The fallacy of the Successful & Certain leader

How your persona of success undermines your efforts to lead

Welcome, entrepreneurs.

This week is part-1 of a two part examination of leadership. Here is part two. Over the next two weeks we’ll first look at the weaknesses of a particularly popular form of leadership (that of the Successful & Certain leader, the one who is always “crushing it”), and then explore a structure of leadership that is already practiced by many of the best leaders in the world (those brave souls who are both Vulnerable & Committed).

Let’s get to it.

In 1982, scientists conducted an experiment in which they strapped shock collars to rats and put them into a two-room environment. Inside one room, the rats would be shocked intermittently at a strength of between 0% - 75%, whereas in the other room they would be subjected to a constant shock of 100% strength. Within a short while, all the rats had migrated into the second room, in effect choosing constant torture to intermittent pain. The same has been shown in (less painful) experiments with humans, illustrating the perhaps counterintuitive conclusion that humans generally prefer actually getting bad outcomes to the feeling of being vulnerable to potentially bad outcomes.

Entrepreneurs are inherently vulnerable to potentially bad outcomes. No wonder we’ve evolved the remarkable adaptation to present an image of success and certainty, even when the reality is anything but. “Crushing it,” I’ve heard it called.

I used to do this better than most. I would project success at all times, carefully curating an image of the leader who was certain where he was going, and that he would get there. A never ending path up and to the right.

To some degree people respond to that, what I call “Success & Certainty” leadership. Others, being just as uncomfortable with uncertainty as the entrepreneur, can flock to a leader who seems to know the answer. However, despite our lizard brain’s millennia-old discomfort with vulnerability and uncertainty, I’ve found that there are a few major costs of Success & Certainty leadership, which collectively outweigh the benefits.



There’s an old Buddhist parable about a group of blind men who stumble upon an elephant for the first time. In trying to collectively determine the nature of the creature they’ve met, they each touch different parts of the animal and describe their experience to one another. Feeling a tusk, one man describes elephants as hard like a rock, long and smooth. Another, feeling a leg, claims that elephants are as wide like a tree trunk and rough to the touch. A third, feeling an ear, states that elephants are paper-thin, hairy and wing-like. And so on.

Business is like this. No matter where you are, C-suite or entry-level, you only have the ability to see part of the elephant. By projecting certainty in her beliefs (particularly if that certainty is bolstered by actual authority), a Successful & Certain leader inhibits her team from providing the additional perspectives necessary to help her see the whole elephant, and thereby makes worse decisions. Even if she has strong-willed leaders around her who put themselves at risk to help her see her blind spots, a Successful & Certain leader often experiences their opinions as challenges to her competence, and accordingly focuses more on defending her position than learning from other perspectives. Accordingly, Success & Certainty leaders tend to learn slowly on their own (often by painful experience), rather than learning quickly from the wisdom of their team.

Incidentally, while this dynamic happens all the time within teams, it is just as prevalent with investors in the board room. Their lizard brain on alert, many CEOs try to impress their board with their competence even after they’ve received investment, even through the inevitable problems. They gloss over problems and instead focus on their solutions and how sure they are of them, making themselves feel safer while simultaneously preventing their board from actually helping.

Better decisions come from a better understanding of the problem. This happens much more rapidly when you realize you can’t see the whole elephant, and stop acting like it.


For a long time running a startup, I had different responses to “how’s it going” depending on the context, such that if an investor asked I’d spout off an anecdote about the growth of the market and an upcoming revenue milestone, while if it was an employee I’d offer up a cherry picked metric that showed the tremendous traction of the product. Either way, the impression the other person was left with was that we were “crushing it.”

Meanwhile, like all startups we faced tons of problems. Competition, software crashes, missed revenue milestones. The works. The juxtaposition between maintaining a public persona of success while frantically trying to solve life-threatening problems behind the scenes can feel a lot like living a double life. Like a kind of startup kabuki, where you have to strap on a mask to go to work.

Anyone stretching themselves to create something brand new is going to battle some amount of imposter syndrome. This is bad enough when it’s all in your head, but deliberately cultivating an image of success and masking real problems can make it much worse.

As an entrepreneur, it’s not your responsibility to blurt out all your business’ warts and pimples on the first date. There’s a reason many women wear makeup and we guys put on nice clothes: presentation makes it easier to attract people, be they dates, employees or investors.

But building a business is inherently uncertain, and everyone involved knows it. Present your business’s best side, but be up front about its weak spots and holes as well. Investors (or employees) will respect you for your transparency, and you’ll have enlisted an ally in solving the actual problems your business faces, rather than a low-key threat with a checkbook.


Imagine if, when you were trying to start your business, all your friends spun up businesses at the same time and all of theirs were successful without any problems. Not only would you have to solve the problems inherent in starting a business, but you’d also have to deal with the uncomfortable possibility that starting a business was actually easy, and you were just uncommonly bad at it.

This is what it feels like to innovate within a company where all the metrics are up and to the right. Or a company in which the leader is so Successful & Certain that it seems that way.

Innovation requires taking a risk. Creating something new requires putting some part of yourself on the line, emotionally taking the chance that the thing you create might suck and everyone might laugh at you. Leaders that seem like they’re successful all the time (whether or not it’s true) make their employees less likely to take the risks necessary to innovate, because employees don’t want to be the only one who fails.


So, if we’ve thoroughly debunked the efficacy of leading from a place of Success and Certainty, what’s the alternative? Failure and uncertainty leadership? We’re supposed to go around unsure of ourselves and telling everyone about each thing that goes wrong?

Definitely not. Clarity of vision is critical in leadership, despite the uncertainty of achieving it. Otherwise you’d never know where you’re leading.

The key to strong leadership, I’ve found, is in being at once both Vulnerable and Committed. Vulnerable, as in fully human, warts and all, with nothing hidden. Committed as in acknowledging the difficulty of what you’re doing in building a company, and fully dedicated to marching forward toward your vision anyway.

Next week, we’ll dive into what this looks like.

Here is part two.

Two cultural norms that support effective decision making

There’s nothing worse than spending days on a strategy with your team, working through every last detail, and then a month later, at the first sign of a real challenge, having someone say they didn’t really agree with the direction all along.

This Monday morning quarterbacking can cause real problems, undermining the ongoing efforts of the rest of your team to make the initiative successful.

Enter one of my favorite cultural norms: “No Silent Disagreement”

The norm states that if you have any issues, any doubts, no matter how slight, about whatever your team is working with, it’s your responsibility to voice those. It’s your job. As in, if you don’t, you didn’t do your job and there’s a different problem.

It’s typically invoked at the end of meetings, where after a long discussion and some agreement on direction the leader will say “No Silent Disagreement” and then pause (sometimes uncomfortably) to give people the space to jump in with anything that’s on their mind.

This does two things, both of which are good:

  1. It completely eliminates the Monday morning quarterbacking.

  2. It draws out those who talk less in meetings to share their perspective, helping to better inform decisions.

Now this isn’t to say that someone raising an objection via NSD time automatically reopens the discussion. It’s also reasonable for the team or the leader to decide that while an objection may be valid, it doesn’t change the plan. The point is only that it’s everyone’s responsibility to raise their objection, so the team has the opportunity to process all information available to them through every perspective, and then move forward cohesively.

This leads us to our second norm, “Now We March”, which is particularly valuable when an objection was overruled.

NWM states that once the decision is made, the time to voice disagreement is over and everyone’s responsibility is now to execute the direction. To state it explicitly, NWM mandates that all reservations or disagreements must be left in the meeting room, never to be brought up again (unless and until the group calls another meeting). Even if one has a remaining reservation, it’s their responsibility to execute the direction despite their reservation, and never voice their reservation to their team.

The stakes are high here. I’ve worked with teams in which, after participating in making a decision in the meeting, one of the managers would share his reservations about the decision with his subordinates. This is incredibly toxic behavior which at best undermines the success of the initiative and at worst can lead to intractable resentments between the leader’s team and the company. After all (as it looks to the team), if our manager doesn’t think the initiative is a good idea, the company must be doing something either stupid or willfully blind. So why on earth should we support it?

NWM as a cultural norm nips this in the bud. Combined with NSD, it’s a recipe to great decision making.

A team’s efficacy often comes down to their alignment, and getting to alignment comes from a good, inclusive decision making process. I’ve seen No Silent Disagreement and Now We March work well across many companies, and I hope they work for you, too.

A powerful question to ask yourself as you head into your next conversation

Am I listening to win, fix, or learn?

No right answer, but the outcomes can vary widely.

(HT: @schlaf)

Many entrepreneurs come to similar realizations in different ways/timelines

I’ve been sober for 13 years, exercise 5x/wk (slightly less since COVID killed basketball), and hired my first executive coach when I was burned out and raising series B.

Add meditation as a key practice, and you have the foundation of very sustainable success.


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