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:
Have them regularly. (read why below)
Limit the number of agenda items.
Get more feedback than you give.
Start with wins and increase your positive to negative feedback ratio.
Use 1:1s to coach your team to solve their own problems, not to solve problems for them.
Align on a time horizon to focus each conversation on.
Listen actively and deeply before responding.
Follow up on past conversations.
Flip who runs the show
Create a standard agenda with each direct report.
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.
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.
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.
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.
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.
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.” ”
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.”
”
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:
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)
What has your attention right now?
What's driving you crazy these days?
What's making you happy to come to work these days?
What is the general mood and morale of the team(s) you're on?
How are things outside of work?
How is stress at work?
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:
What's your next step?
What was most useful to you?