Delegating work

One of the hardest skills to learn as a new manager moving from an individual contributor (IC) role is how to delegate. How to use the power of a team to achieve more.

Delegation by its nature is a hard task. There is a balance between being absent as a leader and being too involved. It's the balance between micro-managing a project or a team and giving them space to operate.

Delegation is hard for many reasons. It adds a layer or more between you, as a leader, and the outcome of your team. Although you continue to be responsible for the outcome, you no longer tightly control it. Moving from an individual contributor role makes this particularly hard. Generally, your team is still performing tasks that you generally know how to do. Being able to hold back and not jump in is a difficult skill to learn.

As you start delegating work, you're also establishing a different kind of relationship with your team. You're trusting them to understand expectations, take action, and deliver work. Trust is a difficult thing to build and for most people, it takes time. Many new managers skip that trust building relationship because they lose the patience with stepping back and letting the team operate. Building trust also means allowing mistakes to happen, even if you knew they would as long as they're not completely destructive to the individuals or to the team.

The difficulty to detach yourself from the tasks you enjoy is another barrier. For example, I still enjoy doing product design. Sitting down in front of a Sketch file, brainstorming ideas, putting pixels to the screen is still an enjoyable experience for me. I don't do much of it anymore on daily basis, at least not for work. Not being able to jump in and spend time on it is difficult but important.

There are many more angles to explore but I'll focus on a few below.

Why delegate?

Let's start with the basics. Why delegate?

If you decide to go into management, the role you play in the outcome changes. It moves from a direct line between the work you do and the outcome you achieve to a very indirect line between the two. Your focus changes to setting direction and expectations, providing resources, and removing blockers to allow your team to execute. The joy is that as a team, you end up achieving a lot more that you could individually do. This is basic stuff.

You are no longer as effective of an individual contributor. You don't have the same amount of time to do things right and any time you're spending on pure IC work is time you're not spending on other things.

To manage teams effectively, you need to remove yourself as a blocker to progress. In my career, I worked with many managers who spoke highly of their ability to remove blockers away for their team but never stopped to realize that decision-making going through them and them alone, or that their micro-management style was actually one of the biggest blockers to their team's progress.

How to get better at delegating?

There are concrete things you can do to get better at this. These are not meant as silver bullets, but they do represent a set of core steps you can take as a manager to ensure you are delegating effectively. They're the steps that have personally helped me throughout my career.

Measure the outcome

For much of the work your team is doing, you already know of a way to do it. Your natural process of evaluation starts from the process by which the outcome was achieved. This is a mistake.

Trying to re-align the outcome your team achieved to the exact process and outcome you've envisioned as you thought of a project means you're almost guaranteed to set your team up for failure.

Instead, focus on the core principles that would make this work successful. What are the core set of elements that would mean this project succeeds. Make those clear to the team and set expectation around deliver, time, etc.

As the team is delivering, evaluate the work on those principles. If the work matches those principles yet still doesn't match your expectations, you'll have to think deeply as to where the delta comes from. Is it that the principles you outlined were lacking or is it that the work simply doesn't match your exact mental model of the results? If it's the latter, you need to start considering how to accept work that might look different from you yet meet the need and quality requirements.

This does not mean that you shouldn't look into the efficiency of the process by which the work was achieved. Of course you should. However, looking at the process first might blind your ability to still evaluate the outcome.

Allow mistakes, even when you know they're coming

Research tells us that people learn better from their own mistakes. There is a difference between someone pointing out why something could've failed and between learning that yourself by going through and observing that failure.

One of the biggest mistakes a new leader does is putting their team in a bubble to protect them from making mistakes. I've done this.

Don't do this. Teams will make mistakes. It doesn't matter how close you keep an eye on them or their process, mistakes are a natural part of how we do things.

It's generally more difficult when you can anticipate a mistake.

If the mistake is new, not critical, and is a bump on the road vs. a direction-altering mistake, you should let your team face it. On one hand, they might surprise you, and on the other, it is a learning experience. When thats mistake happens, don't use it as a way to show your knowledge or point fingers. This is easy to do. I've done it before too. Instead, use it as a way to understand why that mistake happened and how similar mistakes shouldn't happen again. Learn alongside your team don't simply team them.

Build trust

This is probably are the core of why new managers can't delegate well. Trust. The above is how you do it. Building trust takes time. As much as you need to trust your team to perform, meet expectations, and learn, they're also looking at you to see how much space you're giving them to execute. Remember that trust goes both ways.

Give credit, take blame

You are by default credited for your team's work. Never claim credit for something your team has done. Always give the credit to those doing the work. Everyone looking at you understands that your direction, leadership, and management has allowed this to happen. You don't need to say it.

Never be afraid to direct credit to your team and specifically to the individuals who've executed well. Take steps to ensure you are giving credit both in front of your team and in other forums where they might not be.

When things don't work, take the blame. Be clear about the reasons why something might've failed. Analyze the failure, learnings, and the impact but don't point fingers. Be positive as you talk to a general audience and direct as you give specific feedback to the individuals on your team.

Overall, delegating work is generally hard. None of the above is a silver bullet to solve these issues but it is a combination of learnings that worked for me.

Thanks to Dima  for reading earlier drafts of this.