Growing Leaders

Nick Rockwell
8 min readDec 2, 2021

I was recently asked to give a talk on building leaders, so I did, and I thought I would share an adapted version here.

The framing of “building” leaders is OK, but I prefer “growing”, in the agricultural sense, rather than in the sense of personal growth. “Building” implies a plan, a blueprint, a deterministic process of leader-building — brick by brick, as it were. I’m pretty sure you don’t have to be born to lead, but I know it’s not that simple, either.

Growing, agriculturally, captures the sense of influence rather than control. There is a lot the farmer can do to influence growth, but there is also much that is out of her control — such as the weather. Similarly, when it comes to growing leaders, we can do a lot — but we rely on the right conditions arising, and we have to be alert and opportunistic.

Why might that be? When we break leadership down to smaller pieces, we end up with qualities, rather than, say, skills: things like determination, authenticity, courage, and so on. When growing leaders, we are cultivating qualities. You can teach someone a skill, but you can’t just teach them to be a certain way. Only experience can do that.

So, what are some of the qualities we may want to cultivate in a leader that we may actually be able to influence?

First, independence. We want leaders to collaborate, to still be part of a team, and to ask for the help they need, to be sure. But we also need leaders to be independent. Leaders have to be able to work things out for themselves — to take initiative, and to act when they don’t have all the information or support that they’d like. Not all the time, but when necessary.

Managing implies following a pattern, working within some expected range or bounds. As a manager, when something becomes unmanageable, you probably aren’t expected to manage it. As a leader, however, you are. You are expected to deal with the unexpected, and expected to have the independent agency to adjust, without being shown the way.

Second, creativity. When novel challenges arise, we expect leaders to craft a novel response. We need leaders to cultivate and demonstrate creativity. Inventing requires leadership, and leadership requires invention. Leaders need to generate — options, ideas, Plan A’s and Plan B’s. We need growing leaders to develop the confidence to exercise their creativity.

Next, resilience: when we try new things, failure is guaranteed. And of course we want leaders to hold, not pass, responsibility for failure. Leaders should be load transferring much of the time — delegating — but we also have to be load bearing, especially when there is no well-understood, tested delegation path.

Often the hardest part isn’t the failure itself, but the fact of disappointing people. Disappointing someone is part of the daily life of any leader, and it’s hard emotional work. We’d better have the emotional resources to absorb the disappointment and keep going.

Very similar to resilience, but a little different, is willingness. Because failing is hard, disappointing people is hard, so leadership is hard. If you aren’t driven to do it — even by insecurity, as is sometimes the case — soon enough you won’t. We may all get to that point eventually — leading is exhausting! But in the meantime, we’d better want to do it, despite the difficulty, or we’ll have a hard time pushing ourselves through the inevitable adversity.

Speaking of adversity, we are actually lucky that it’s inevitable, because It’s a key ingredient to growing leaders. So is support of course — they are like the sun and the rain — both absolutely beneficial and necessary, and both destructive in excess.

Adversity is beneficial? Some may think that’s an old idea. And it is, in fact, very old — millions of years old. We all have personal experience of what’s called hormesis in biology — moderate stress inducing growth or robustness. No doubt, life will take care of supplying adversity, but do we perhaps, as leader-growers, have a responsibility to take a more active role? I think so. Here are a few reasons why, and a few ways to approach that task.

First, you and your growing leader can find failure together. We’ve said failure is a daily affair for leaders. It’s hard to learn to tolerate it. Wouldn’t it help to experience failure in controlled conditions, with a teacher alongside? Finding limits and figuring out how to move past them is part of how we learn anything.

We’ve heard we have to let our people fail — but that’s too passive. We need to help them seek failure, or even engineer failure, where we can see it, talk about it, even analyze it — and blunt the negative impact either through timely intervention or hedging. Doesn’t that maximize the learning while minimizing the pain and consequence?

Next, find the aversive thing, and demand that thing. We all hate to do something: it could be giving tough feedback, or it could be giving praise. It could be public speaking, or it could be 1 on 1 conversations. It could be dealing with crises, it could be dealing with the day to day. As leaders, we can compensate for our people’s aversions, and we often do, by tailoring their roles or taking things on ourselves. But, sadly, as leaders, we have to deal with our aversions.

While we may often be able to outsource the work that we want to avoid, eventually, circumstance will require us to do the thing we hate to do. Part of leading is being a backstop, being independent, being resilient. So as a leader-grower, you have to compel your budding leaders to do the things they hate to do, so that when they have no choice, they are prepared. They have already figured out strategies to manage or overcome their aversion.

Last, when our growing leaders face failure, the risk must be real. As leader-growers, we want to protect our people. But if the risk isn’t real, we will deprive them of the ability to cultivate their resilience, to learn how they deal with failure, to test and strengthen their willingness or resolve. We can protect the humans in many ways — by offering support, sympathy, helping them to learn, or even offering paths to success outside of leadership, but we must allow the questions of leadership to be fully asked if they are truly to be answered.

So we can support leaders as people, but we shouldn’t shield them from failure, aversion, or real risk. How do we do that?

It’s a commonplace that a good leader mostly coaches, rather than directs or controls. It’s easy to just coach when things are going well — it’s harder in a crisis. But that is when it matters most. You will not feel like you are doing enough. Your boss will not think you are doing enough. Even your growing leader, at that moment, will probably be unsatisfied with “just coaching”.

However, if you cave at that point, you’ve revealed that you don’t really mean it — you don’t really trust your growing leader, that they can handle the crisis on their own, and you’ve signaled to your boss that they can’t — you had to save the day. You’ve robbed them of the opportunity to learn, to hormetically grow from the actual experience of the crisis.

That requires creating a real void — a gap, a space between your accountability and theirs. The problem is, as nature abhors a vacuum, so organizations abhor gaps in accountability. It can’t last long, but it has to be there, and it has to be real, or your growing leader has nowhere to grow.

Next, as leaders, we can be reluctant to engage emotionally — we might say, “I’m your leader, not your friend”. However, this may be a strategy leaders use to protect ourselves — not to help the growing leader. To be clear, I’m not saying leaders should try to act like peers, or deny or obscure the real power that we hold. But nor should we withhold real connection and empathy — elements of friendship — from our growing leaders.

We need to engage emotionally with them. Otherwise, what is your investment in that growing leader? How can you expect them to trust you when you ask them to take real risk? A relationship with real emotional valence, capable of sustaining trust, rooted in genuine caring, is something you owe to your growing leaders. And like all relationships, that requires you to make emotional investment and to take emotional risk.

The topic of risk brings us to the real work that you, as a leader-grower, have to do yourself.

We mentioned creating a void or gap in accountability. That happens within a crisis, on a discrete or acute scale, but it also has to happen on a larger scale, and that is called succession. I think succession is an imperative, one that we must take seriously, and the consequences of which we must accept. The thing is, once a leader starts to grow, they must not stop. They have to see progression. If you stop them, you seriously damage their development as leaders, possibly permanently.

If you are atop or near the top of your hierarchy, you may want to hold on to that spot. You worked hard to get there! But if you do, eventually you arrest the convection within the entire organization. And the whole organization starts to atrophy. So recognize that once you start seriously developing leaders, you have to start figuring out how you will create space — by moving (growing?) up yourself, or by moving aside. That can be hard.

Next, if you are in a hierarchical org, like 99.9% of companies, you likely have the typical 5–8 reports, and they cannot grow and advance evenly. You will have to choose. You will have to recognize that these people, who you spend so much time trying to get to work together, are in fact in competition, to varying degrees, and you will have to choose who advances. You may not want to, and they may not even want you to either, but you have to, eventually. And that can be hard.

Last, when you selflessly step aside and allow the growing leader that you have painstakingly mentored to succeed you, do you know what they will do? They will fix all the things you messed up. And it will make you mad — if you are around to witness it. If you are, and I hope you are, either because you continue with that same organization or because you continue to have a meaningful relationship with that person — you had best deal with it. That is what they are supposed to do! That is what you helped teach them to do. The things that are broken are necessarily the things that you were blind to, or didn’t know how to fix, and they will have to address them. But, it will still be hard, because you will be confronted with your failures.

Let’s end with a thought about leadership as a craft. We celebrate the brilliant leaders, the special ones, the people who really were born that way, perhaps. And we despise the terrible ones so much — they are terrible! We give little thought to the ones in between — that’s not leadership! Leadership is a big deal — either great or terrible! Actually, we can be ok leaders, we can be good leaders, if we can’t all be great, and it makes a difference.

Showing up, testing our willingness and recommitting, confronting our aversions, investing emotionally, putting ourselves at risk, creating space — we can work at these things, and if we do a little better, it’s worth it, and it matters, for the leaders we are growing, and those who will follow them. So do it!

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Nick Rockwell

SVP Engineering at Fastly, ex-CTO at NYT. Passionate about tech, music, science, art, helping others be their best.