The Delegation Dilemma.

Why leaders struggle to let go and what it costs everyone.

When Delegation isn’t really Delegation.

Most leaders know they’re supposed to delegate.  The advice is everywhere.  Empower your team, avoid micromanagement, focus on strategy and not detail.  

Reality can sometimes be quite different, because practicing delegation is one of the hardest leadership skills to master.  Not because people are unwilling, but because the emotional risk feels too high.

To delegate well is to let go.  

To allow others to own decisions, not just tasks.  To trust that something will be done differently, maybe even imperfectly, without stepping in to correct or control.  

That’s easy to say.. it’s much harder to live.

So instead, we often see delegation by name only.  

A handover that’s still tethered to oversight, a transfer of responsibility that’s quietly pulled back the moment pressure rises. 

This isn’t a character flaw, it’s a human response to the reality that, in most organisations, the consequences still flow uphill.

Leaders are accountable for what happens, even when they’re not the ones doing it.  So, understandably, they hover and they double-check. 

They quietly rewrite, rework, or reroute.  In this environment the task gets done, but trust gets quietly diluted.

Over time, people stop believing that delegation is real.  They wait to be told and they act with caution.  They disengage from ownership because the space never really belonged to them.

This is the delegation dilemma.

We say we want empowered teams, but we don’t build the conditions for empowerment to hold and the result is friction, fatigue and slow erosion of initiative.

In Part 1, we explored the risks of deferring blindly to authority, but the inverse is also true: when authority tries to do everything, the system becomes just as brittle.

Delegation is passing the weight of ownership.

Delegation as a Transfer of Ownership.

Real delegation is not about offloading work, it’s about passing the weight of ownership.  It means that the person taking on the task also takes on the decision-making, the responsibility and the freedom to execute with judgment.

This kind of delegation is rare, not because people are incapable, but because systems often don’t support it.

To delegate well, leaders need:

• Clarity: what’s being handed over and what boundaries exist

• Confidence: in their people’s ability, even when outcomes are uncertain

• Courage: to let someone else carry the consequence and to support them regardless

  
  
  
  

And teams need:

• Permission: to make decisions without second-guessing

• Trust: that their judgment will be respected, not reviewed

• Support: access to the leader when needed, without fear of overreach

  
  
  
  

This could feel like a checklist of sorts, but in reality what described is a relationship.  

Delegation is best when it’s relational, not transactional.  It only works when there is shared understanding and psychological safety on both sides of the handover.

In aviation, delegation happens constantly and visibly.

What High-Reliability Industries Teach Us.

In commercial aviation, the captain is legally accountable for the flight, but delegation happens constantly and visibly. 

A well-functioning flight deck is not a solo act, it’s a fully mirrored, shared, synchronised effort that depends on role clarity, mutual respect and clean transfer of control.

There’s a phrase used in command training: “You can’t hold the stick and train someone else to fly.”  If a captain constantly overrides, re-corrects, or takes back control, the First Officer never truly learns to lead.  

First Officers enter most airlines not as a subordinate, but as a captain in waiting and their skills are developed constantly whilst on the job. 

The most effective leaders seek to fully empower their first officer in all regards, so that when the time comes for them to step into command, they’re already mostly prepared.

Aviation solves the gap between mostly prepared and fully prepared with Command training processes which involve months, even years of behavioural observation before a pilot is invited to be assessed for command.  

During this time, they’re deliberately given more decision-making space.  They’re asked to speak first, act first and build their own judgment.  Instructors and captains observe, support, and coach, but they don’t rescue unless safety is at stake.

In the simulator they are expected to simulate command and are presented with vast arrays of simple, complicated and complex issues that require not just piloting skill or knowledge, but management expertise. 

These are live examples of what real delegation looks like: support without interference.  Trust with visibility and a clear understanding of when to step in, because in aviation, intervention is a trained skill.

Agreed intervention methods, allow people to speak safely.

Intervention: how to speak up and when.

There are three levels of intervention, taught and rehearsed in the simulator:

1. Hinting and tipping: subtle cues that something’s off: “How are you seeing this approach?”

2. Tell me what to do: direct re-brief or request for shared action: “Let’s talk through this together.”

3. Do it for me: taking control to protect safety: “I have control.”

   
   
   
   

These phrases form a common mindset, language and method. 

They reduce ego, clarify intent and they make it possible to intervene without shame or conflict, because everyone understands that adaptive capacity fluctuates and the team outcome matters more than individual pride.

This structure removes ambiguity, it removes the fear of overstepping and it allows leadership and followership to flow between people based on the moment, not the job title.

In business, we rarely have this language.  

Without it, leaders can become conflicted and either overcorrect or disappear.  Teams either feel micromanaged or abandoned, but if we introduced this kind of graduated intervention backed by training, not instinct, delegation would feel safer on both sides.

Because here’s the truth: micromanagement doesn’t come from a desire to control.  It comes from fear. 

Fear of being blamed, fear of failure and fear that things will unravel if we don’t stay close.

Each fear is totally valid, but left unchecked, they create the very fragility we’re trying to avoid.

The Quiet Cost of False Delegation.

When delegation is offered but not supported, it erodes confidence on both sides.

• Leaders feel frustrated when outcomes differ from expectations.

• Team members feel undermined when decisions are questioned after the fact.

• Everyone spends more time circling clarity than doing meaningful work.

  
  
  
  

Worse, it creates a kind of professional learned helplessness. People stop offering their best thinking and instead default to asking permission. 

They become careful, not creative.

Slowly and quietly, the system breaks, not from a single moment, but from a thousand micro-signals that say: You don’t really own this.. I do. 

Strong relationships grow from the empowerment delegation brings.

Delegation Is a Relationship, Not a Handoff.

Delegation should be about giving someone else the space and the support they need to carry out their designated task.

To make that work, leaders must become comfortable with discomfort.  They must build clarity around roles, communicate expectations openly and remain available without being intrusive.

Teams must then rise to the invitation.  Not with perfection, but with presence and a willingness to think, decide and learn. 

Especially, when they don’t get it right the first time.

The good news is that this kind of delegation is teachable.  It’s not a personality trait, more a practice grounded in behavioural clarity, shared language and trust.

High-reliability industries have shown us what that looks like.  Business can learn from it, not by copying the cockpit, but by understanding what sits underneath it: belief in people, clarity in roles and courage to let others lead before they’re perfect.

Because even when delegation is working, another question remains:

How do we maintain trust without disappearing?

How do we lead without watching from the shadows?

That’s where we turn next.