Koan #18: Ready... Steady... Delegate!

We usually send the situation in one newsletter and results in a following newsletter. Here the situations and results are copied verbatim into one post. Hence, when it says 'you' - it means the subscribers who voted in newsletter, not readers of this archive.
This situation was published in the 01 Jun 2021 newsletter.


You have two big tasks ahead of you. One task you have done before and know how to do, we’ll call it ‘The boring task’. The other task is in somewhat uncharted territory with the result not clearly defined and may require trial & error; we’ll call it ‘The challenge task’. Both tasks will take a significant amount of time, and your calendar only has space for one of these. The good news is that you manage someone, Alice, who just recently passed their probation, and in your 1:1s has expressed that they would want some challenging work. What would you do?

Option A - You give ‘The challenge task’ to Alice and focus on doing ‘The boring task’. Alice gets their challenge. You might also finish the boring task faster and take on a new task sooner.

Option B - You give ‘The boring task’ to Alice and take on ‘The challenge task’ Alice may still learn something, and you get to do something interesting.

Option C - Work on both tasks together.

Option D - Ask Alice which task they would like to take on, and you complete the other one.


Delegation is one of the most important skills new managers have to learn if they want to be effective, but it is also easy to make mistakes when you delegate. To make matters worse - it is hard to notice when it is done poorly. If delegation is done poorly, the result of the delegated task(s) may look poor, and more often than not this will be judged as poor performance.

One of the best rules of thumb for effective delegation is summed up in this quote by Andrew Grove in his book “High Output Management”:

“Delegation without a follow-through is abdication.”

This can be interpreted in at least a few different ways. One approach may be delegating a task, and then regularly haranguing the person with “is it done yet?” and “if not - why not?” That is not a great follow-through because it can quickly devolve into micromanagement. Another way to think about this is to consider what you can do as a manager to follow through effectively. In the context of last week’s situation, there are two tasks - one we know inside out, and another that is unclear. Put in this light it should be clear that delegating the boring task makes the follow-through more effective making option B the best one out of the four.

Considering the almost even split between last week’s options, it is worth explaining the remaining options. A lot depends on the context, but we think the key aspects of last week’s situation were the fact that the two tasks will take a significant amount of time, that Alice just passed their probation, and that Alice asked for more challenging work.

Giving the challenging task to Alice, as in Option A, might make it difficult to follow through, because it is not clearly defined even for the manager. If Alice encounters a problem, it may quickly lead to frustration on both sides. Alice may feel thrown in at the deep end without support. Their manager may feel like Alice is performing poorly. As the task is ill defined, it may be hard for anyone to get a grasp on what exactly went wrong and mean that Alice and the manager end up both working on the same task in anger.

Starting off working on both tasks together, as in Option C, sounds like a good plan. It could be, for a quick task that Alice may need to learn to do repeatedly, or when teaching a crucial skill. In such a case Alice can be up-skilled by feedback being given in real-time. However, in last week’s situation there are two long tasks that need to be done. If working on them together at the same time, the manager would most likely feel pressure to do both at a decent pace to make it in time. This raises tension between the manager’s goal of trying to finish the tasks and Alice’s goal of trying to understand what’s happening, thus slowing the process with questions. Or, Alice may even be in the back seat the whole time and not learn anything when similarly well or poorly defined tasks come along.

Giving the option for Alice to choose their task may work if they choose the boring one. However, having asked for something challenging, and presented with a choice between boring and challenging, Alice may be inclined to take the challenge. And this leads to the same issues of follow-through, as summarised for Option A above. One important detail is that Alice just passed their probation, and it may as well be that what a manager considers boring and routine can be a challenge or a learning opportunity for Alice, just as they wanted, as in Option B.

One of our subscribers summarized all of the above in a very concise response:

“You will be able to support Alice if they are doing the boring task. Doing one each will be very inefficient and most likely lead to confusion. As the outcome of the challenging task is ill-defined, you will need to work on fixing that before you can get started and whilst this could be good for Alice, it may hinder their great progress so far.“