When a Leadership Problem Isn't a Leadership Problem

By Jill Barrett, Evolve Impact Founder & Managing Partner

Organizations often come to us because of a person.

A senior leader has been promoted into a bigger role and is struggling. A technically brilliant executive needs to become better at leading people. A founder knows she needs to let go of some things but can't quite do it. A successor is preparing to take over. Two executives who are both very good at what they do cannot seem to work well together.

The question is often some version of: Can you coach this person?

Sometimes the answer is yes.

Executive coaching can be extraordinarily powerful. I have watched leaders become more self-aware, learn to regulate themselves under pressure, have conversations they had been avoiding for years, understand their impact on other people and fundamentally change how they lead.

But after years of doing this work, I have become increasingly interested in a different question:

What if the person isn't the problem?

Or, more accurately, what if the problem doesn't belong entirely to the person?

Looking Around the Leader

Years ago, I was more likely to accept the presenting challenge as the coaching challenge. Someone needed to become a better communicator, delegate more effectively, develop executive presence, manage conflict or prepare for a larger role. We would work on that.

I still do.

But now I also look around the leader.

What is happening on the team? What is expected of this person? Do those expectations make sense? Does the person have the authority to do what everyone says they want them to do? What does the CEO do when this leader actually exercises that authority? How are decisions made? Where is information held? What happens when someone disagrees? What behavior gets rewarded around here?

And one of my favorite questions: What aren't we talking about?

Sometimes the answers change the work entirely.

We have worked with founders and CEOs who genuinely wanted other leaders to step up while still holding tightly to decisions themselves. We have coached technically accomplished people whose organizations kept rewarding them for being the expert while simultaneously asking them to stop being the expert and lead. We have supported successors preparing for greater authority when the organization itself had not fully worked out what authority was actually transferring.

We have also worked with executive teams where what initially looked like an interpersonal problem between two people was connected to something larger: unclear roles, competing priorities, different understandings of strategy or decisions that had never really been made.

In those situations, coaching one person harder isn't the answer.

Organizations Develop, Too

Photo: Shawmut Design and Construction

This is particularly important in the architecture, engineering, construction and design industries, where technical excellence matters enormously.

People become leaders because they are excellent architects, engineers, builders, designers, project managers or business developers. Then the organization grows and suddenly what made them successful is no longer enough.

Now they need to develop other people. They need to delegate work they could probably do faster themselves. They need to have difficult conversations with colleagues who may also be friends. They need to think beyond their discipline or business unit. They may need to help run the enterprise rather than simply excel within it.

That is genuine leadership development.

But something else is happening at the same time. The organization is being asked to grow up, too.

The informal ways of working that were perfectly adequate when everyone could fit around one table stop working. Decisions need to move. Roles need to change. Information needs to travel differently. Founders have to release things. New leaders have to pick them up. Executive teams have to become teams rather than collections of successful individuals.

This is where leadership development and organizational development begin to meet.

What Is the Problem Telling Us?

I have come to think that strain inside an organization is often useful information.

A succession gets messy. Two executives repeatedly collide. A leader can't seem to delegate. The CEO is overwhelmed. A promising person keeps bumping against the limits of a role. The executive team spends hours together but the important decisions somehow happen elsewhere.

It is tempting to decide who is at fault.

It is more useful to get curious.

What changed? Why is this becoming a problem now? What has the organization outgrown? What is this person being asked to do that the surrounding environment makes difficult? What pattern keeps repeating?

And importantly, what does the individual leader actually need to own?

Because this isn't an argument for letting leaders off the hook. Quite the opposite. People have tremendous agency inside organizations. A leader's defensiveness, avoidance, inability to listen or need for control can create consequences far beyond that individual.

We need to see that clearly.

We also need to see everything else.

The Work Can Start Almost Anywhere

This has changed how I think about our work at Evolve.

Sometimes we begin with an executive coaching engagement and discover that the leader's team needs attention. Sometimes work with an executive team surfaces an individual development need. Sometimes succession work reveals that the real challenge isn't choosing or preparing the next leader, but helping the current leader release authority and helping the organization reorganize itself around a new center of gravity.

There isn't a tidy line separating the person from the organization.

They are affecting each other all the time.

This is one reason I remain so interested in coaching. Deep individual change can alter an entire system. A CEO who learns to tolerate disagreement creates room for other people to think. A founder who genuinely releases authority allows another leader to grow. An executive who becomes less defended can change the quality of conversation across a team.

But the reverse is also true. Clearer roles, healthier team dynamics, better decision-making and thoughtful organizational structures can release capacities in people that were there all along.

Leadership development works best when we pay attention to both.

So when someone calls us and says, "We need coaching for this leader," I still listen closely to what is happening with that leader.

I just don't stop there.

I want to know what is happening around them, too.

Because sometimes the person sitting in front of us needs to change.

Sometimes the organization does.

And very often, they need to evolve together.