The art of entrepreneurship is, in part, knowing when to delegate.
Delegation is a tricky thing. Generally speaking, if you’re a leader, you’ll be able to do most, if not all, of the responsibility of your subordinates at a higher quality than they can.
But, you cannot do ALL the work of your subordinates. There is just simply too much to do.
And, if you try to do all the work of your subordinates, you will quickly become bogged down, and your business will suffer.
And so, enter delegation.
You need others to be able to do work required to a specific standard — it doesn’t have to be your standard; it just has to be good enough to be acceptable and move things forwards. And sometimes, you may get even higher quality work than you could achieve, especially if you hire the right people.
It is important to remember that delegation is not abdication. You are still responsible for the work being done — you are just delegating the actual work.
Before we get into the mechanics of delegation, it is worth pausing to discuss the role of deep work. Suppose anyone on a team has technical responsibility, and I mean anyone who is supposed to generally do one thing (i.e. an accountant, a software developer, a designer, a data analyst, and so on). In that case, the critical thing is that they spend as much time as possible working on the right thing without disruptions and changes to the direction of their work. This ensures that they can regularly get into deep work, which is where the highest quality work is done by individuals.
To make this happen, it is the leader’s responsibility to protect their time and work. This may mean saying no to requests for help or delegating tasks to others on the team. But, whatever the case may be, the leader needs to ensure that each individual on the team can get into deep work as much as possible.
Managers (not leaders) often fail to understand this, because the role of a manager is almost diametrically opposed to the role of a technical worker. The manager is there to align, coordinate, unblock, and report. This, if done badly, can mean a significant number of meetings. After a long enough career, the number of meetings themselves is seen as progress, and this thinking is extended to technical workers themselves, who should actually be protected from meetings as much as possible.
So, back to delegation.
The key thing a leader needs to identify is what work they should be delegating and which work they should handle themselves. This is often not as straightforward as it may first appear, especially if one does not have a model or framework in place to evaluate work.
I discussed this at length in my essay Prioritization for Leaders and I will reiterate the same point here:
Leaders should spend the majority of their time working on the point of constraint; everything else should be delegated to someone else.
And if we extend delegation not to just handling work but to making decisions, then another way to see this is that anything that is highly consequential and irreversible should never be delegated, and anything under a specific amount of consequentialism (let’s set an arbitrary cap of 50%) should always be delegated.
So, what is left? A sweet spot of sorts, in which the leader needs to use their judgement to decide if they should delegate a task or not.
A leader needs to remember when delegating that they are delegating work, not responsibility. The leader is still responsible for the work being done; they are just not doing the work themselves. This means that the leader needs to be clear about what is expected from whoever they are delegating to, and they need to be clear about what the standards are.
The leader also needs to be available to provide support and answer questions, but they should not be expected to do the work themselves.
Delegation can be difficult for many leaders, especially those who have come up through the ranks by being “go-getters” and taking on everything themselves. But, it is a necessary skill for any leader and a skill that can be learned.
The critical thing is to start small, with tasks that are not too important and not too consequential. And, as one gets more comfortable with delegation, to delegate more and more.
So that is when to delegate, the next question becomes how to delegate. There is a continuum between giving clear instructions and getting precisely what you want out of people, and being a suffocating micro-manager that does not let individuals use their brains and initiative to tackle work and decisions the best way they see fit based on the unique circumstances at the time.
I generally prefer to try and let individuals I trust figure out as much as possible by themselves, but that requires trust, which is not something that is gained immediately but builds up over time.
So, I tend to be closer to the micro-manager with individuals who I have not had the chance to work much with, and far looser with individuals who I have worked with for an extended period of time.
When it’s the latter arrangement, I like to focus my brief of the work on some of the key risks, the key expectations of results, and specific hard timelines. I always let the individual know that I am a resource they can access at any time if they have questions or get stuck, and I trust them not to abuse that level of accessibility. If the specific task or decision is something I am an expert in, I may also give general pointers towards the “how” of the execution. Still, I think it is generally best to let people figure things out themselves and build their skills in this manner.
On the other hand, when it’s the former arrangement, and I am working with someone new or on something highly consequential, I tend to be much more specific in my delegation. I will go over not just what I expect as an outcome but how I want that outcome to be achieved. This level of detail can lead to micromanagement if one is not careful, but it can also help avoid major disasters.
The key here is always to keep communication open so that the leader knows what is going on and can provide guidance without stifling initiative and creativity.
I am going through an interesting transition now at Mäd, where I have always delegated substantial parts of the work — almost all of the client work has always been done by subject-matter experts while I run the firm itself.
Now, I have delegated the firm’s running, which is an interesting experiment. The focus of delegation becomes much narrower — how do you enable one individual to flourish and do outstanding work running something that you have previously been running?
At a certain level of delegation, especially when there are layers of managers involved, metrics and data play an important role. We’re disciplined at Mäd with our financial reporting. Blue is even more fortunate that, as a software company, almost every metric I could dream of accessing is trackable via a dashboard.
This is good because it can enable discussions to centre around outcomes, not just inputs. Delegation becomes far more about providing clarity about the long-term outcomes than the short-term inputs.