Why We Struggle with Delegation.
“It will be quicker if I just do it myself.”
It is such a reasonable sentence. You know the work. You know what is required. By the time you explain it, answer the questions and check what comes back, you could have finished it.
So you do.
Then you do it again next week.
Eventually, you are wondering why everything still depends on you.
Delegation can trigger interesting responses. Some people seem comfortable handing work over. That does not mean it was always easy for them. They may have learnt how to tolerate the uncertainty, have the conversations and make peace with someone doing things differently.
For those of us who flinch at the suggestion, another delegation framework may not be enough. We can understand the steps and still find ourselves saying, “Leave it with me.”
That is where I get curious.
What feels difficult about letting this go?
The same behaviour can have a different story beneath it
Two leaders can hold onto exactly the same task for entirely different reasons. One worries about quality. Another worries about burdening the team. Someone else feels uncomfortable depending on another person.
From the outside, we see a leader who struggles to delegate. We cannot know their motivation from the behaviour alone.
The Enneagram offers a useful lens for exploring this. Its nine types describe different patterns of motivation, each of which can influence what handing work over means to us.
These are possible inner conversations, rather than rules about how each type behaves. Any type can delegate well, and you may recognise yourself in more than one example. You do not need to know your type to notice which sentence feels familiar.
Type One: What if they do not do it properly
For a One, delegation can bring up concerns about standards and getting things right.
“What if they miss something? What if I have to redo it? I may as well do it properly the first time.”
The care behind this matters. You want to deliver work you can stand behind. Yet it is easy for “done well” to become “done exactly as I would do it”.
You hand something over, but remain mentally involved in every detail. When it comes back, you make changes that the person may not understand, particularly if you never explained the standard in the first place.
A question to sit with: Does this need correcting, or is it simply different from how I would have done it?
Type Two: What if they need me less
For a Two, keeping the work can feel like an act of care.
“My team already has so much on. I do not want to add to their pressure. I will take this one.”
Sometimes that is a thoughtful leadership decision. It is also worth gently asking whether being the person who helps has become part of how you know you are valued.
If someone else can manage without you, where does that leave you?
You can care deeply about people and still allow them to carry responsibility. Before deciding they cannot take something on, have the conversation about their capacity.
A question to sit with: Am I responding to what they need, or to my need to be needed?
Type Three: What if this slows us down
For a Three, delegation can feel inefficient.
“I can get this done in twenty minutes. Why spend forty minutes explaining it?”
When results matter and time feels tight, taking over makes sense in the moment. The difficulty is that the team never gets past the slower learning stage if you keep stepping in to finish.
You get the result today, but the work returns to you tomorrow.
A question to sit with: Am I measuring efficiency by how quickly I finish this task, or by how capable the team becomes over time?
Type Four: What if something important gets lost
For a Four, a piece of work can carry personal meaning. There may be a particular tone, creative intention or quality that feels difficult to explain.
“They will not quite understand what I am trying to create. It will lose something if I hand it over.”
The challenge is to make that intention visible. Share what matters and why. Give examples. Invite the other person into your thinking, while leaving room for their contribution.
A question to sit with: Have I helped them understand my vision, or assumed that only I can bring it to life?
Type Five: What if this takes more energy than doing it myself
For a Five, the anticipated demands of delegation can feel exhausting.
“There will be questions, interruptions and explanations. It will be easier to work through it on my own.”
There may also be concern about competence: if the work is inaccurate or incomplete, what will that say about your expertise?
Keeping it can protect your energy today while committing you to doing it indefinitely. A clear brief and an agreed time for questions can make the process more manageable.
A question to sit with: What could I explain or document once that would save me from carrying this repeatedly?
Type Six: What if something goes wrong
For a Six, holding onto work can feel like the responsible thing to do.
“I need to know this has been covered. What if they overlook a risk? I am still accountable.”
You may anticipate problems that others have not considered. That awareness is valuable. Share it, along with clear checkpoints and agreement about when to ask for help.
The difficulty comes when taking responsibility means feeling you must do everything yourself.
A question to sit with: What agreements would help me trust the process without needing certainty about every step?
Type Seven: What if this becomes uncomfortable
For some Sevens, delegation becomes harder when it involves disappointing someone, setting limits or following up on a difficult issue.
“I do not want to make this heavy. I will just sort it out.”
Keeping things positive can mean leaving the less comfortable parts of the conversation unsaid. Perhaps ownership remains vague, or you avoid telling someone that the work needs another attempt.
You can bring warmth to a conversation and still be clear about what is needed.
A question to sit with: What discomfort am I postponing by taking this back on?
Type Eight: What if I lose control
For an Eight, handing work over can mean relying on someone whose pace or judgement differs from your own.
“If I keep hold of it, I know we can move.”
You may delegate the task while continuing to make every decision. The person has responsibility, but very little authority to act.
Trust needs something concrete behind it. Agree on which decisions they can make, where your input is required and what you need to be kept informed about.
A question to sit with: Have I given them enough authority to own what I have asked them to deliver?
Type Nine: What if asking creates tension
For a Nine, doing the work can seem easier than disrupting the peace.
“I do not want to put pressure on them. And if it comes back wrong, I will have to say something.”
So you avoid the request, soften it until it sounds optional, or quietly redo the work instead of explaining what needs to change.
The immediate tension disappears. Your workload grows, and resentment may grow with it.
A question to sit with: What needs to be said clearly now so I don't carry it silently later?
There is a cost to keeping it all
Whatever the motivation, the work still takes up space in your day and in your mind.
It can show up as exhaustion, overwhelm or a shorter temper. You become frustrated by interruptions, even though people have learnt that you are the person who knows, decides and fixes.
Meanwhile, your own work waits.
If you lead a team, that may mean less time for strategy, relationship building and the conversations that help you anticipate what comes next. The important work keeps being postponed because the day-to-day work always has a louder voice.
There is a cost to the team, too.
People need opportunities to stretch, exercise judgement and work through something they have not mastered yet. They need support, and they also need the experience of discovering that they can do it.
If we keep stepping in at the first sign of discomfort, we can interrupt that discovery.
It is worth asking: What am I preventing someone from learning by continuing to do this for them?
Make the brief clearer than you think it needs to be
Understanding your resistance is one part of the work. Giving someone what they need to succeed is another.
“Please put the presentation together” may sound clear to you. In your mind, you can already see the audience, the format and the level of detail.
They cannot see that picture unless you share it.
Someone can have been in a role for more than a year and still not know your expectations for this particular task.
Explain the purpose, what a useful finished result looks like and when it is needed. Share the template or a previous example if there is one. Be clear about what is essential and where they can use their own judgement. Ultimately – what does done and doing look like?
Discuss their capacity, too. If this becomes a priority, what else may need to move?
Then ask them to talk you through how they understand the task. You may discover a gap while there is still time to clarify it.
A few extra minutes here can prevent hours of rework, along with the frustration of judging someone against an expectation they never knew existed.
Stay connected to the work
Something else I see leaders do is delegate a task and only check in the day before it is due. Sometimes, on the deadline itself.
By then, there is very little room to clarify a misunderstanding or help someone change direction.
Agree on a halfway check-in when you hand the work over. A simple conversation can be enough: “How are you getting on? Talk me through where you are. Is there anything you need clarity or support on?”
You can stay interested in the work while leaving ownership with the person doing it. A check-in gives them an opportunity to ask questions and gives you both time to notice what needs attention.
Without that conversation, the assumption that “they know exactly what to do” can remain untested until the work arrives.
Then comes the disappointment, perhaps the anger, followed by a familiar conclusion: “This is why I should have done it myself.”
Before you decide that delegation was the mistake, ask yourself: ‘Did I create an opportunity for us to check our understanding while there was still time to do something about it?’
Make it safe to learn
Your team learns what is safe from how you respond when something goes wrong.
If you say, “You can ask me anything,” but appear irritated when they ask, they will notice. If an imperfect first attempt leads you to take the work back, they may become reluctant to try again.
Psychological safety becomes practical in these moments: can someone tell you they are unsure, raise a concern or acknowledge a mistake without fearing humiliation?
You can hold a clear standard while helping someone learn how to meet it.
Try asking: “Talk me through your thinking. Where did you get stuck? What would help you approach this differently next time?”
Leave the work with them to revise where possible. Give feedback they can use, rather than silently fixing it yourself.
Choose the scope thoughtfully. A first attempt might be a draft reviewed before it goes to a client, or a meeting they lead with preparation beforehand and a conversation afterwards. Allow room for mistakes within boundaries that suit the work.
And when they succeed, let them own that success.
Give yourself one experiment
Choose one recurring task or meeting that someone else could learn to own.
Notice the sentence that comes up when you imagine handing it over. “They are too busy.” “It will take too long.” “I cannot be sure.”
Get curious about what that sentence is protecting.
Then have the conversation. Make the expectations clear, agree on support and allow the other person to do the work.
It may take more time today. You may need to explain something twice or sit with the discomfort of a different approach.
Now imagine your diary a few months from now, with that piece of work no longer depending on you.
What could you give your attention to?
What might your team become capable of?
And what could you create with the space you have finally allowed yourself?
Here’s to the gift of delegation,
Warm wishes
Lori