In 2020, I sat down with Forbes contributor Ian Mathews to talk about my transition from active military service to starting The Eighth Mile with Jonathan Clark.

We talked about starting a business, but much of the conversation came back to leadership.

Some of it was about what worked. More importantly, some of it was about what I got wrong.

Looking back at that conversation several years later, there are a few lessons I've carried with me.

I Didn't Make the Hard Decision Early Enough

As a young officer preparing to deploy to Afghanistan, I had concerns about someone in a leadership position within my team. I knew there was a problem. But I didn't want to disrupt the team immediately before deployment. I thought I could develop the person. Give them more time. Make it work. There was probably some ego involved too.

I'd spent four years in an environment where everything was assessed. We were graded, compared against our peers and eventually ranked against our cohort. I wanted to be a good leader. And part of me believed a good enough leader should be able to fix the problem.

I WAS WRONG.

During a gunfight in Afghanistan, that person froze at exactly the point when I needed them not to. The warning signs hadn't disappeared because I'd chosen not to act on them. I'd simply delayed the consequences. That's something I've carried with me ever since.

Avoiding the difficult decision doesn't mean we avoid its consequences.

Sometimes we're genuinely giving someone an opportunity to improve. Sometimes we're avoiding our own discomfort. Knowing the difference matters.

My Avoidance Turned Into Micromanagement

After that incident, I had a problem. I couldn't completely trust that role to function without my involvement. So, I compensated. I checked things. I became involved in decisions that should have happened below me.

In short, I micromanaged.

Given where we were and what was at stake, ensuring my soldiers came home safely mattered considerably more than demonstrating perfect delegation. But there was still a cost. Every time I operated at somebody else's level, I had less capacity to operate at mine and that experience changed the way I think about micromanagement.

Sometimes it's simply a leader who likes control. But sometimes it's a symptom of something else. A capability issue. Unclear expectations. A previous failure. A lack of trust. Or a difficult conversation that hasn't happened.

Before we tell a leader to stop micromanaging, there's another question worth asking:

What has made them believe they need to?

I'd Spend Another 60 Seconds Explaining Why

If I could give my younger self one simple piece of leadership advice, it would be this:

Spend another 60 seconds providing context.

Some of the times my people were most frustrated with me weren't because they disagreed with the decision. They didn't understand it. They knew what we were doing. They didn't always know why.

Context changes the quality of the decisions people can make without us. If our teams understand what we're trying to achieve, why it matters and the conditions we're operating within, they don't need an instruction for every possible situation. They can exercise judgement.

If people can only make good decisions while we're standing beside them, we haven't necessarily developed capability. We may have developed dependence.

Rank Gave Me Authority. It Didn't Give Me Influence.

While deployed, I remember an American lieutenant being surprised by how casually my soldiers interacted with me. They'd call me “boss”. He couldn't understand it. From his perspective, there was a rank structure and our interactions should reflect it.

But within our team, that informality wasn't disrespect. Quite the opposite. If my soldiers suddenly started calling me “sir” all the time, I'd probably have wondered what I'd done wrong. It taught me something about the difference between authority and influence.

Our position can require people to comply with a decision. It doesn't make them trust us. And it certainly doesn't guarantee they'll tell us when they think we're wrong.

Sometimes one of the better indicators of a healthy leadership relationship is what people are prepared to say in front of us.

Vulnerability Made Me More Credible, Not Less

For a long time, I thought leadership meant protecting an image of competence. We should know. We should be composed. We should have the answer. Over time, I found almost the opposite.

The more comfortable I became saying: I got that wrong. I don't know. This is where we're weak. We haven't delivered what we said we would. the stronger some of my relationships became.

People didn't have to go looking for the bad news. They knew we'd tell them.

That doesn't mean leaders need to broadcast every insecurity they have. But protecting our reputation at the expense of honesty doesn't create trust.

Jono and I Didn't Need to Be the Same

When Jono and I started The Eighth Mile, we deliberately took different roles. I'm naturally more inclined towards finding gaps, opportunities and relationships and asking what might be possible. Jono brings considerably more structure, systems, process and operational discipline. Those differences have been useful.

I've become increasingly sceptical of the idea that there is one ideal version of a leader that everyone should eventually become. Teams don't necessarily become stronger by making everyone more alike. Sometimes they become stronger by understanding where people are different and using those differences deliberately.

That requires enough self-awareness to know where we're useful. And enough humility to know when someone else is better placed to lead.

The Problem Isn't Always What It Looks Like

One of the reasons Jono and I eventually started The Eighth Mile was what we saw after leaving Defence. We'd encounter what appeared to be a process problem. A project problem. A systems problem. Then we'd look underneath it.

Two people weren't talking. Expectations weren't clear. Nobody wanted to challenge the boss. Someone didn't trust someone else. A difficult conversation had been avoided for six months, and the organisation had gradually built processes around it. Then somebody suggested buying another system.

Not every organisational problem is a people problem. But enough of them are that it's worth checking before we spend a fortune solving something else.

The Leadership Problems Change

At 22, leadership felt incredibly immediate. People. Decisions. Consequences. But, as my responsibilities changed, so did the leadership problem. The question gradually moved from:

What decision should I make? to: How do we create the conditions for other people to make good decisions without me?

That means giving people context. Developing capability. Being clear about expectations. Having difficult conversations early. Creating enough trust for bad news to travel upwards. And resisting the temptation to continually operate at a level below where we're supposed to be.

The fundamentals don't necessarily change. The way we apply them does.

I'm Still Learning

When I spoke to Forbes in 2020, I'd already moved from Defence into business. But I don't think we ever really finish transitioning as leaders. Experience keeps challenging what we thought we knew.

• Be patient with people, but don't use patience to avoid accountability.
• Give people autonomy, but don't abandon them.
• Be confident enough to make a decision, but humble enough to change it.
• Stay close enough to understand what's happening, but far enough away that we don't become the bottleneck.

There aren't neat answers to all of those contradictions. That's leadership.

And perhaps that's the biggest thing that's changed since I was a 22-year-old lieutenant trying very hard to have all the answers. Leadership isn't knowing what to do every time. It's developing the judgement to understand what the situation requires from us this time.

This article draws on David Neal's original interview with Forbes contributor Ian Mathews. Read the original Forbes interview for the full conversation.