Khan Academy, but for learning leadership

Leading teams is hard, but it’s not complicated.

Leadership has all this mystique around it, and it drives me crazy. It’s like you have to be one of the chosen ones, have some purported “natural” aptitude, or go to a fancy graduate school to be a veritable leader.

I think all these stories we tell ourselves about leadership are dogma. And hogwash.

The way I see it, leadership is a choice. If you choose to lead, take the responsibilities that come with leading, and work hard to get better at it, you’re a “leader”. Full stop.

The way I see it, the demand for people who choose to lead outstrips supply. For a peaceful, prosperous, vibrant, sustainable world we need SO many capable leaders.

We need leaders on every block in every neighborhood. We need leaders on every team in every company, large or small. We need leaders for every book club, sewing group, community service organization, and every non-profit organization. We need leaders in every family and circle of friends, probably more than one each. We need leaders in every civic group, every bible study in every church, and every youth sports team, every library, and school classroom.

I don’t have empirical data to back this up, but here are some illustrative numbers, to size up the prize here.

Let’s say…9 out of every 10 people above the age of 14 are capable enough leaders. That may be generous, but roll with me on this.

Let’s also say that after you count every neighborhood block and every church, every team and company, and every group - large or small - that needs capable leadership, the numbers say that requires 93% of people above the age of 14 to be capable enough leaders.

Let’s say that 93% figure assumes people who are capable of leading will lead in more than one area of their life.

If the demand for leaders is 93% of people over age 14 and the supply is 90% of people over age 14 - that means we’re 7.9 million leaders short. And that was (hopefully) being generous that 90% of people are capable leaders. (Here’s the link to population estimates used).

Even if those numbers are not precise, and are merely direction, the conclusion stings. Unless we’re incredibly close to the pin, we could have a leader deficit in the millions.

In my experience, being trained or designated as leader is some ridiculous, exclusive club you have to be anointed into, which is the exact opposite of what we need. We don’t need to be thinking about developing capable leaders by the dozens, thousands, or even the hundred thousands. We need to be developing leaders by the millions.

Leadership is hard, but it’s not complicated.

It can be explained. I personally feel like it’s made to feel like a secret club, because it benefits the people who are in on the joke, so to speak. If there’s a shortage in the supply of leaders, those who figured it out can raise their prices - whether that’s charged in money or status.

I’ve started an experiment to try chipping away at this problem.

Why not try to explain some of the basics of management and leadership that apply to every team in any domain, just like Khan Academdy does for so many other subjects? Why not try to make leadership simple enough for anyone who wants to learn?

You can check the first video I’ve posted on a new YouTube channel called “Leadership in 10 minutes”. It takes a simple, universal, concept of leadership and explains it in 10 minutes or less.

The first video is on “strategic planning”, which is a super complicated way of saying, “figure out what to do.”

Good, bad, or ugly, I’d love your feedback on how to make it better or your guidance to abandon the experiment if what I’ve tried to do is just not helpful at all.

Status fights and wasted talent

Companies, and really any organization, can function like a fight for status. This “fight” plays out in organizations the same way whether it’s a corporation, a community group, or a typical school cafeteria.

There’s a limited number of spots at the top of the pecking order, and the people up there are trying to stay there, and those that aren’t are either trying to claw to the top or survive by disengaging and staying out of the fray.

If you’re engaged in a fight for status there are two ways to win, as far as I can tell: knocking other people down or promoting yourself up.

Knocking other people down is what bullies do. They call you names in public, they flex their strength, they form cartels for protection, and they basically do anything to show their dominance. They become stronger when they make others weaker.

This is, of course, easy to relate to if you’ve ever been to middle school or have seen movies like Mean Girls or The Breakfast Club. However, the same sort of dominating behavior that lowers others’ status occurs in work environments.

“Bullies” in the work environment do things like interrupt you in a meeting, talk louder or longer than you, take credit for your work, exclude you from impactful projects, tell stories about your work (inaccurately) when you’re not there, pump up the reputation of people in their clique, or impose low-status “grunt work” on others. All these things are behaviors which lower the status of others. In the work environment, bullies get stronger by making others weaker.

The other way to win a status fight is to promote yourself up and manage your perception in the organization. In the work environment, tactics to promote yourself up include things like: advertising your professional or educational credentials, talking about your accomplishments (over and over), flashing your title, hopping around to seek promotions and avoid messy projects, or name dropping to affiliate yourself with someone who has high status.

Let’s put aside the fact that status fights are crummy to engage in, cause harm, and probably encourage ethically questionable behavior. What really offends me about organizations that function as a status fight is that they waste talent.

In a status-fight organizations people with lower status are treated poorly. And when that happens they don’t contribute their best work - either because they disengage to avoid conflict or because their efforts are actively discouraged or blocked. 

Think of any organization you’ve ever been part of that functions like a status fight. Imagine if everyone in that organization of “lower status” was able to contribute 5% or 10% more to the customer, the community, or the broader culture. That 5 to 10% bump is not unreasonable, I think - it’s easy to contribute more when you’re not suffocating. What a waste, right?

Of course, not all organizations function like a status fight and I’ve been lucky to have been part of a few in my lifetime. I think of those organizations as participating in a “status quest” rather than a “status fight”. In a status-questing organization, status actually creates a virtuous cycle rather than a pernicious one.

A status quest, in the way that I mean it, is an organization that’s in pursuit of a difficult, important, noble purpose. Something that’s aspirational and generous, but also exceptionally difficult. 

In these status-questing organizations the standard for performance (what you accomplish) and conduct (how you act) is set extremely high, because everyone knows it’s impossible to accomplish the important, noble, quest unless everyone is bringing their best work everyday and doing it virtuously. 

And when the bar is set that high, everyone feels the tension of needing to hit the standard, because it’s hard. Whether it’s to achieve the quest or be seen by their peers as making a generous contribution to the organization’s efforts, everyone wants to do their part and needs the help of others. 

And as a result, the opposite dynamic of a status fight occurs. Instead of knocking other people down, people in a status-questing organization have no choice but to coach others up, which ultimately raises everyone’s status. 

If you’re on a noble quest, there’s plenty of “status” to go around and the organization can’t afford to waste the contribution of anybody in the building - whether it’s the person answering the phone or a senior executive. In a status-questing organization, the rational decision is to raise the bar and coach instead of throw other people under the bus.

And what’s nice, is that in an organization with that raise-the-bar-and-coach-others-up dynamic is that the bullies don’t succeed, because their inability to raise and coach is made visible. And then they leave. And so the virtuous cycle intensifies.

So if you’re in an organization that feels more like a high-school cafeteria than an expeditionary force of a noble, virtuous quest, my advice to you is this: raise the bar of performance and conduct for the part of the organization you’re responsible for - even if it’s just yourself. And once you raise the bar, coach yourself and others up to it. 

And when you do that, you’ll start to notice (and attract) the other people in the organization who are also interested in being on a noble quest, rather than a status fight. Find ways to team up with those people, and then keep raising the bar and coaching up to it. Raise and coach, raise and coach, over and over until the entire organization is on a status quest and any “bullies” that remain choose to leave.

Of course, this is one person’s advice. Looking back on it, it’s how I’ve operated (but I honestly didn’t realize this is how I rolled until writing this piece) and it’s served me well. Sure, I haven’t had a fast-track career with a string of promotions every two years or anything, but I have done work that I’m proud of, I’ve conducted myself in a way that I’m proud of, and I have a clear conscience, which has been a worthwhile trade-off for me.

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Note: this perspective on equality / the immorality of wasted talent is well-trodden ground, philosophically speaking. John Stuart Mill (and presumably his contemporaries) wrote about it. Here’s an explainer on Mill’s The Subjection of Women from Farnam Street that I just saw today. It’s a nice foray into Mill’s work on this topic.

Damn it, let's give our kids a shot at choosing exploration

In retrospect, this isn’t the vocation I was supposed to have. It was put on me, or at least started, by an act of God. But my path within the universe of organizations  - a mix of strategy, management, public service, and innovation - was never supposed to happen.

I had always, in my heart of hearts, set my mind on space. I knew I would probably never be an astronaut. For a multitude of reasons I would’ve never had a path to the launchpad - being an Air Force pilot or bench scientist wasn’t me. I won a scholarship to Space Camp when I was in 4th grade and I got to be the Flight Director for one of our missions. And from then on, I dreamed of being on a team that reached outward and put a fingerprint on the heavens.

Five years later, a mosquito was never supposed to bite my brother Nakul -when I was 13 - thousands of miles away in India. That mosquito was never supposed to give him Dengue Fever. He was never supposed to be patient zero of the local outbreak and die from it. None of that was ever supposed to happen, but it did.

And, when he died, I got hung up on something. I didn’t get caught up on curing the illness itself. I didn’t feel called to become a biologist, epidemiologist, or a physician. What I couldn’t for the life of me understand is how in the 20th century, with all its wealth and medical progress, could Nakul not receive the treatment - which humankind had the capability to administer, by the way - he needed to survive Dengue Fever? How was Dengue Fever still a thing, in the first place? How could governments and health care systems not have figured this shit out already?

The problem, as I saw it then, was institutions. His death, and millions of others across the world, could be prevented with institutions that worked better. And the vocation that called out to me shifted, and here I am.

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Watching kids watch Christmas movies is interesting. You can see their body language, facial expressions and language react to the imagination and wonder they’re observing. Their bodies seem like they’re preparing to explore, just like their minds are. They light up, appropriately enough, like Christmas lights. It’s really something to see a child imagining. 

For our boys, right now, anything in the world is possible. Any vocation is on the table for them. They can dream of exploring. They can dream of applied imagination. They can dream of storytelling and art. They can dream of so much. At this age, I think they’re supposed to.

What occurred to me, while watching them watch Christmas movies, is that I don’t want them to be drawn into the muck like I was. 

I was supposed to be exploring space, but plans changed and now I’m firmly planted on earth, in the universe of human organizations. I am definitely not charting new territory, rather, I’m fixing organizations that should never have been broken in the first place. I am not an explorer, I am a reformer. There was no choice for me, the need for reform here on earth was too compelling for me to contemplate anything else.

But for our children, mine and yours too, let’s give them a choice. Let’s figure out why our institutions seem to be broken and do something different. Let’s figure out why our social systems seem to be broken and do something different. Let’s not let institutions be a compelling problem anymore. Let’s take that problem off the table for them. Let’s complete this job of reform - both of our organizations and our individual character - so they don’t have to.

Maybe some of our children will want to follow in our footsteps and be reformers, but damn it, let’s give them a chance at choosing exploration instead.

Management is moral

These are the three questions I think about a lot, with regard to my professional role as a people manager:

1. Am I here to enrich the lives of others (customers, colleagues, owners) or my own?

2. Are my expectations for my team (starting with myself) going to be high or low?

3. When my team doesn’t meet my expectations (which is bound to happen sometime) am I committed to coaching them, or merely shaming them into compliance with my wishes?

Don’t be fooled, these decisions are all moral in nature. Being a manager is not merely transactional, tactical, or even just strategic. Management is moral. Or I should say, depending on how one answers these questions, management might be moral. In my view, it ought to be.

As managers we are the stewards of whether the talent of the people we manage is wasted or not. And we steward tens of thousands of dollars worth of people’s time, if not more. For that reason, I think management ought to be a moral endeavor where we consider its moral implications.

And it starts with the expectations we set for ourselves and, in turn, others.

I persist, management is moral. We should take it that seriously.