Delegation 101

Delegating well is a superpower. It frees founders from some of their operational responsibilities, giving them much-needed headspace for strategic thinking and big decisions, it prevents them from becoming bottlenecks for their organisations, and it empowers their reports and gives them room for development. What’s more, everybody can learn it. It’s a skill, not an innate quality. But it takes some awareness and attention to get it right.

This is a snapshot of a slide that I once made for myself to compare organisational theories. The topic of delegation comes up in most of them, marking it as a turning point in the development of a company that will decide whether a company manages to continue to grow or stalls.

In my work with founders, I often see that delegation first becomes an area of concern when a business reaches about 30 people. This is when one or more of the following issues appear:

- Founders are being drowned day-to-day operations and fire fighting
- Progress stalls when the founder is not personally involved (or at least it seems so)
- Founders feel like they cannot get rid of workitems, that they are coming back to them, and people around them seem to be more problem- than solution-oriented.

All of these can be signs of under-delegation, but in my experience, it’s much more likely that they are caused by under-managed delegation. Founders are often prepared to hand over operational responsibility because they fully realize that they need to make space for more strategic work, but they are unaware of whats needed to make delegation a success and end up in delegation hell, where they have less visibility & control over workitems but are still involved in handling them.

So how to do better? What’s needed for good delegation?

First of all, it’s important to realize that delegation is a process (and not an act) that requires some attention. It requires attention before a handover takes place and it requires attention afterwards. This is often overlooked, and delegation is handled too much in the moment. Also I think it helps to view delegation as a contract. It requires mutual consent about its goals, reasons, rules and process aspects to work well.

This implies - correctly - that you should think of the most relevant aspects of the delegation at hand before you delegate and make them explicit and agreed upon. For this purpose, I have often used a checklist to ensure I think of everything that matters before entering into delegation. I go through the list, write down what I think is necessary, and go through these items one by one with the delegatee. Sometimes, I forward my notes to them afterward.

Delegation Checklist

Goal of the Delegation

What is my desired outcome (& intermediate outcomes, if any)? What is an acceptable deviation in quality or quantity?
What are deliverables? How can success be measured?
What is my timeline?

Reasons for the Delegation

Why do I need to get it done?
What are important elements of context or assumptions of mine that lead me to believe that?
Why do I think the delegatee is right for the job?

Key Rules

Do I have particular expectations on how the results are achieved (way of doing things)? Is there a level of discretion to it? Why?
What is the delegatee’s role? What powers come with (in particular, what can he ask of others in the organisation)? What are limits to said powers? What resources are available to the delegatee?
What is the priority of the delegation compared to the day-to-day responsibilities of the delegatee? How do I imagine their time should be used?

How do I wish to be kept up to date on progress? What other reporting modalities matter to me?
When do I want to be involved or asked for direction or feedback? When don’t I?

*Sometimes, a “Decision Tree” like this one can help to clarify the rules and expectations around approval and involvement of the delagtor*

Do you need to do the complete list every time you delegate something? Initially, I would, yes. Practice makes perfect, and it’s helpful to develop a routine for delegation. But after a couple of times, it depends on the object of the delegation and the experience of the delegatee. The more extensive/complex/longer-running the object of the delegation is, the more thought should go into this. I think it’s particularly important to be very clear about reporting and alignment modalities when the delegation will span some weeks or months and to go really into role/powers/resources and potential conflicts if the work item is likely to collide with day-to-day work in other areas of the company a lot. But if you are just delegating a small work item, then I believe it’s mostly fine if you are clear about the goal, deliverables and measurement of success. Likewise, a more experienced delegatee will require less context and guidance than a less experienced one. In any case, if in doubt, prepare it.

Notice I said above delegation requires mutual consent. It is not enough that one side delegates (that would be dereliction). The other side must accept it. Think of these questions to ask the delegatee:

Is anything unclear to you? Do you feel that information is missing?
Do you disagree with anything?
Do you have doubts or insecurities about any aspect of the delegation? Or is there an area of discomfort for you?
Do you foresee potential conflicts with your current work environment or colleagues arising out of the delegation?
From your point of view, what are the next steps?
And finally:
Do you want to take over this responsibility?

In contrast to the preparation, I think these questions are always helpful - regardless of the size of the delegated responsibility and the experience of everybody involved.

This sounds like a lot? Maybe. But it’s much better to think these through beforehand and to make them explicit than trying to correct them afterwards. And it will save you time and - even more importantly - worry. Trust me. Plus, this scales pretty well. You will only delegate to a handful of people. By doing this conversation diligently once or twice, you will build a shared understanding of what’s expected and needed and the third time around will be much quicker already.

Last but not least, it will make the delegation more successful because it minimizes disturbance and maximizes a feeling of autonomy and trust in the delegatee. It makes a huge difference for the delegatee if something was clearly discussed and agreed to from the very beginning or if it was introduced after the fact by way of corrective action of the delegator. The former gives clarity, the latter feels like micro-management.

And that brings us neatly to an important aspect of delegation. Delegation is vastly more successful, if the delegatee feels a real sense of ownership and not just mere duty.

And you only ever feel ownership for something that you have been entrusted to do. It’s your job as the delegator to convey that trust. And to not destroy it carelessly (e.g. because you become itchy and want to involve yourself above and beyond the agreed rules for feedback and consultation).

Does that mean that you can never add granularity or tighten the rules? Of course, it doesn’t. As the delegator, you have accountability for the outcome of what has been delegated, and that is more important than anything. But it might make the delegation less effective, so if you can avoid it by being more thoughtful, you should.

The last thing that is required of you: you need to keep track of the delegatee adhering to the agreement. If, for example, the delegatee does not report back as agreed, remind them of the agreement and that you expect it to be honored. Doing this diligently goes a long way. Not only for the delegation in question, but it also sets an example for the whole company of what good work ethics are. Also, you want to encourage action before safety. Some delegatees like to play it safe by ensuring your approval for all they do. While this might even appeal to you (because it gives you a sense of control, and, well, it’s flattering to be needed), it limits the potential of the delegation. And it’s slow. Again, the goal is that the delegatee owns the object of the delegation and that you get it off your to-do list. It’s ok develop this over time, but develop it must.

In summary, delegation is a lot of work for the delegator. But it’s worth it. It scales well and if you get it halfway right and build a group of capable delegatees to support you, it makes your life so much better and you so much more impactful. It’s a superpower.

Founder Mode (Part 2)