Monkeys, Eisenhower, and why I need to stop doing things myself

One of the most valuable skills as a leader is delegation. Without delegation, you may be the boss, but you’re not a leader. In many ways, effective delegation is the surest measurement of the quality of a leader. Trusting your team to do a job really well, giving them the freedom to do so, and basking in the success that comes when all of that comes together in just the right way, is the secret sauce that makes an effective organisation.

I’m terrible at delegating.

Phew, there. I said it. It’s not that I don’t know how to delegate, I just haven’t mastered the recipe yet, and I’m starting to get a handle on why.

One of the best books I’ve ever seen about delegation is Kenneth Blanchard’s The One Minute Manager Meets the Monkey.

The essence of the book is very simple. Every time someone comes to you with a problem, that problem is a monkey on their back. When you say things like “leave it with me” or “I’ll look into that”, then congratulations! That monkey is now on your back. Now, having a monkey on your back is fun and a little bit exciting at first. After a while it gets old. Having two monkeys on your back gets old faster. More than two monkeys is just not fun any more.

The aim, is to send that person away with the monkey still firmly on their back. Ideally – send them away with one of your monkeys too. Chances are, if you’re a leader, you’ve got a veritable circus on your back.

The book does a great job of highlighting the behaviours that inhibit delegation – and it has stuck with me since I read it about eight years ago. I’m not going to re-state the entire book here – I encourage you to read it – but it’s a great guide to delegation.

About five years ago I was introduced to Eisenhower’s Urgent & Important Matrix. You’ve probably seen this too – and maybe you’ve used it. If you haven’t, here’s an example.

When you have your tasks categorised into each of these four quadrants, it’s easy to see how you should proceed with getting them done.

Again – I know exactly how this works, and I must admit, that within the business, I have delegated most of the things that fall into the Urgent & Not Important quadrant. I don’t have a problem with knowing what to delegate. I still have a problem with delegating successfully, however, and I think I’ve figured out why.

One of the most difficult things for me to delegate is the thing that I have hired teams of people to do – developing software. Yes; I’ve hired seven software engineers and I still feel the need to muck in and do it myself way more often than I should.

I started to get frustrated with this recently, because although I absolutely love coding, and I have over twenty years experience doing so, it is fundamentally not my job. So I set about figuring out why I am so bad at delegating this particular job.

Being that it’s my specialist subject, if you will, I just can’t help myself. I am the guy for the job. Except I’m not. I have specifically hired very smart people to do that job for me. So what’s going wrong?

There are two fundamental problems with me delegating my specialist subject.

The dip before the climb

As a leader who has to delegate their specialist subject, you have to be ready to deal with the huge dip in productivity that comes at the exact moment you delegate your responsibility to someone else. Even when delegating to multiple people, there will be a dip.

In Fred Brooks’ legendary book The Mythical Man Month he explains one of my favourite pieces of leadership wisdom. Ten people cannot do the same job as one person ten times faster.

For example, if a person can dig a hole in ten hours, can ten people dig the same hole in one hour? Probably not. For a start, they’d probably all get in each-other’s way.

The logic is that the number of relationships that need to be maintained, and the number of communication channels that arise as you add more people increases exponentially, which hampers progress.

There’s also the learning curve to think of. When you delegate something that you’re particularly good at, it will inevitably take some time for those you delegate to to reach the level of knowledge required to hit the pace you had.

You need to get comfortable with there being a significant period of time when the work that you would normally do will be done much slower. If you get restless and decide you can’t wait for the team to climb back out of this dip by themselves, you will never delegate successfully. They need to be given that space.

The communication gap

When you delegate something that you would ordinarily have done yourself, you will never obtain the same quality of results if those to whom you delegate don’t have access to everything you know that would empower you to do the job. Now – I’m not saying you need to find a way to impart all of your knowledge – that would be crazy – but you need to plan a level of knowledge transfer that will produce good enough results within an acceptable period of time. It’s not just knowledge of the “how” – but also the “what”. Ensuring the team has enough detail about the conditions of satisfaction, or acceptance criteria will make or break the delegation of any task.

This is the part that I struggle with most. I carry a lot of information in my head, and rarely take detailed notes because I don’t need to. The lack of detailed notes, while acceptable for me, means that when I delegate the task, I then need to write very detailed instructions from memory – and crucially – not leave out anything that I would take for granted. It’s this filtering based on assumptions that is the most dangerous threat to the communication gap in delegating.

So what can I do to improve my delegation of tasks that I feel I’m extremely well qualified to do?

Don’t be a proxy

In many client relationships, the team leader acts as the liaison between the team and the client. The problem with proxying all questions and instructions through the team leader, is it increases the communication overhead and unintentionally breaks down the opportunities for those doing the job to get all of the information they need.

Open up the lines of communication. Empower your people to talk directly to the customers, and give them the opportunity to do so. Give customers the confidence in the team too – but stay in the loop. Don’t drop the ball in terms of leadership or oversight – but don’t be the man (or woman) in the middle.

Slow down and have patience

Don’t delegate everything in one fell swoop. Accept that there are some things you’ll have to do yourself for a while, otherwise you’ll end up taking back the things you’ve delegated. Get comfortable with the dip in productivity that will inevitably happen when you delegate a task for the first time. Discuss it with those you delegate to and make a plan to monitor it and regularly revisit what’s working and not working.


Delegation is a very delicate art. I am still learning how to make these approaches work, but so far I am seeing improvements in my own levels of comfort and the team’s delivery of tasks that I would have done myself.

I usually recommend books I’ve read. The Mythical Man Month is the primary source of one of the most powerful pearls of wisdom in team leadership – but as a book, it is extremely difficult reading. I recommend you only read it if you’re intent on doing so. If you just want the gist – try this nice summary.

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