Don't Emotionally Bootstrap Your Startup

“Sure, my co-founder and I have mild PTSD...but we’re just knuckling through”

“You’re just knuckling through?” I replied.

“Yes”

(I paused)

“If I was a friend of yours and I told you that I had PTSD and that I was just knuckling through it, what would you say to me?

…

A few weeks ago I sat down for a catchup call with an old friend that turned into a mini-coaching session with that simple act of reflection - repeating back what I had heard. It slowed the conversation down enough so that we could both hear what was happening. (this is one of the reasons that cadence is an essential element of my Conversation OS Canvas)

I could have just laughed along with the inside joke. Hah Hah, isn’t repressing trauma funny?!

But my interest is always in taking a conversation deeper, to the heart of the matter.

I asked her if I could offer an alternative perspective.

Now, some folks will tell you that coaching is *never* ever about offering advice. But I knew how to pivot her understanding of an essential startup philosophy and learn to apply it to herself. 

Also, I’m her friend, and you can’t coach friends, right? 

In my defense, I asked for permission first. Key point. Advice without permission is...well, it sucks. (Invitation and Power are also key elements of the OS Canvas, just saying)

See, this friend of mine has been starting up a company for the last few years. It’s taken off...they’ve been selling well, and getting some great placements, requiring bigger orders...which are complicated. Pricing a product depends on how much you are planning to make over time, the amounts you make may determine the manufacturing process. (This is, by the way, a physical product. They are, for lack of a better word, hard. (It’s a pun.))

The uncertainty in demand was making it hard to price the product competitively. The difficulties in pricing were making it hard to negotiate with bigger buyers quickly. No one likes the phrase “negotiations were dragging on” ...but they were.

On the call, she’d admitted to me that if today, she was handed her company, with all of its challenges, she’d be thrilled. She’d get right into problem-solving mode and knock ‘em down, one at a time, like the boss that she is.

But most of these problems are ones that she’d created, herself. As she’d been explaining to me during our conversation, she had bootstrapped her company, launched the product as an MVP, and had been scrambling ever since to scale it properly, mostly by rebuilding it from the ground up. She had already shared with me how bootstrapping had created all of these challenges for her, and how she was being more intentional about building her product’s solid foundation. 

So I knew that the word “bootstrapped” meant something to her. She had been living it. And she knew all about how, eventually, you have to start over...sometimes from the ground up and (re)build a solid foundation. 

She just wasn’t using that language on herself. Nor had she realized that the emotional state of her company and her own emotional state were so intimately intertwined. 

I am a total bootstrapper, so I empathized. Maybe you are, too? I love to just get an idea out there and see what traction we can get. But that is outer bootstrapping. 

What she was doing was inner bootstrapping.

A few years back, I wrote on a sticky note:

“Don’t emotionally Bootstrap your Startup”.

Since I wrote that sticky note I’ve done a lot to reduce my own inner-bootstrapping. I have a coach, I work with an executive coaching mastermind as I deepen my own executive coaching practice, I have a men’s group that meets weekly (it’s like crossfit for my emotions), a therapist and a slack channel filled with innovation consultants who are all more talented than me, and generous with their insights. And...yet...It can still feel lonely and hard sometimes. 

Some people will tell you that a coach can’t tell a personal story, or offer advice. In this case, I knew that sharing my sticky note and its back story with her would help her rethink her inner-bootstrapping mentality.

When I shared this idea with her, I watched her shoulders lower an inch. She took a deep breath. She started to step back from being inside of her pattern to watching it from the outside. She felt seen.

She could begin to ideate about what *she* could do, and wanted to do, to help herself put on her own oxygen mask. 

But this was just the start. Trauma takes time. So we got to a deeper question: How could she forgive herself for creating her problems? 

Self Empathy, or empathy for a past version of yourself, is a powerful tool. Having a conversation with your past self is possible. Having a conversation with your future self is possible too. 

In fact, that’s where we finally got to. What did her future self want from her? What path would get her towards meeting that version of herself?

These are conversations worth leading with yourself and for others.

The Secret to Engaging people remotely

Giving People an Out helps them be all in

Today, people have a lot on their plates. Their calendars are full. So, getting people to carve out time in their lives for your meeting is, let’s say, non-trivial. It’s even more challenging to get them to stay engaged during the time you have booked with them.

People are at liberty to leave your session at any time. Back when we met “in real life” it took guts to follow the “Elon Musk Rule” and leave a meeting you thought wasn’t leveraging your time well.

(This rule is sometimes better known at the Law of Two feet in the world of Open Space Technology...and has been renamed the Law of Mobility to be more inclusive.)

Now, people can leave in an instant, at the touch of a button.

In “Finite and Infinite Games” (one of my favorite books) author James Carse suggests that 

“anyone who must play, cannot play.”

In other words, you can’t force people to show up at their best. 

Creating a space where people feel safe to bring their best is one of the most important skills right now. It’s one of the reasons why I’ve been musing on past emails about how to create these kinds of spaces.

I’ve also been musing about this topic, because over the last weeks, I’ve been facilitating a session about creating safety for authenticity for the Google Relay Conference. Over the past 4 years it’s been one of the most powerful conversations I’ve been part of, bringing together top consultants in Design Sprints and Innovation with top experts from inside of Google to talk about the future of Design Sprints. Stay tuned for a set of materials and outcomes from the session.

Extrinsic vs Intrinsic Motivation

You can try to leverage extrinsic motivations, like duty, money or habit to get people to show up...but they'll only show up in the most mechanical of ways.

If you want people’s creativity and engagement, you need to evoke their sense of play or their sense of purpose.

People are free. They don’t have to be in your meeting. 

Respecting and acknowledging that essential freedom is the most powerful secret to engaging people.

If you think about earning people’s attention instead of “getting them to pay attention” you will find a subtle internal shift in how to attempt to lead and facilitate groups.

Giving people an out helps them to be all in: Four layers to shift

This is an internal, mental model shift. There are at least four layers in this shift towards acknowledging that we have to earn people’s attention.

1.Showing Up: One layer is getting people to show up for the session, the meeting, the workshop, the kickoff. For that, we must refine our skills in Invitation, one of the core elements of my Conversation OS Canvas. Why does it matter for them to be there?

2. Participation: Another layer is allowing people to participate at their own comfort level once they’ve arrived in the session. This is why I always let people “pass” on a check in, or hang back on an exercise. I make it clear that we need them fully here, but acknowledge that they might have other things going on, so they might need to step back. Or, they might want to just watch for a bit until they feel ready to jump in

3. Payoff: People need to believe that the outcome of their participation will be worth MORE than time they put in. In other words, “is the juice worth the squeeze?”.

4. Variety: People get bored. It’s life! Think about switching up your approach as often as relevant and possible: Chat. Video. Using physical activity and digital whiteboards.

eight types of variety to boost engagement

VARK refers to “Visual, Auditory, (W)ritten and Kinesthetic learning types. Although the theory is contested, it’s still a good shorthand for engagement. While you can’t really diagnose and customize for a specific learning style, adults usually claim to excel in one over the other. I like to make sure I move around the VARK circle early and often.

When I work with leaders on developing their facilitation approach I like to get them to think about what other types of variety they might use to engage people. Any one of these modes of engagement can get boring if overused! The code word is variety!

Spectrums to create variety across include:

1. Visual: I love to get people to sketch their ideas on paper…it’s a cheat, because it also uses written communications and is highly kinesthetic. It’s a 3-for-1

2. Auditory: Clear instructions, judicious use of music (one facilitator invited folks to play their own music during a silent, muted brainstorm.

3. Written communications: Anchoring the conversation in written text, either in slides, in chat or in a shared document can create engagement if not overused.

4. Kinesthetic modes: Like stretching, or using objects in their space.

5. Conversational Size, Interpersonal to Intrapersonal: ie, making time for small and large conversations, including time for individuals to think.

6. Tempo or Cadence: making time for short, focused bursts and more slowed down conversations.

7. Control or Power: Making space for structured work as well as creating space for unstructured, decontrolled or decentralized conversations.

8. Patterns: I am a huge fan of breakouts and “think-pair-share” but even that can get boring if over-used. Leveraging a greater variety of group conversational patterns, like round-robin, popcorn-style share outs or fishbowl conversations.

Whatever you do, the core mental model is that you are earning their attention, by inviting free folks to participate freely, to make the payoff clear and tangible, and to continuously engage them across any and all channels that work.

As with all human challenges, your mileage may vary. Experiment and try new things, and see what works for your team.

Leadership is the Art of Showing up on Purpose

The Art of Showing Up (on purpose)

Outside of time travel, there is only one chance to do a moment right. Each conversation, meeting, first date, only happens once. There’s only one today, one time we’ll experience this hour, this minute, and this second.

We can rise to the occasion, meet what the moment demands of us...or we can replay a series of "if only I had..." options in our heads.

Leadership is the Art of Showing up (on purpose).

This is about being a mindful and intentional leader, instead of showing up based on how we've always done it in the past, or showing up out of habit, unconsciously or mechanically.

It's about asking what the moment demands of us and finding a way to bring the best out of others.

How do you need to show up more in 2021? How are you finding the resources in yourself to do it? Share your thoughts with the community here, where I posted a painting of this idea, on LinkedIn.

How we talk together is how we work together

How we talk together is how we work together.

Our lives are defined by the conversations we can and can't have.

Our organizations and teams are also defined by the conversations they can and can't have - if there's more truth in the hallways and side conversations than in the boardrooms, there's a problem.

How we talk together is how we work together.

If we can't really talk together, we can't really work together.

If you want to see a change, it's your job to lead the conversations you want to happen. It's your job to ask "what does this conversation need?" and then to show up and bring what it needs.

Leadership is the art of showing up, on purpose, to serve the conversation and the people in it and to facilitate that conversation.

I posted these ideas on LinkedIn and was thrilled with some of the responses (feel free to add yours).

One commenter pointed out that we should start to become aware of power dynamics in conversations:

these narratives can often leave out elements of (real or perceived) power and control, earned and unearned privilege, and the systemic unresolved trauma built into our organizations, systems, and - by default - our leaders.

And to that I say…these elements exist at the level of the individual conversation. Each conversation can be an opportunity to call these dynamics out and resolve them. And let’s be even clearer: this process takes energy. Shifting a system doesn’t happen by accident…It happens conversation by conversation. And leading the conversation you want to have can take effort.

These Japanese words for space can change the way you lead

These Japanese words for space can change the way you lead

Where Does a Conversation Happen?

What is the medium for the conversation…and does it support the conversation you want to have happen?

All the other elements of a conversation converge in one place: the interface for that conversation. (Learn more about the other elements of the Conversation OS Canvas here)

The interface can be physical. The interface of (formerly) regular, everyday conversations is the air we breathe. We vibrate that air with our vocal cords, those vibrations strike our ears and we convert those patterns to sounds, sounds to language.

The interface can be digital. We also communicate through texts, emails, Facebook, Slack, Twitter. Some of these interfaces are more conducive to dynamic communication than others. Others are better for focused interactions. Zoom is a little bit of neither.

Each of us has habits and preferences for where we’d like a conversation to take place. Who hasn’t gotten annoyed with someone for calling when a simple text would suffice? Who hasn’t judged someone for sending a text when a call was appropriate?

. . . . .

These ideas are extracted from my recent book, Good Talk: How to Design Conversations that Matter. You can find free chapters and downloads here.

. . . . .

A Tale of Two Spaces

I was running a working session some time ago with a team, and they’d set up the room in a traditional boardroom-meets-classroom configuration.

What does the space at left say to you? With a screen at one end and everyone facing the center, the space was about focused listening. But we were there to collaborate!

So, during the break, I rotated the center table, creating the space in the diagram at right. Coming back from the break, people stopped in their tracks. The room had changed: they could feel it. What had I changed, they asked?

I had made the space more relational, more inherently collaborative, inviting people to connect with one another more intimately. That relational quality was felt before it was seen.

In the Japanese conception, an empty room can be full of qualities and potential. There are four concepts for space in the Japanese language, which are useful to think about when designing a conversational space.

The Four Qualities of Interfaces

Relational Space

In the example above, I shifted the relational quality of the space. If a room is too small or too noisy, or too big or too quiet — it might hinder the kind of relationships that can form. This is called Wa.

If you’ve ever seen the first Batman movie, you might remember the “super-long dining table” scene…even if you haven’t, you’ve seen the trope before. It’s funny because an intimate dinner for two just needs a smaller, more intimate table.

can you please pass the salt?

Knowledge Capacity

Air is a conveniently handy interface for conversations, but the conversation fades without leaving a mark. Whiteboards and sticky notes are more durable interfaces for conversation, and so they help increase knowledge capacity or the bandwidth of a space. This is called Ba. Seating teams together in a rooms with walls, where they can leave ideas up and add to them over time can also increase Ba.

Place as Space

Going to a remote location can help focus a discussion or make it challenging to attend. In this model, a building can’t be in Tokyo without Tokyo being in the building. Place is space. This quality of space is called Tokoro. This is what real-estate brokers are talking about when they use the phrase “Location, location, location.”

A few years ago I hosted a workshop at a lovely space on the grounds of an art museum. The room was octagonal, with large windows looking out on sculptures and elegant trees. This was not some dingy office cube with fuzzy walls. The space told people something about the event, instantly.

Negative Space

Packing things together can mean no space to move or wander. Negative space, or Ma, allows silence and openness between things and events.

An architect friend of mine told me that this concept is taught as “the space between the stones” …in a conversation, Ma can be the space between breaths or turns taken.

Recently, I put together a virtual, 3-session deep dive on a critical set of tools and skills for a large retail concern. At the last minute, my client informed me that the CEO would be stopping by for “5–10 minutes tops”…they wanted to encourage this initiative and share their stamp of approval on the initiative — this training was the first of many to come. My client assured me that since the CEO was making a bunch of media appearances around a recent big product announcement, they wouldn’t stay long.

The CEO spoke for 15 minutes…then decided to take questions! It was 30 minutes later that they dropped off.

I was slightly panicked as 10 minutes stretched to 20. I looked over the last hour of my agenda. What could I remove? What could I shorten? Luckily, I always add a fair amount of Ma to my agendas so the process wasn’t agonizing…but it wasn’t painless. Going into a session with Ma to spare is always a safer place to be.

Taking something out of your agenda is the best and easiest rule of thumb. It will always be possible to add more later. And the space and time that Ma opens up can be transformative. Planning for emptiness is a paradox, to be sure…but one we all must solve if we want teams to do deeper work.

Negative Space is a huge opportunity

While Ma is impossible to “see” is can be the most impactful way to shift the spaces you create. You can “add” more negative space by creating moments of silence and reflection in your meetings and workshops. Another is by removing activities and not packing the agenda too tightly.

In my coaching work, I’ve increased the negative space by meeting with people for 2 hours. The standard hour put too much pressure on our conversations…increasing the time we had allowed the conversation to drift and deepen and find a center.

Change the Interface to Change the Conversation

Interfaces have a bandwidth, the amount of information they can support (or Ba in Japanese parlance.) Texting is a “skinny pipe,” sending only a single dimension of data (words) in chunks. Reality is a “fat pipe” that throws a broad band of data at us all at once. Tone, body language — even scent! All of those “channels” sent at once can help us read a situation. Texting is great for sending simple information…not breakups.

Changing the interface changes the conversation. If a text interchange gets stuck, switching to a phone call can help. If that fails, asking for a face-to-face meeting can smooth things over. More information bandwidth and lower latency in the interface can help bridge misunderstandings.

With air as our interface, each moment of the conversation slips away with only our brains to hold it all together. We can design our conversational interfaces to support different modes, enhancing our communication. One way is to make the interface “sticky.” A whiteboard or actual sticky notes make our conversations more visible, durable and flexible. These surfaces create more intersections for communication, turning our spaces into super-fat interfaces.

I’ve been having dinner with a group of people Sunday evenings for several years. At first, the interface for our conversation was at the corner of Elizabeth and Houston, at a bar called Jo’s. At some point, someone started a group chat. That channel created a second interface for our conversations, allowing us to meet more frequently and deepen our connections…and go drinking more often.

How can an additional interface enhance your communications?

What conversation do you want to shift?

Interface is at the center of my Conversation OS Canvas because it’s the place where all of the conversational elements intersect and interact.

One of the easiest ways to change your conversations is to change where they happen and the tools you use. Buying whiteboards, sharpies and sticky notes won’t fix anything overnight, but shifting tools can shift communication. Adding an additional interface can help cultivate shared understanding.

Think about your own Conversation OS. Where do you feel comfortable holding conversations? Are your chosen spaces supporting your communication goals?

Think about a critical conversation you want to shift.

How can you rethink the interface of the conversation? Which of the four interface qualities could shift the conversation?

…

Learn more about these ideas in my book Good Talk: How To Design Conversations That Matter. You can download a few free chapters here or find links to buy the audio book and physical books online.

Your next meeting should be silent

Your next meeting should be silent

Here’s how to change the conversation

Meetings can be completely sidelined in the first 30 seconds. There’s one in every group: the guy who opens his mouth first. (and it’s likely a guy…sorry, guys)

What’s the big deal? Someone has to break the ice, right?

The deal is this: The first speaker sets the tone for the rest of the conversation, anchoring the entire conversation.

After the first speaker sets the tone, the second speaker builds a thread from that first turn, whether they agree with the first speaker or oppose them. Before you know it, the rest of the conversation is a response to that first comment.

I call this conversational cascade “first speaker syndrome.”

Having someone speak first feels like a necessary evil, especially if we’re going to fill up an hour’s worth of conversation in a meeting. But what does first speaker syndrome actually do?

The Impact of First Speaker Syndrome

→ People respond instead of think.
When someone shares their first thoughts and opinions on a particular idea, we frame what we say next based on a response to what the first person said. We agree or we don’t. We offer a “Yes and…” or a “No, but…”

And even if we suggest a new thought altogether, that first comment has still influenced our thinking and everyone else’s. There’s no longer any opportunity to have our first thoughts on the issue, unaffected by the first speaker.

→ We run with tangents.
One person’s opinion can easily (and quickly) send us off into a tangent or in a certain direction. What about all the other good ideas that are suddenly pushed off the table to explore the first person’s tangent? First Speaker Syndrome doesn’t always let us explore the best ideas, just the ones that were brought up first.

→ Some people don’t speak at all.
I’m personally on a mission to protect the introverts from the extroverts and the extroverts from themselves. It’s true…Extroverts don’t often even realize the impact of their habit of thinking out loud. ( I hope…)

Speaking up in a meeting can be hard. Extroverts have had more practice. Introverts are often more reserved, calculating their thoughts while the discussion rages on. The problem is: there’s no diversity of thought if we’re always listening to the people who are always talking.

→ Our Fast Thoughts Stop Us From Listening
We think too fast. Researchers have clocked inner speech at a pace of 4,000 words per minute — which is about 10 times faster than verbal speech. That kind of inner speed means that most of us can’t possibly be listening to everything someone else is saying…we’re already thinking about what we could say next.

This problem isn’t just a once-a-year issue. It happens in meetings every day.

At work alone, some estimates figure that the average worker spends about five hours in meetings each week. For managers, that number rises to 12 hours. In the public sector, it’s 14 hours. Most of these hours are reported to be “ineffective” at delivering solid outcomes. That’s a huge financial loss in productivity. That loss could be as much as 37 billion (with a B!) according to one study. And that’s just official meetings.

I think we can agree, traditional meetings like these don’t actually provide space for productive conversations. So, what can be done? How can we design our conversations to be more effective?

I wrote a book about conversations and how we can (and already do) design them — even our internal conversations. Some people feel like “conversations” is a squishy word and that “design” excludes people. I say: design belongs to everyone now. And I believe that we are all designers of our conversations.

What you’re reading is based on ideas and concepts from that book, Good Talk: How to Design Conversations that Matter. Read on or click that link to get free chapters of the book.

We need time to think about what we think

What if there was a better way to meet? What if we didn’t talk at all? What if the meeting was actually…silent?

A silent meeting isn’t getting everyone in a conference room to stare at each other in awkward silence for an hour. It looks more like reading, writing, thinking, and processing ideas and solutions internally before sharing them with a group. We’re slowing down our inner dialogue and thinking our own thoughts and opinions before anyone has the chance to tell us what they think.

If we’re not thinking in meetings and we’re in meetings all the time…when DO we think?

Silent meetings most often start with everyone reading a shared document silently (surprise surprise), making notes of their thoughts as they go. The meeting is facilitated by someone who leads the group through a series of questions and eventually helps moderate a conversation between the group, working towards whatever level of consensus is needed… (This conversation can be silent too.)

This silence, paradoxically, allows us all the same amount of time to speak our mind….except we’re doing it in our heads first, and on a shared canvas second. Everyone’s voice can be heard equally in this way.

Most of my meetings are now Google doc-based, starting with 10-minutes of reading and commenting directly in the doc. This practice makes time for everyone to get on same page, allows us to work from many locations, and gets to truth/critical thinking faster. Good thread 👇🏼 https://t.co/YRsxT3kMAZ

— jack (@jack) April 20, 2018

The impact of leading meetings in this way speaks for itself (pun intended and apologized for). A silent meeting concludes with a diverse list of thoughts, ideas, and solutions for the topic at hand, without anyone dominating or feeling excluded.

Participants are more likely to feel like their expertise is utilized and their time was productively spent.

In a traditional meeting, the end results look more like an exasperated speaker, and attendees who have been checking their watch waiting to get back to the pile of work at their desk. Some participants may have not spoken or voiced an opinion at all while others, the “talkers” may have hijacked most of the conversation.

It might seem like a big leap to go from traditional, loud meetings to a 60 minute silent meeting. And if you’re doing it for the first time, it’s sure to make the attendees feel a bit uncomfortable. There’s no rule that you have to be silent the entire meeting. If you and your team want to give it a spin…

Try this Silent Meeting Agenda

→ A silent table read for the first 15 minutes on Google Docs

→ Allow each person has time to gather and record their own thoughts. (5 minutes)

→ Capture those reflections in a shared document, and allow everyone to read those over. (another 5 minutes) (Mural is a great option to make this process more interactive, even if you’re in person)

→ Only then allow people to have an out-loud conversation as normal. (your last 20 or so minutes)

Try a silent meeting if you want meetings that don’t suck. (And provide real results.)

Learn more about how to run better meetings, host better conversations and new patterns for communicating, check out my book. Learn more and pre-order Good Talk: How To Design Conversations That Matter.

You can also find free chapters and downloads here.

PS - if you want to learn even MORE about silent meetings, be sure to check out David Gasca’s Silent Meeting Manifesto, an excellent resource.

How to Talk to Yourself

How To Talk To Yourself

What’s in Your Head, in Your Head?

Shel Silverstien (and the Cranberries) vastly undercount the voices echoing in the average head; it’s certainly more than one.

There is a voice inside of you
that whispers all day long,

Shel Silverstein, The Voice

The idea of having voices in your head isn’t particularly flattering. It conjures 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. Who gets to sit on your inner committee and how on Earth did they get appointed?

It’s easy to overlook our internal conversation in the bustle of life’s duties. Our culture’s outward focus keeps us from taking time to look inward, and it’s a shame, since your inner conversation is the foundation for all the other conversations you engage in. In a conflict, it can be tempting to think that other people are the problem and that they need to change. The shifting of your inner conversation is another approach.

I wrote a book about conversations and how we can (and already do) design them — even our internal conversations. Some people feel like “conversations” is a squishy word and that “design” excludes people. I say: design belongs to everyone now. And I believe that we are all designers of our conversations.

What you’re reading is an excerpt from that book, Good Talk: How to Design Conversations that Matter. Read on or click that link to get free chapters of the book.

Your Mind is Racing

I heard a story on NPR about a woman who would leave herself voice messages, talking to herself about her challenges, while she was out walking her dog. Later, she would listen to the recordings. She could then take a step back, and listen to herself, as if she was listening to the problems of a friend. We all know how much better we are at solving other people’s problems than our own.

Many of us are also kinder to other people than we are to ourselves, applying a very different and more forgiving error recognition OS with friends or family. Taking her internal conversation outside shifted how she related to it.

Externalizing her inner conversation also slowed down its cadence. Self talk is fast — really fast. Researchers have clocked inner speech at a pace of 4,000 words per minute — which is about 10 times faster than verbal speech. The voicemail method slows self talk down. Like taking in a landscape at a stroll vs a bullet train, she was able to hear nuances in her own perspective that would be easy to miss otherwise.

Comedian George Carlin said “The reason I talk to myself is because I’m the only one whose answers I accept.” Even with externalization, there is a tendency to agree with ourselves, especially if there’s an issue we’re passionately, stubbornly stuck on. It can be hard to break the thread of a circling thought. Our internal conversation can cut a deep groove and get stuck in a rut.

Who’s invited to the Party?

Powerfully motivating invitations are magic when you’re looking to engage anyone, whether it’s inviting someone to come to a party or be your mentor. We take care in external invitations because we know that force and coercion rarely brings out the best in others, and yet we try to use force on ourselves.

Invitation is even more critical in our inner conversation. What voices would you like to invite to your inner party? And what voices would you like to politely ask to leave?

Inner stakeholder mapping can be an enlightening exercise. It’s worth taking 15 minutes and trying this out:

1. Who are your inner stakeholders? Capture 3–5 “people” in your inner conversation on sticky notes.

2. Who talks to who, when? Draw the interactions and conversations between them as arrows.

3. Which voices would you like to ask to leave?

4. Which voices would you like to work together better?

If you want to learn how to have better conversations with yourself, in your life and in your work check out my book.  Get free chapters and downloads here.

Four ways to Create Safety for Others by Learning how to Create it for yourself

One of my deepest wishes is to always create a safe space where everyone's voice can be heard and matter. It's more like a horizon to reach for than a shore I arrive at. And I go off course plenty.

Fostering psychological safety in groups is essential. How else can we ensure that people feel truly able to say what needs to be said, to offer their deepest creativity, to challenge the status quo?

The work of folks like Amy Edmonson and Ed Schein make it clear: When people don’t feel it’s safe to speak up, then things can become unsafe fast. Mistakes happen. Standards slip. Lives can get lost.

Without a deeply safe environment, people also literally can't think: Stress marshals the body's resources for survival, leaving everyone with less energy to bring their best selves.

If you are trying to innovate or get your team to be creative, an unsafe environment is the opposite of what you want to foster. Without safety, teams are living in an environment that focuses on survival, not excellence.

The core of creating safety for others is creating safety for yourself.

I don't think we can create safe spaces for others unless we know what safety is for ourselves. It can be challenging to lead people deeper than you yourself have gone. And we can't continuously foster a safe environment if we don't understand how fragile this state can be for ourselves. This is about applied empathy.

I posted a painting I made about these ideas on LinkedIn and Twitter...I'd love for you to join the conversation and share what helps you create safety for yourself and others.

Some ways I create safety for myself:

1. Slowing Down. As the Navy Seals like to say “slow is smooth smooth is fast”. As Mario Andretti says “If everything feels under control, you’re not going fast enough.” So, slowing down, taking a breath, taking a break, always helps create more safety, a deeper sense of control, and ultimately, smooth speed.

2. Connecting to my own body. The best way I know to slow down is to ask myself and others to “Mentally arrive where we physically are”. I learned this simple, direct and powerful phrase from my friend Uli Beutter Cohn, who hosts the Subway Book Review. Mindfulness is a concept that can attract some people and repel others, so I use this phrase to make it simple and straightforward.

Everyone has a lot going on. We don’t know what people had to endure before turning on their video chat…so it’s great to take even a single minute to connect with where we are now: together.

3. Being curious about what other people are experiencing. What is their world, right now? If I can slow down, I can ask to know more about what someone meant or intended to mean before reacting. I can connect to others and empathize with them if I can first do that for myself. Then, we can explore: What is their current mental model? Empathy and curiosity reduces any need for being defensive, which is an unsafe feeling. Find more on exploring mental models here.

4. Resistance is Information. Recently I was coaching a CEO of a startup who was struggling with a conflict: to work on his product-market fit or to do a fundraising round. In this case, it wasn’t about making the right choice…it was about understanding why he was conflicted. Getting to the heart of the conflict helped him realize how to solve the challenge, not as an either/or choice, but as a set of values to live.

Being curious about conflict helps in conversations with ourselves and in conversations with others. I create safety for myself in group situations by reminding myself that conflict isn't bad, it's information about how other people are feeling and thinking. Getting curious about their position (see above) can be transformative. Curiosity can help show that the way forward can be better than either of us could imagine, if we work together from a place of safety.

As I mentioned above, I posted a painting I made about these ideas on LinkedIn and Twitter...I'd love for you to join the conversation and share what helps you create safety for yourself and others.

Transform your Leadership with the Systems Thinking Iceberg

How Systems Thinking can help you lead more intentionally

A few weeks back I wrote about how reflecting deeply can be transformative. Most often we react to events - we experience a challenge or a gap and go with our gut on a response. Stimulus and Response.

A Systems Thinking approach can make our responses more intentional, more focused and more effective. As the model above suggests, the more deeply we understand a system, the more leverage we have to transform it. Systems thinking, and the iceberg model were both popularized by Peter Senge in his 1990 book, The Fifth Discipline: The Art and Practice of the Learning Organization. Systems thinking provides a vocabulary and a set of tools that can help you understand why things are the way they are and most critically, where the leverage points for effective change are. But systems thinking has it’s roots much further back. Check out The Universal Traveler from 1974 for a deep dive into trippy, counter-cultural Soft-Systems Theory that smells and tastes a lot like Design Thinking. You can go back even further. I’m currently reading Peter Checkland’s Systems Thinking, Systems Practice from 1981…which includes a 30-year retrospective on System Thinking!

Anticipation over Reaction

Who wouldn’t prefer to see around corners and anticipate challenges before they unfold? Systems Thinking suggests that the path towards anticipation lies in seeing the unseen. We can only see the visible world - Trends and Patterns are seen with the mind’s eye if we sit with the questions “What has been happening?” Only then can we begin to deduce trends.

DESIGN IMPLIES A THEORY OF CHANGE

Once we start to see a pattern or trend emerging we have two options - intervene now to make a change and/or make a change next time, before it happens. This is the dream of every time-travel movie - go back before something terrible has happened and make sure it doesn’t.

As facilitators, leaders and change agents, the question is always: “What can be shifted?” …but more critically, which changes will stick? Which will be most impactful? To answer those questions, we need to have our own theory of change.

Which is more impactful for an organization? An intensive workshop or long-term coaching? What is more effective, a training for select senior leaders, or video learning for a whole division? It depends. On what? Evidence, sure, but we all select our own evidence. It comes down to what you, the change agent, thinks is possible. We can and should check your hypothesis later, but the intervention you choose will be the one you believe in.

Mental models built the system

The deepest level of change for a system is shifting the way the people in the system think. Most systems are co-created and co-evolved, over time. People with positional power set certain rules and structures, and people give those structures power by participating in them, giving them legitimacy. Over time, people shift the system just by using it in their own ways (Google Desire Paths for more). If you can understand and shift the assumptions, beliefs and values that sustain the system in its current state, the system will shift, inextricably.

This is one reason why I believe in coaching as a theory of change. A conversation, for me, is the smallest unit of a change. And deep, sustained conversations over time are, I have found, to be the most effective approach. To connect with me about coaching head over to my coaching page.

HOW to bring Systems thinking into your work

The main way is by taking time to think. It’s rare, and hard to do, but reflection time is always productive. Linked above is my essay on reflection. It’s specifically about year-end reflections, but the models and frameworks can be applied to any project or team. Retrospecting is key to any leadership practice. Set aside an hour by yourself or with a team and ask people to consider each of these levels of perception.

Reflections over Resolutions

Don’t set New Year’s Resolutions. Use Design Thinking, Lean and Systems Thinking Instead.

New Year’s resolutions are declining in popularity — A Forbes survey showed that about 75% of people over 45 don’t bother with them anymore. And good riddance. Research shows that resolutions are not very effective at changing behaviors — after a month, nearly half of resolvers had failed at whatever they were resolving to do.

Resolutions are driven by what we think we should do

The top ten resolutions should look pretty familiar to you:

Exercise more, Lose weight, Get organized, Learn a new skill or hobby, Live life to the fullest, Save more money / spend less money, Quit smoking, Spend more time with family and friends, Travel more, Read more.

Most of these are driven by an idea of what we *should* look like, *should* have or *should* be like. Resolutions are driven from the outside.

Resolutions are also problematic because they are focused on the goal, devoid of any plan or process to make them happen. So let’s peel these two issues back to the heart of the matter: How to Reflect so you develop deep insights about how you want to be and How to Resolve so you accomplish what you want.

Reflect before you Resolve

Towards the end of 2020, I packed up my laptop, my sketchbooks from 2020, a mess of post-its and markers and loaded up my bicycle panniers. I took a 30 mile ride North up out of New York City to a quiet town in the woods. I booked a small AirBnb for myself and took a few days to think about the year.

I was exhausted from the emotional roller coaster that was 2020 and couldn’t really think about the new year. So all I knew was that I wanted to do a deep dive on the year that had just passed.

How to Reflect: Use a Process

There’s nothing wrong with randomness or improvisation in your reflection process…but even Improv has some fundamental rules with coherent internal logic. So I wanted to use a simple format to guide my process. Reflection is a conversation you have with yourself and I believe that we can, do and should design our conversations — both with others and ourselves.

I’ve found that the best processes have a deep, internal logic. That’s why I fell in love with Design Thinking more than a decade ago. Discover, Define, Develop and Deliver are four words that can move any creative conversation forward with clarity, regardless of the challenge. And Reflection is the perfect process to make the “Discover and Define” upfront part of the process effective.

Some of my favorite reflection prompts come in groups:

Plus/Delta is the simplest of all of the approaches I’ve used, and I learned it from Gamestorming, a powerful library of group process designs. Plus is positive and Delta is the symbol for change. This model of reflection asks us to ask ourselves “what worked?” and “what would you want to change?” . This simple process is a great reflection format because negativity is removed from the conversation — if there’s a “minus” we’re asked to turn it into a “delta”, which is a fundamental approach to reframing challenges.

Rose/Thorn/Bud (RTB)is attributed to the Boy Scouts of America. I first learned about this format from a co-worker of mine who used this format to facilitate a better dinner table conversation with his three daughters. He’d ask each of them for something nice that happened that day (A “rose”) and also would ask them for something not-so-nice that happened that day (A “thorn”). While Plus/Delta removes negativity on purpose, RTB includes it, on purpose. Knowing that negativity is included in the conversation can create clarity and safety. If you’ve ever seen the Pixar movie Inside Out you know how damaging it can be to focus only on the positive side of things.

“Buds” are like little roses…they’re not in full bloom, but they might develop into a rose with the right support. Buds can be something on the horizon, something emergent, something hopeful. A very simple way to put RTB is “Positive/Negative/Potential”.

Facts/Feelings/Insights/Potential: This approach has many mothers. A foundational approach in Non-Violent Communication (NVC) is separating out Observations, Feelings, Needs/Values, and Requests (OFNR). Disagreements in groups of people usually happen when we dance around and between each of these elements or combine them haphazardly. Using the OFNR approach as the foundation for a reflective process can be powerful, and it’s the approach I used for my personal retreat. The ONFR approach smells a lot like What/So What/Now What, another favorite for group reflections attributed to Rolfe et al in 2001.

Separating Facts and Feelings is powerful. The key reflection questions here are: “What Happened?” and “How did it Make me Feel?”

These two questions are extremely neutral, which is an advantage, but also very general. I use these two questions in my workshops often because I don’t want to put my thumb on the scale when teams are thinking. But looking with more specific detail can be helpful.

Positive/Negative/Potential is one more detailed way to look back over the year: What happened that was awesome? What happened that was awful? What happened that has potential? These questions address the first phase of the Design Thinking process to help us Discover “What Happened” in a more balanced way.

A friend recommended Alex Vermeer’s 8,760 Hours as a guide to my retreat. Vermeer’s approach is to do a mind map of 12 life areas: Values & Purpose, Contribution & Impact, Location & Tangibles, Money & Finances, Career & Work, Health & Fitness, Education & Skill Development, Social Life & Relationships, Emotions & Well-Being, Character & Identity, Productivity & Organization and (finally!) Adventure & Creativity.

Doing a RTB on *each* of these areas will give you a much clearer picture of “what happened” over the last year and a much deeper sense of how you feel about these elements of your life. If you don’t like Alex’s 12 life areas, choose your own or synthesize some other approaches.

Alex has his own suggested Reflection Questions for each element:

1. What went well?

2. What did not go well?

3. Where did you try hard?

4. Where did you not try hard enough?

By the end of a half-day, I had flipped through my sketchbooks for the last year and captured a series of nuggets of inspiration and sketched a host of mind maps for each area of my life. I was also beginning to feel energized about possibilities for 2021 (which surprised me).

Don’t Forget Gratitude

I talked over my plans for a retreat with my wife and my therapist and they both had the same advice: Don’t forget gratitude. Looking over the year (as difficult and chaotic as it was) and finding moments of brightness was profound. Gratitude and joy, in this context are data about how I felt. Many years back I diligently kept a gratitude journal: Three things I was grateful for, each evening. At the end of the year, I copied all of my entries to sticky notes and made a huge wall-sized map of what triggered gratitude for me. This map was a map to my happiness — it was pretty clear what elements I needed to keep cultivating in my life to keep me alive inside and out.

How to Resolve: Run Some Experiments

Using the “Discover” mindset from Design Thinking along with a series of thoughtful prompts can help you begin to “Define” what areas are most in need of support. Support to continue flourishing, and support to get on track.

Resolving to achieve ALL of the top ten resolutions will leave you pretty spread out and exhausted. You can’t Exercise more, Lose weight, Get organized, Learn a new skill or hobby, Live life to the fullest, Save more money / spend less money, Quit smoking, Spend more time with family and friends, Travel more, Read more ALL at the same time. So pick 2–3 areas from your reflection to work on.

So when I suggest “run some experiments” I mean SOME not all. Pick 2–3 areas from your reflection map and decide how you want to shift each of them.

Leverage Lean Startup for your Life experiments: Measure-Build-Learn

There are a lot of versions of this multi-circle diagram and they are all dizzying. The key idea is that there is a Design Thinking — Lean Startup handoff at the midpoint of the traditional double diamond, expanding and adding more detail to the “Develop/Deliver” phases.

We’ve leveraged a self-empathy process with our reflection questions to address the upfront, problem solving phase in the below diagram.

In the Lean mindset, you build as little as possible, try something out and then measure the results. We pick something we want to learn about, build something to help us do that, and measure the results.

Here I’ve taken one of the many “circles” diagrams from the internet and overlaid the reflection process.

Define your Approach Clearly

“Get in Shape” is a pretty broad goal. Round is a shape, after all.

Do you want to run a marathon? Lift your body weight? Swim the English Channel?

Regardless of your goal asking about your Why is critical. Why do you want to run a marathon? Asking 5 Whys is a minimum — 9 Whys will potentially get you to the heart of the matter.

As Nietzsche said, He who has a why to live for can bear almost any how. When the going gets tough (and it will) knowing your why will help pull you through.

In essence, instead of resolutions, frame a hypothesis:

If I sign up to run a marathon I’ll get in better shape. (maybe)

If I sign up for a running group I’ll train for the marathon. (much more likely)

Behind this hypothesis is a tacit assumption and a deeper Why: If I’m in better shape, I’ll be happier.

One of my goals is to read more so I can learn more and be smarter. I like being smart since it makes me better at my job. One of the ways I’m going to make that happen is having more authors on my podcast. I think it’s rather rude to invite someone for an interview and *not* read their work. In essence, my podcast is a system I’ve set up to enforce my goals.

Systems over Events

Getting in Shape and Reading More are not events…they’re processes that occur over time. Wishing to “get in shape” doesn’t make it so. Not smoking a single cigarette doesn’t a quitting make (although not smoking a single cigarette is much easier than never smoking a cigarette ever again. Check out the behavior grid for more.)

Signing up for a running group is changing the system your fitness approach exists in. Telling my wife that I want to stop looking at my phone after 10PM is changing the system my sleep habits exist in. I see the events and the patterns…but unless and until we shift the system our lives exist in, the effort to stick to our goals will be more challenging than it has to be.

The Iceberg Model is a key mindset for reframing your goals in terms of increasing impact.

A few years back my friend Rob struggled with quitting smoking. He noticed that he smoked the most when he was working from home during the week. So over the weekend, he’d throw out his cigarettes and give his wallet to one of our friends. He didn’t need money during the week — He could order nearly anything over the internet with his credit cards stored in his computer while his corner bodega, where he would buy cigarettes, would only take cash.

Rob decided to take the events and the patterns out of his hands by shifting the system, a place of much higher leverage to foster change.

How can you change the system, rather than just relying on your willpower to shift events one at a time?

The Iceberg Model: Events, Patterns and Systems

Inspect the Results Regularly

In essence, the problem with resolutions is that they are the ultimate waterfall approach. It’s no surprise that making resolutions once a year with no check-ins along the way fails 81% of the time over two years.

How often should you check in with yourself? (in essence, how often should you re-reflect?)

In Scrum, there’s a daily standup. And that’s not a bad suggestion, but a little lightweight according to Ben Franklin, who suggested a morning standup and an evening check-in! He suggested that each morning one should ask “What good shall I do this day?” and at night to check back in with “What good have I done this day?”

My wife and I actually have a RTB conversation at the dinner table most nights, so, I’m not against this approach. For me, I’m planning weekly check-ins with myself and a 90-day retreat. That’s just for my business. I have a weekly men’s group as well as therapy to check in on my emotional wellbeing.