I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack in downtown San Francisco.

No problem.

Practiced talk, small group, low stakes. I was editing the title slide to update the location and name of the event. No practice necessary; again, I’d done it before.

The piece was based on this piece called Stables and Volatiles. The brief pitch. Stables are those who happily work with direction and appreciate that there appears to be a plan and the calm predictability of a well-defined schedule. Volatiles are the opposite. Read the piece; I like it.

Finished quickly. I was told this was more about a discussion than a presentation. Fine with me. Q&A tells me precisely how well the deck landed, and I’d done this talk enough to believe the Q&A would be rich. Healthy banter. It started that way. Questions about my first stint at Apple and whether well-known people were Stables or Volatiles, but then Leo in the Back Row lost his shit.

“This is bullshit. It’s a false dichotomy.” Leo, the CTO in the Back Row, was pissed about my presentation. For those without ChatGPT at the ready, a false dichotomy is “the fallacy of presenting only two choices, outcomes, or sides to an argument as the only possibilities, when more are available.”

After some back and forth, I told Leo, the CTO in the Back Row, that, like most of my writing, I liked to describe humans in stark, clever ways. This often took the form of a “THIS or THAT” black-and-white structure, but I was 100% clear that the answer to humans was a hard-to-define grey area. My job was to get you to think, not to define every possible configuration of human behavior.

I’d delivered that answer before, and it worked, but Leo, the CTO in the Back Row, was having none of it. He was still angry and — now, I am guessing — because I’d wasted his time. He was promised a structured model, and I delivered confusing poetry.

Leo, the CTO in the Back Row, was the Police. And the Police don’t like poetry.

Guess What, Leo

I have another false dichotomy for you: the Poets and Police.

Poets:

• Finish things. Usually.
• Use rich language to describe abstract situations.
• Believe well-formed, highly descriptive ideas make the world an understandable place.
• Are fine with ambiguity because they understand it’s all just shades of grey.
• Fall in love with ideas. They’ll fall in love with a single choice word.
• Like to use the word “feel” because feelings are distilled intuition expressing themselves as inspiration.
• Love thoughtful compliments.

Police:

• Finish things. Wow, they finish things.
• Crave well-defined structure and rules.
• Believe rules make the world an understandable and measurable place.
• Hate ambiguity because it provides no direction.
• Deeply enjoy both debating and enforcing those rules. They believe this is how you make future measurable progress.
• Will debate a single word that is out of place until clarity is achieved. (Poets do this, too.)
• Are excellent at measuring anything with metrics. Are unlikely to believe unmeasurable truth.
• Never use the word “feel” because feelings are irrelevant to getting the job done.
• Appreciated well-defined accomplishment.

Two things.

First, as a Poet, I know I am describing the Police from my perspective. Police will profoundly disagree with many of the attributes I describe. I am eagerly listening.

Second, yes, this article is similar to my much earlier piece on Organics and Mechanics, but I feel it’s stronger writing.

Third, I am making up a third thing. To annoy the Police who were keeping count because that is how we Poets roll.

Success is Both

As a self-declared Poet, I can confidently describe the Police because it is a job requirement that develops strong working relationships with these essential humans. I need them because the Police do the challenging work of keeping the trains on time. This isn’t simply holding conductors to a schedule but also maintaining the trains, taking care of the track, and ensuring we have a qualified staff of humans to do all this work. Oh, and how about a budget? How are we going to afford all of this? Someone needs to build a credible business plan for this train company so we can afford to keep the trains on time.

As a self-declared Poet, we also need to understand the aspirational goals of this train company. I also understand the importance of consistently sharing this vision with everyone. I know we need to listen because we need to understand how the company feels. I’m adept at organizing teams of humans with differing ideas and skills. It’s an endless puzzle that I enjoy attempting to solve. I love celebrating our victories. I feel our failures deeply, but I know that with the Police, we will learn from these failures.

Listen. Leo. The CTO. You there — in the back row. I get why you’re mad. See, while we differ in how we view the work, we are the same regarding what’s essential. We want the team to succeed, and we want them to advance. I’ve learned some of my favorite moves watching you work, Leo. I’ll work hard to try not to waste your time with too much poetry if you work hard to understand that poetry is part of how we describe and achieve the impossible.

I’ve worked at three successful start-ups and one failure. I’ve also worked at post-IPO successes such as Borland, Netscape, and Apple, which means I’ve seen a lot of different founders who, if you measure success financially, were quite successful.

My backstory aside and with deep respect, most founders fail. You’ve heard of the stories of sucessful founder because they’ve become famous (or infamous). However, the majority of start-ups fail. No one tells and retells the stories of these companies because they never launch. No one became rich or famous. It is their defining characteristic. In his recent essay, Paul Graham talks about the successful founders. However, it’s not “Founder Mode,” it’s “Successful Founder Mode.” Lumping all Founders together would mean we should — statistically and more descriptively — call this “Failing Founder Mode,” which is neither clever nor inspirational.

As a person deeply in love with naming things, I like the framing of Founder and Manager Mode because it’s clever and instantly useful. If you’ve been reading me over the years, you’ve noted I’ve begun to detest the term manager for some of the reasons Graham highlights: unfamiliar with the details, management at a distance, lousy hiring, and siloed decision-making. I’ve gravitated towards the word leader both because I want to make it clear any motivated human can execute the skills of a good manager — leadership comes from everywhere — and, more importantly, I believe managers tell you where you are. Leaders tell you where you are going. It’s a philosophy thing.

It’s less clever and symmetric, but I would define these two modes as: “Founder Mode” and “Scale Mode” because one of the many things you need to do as a successful start-up is scale. Landing managers is one of those tactics, but it’s just one essential investment you make as you scale. Other tactics are equally important. Focusing on managers as the thing that makes you a larger successful company gets you… more managers. Gross.

My observation from three successful start-ups, three post-IPO starts where the founders still ran the show, and one failure: the founders were all eccentric humans. In a hypothetical room full of humans, which included these founders, you would eventually notice their behavior or conversational pattern. You would single them out in your head because the hair on the back of your neck stood up and wonder, “What… is going on there?” My one start-up failure? The founders? By the book, MBA types. Standard vanilla leadership. Trust me, you’ve never heard of them or the start-up.

Graham hints at some of the attributes of Founder Mode but mostly says it’s not as well-defined. It is. Founder Mode is the culture of a company, and a culture is defined by the character of the founders. Here are the values I’ve discovered over and over again working with these humans:

• The whole team is involved in the details. Anyone can argue about the product because everyone works to be a product expert.
• Everyone does the work. The stratification of responsibility is a red flag not just in rapidly growing team, but any company. Everyone files bugs because everyone uses the product. Yes, there is job specialization, but there is also a belief that we are equally accountable for the product.
• An organization chart doesn’t tell you who can speak with whom; it tells you who is accountable for what. It’s a map. Not a power structure.

And finally, hire leaders, not managers.

Awkward.

Seven of us now. Sitting around the table. Five minutes since the start of the meeting. We’ve used up our chit-chat allowance and wonder if you will show.

In the scheme of things relevant to a company’s success, showing up late to a meeting is not the end of the world. When it happens a lot, when it’s always the same person and that human is a leader, I have a severe tick when it comes to this human. Here is my chain of increasingly frustrated and snarky reasoning:

Here’s my inner dialog:

• Do you know that you are late?
• Do you understand why you are consistently late?
• Do you understand the total cost of this lateness? It’s the room full of humans waiting for you, plus the repeat of the information they’ll need to hear when you arrive.
• Do you understand the subjectively immeasurable credibility hit you take each time this happens?

With that out of my system, let’s get to the heart of my concern. If you understand the problem and further understand the cost of this behavior, why is it continually happening?

Many meetings are predictable. Look at your calendar first thing in the morning. Is this an achievable set of work? No double bookings. Good. Do you see where you are likely going to be time-constrained? You’ve got a meeting you must attend that always runs long — ok, move the meeting after it. You’ve got one meeting on the opposite side of the campus? Ok, build in travel time and adjust the calendar as necessary.

Some meetings are not. Day has started, and the universe is throwing you curveballs. It happens. A reliably stable meeting ran long. Did you tell the next meeting to move on without you? Wait, you need to be there? Ok, move to the next available slot — quickly and alert attendees. Loudly. An important meeting landed in the middle of your everything? Ok, what needs to shift? Shift it. Loudly and promptly.

But it just keeps happening. Five minutes late to everything. Too much on the calendar, too many curveballs. You are in a constant state of stress, and this is where I will stop us for a second to state the obvious.

There are leadership types who believe this level of busy is correct. They believe a key part of the job is this level of stress and scurrying hither and fro. Some humans find a modicum of pride in this state. You know, the meeting doesn’t start… without me.

To all the serial show-up-laters who meet this criteria,

You are a failing leader.

Strong words. You thought your consistent five minutes late was a quirk. A minor operational error, but in my book, it’s a strategic flaw because you are not identifying and fixing the fundamentals. There are so many minutes in a day, there are only so many meetings you can personally attend, and these are knowable quantities. Failure to address these fundamentals means you are not growing as a leader.

Who can go instead of you? No one? Why? What is so essential about you? Experience? Really? How does one gain experience? You give others the same opportunity that someone else gave you. You ask them, “Can you attend this review?” They look panicked, so you tell them, “Here is the essential context you need. These three things will likely happen; here’s what I do when they occur.” They look less panicked, and you finish with, “I know you can do this.” They grin. Nervously.

Delegation. This is one solution. There are many more, but I’m not listing them because it is your job as a leader to identify the problem that ails your team and be accountable for properly and permanently fixing them.

So you can show up for a meeting on time.

1. Say their name if you think they aren’t listening. In a meeting with five or more humans, it’s ok if someone checks out of part of the conversation. Not every topic is of equal interest to all humans. When you know the conversation is steering back to a human who isn’t listening, say their name.
2. Repeat the hard part when you don’t understand. Or, repeat the last thing they said and add a question mark. Ask questions if you don’t understand.
3. Pause if you need more time to think. Let the conversation breathe.
4. Move your line of sight below theirs. Hunch over a bit. This changes the sense of who is in charge of the conversation. I learned this subtle move from a fascinating book about improv. We, as humans, react to the relative position of another’s gaze. Higher, they are driving. Lower, they are receiving.
5. Look them in the eye if you think your point isn’t landing. Or if it’s important to them. Repeat the point. Once. A variant of saying their name, except in this scenario, you have their attention, but it’s unclear if they understand the point.
6. Stop talking. Ask them what they think. Or slow your cadence. I get on a roll often, conversationally, and what feels like a delicious conversational tale to me is rambling. When the room starts to tell me this, I stop. I stop for five seconds. In five seconds, you can effectively reset the tempo of a conversation. Possibly my favorite conversational move. s
7. Listen to the room when you are done to see and hear what they heard. Does the conversation continue immediately on the same or related topic? Excellent. Is there a painful, long silence where it’s clear you didn’t deliver your message? Keep trying.