The Inner Work Most Leaders Avoid

There is a side of leadership we spend a lot of time learning about because it's relatively easy to see. We learn how to communicate, manage people, build teams, set goals, make decisions and create a culture people want to be part of. There are books, courses and entire industries built around helping us become better at those things.

Then there is another side of leadership that is much harder to put into a framework.

Why did that person's criticism bother me so much? Why do I keep stepping back into things I've supposedly delegated? Why does slowing down make me uncomfortable? Why am I frustrated that my team doesn't take more ownership when, if I'm being truthful, I still want to have the final say on almost everything?

Those questions are less enjoyable because the problem can't always be solved by changing a process or having a conversation with somebody else. Every now and then, the person who needs some attention is the one doing the leading.

I've spent a good portion of my life building and leading businesses, churches, nonprofits and other things I believed were worth building. I've also been around enough leaders to know that you can become remarkably successful without ever doing much of this inner work.

For a while, anyway.

Success can hide things surprisingly well... One of the strange things about leadership is that some of the qualities that help us succeed can also become the things that eventually hurt us.

Take the founder who feels personally responsible for everything. In the early years, that can be exactly what the business needs. Nobody cares as much as the founder does, so they're the first one in, the last one out and the person willing to solve whatever problem appears. That level of ownership can build a company.

Ten years later, the same person may have fifty employees and still feel personally responsible for everything. Now the quality that helped build the business has become the reason nobody around them can fully lead.

The same thing happens with perfectionism. High standards can produce excellent work, but somewhere along the way excellence can turn into an inability to accept anything that wasn't done exactly the way you would have done it.

Even ambition can play both roles. There is nothing wrong with wanting to build something meaningful or create financial security for your family. But if you never stop to understand what's underneath that ambition, you can spend a very long time feeding something that never seems to get full.

That's what makes the inner work difficult. Our unhealthy patterns don't always look unhealthy. Quite often, they've been rewarded.

I think leaders become very good at looking outward and it makes sense when you think about it. Leadership trains us to look for problems and solve them. If sales are down, we look at the sales process. If someone isn't performing, we look at the employee. If margins are shrinking, we look at costs. If the business has outgrown its systems, we build better systems.

There is usually something tangible we can work on.

Looking inward is messier because there isn't always a neat action plan waiting at the end of it. I can improve a process much more easily than I can answer why I need everybody to approve of me. I can restructure a department more easily than I can admit that I've avoided dealing with someone because I hate conflict. I can read another book about delegation without ever asking myself why I find it so difficult to trust someone else with something important. That's where I think many leadership problems become mislabeled.

We think we have a time-management problem when we've actually said yes to far too many things because disappointing people makes us uncomfortable. We think we have a delegation problem when a large part of our identity comes from being the person everybody needs. We complain that people won't take ownership while quietly making sure they never have enough freedom to do so.

A new system might help with those things, but it won't solve what's underneath them.

What are you still trying to prove?

This is a question I've become more interested in as I've gotten older, partly because I think a surprising amount of achievement is connected to it.

Most of us probably don't wake up thinking, Today I'm going to prove my worth through professional achievement. Life is rarely that obvious. It shows up more subtly.

You want the bigger company. Then you get it and immediately start thinking about the next stage. You reach an income level that once seemed extraordinary, but somehow the number that would make you feel secure has moved again. You finally get the title, recognition or independence you wanted, enjoy it for a little while and then discover another mountain that apparently needs climbing.

There's nothing inherently wrong with any of that. Growth is good. Ambition can be good. I've spent much of my own life building things and I still enjoy it.

But I think it's worth asking occasionally what is doing the driving.

Maybe you're trying to prove something to a father who never thought you'd amount to much. Perhaps there was a boss who underestimated you twenty years ago. Maybe you grew up without much and promised yourself you'd never feel financially vulnerable again.

Or perhaps you've simply spent so many years being “the successful one” that you don't quite know who you'd be if you stopped achieving for a while.

The strange part is that the person we're trying to prove something to may not even be watching anymore.

We still are.

Leadership has a way of exposing what we haven't dealt with and the more responsibility you carry, the more opportunities there are for whatever is happening inside you to affect somebody else.

An insecure employee may struggle privately with criticism. An insecure CEO can build an entire culture where nobody feels safe disagreeing with them. A person who avoids conflict may leave an uncomfortable conversation for another day. A leader who avoids conflict can allow a toxic employee to damage a team for years because dealing with the situation feels worse than tolerating it.

The scale changes... That's why I don't think self-awareness is some soft addition to leadership. It has practical consequences for the people around us. It doesn't mean we need to analyze ourselves endlessly or turn every difficult business decision into a journey of self-discovery. There are times when the problem really is the strategy. There are employees who really aren't performing. Markets really do change and customers really can be unreasonable.

But mature leadership requires enough honesty to recognize when the common denominator might be us.

I've had to learn that too.

There have been decisions in my life that I believed were entirely rational at the time. Looking back with a little distance, I can see pride mixed into some of them. Fear in others. A desire to be needed. A reluctance to disappoint somebody. The belief that if I just worked harder I could somehow control an outcome that wasn't entirely mine to control.

Age gives you the rather inconvenient gift of being able to see yourself more clearly in the rearview mirror. The hope is that eventually you learn to recognize a few of those things before they disappear over the horizon.

Every leader needs somewhere they can stop performing and I think this becomes harder as people become more successful.

When you're responsible for an organization, people naturally look to you for certainty. They want decisions. They want direction. During difficult periods, they want reassurance that somebody knows what happens next.

Quite often, you don't.

You simply have more responsibility for making the decision anyway. Do that for long enough and it becomes easy to confuse leadership with always needing to appear certain. That's a lonely way to live.

Every leader needs a few relationships where the title doesn't matter very much. Somewhere you can admit that you don't know what to do next, that you're tired, that you handled something badly, that you're questioning a decision or even that something you worked incredibly hard to achieve hasn't made you as happy as you expected.

Not everybody needs access to that part of you. Leadership does require judgment about what you share, where you share it and with whom.

But somebody should.

If there is nobody in your life who can challenge you, disagree with you and tell you something you don't particularly want to hear, success can become an echo chamber surprisingly quickly.

You can't delegate this part...

There are very few parts of building an organization that can't eventually be handed to somebody else.

You can hire people who are better than you at finance, operations, sales, technology, marketing and strategy. In fact, if you're building something substantial, you probably should.

The inner work doesn't work like that.

Nobody else can become self-aware on your behalf. You can't hire someone to deal with your ego while you get on with running the company. A consultant can't decide what success means to you, and no executive team can determine whether the life you're building is still one you actually want.

Those questions belong to us.

I don't think the goal is to eventually become some perfectly self-aware leader who has resolved every insecurity and responds wisely to everything. I'm certainly not there, and I've yet to meet anyone who is.

Perhaps the goal is simply to become a little quicker at noticing.

To recognize when fear has entered the decision. To notice when your reaction is larger than the situation probably deserves. To become curious about why letting go of something feels so difficult. To catch yourself when ambition has stopped serving your values and your values have started serving your ambition.

That kind of work isn't particularly visible, which may be why it's easy to avoid. Nobody applauds when you change your mind, deal with an insecurity or finally admit something to yourself that you've known for years.

But the people you lead will eventually experience the results.

So will the people you love.

And perhaps that's why the inner work deserves at least as much attention as all the leadership work we're much more comfortable doing.