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How to Win the Race for Leadership Roles.

In every business there are leadership voids. These voids represent unsolved problems that have no person or persons working to solve them.

These voids get filled in one of three ways.

#1. The problem inside of the void becomes so troubling that an existing leader in the company, often a manager, devises a solution and then assigns someone to implement the solution. The person doing the implementation is often called an individual contributor (IC for short).

#2. Instead of devising a solution, the manager assigns one of their individual contributors responsibility to design and implement a solution. Typically the IC is overwhelmed by a sense of “Why would you ask me? I don’t know the answer.” This sense rarely acknowledges that obviously neither does their manager.

#3. An enterprising IC decides this is their moment to make an impact by taking initiative.

Options 2 & 3 are the pathways that mint new leaders. This pathway is won in one of two ways, by hubris or by competence. Think of it like a race between good (competence) and evil (hubris).


I’m taking this framing of hubris vs. competence from an HBR article, Why Do So Many Incompetent Men Become Leaders?

In my view, the main reason for the uneven management sex ratio is our inability to discern between confidence and competence. That is, because we (people in general) commonly misinterpret displays of confidence as a sign of competence, we are fooled into believing that men are better leaders than women.

Essentially, the race for leadership spots is being played on an unfairly tilted field because men are both more likely to display undeserved confidence and also to be perceived as confident. But confidence doesn’t correlate with competence — thus people who believe in merit or winning or getting things done or actually making successful, profitable businesses experience this situation as unfair.

I’m talking about unfair to men and women now (competent men are disadvantaged, just to a lesser extent than women and minorities). And this is also unfair to society. And to the people who report to these terrible leaders that organizations are biased toward promoting. It’s just a terrible situation for practically everyone.

We should change this, both by changing how we evaluate potential leaders and by supporting competent people to move into leadership sooner.

So, lets assume that you aim for competence. (I used a very specific phrasing there, “aim for” instead of “are”— competent people are often so aware of their own flaws that they have trouble identifying themselves as competent.)

The playing field isn’t level. That’s true. But you still want to compete and you want to win more often. How can you, the competent future leaders of the world, compete most effectively?


How to win the race (Advice for up-and-comers)

Naively, many people assume that to reach leadership they should develop more hubris. (BTW, I’m saying leadership over and over to refer to people who take responsibility — everyone in a company, starting with reception, can display leadership.)

Thankfully (for you and the entire world), trying to develop hubris as some sort of twisted virtue never works out. The reason competent people aren’t full of shit is because they respect results over promises. You’re not going to win your New Years “Become a bullshit artist” resolution. You’ll give up in a bout of self-loathing.

The actual best way to compete is much more appealing.

Think of hubris as fake confidence. It’s irrational because there’s no actual knowledge or research backing it up.

Merit based leaders develop real confidence based on real knowledge and expertise. Rather than being irrationally aggressive, they become overwhelmingly grounded by their preparation.

Preparation and data gives you an incredible backbone.


A lot of people don’t know what strong preparation looks like though, so I’ll give you an anecdote from the first time I successfully stood up to an overbearingly bad manager (and, please note, I had many weak attempts completely rebuffed before this).

I was on a death march, i.e. a project that was riddled with schedule, budget and quality problems with no acknowledgment or plan for fixing these problems. I got fed up with failing, which prompted me to take an unusual amount of initiative:

  • I bought a book on project management on a Friday after work.
  • I read this entire book over the weekend, taking my knowledge of project management from zilch to pretty good in just two days.
  • On Monday, I moved my computer to a little known corner of the office and turned off my email.
  • For three days I created a full specification, project plan, and estimate for the entire project including the pieces that other people had to do.
  • On the fourth day, I scheduled a meeting with the project manager who should have done this work themselves.
  • I presented my reality-based, well thought through plan and estimate for the rest of the project.
  • Surprisingly, the project manager responded by saying, “That estimate is too long. I can’t get my manager to agree to this.” Despite my surprise at not being immediately recognized as a hero, I didn’t back down. I told the project manager to either let me present to his manager or to present me with a new reality-based plan that would fit his target estimate. My preparation was so much better than his, so my competence beat his confidence.

Who buys a book and reads it over the weekend just to win an argument with their manager?

The answer: people who want to win the race against their irrationally confident competition. I was promoted immediately after this.


The good news about preparation is that it’s exactly what you’re naturally inclined to do. And it’s the right thing to do. Preparation and competence are close friends.


A shitty, but common way to win the race is with patience.

I often observe competent workers who also cary a long term sense of obligation. So despite bad management decisions, these workers persevere.

In a moderately well-run company (remember, bias toward irrational confidence is rampant and normal), bad managers will be promoted, flame out and then be fired.

Out of exasperation, and lacking any candidates with excessive hubris, the quietly competent workers will start getting promotions.

But let’s be real. This is a crummy strategy to rely on. You want something that works faster.


“Go with your gut. Worst case scenario, you’ll learn why your gut is wrong.” ~ Marc Hedlund

Your gut tells you when you have preparation work to do. If you have a bad feeling, take the time to examine it.

Here’s a scenario. Your manager comes to you with a ton of work and asks you if you can get it done by tomorrow.

  • A rookie says, “Ok.” and then tries their best.
  • A novice says, “I’m not sure.” and then tries their best.
  • A new leader says, “Ok,” lets their manager leave, notices that the experience left a bad taste in their mouth, back-of-the-envelopes the actual amount of work as three days, and emails back to their manager, “I just went through the details and I think it will take three days.
  • An experienced leader says, “Let me take a look and get back to you today,” estimates the time, compares it to existing company priorities and then either responds, “It’s going to take three days but I think we should still do it because…” or responds, “It’s going to take three days and I don’t think it’s worthwhile because it gets in the way of this other, better thing to do.

But that’s all triggered by your gut.

This is a speed hack. Often months go by between gut feeling and utter certainty.

It would be hubris to act immediately off of a gut reaction. Those are the people we’re trying to replace.

Instead, your gut is the trigger for you to do some actual, competent work. Stop waiting until everything has fallen to pieces and start listening to your gut.


Meditate. That’s the best answer I have for people that want to learn how to trust their gut.

I’m serious. Meditation is a very specific form of brain training. You practice becoming aware of your thoughts.

Lets go back to the scenario where your manager drops a ton of work on you. There’s actually a lot going on in your head when that happens.

  1. You may have been interrupted and your mind is still focused on the unrelated work you were in the middle of.
  2. You may intuitively disagree with the rationality of the request.
  3. You may subconsciously want to please your manager and/or avoid conflict.

So, in order to have a good conversation you need to be able to recognize that jumble of thoughts so that you can address them. Otherwise you’ll say yes no matter how bad the request is.


Build up your principles.

Principles are things you’ve pre-decided and have at the ready. They make it possible to answer quickly when you don’t have time to prepare.

Peter Drucker, famed business writer, gives the advice that the idea of the hard-charging CEO who is rapidly making decisions is bogus and dangerous. A CEO, and any leader really, should respond to any request from a coworker with the principle that would let that coworker make the decision on their own.

Of course, principles get refined over time. You don’t start your career with any, and then through experience, you start to build them up.

For example, one of Steve Jobs lesser known principles was that Apple “sells dreams, not products.

You see this in every Apple product description. Every feature is explained in terms of what it allows you to accomplish rather than merely what it is or how it works.

So, when some new marketing hire comes up with the great idea of applying sales psychology hacks from Cialdini’s Influence book, the rest of the team can say, “That’s a fine idea for some other company — but it’s not what we do.”

That leads to consistency and efficiency — every decision isn’t held up by a negotiation over an entire universe of options. They’ve narrowed the options in order to keep moving.

Also important there, by narrowing the options Apple gives themselves room to become world class at the option that they did choose.


How to level the field (Advice for hiring managers)

The above is basically how to turn yourself, a competent worker, into a leader who helps solve problems around the company. You get better at preparation, you develop a habit around turning gut feelings into articulated positions, you develop a solid foundation of mindfulness, and then you build up a library of principles to work from.

If you do that, you almost always end up with promotions, raises and increased results.

But what about those of you who play a role in picking leaders?


Why does hubris work? So far, I’ve placed a lot of the blame for bad leadership on people with unwarranted confidence. But what about the system that supports them?

In most companies (i.e. yours), leadership opportunities are filled through a volunteer process. You ask, “Can anyone help?” and then you reward the first person to answer yes. The only qualification in this situation was confidence, the volunteer is telling you that they can do it.

Imagine if you hired this first-come-first-serve way? That would be insane. But this is how we fill minor roles inside of our own companies (larger promotions often have more process at least).

Initiative is good. In fact, it’s absolutely annoying when your most competent people refuse to take initiative because they don’t feel ready.

But a system that relies entirely on initiative for assigning leadership opportunities, is a system that rewards confidence over competence.


You do not need to rely on volunteerism. That’s a copout.

Holocracy has a meeting facilitation technique that I stole and just refer to as Round Robin.

The technique is that when you need to get a contribution from everyone in the group you go around the room and ask each person individually. The person on the hot seat can either give a contribution or pass.

Imagine applying this technique to your standard brainstorming meeting. Instead of only getting ideas from your volunteers who shout out or raise their hand, you’re explicitly soliciting ideas from everyone.

The magic of this technique is that you stop waiting for your best, most competent employees, to volunteer and you stop allowing your most confident, least competent employees to monopolize the conversation.

Essentially, you can often kickstart someone’s leadership path by volunteering them for leadership.

If you regularly give people small opportunities to shine, then you’ll spot the moment when they’re ready for bigger opportunities.


Last, all of us carry this bias that confidence means competence. You just have to acknowledge that you’re human and filled with biases.

Admitting is the first step. Then you can catch yourself (because you have a mindfulness practice) and adjust.

From there you can stop pretending that you have a pipeline problem that’s only submitting blowhards for your leadership positions. Leaders are out there and trainable.

Personally, as a hiring manager, I like anything that makes me feel in control. (Even if getting there means I need to admit I’ve been making critical mistakes about people’s potential.)


In 2005, I was an engineering manager for a 15-person startup.

One day, the CEO of the startup gave everyone in the company a very heady assignment. He asked us to take half a day and jot down our best ideas for where we might take the company.

He asked everyone. And he demanded that we comply because everyone had to present their idea afterward.

There were basically six engineers and I was their boss. Two of those engineers were anarchists — they’d tell you that. They were really a huge problem to work with for big and for little reasons. One wouldn’t even stand up at the stand up meeting because he considered that too compliant.

The other three were intermittently challenging — in that occasionally they’d push for big ideas but they weren’t anarchists or threatening to punch their coworkers (it was a weird group).

The sixth was almost not worth talking to. He got his job done, never said no to an assignment, his code always worked. I basically only talked to him to award him a bonus and then a raise.

Going into this brainstorming session assigned by the CEO, I already knew what the two anarchists were going to do. They were loud and obnoxious and had already been throwing out ways for the company to make a U-Turn.

But it was the sixth engineer, the quiet, reliable one, who was actually sitting on a good idea. He’d been thinking for years about the idea of status messages over text messaging.

He told us that idea because we asked him to. And we loved that idea. And we asked him to build it. And he turned that idea into Twitter. And he was the first CEO of Twitter.

And that’s why getting better at coaching and identifying leaders matters.