
Hard-learned leadership lessons from both the military and the corporate world
Giving someone responsibility is easy. Living with what they do with it is considerably harder.
Delegation sounds simple. Give someone responsibility. Explain what needs to happen. Step back and let them get on with it. Until they do it differently. Or more slowly. Or make a decision we wouldn't have made. Suddenly, stepping back becomes considerably harder.
This is where delegation gets interesting. Leaders remain accountable for outcomes they are deliberately allowing someone else to influence.
That creates an uncomfortable contradiction: We want people to take ownership, but ownership requires us to give up some control.
Most leaders are comfortable with the first part. The second is where things tend to unravel.
There are legitimate reasons leaders hold onto work.
They have more experience. They understand the stakeholders. They can see problems coming. They can probably complete the task faster themselves. So, they remain involved.
Initially, this can work remarkably well. Decisions are made quickly. Problems are intercepted. Quality remains high. The leader looks effective. But over time, decisions continue travelling upwards. People wait for approval. Knowledge remains concentrated. The leader becomes increasingly busy while everyone around them becomes increasingly dependent on their involvement. Eventually, the leader's competence becomes the team's constraint.
The very thing making the leader valuable can prevent everyone else from becoming valuable without them.
This is where many attempts at delegation come unstuck. A person is told: "This is yours." But every meaningful decision still requires approval.
Technically, responsibility has moved. Practically, very little has.
If people are expected to own an outcome, they need to understand the authority that travels with it.
Without that clarity, people quite reasonably escalate decisions. The leader then becomes frustrated that nobody shows initiative.
Sometimes people aren't reluctant to take ownership. They've simply learned where ownership ends.
There is an opposite mistake. Hand over responsibility, disappear and call it empowerment. That's not delegation either. The amount of oversight required should depend on the person, the task, the consequences and the context.
An experienced person dealing with familiar work probably requires very little intervention. Someone developing a new capability may need considerably more. A high-consequence decision may warrant checkpoints regardless of who owns it.
This is why "just trust your people" isn't particularly useful leadership advice. Trust matters. So does judgement. Good delegation isn't maximum autonomy. It's appropriate autonomy. The objective is not to remove the leader completely. It is to make their involvement proportionate to what is actually required.
A leader can delegate a task relatively easily. Delegating judgement is harder. Judgement requires context.
People need to understand what is being attempted and why. What matters most? What are the constraints? Which risks are acceptable? What happens when two priorities conflict?
This matters because reality rarely behaves exactly as the plan predicted. Detailed instructions work beautifully while circumstances remain stable. When they don't, the person either needs to return to the leader or exercise judgement. Context makes the second option possible.
Instructions tell people what to do when the plan works. Intent helps them decide what to do when it doesn't. That is where delegation starts developing capability rather than simply redistributing workload.
Developing people is inefficient. At least initially. It is often quicker to make the decision ourselves. Quicker to rewrite the document. Quicker to fix the mistake. Quicker to have the difficult stakeholder conversation. Quicker to say: "I'll just do it."
Sometimes that is absolutely the right decision. Deadlines exist. Consequences matter. Not every problem needs to become a developmental exercise. The problem is when "I'll just do it" becomes the default.
Every time a leader takes something back because doing so is faster, they solve an immediate efficiency problem while potentially creating a longer-term capability problem. The team remains dependent. The leader becomes overloaded. And because the leader is overloaded, there is even less time available to develop the team.
Short-term efficiency can create long-term inefficiency remarkably effectively.
There is usually a point in delegation where the leader becomes uncomfortable. The person is struggling. Not catastrophically. Just enough that the leader knows they could step in and resolve the problem considerably faster. This is an important moment.
Difficulty isn't always evidence that delegation has failed. Sometimes difficulty is how capability develops.
People need opportunities to deal with ambiguity, recover from small mistakes, make decisions and experience the consequences of those decisions. Remove every obstacle and we may also remove the learning. This doesn't mean allowing preventable disasters in the name of development. There is a difference between preventing unacceptable failure and preventing discomfort.
Good leaders need to know which one they're looking at.
There is a very safe version of delegation. Give people administration. Low-risk tasks. Work the leader doesn't particularly want to do. Anything where failure won't matter very much. That might reduce workload but it doesn't necessarily build capability.
People become capable of carrying meaningful responsibility by eventually carrying meaningful responsibility. That exposure should be proportionate and supported. Nobody is suggesting handing the newest employee the largest client and wishing them luck. But development has to contain some consequence.
If leaders retain every difficult decision, important relationship and meaningful piece of work, the team never gets to practise carrying them. Then one day the leader genuinely needs somebody to step up and discovers nobody is ready.
Capability built only when it is urgently required has been built too late.
One of the simplest tests of delegation is what happens when the leader isn't there.
If so, the organisation may not have developed an exceptionally valuable leader. It may have developed a single point of failure. This is one of leadership's stranger contradictions.
We often demonstrate our value early in our careers by becoming the person who can solve difficult problems. As leadership responsibility increases, success increasingly requires building other people who can solve those problems without us.
The behaviours that made someone valuable can eventually become the behaviours they need to let go of. Delegation therefore distributes much more than work. It distributes knowledge, judgement, confidence, relationships and decision-making experience.
Over time, fewer things should require the leader personally. That isn't evidence that the leader has become less important. It may be evidence that they've done their job.
Delegation is often treated as a time-management technique. And yes, it should create capacity. But that's probably the least interesting thing it does.
Done well, delegation develops judgement. It exposes people to consequence. It distributes knowledge. It tests capability before that capability becomes urgently necessary. There will always be decisions leaders should retain and moments where intervention is necessary. The skill is knowing the difference between being needed and needing to be involved.
The real measure of delegation isn't how much work disappears from the leader's desk. It's what the people around that leader become capable of doing without them. A leader who remains essential to every decision might feel extremely valuable. They may also have become the team's biggest constraint.
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Drawn from lessons learned in the military, and in business, we make leadership principles tangible and relatable through real-world examples, personal anecdotes, and case studies.
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