ISSUE #2 - FEBRUARY 2, 2022
The challenge of delegating
Advice for managers on when, what and how to delegate effectively. Avoid frustration, subpar deliverables and missed deadlines.
As people grow further in their career path, taking up managerial roles, it is usually required that they lead teams of people. One of the most important challenges they face is delegating. The problem lies not in delegating per-se. It is doing it effectively that creates challenges. When you are not delegating effectively, you are struggling to make time to deliver anything on time. Your backlog piles up with more and more urgent tasks and you end up either missing important deadlines or with final deliverables the quality of which is subpar.
For me, being in product, this started once I got into more senior roles. At that point, I had to manage bigger teams of people, with their roles spanning from other product managers, user researchers and analysts to designers, engineers, QA and so on.
Delegating is not a simple matter. Especially when people are new to their senior role it is arguably hard to forgo the need to have control. This leads them to avoid delegating and end up with lower quality deliverables and being overworked. In addition to that, a team whose work revolves around a manager who demonstrates lack of trust and keeps the important tasks to themselves, tends to feel less empowered.
I found that it is not only important to know when to delegate, but also what and how. Even when you acquire the courage to let go and allow other people to come in and contribute, you may find that delegating is not always straightforward. People might miss deadlines or present you with a deliverable which is totally different from what you had in mind (which is not always bad by the way). And this is natural. You cannot have the full picture of other people’s backlog and your mind is not operating in the same way. Consequently, all this leads to frustration (for both sides), lack of trust and ultimately to missing important objectives which hurts everybody.
Further in this post you are going to find answers to the following questions:
- When should you be delegating?
- What should you be delegating?
- How should you be delegating?
When should you be delegating?
Fortunately, this question can be easily answered, mostly because it is pretty simple to see the signs. Think about this: Have you started missing deadlines and this was not the case in the past? Do you feel or have you gotten feedback that your work’s quality is dropping? Do you feel that your tasks list is so full that you do not know where to begin from?
If the answer to the above questions is yes, then it seems that you need help. And in order to to get help, you have to start delegating some of those items to people working with or for you. They are there to get ownership and you are in this together. So, find the courage and give them some skin in the game.
What happens though in case you have no-one to delegate to? In that case, you are going to have to discuss it with your manager or CEO. You have to clearly state the problem and request for assistance. It is better if you have done your homework first, which includes the answers to the following questions:
- What kind of tasks are you spending your time on?
- By spending time on those tasks of high importance are falling behind?
- How much time do you spend on those on a weekly basis?
- Can those tasks comprise a clear role to be hired?
- If yes, what is the role description?
- How hiring a person with the above description would free up your time and what is the value of that?
Having prepared the answers to those questions in advance is going to help you make a compelling case, allowing your manager to empathize with the problem. This way, you would meet less resistance in getting all the involved stakeholders to agree and free up the necessary resources for this hire.
What to delegate?
Once you are in a position to delegate, the first problem that occurs is which tasks should be delegated and which not. What I found to be a very helpful framework for me, was a small tweak on the so-called “Eisenhower Matrix”. Yes, of the US president Dwight D. Eisenhower who was thought to be an expert in time management.
Eisenhower used to make decisions on what he should or shouldn’t and when based on the following framework:
In order to be able to use it, you have to be able to distinguish between what is urgent and what is important. Often people blend those two together. In short, Eisenhower says the following: Whatever is urgent and important at the same time, you have to do it immediately yourself. If something is important, but not urgent, you are going to have to decide on when you are going to do it. In case something is urgent but not important, you should delegate. Finally, in case something is not urgent and not important, then delete it. I find the above framework applicable in modern business environments, however, with a small tweak.
This tweak would affect the actions that should be taken in each combination of urgency and importance as follows:
Important & urgent: Do it immediately
In this case this is something that needs your immediate attention. So, you better start working on it as soon as possible. What happens though if you have more than one tasks of this kind? Then, you should definitely delegate one (or more) of them. We will talk about how in the next sections of this post.
Important & Not Urgent: Delegate it or schedule it for later
In this case, you have the luxury of taking your time and deciding when you are going to do a task or delegate it to someone else. My personal preference is the latter. When you have people that are reporting to you, it is important to allow them to work on meaningful items. Firstly, because you want them to grow and this does not happen by doing “monkey-work”. Secondly, if you keep giving them unimportant work, they will eventually loose their motivation. The result would be to start looking for someone that will be willing to allow them to work on the impactful stuff.
Urgent but not important: Delegate it
If something must be done, however it is not of great importance in the grand scheme of things, then feel free to delegate. What could belong to that category? That could be a report that is going to the upper management on a standard frequency, which is not automated. Since you have a certain deal to deliver it on a standard frequency, it is important to deliver it on time. On the grand scheme of things though, this should not affect the company’s future success.
Not Urgent & not important: Drop it
Plain and simple. You do not have time to deal with stuff that will not have any impact. Moreover, you should not waste anybody else’s time with something like that. An item like this could have ended up in your task list a long time ago and it is now deprecated or irrelevant. Or your initial evaluation about it was not right. Do not hesitate. Drop it and save everybody’s time.
So, the above matrix with the small tweak that we introduced would be transformed as follows:
A good exercise would be this. Take your current tasks list and categorize the items in this list in each of the above categories. How many of those tasks should you be delegating, but you do not? Are there any tasks in there that should not be? Get the answers to those questions right and you are going to have a much easier time dealing with your day-to-day schedule.
How should you be delegating?
Here is the most tricky part. Delegating is not as simple as just asking for a deliverable and giving a deadline. I am sure that the majority of people have learnt this the hard way. If the final deliverable is not what was expected, to my experience, this is for the most part because of the delegator, rather than the delegatee. And the breaking point is at the beginning of the process. When the delegator asks for the deliverable. How could you ensure that the deliverable will be as close as possible to what you have in mind? Let’s see.
Describe the problem
Before handing over a task to someone, ensure that you give them a clear picture of the purpose that this task is going to serve. Also, share a clear definition of the problem you are trying to solve. The above is essential so that the other person will understand the nature of the job at hand. And most importantly, this person might come up with additional recommendations regarding the task at hand that you might not have thought of.
Describe the deliverable. In detail.
This is vital. Giving a vague description of what you are seeking for allows for space for misunderstanding and misalignment. In case you need something very specific, be very clear about what this looks like. Ideally, offer an example or even a sample of the final deliverable. This way you can safeguard that you are on the same page with the person that is going to work on it. Beware though. Allow the other person to share their feedback with you and make sure to listen to it with an open mind. It is possible that their recommendations will be valid and lead to a deliverable of a much higher value than the one you had in mind. Never shut your eyes to a different perspective.
By doing this, you allow the necessary space for the other person to think for itself and not just be an executioner. After all, you do not want to be this “micromanaging” person who is not listening to any input from other people.
Ask the other person to describe you the problem and the task at hand
This is a great way to make sure that what you said is actually what the other person heard. Listen carefully, in order to understand if there are any blind spots. On top of that, when the delegatee is describing the task at hand, then new questions might come up that might clarify the small details of the task. Once the other person finishes, make sure to ask if there are any further areas in need of clarification.
Set a clear deadline
If something needs to be done by a certain time, then be specific about it. This deadline should not be phrased as “in one week”, or “in a couple of days”. Set a certain date. It is important though that you explain why the task needs to happen by that date. Do not set a deadline that came up out of the top of your head just for the sake of it. Also, make sure to ask the delegatee if this deadline is okay with them. Their schedule could be already overloaded with other tasks that you do not even know of. Those tasks could be of equal or even higher importance than the one you are delegating. This needs to be an agreement where both parties are onboard with.
In case the delegatee tells you that the time frame is not sufficient, then look into the possibility of delegating to someone else. In the case where this is not an option and the delegatee is your subordinate, then sit with them and go over the rest of the tasks in their backlog. You can look into the possibility of pushing something else further down the line. If this is not the case, then consider moving the deadline to a later date.
Follow up
Great, you have delegated the task! Is that it? No.
Always follow up. Not in the sense of being paranoid. Just to ensure that everything goes according to the plan. For example, if the deadline expires in one week then check in with the other party three to four days in advance. Ensure that everything is moving according to the plan. There are many things that might occur in between, so in case there is a setback and the delivery is in danger, you need to know early enough in order to take any necessary action.
Following the above steps, you have maximized the probability of having a deliverable of the shape and the quality that you need on time. However this is not all. There is one more step.
Always share feedback
Working with people means that this is a long lasting relationship and you have to help them further improve. Sharing feedback is a cornerstone to that endeavor. When a deliverable is of great quality, acknowledge it and let the other person know. If there are areas for optimization in the future, point them out. Sit with the other person and explain where and how they could improve. This way you are helping the other person grow further, your future deliverables to be of better quality. Consequently this has a positive impact on the whole team and the company.
That was it! By following the above steps you should be on track to get higher quality deliverables from your team as well as avoid any frustration and minimize lost deadlines.
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