trusted conversation partner to turn your monologue into a dialogue.

It can be tempting to go to someone who will let you unburden yourself and hear you out. It can be tempting to choose people in your life to talk with who will just listen. And you should! Finding someone who will deeply listen is incredibly impactful.

Whether you seek out a friend, family member, therapist, coach or advisor, it’s essential to have deeper dialogues with people who will challenge you and expand your frame of thinking. 

To get out of your rut, pick someone who can leverage the mindsets of coaching, mentoring and advising - not just listening to you, but pushing back on your thinking. They should ask you deeper and deeper questions that pull you into thinking differently. When you start to look at the challenge in a new way, you will start to break out of your inner chatter and start to create something new. If a coach sounds like the right approach for you, you can learn more about my coaching philosophy here.

Note: If your inner speech is particularly dark or repetitive and the four approaches you can try on your own, above, are having no impact at all, talking to friends and family isn’t making a difference, and a coach isn’t making a dent in the situation, you might need a therapist or medication.

An inner speech checklist

1. Recognize when your inner speech is turning into chatter.

2. Take a break and do something else. Take a walk, tidy up...shift your space!

3. Learn how to practice mindfulness and meditation in order to be present in the moment and not ruminate on the past or worry about the future. Get into your body and out of your head

4. Develop healthier thought patterns by challenging negative thoughts with positive ones. Consider the worst case AND the best case scenarios!

5. Work on developing self-compassion and self-forgiveness for when you slip up or make mistakes. This is a “Sporting” mindset: you win some, you lose some, and you keep playing.

6. If the chatter persists, talk to someone who can help you find perspective or look at the situation in an alternate light.

7. Engage in activities that bring you joy and help you relax so that your inner speech can take a break from ruminating on stressful topics.

Take the next step

Which of these strategies resonated the most with you? Which are you going to try out?! 

Let me know! 

Did I miss a strategy that you find works really well for you? 

Let me know!