Dear Mathias, I’m a director of engineering working in a 50+ person engineering organization.

I’m a manager of managers, overseeing several engineering teams. I want to delegate more work to my engineering managers. In fact, I know I need to, but I’m afraid of delegating something quickly and potentially setting them up to fail. But, I just don’t have the time to set them up for success, so I keep completing tasks myself rather than handing them off. How can I break out of this cycle?

–– Sam

What’s the purpose of delegating?

Dear Sam, 

Delegating is important, not just for you, but also for the people around you. As you take on new and more senior roles, your responsibilities are bound to grow, not just in size but also in scope. 

While the work you produce begins to grow in the number of people it impacts, and therefore its importance, it can fall down your priority list in favor of work that you can easily plow through and tick off your to-do list, ultimately making you feel good about making progress. With so much to do in your new role, it’s easier to go back to what you’re familiar with and take care of all the other work you were previously responsible for.

Continuing to work on your old tasks while taking on new responsibilities comes down to a simple math problem. There is only so much time you have in a day or a week. This leaves you with three options: you can put in extra hours to get all the work done, do a shoddy job while trying to cram everything into a normal working day, or never really finish anything and make minuscule progress on your work. 

None of these outcomes are fulfilling. Piling on more work for yourself while also putting in more hours increases your chances of burnout. What’s more, doing a poor job or never really finishing any of the tasks you can’t seem to let go frustrates everyone around you, especially those who are dependent on your work.

I suggest you start by asking yourself these questions, reflecting on your personal motivations and hindrances to delegation:

1. How does delegating more help you and the people reporting to you?
2. How does it help the organization, your peers, the people you report to, and the people you’re responsible for?
3. What is personally keeping you from delegating more? Is it time? Is it trust? Is it impatience? Is it a feeling of wanting to be involved? Is it a fear of your report doing a bad job or failing? Or something else entirely?

There’s no judgment in any of these questions. Just be honest with yourself.

What’s in the way?

Establishing your motivation is one thing, making the space to live up to it is another. It takes time to successfully delegate something. 

Let’s face it, calendars tend to fill up entirely on their own, and we are constantly being pulled in several directions at once. When we’re that busy, it can seem like delegating is more time-consuming than just doing it ourselves. You could just choose to hand something off quickly, but as you say, Sam, that’d most likely only set up your delegatees for failure and yourself for disappointment.

The hard truth is, though, that while you may need to invest more time now, your investment is likely to pay off in the future. Over time, your delegatees will be capable of taking on more and more work with confidence, leaving you to focus on bigger ticket items without not worrying about small tasks or decisions.

Let’s start by looking at the first hurdle: your calendar.

1. What meetings do you really need to participate in?
2. Are there any meetings you’re a part of where you don’t really add any value and your participation is more out of courtesy than anything else?
3. Which of these meetings can you drop out of?
4. Where in your calendar can you pre-block a few slots to focus solely on delegation?

The second hurdle is that you may not be confident that your delegates will finish the project to a good degree, successfully, or in a timely manner. Here you need to start looking at yourself and your expectations.

1. What are you afraid could happen when you start delegating more work?
2. Could the delegated projects fail? Could the work not meet your standards or expectations?
3. What could you provide to your delegatees to ensure their success? Perhaps improving or increasing the contextual knowledge they have of a project/task could help clear things up. Alternatively, you could coach or mentor them to pick up skills they don’t yet have  Or, you set up regular feedback cycles to ensure they don’t veer off course, giving you an opportunity to correct or reset expectations.
4. Is there a way to give your delegates the option to fail, allowing them to learn regardless of the outcome? This could look like making the project smaller to reduce the dangers of failing, instead of the delegatee focusing on small iterations and experiments. Can you provide a space to reflect once the project is finished, and try again, helping them figure out a different approach?

A delegation toolkit

Assuming you’ve found time in your calendar to start delegating more, here’s a simple toolkit to get you started:

1. Make a list of projects that you can delegate. Look for projects that would normally be in your own comfort zone – the work you get drawn to out of habit.
2. Assign each project to the person you think is most suited for the task based on the project’s scope, their experience, and what would help them to advance in their career.
3. Write down your expectations for each project, including the project’s goal, the time frame, the cadence of opportunities for feedback, and how often you want to be kept up-to-date on progress.
4. Discuss these expectations with your delegatees. Are they reasonable? What do they need from you to be successful? What isn’t yet clear about the project? Adjust as needed and write everything down into a project brief. The written format ensures that both of you remember what you have discussed and decided.
5. Commit them and yourself to the expectations you’ve come up with. Solidify that commitment in your shared document.
6. Set up a cadence of meeting with them along the way to coach them. A tighter loop can be useful for folks who don’t yet have the right experience for the project at hand.
7. Put each catch-up meeting on your calendar, stick to them, and protect them at all costs.

Delegating effectively is a matter of managing your own time better and bringing about the circumstances so that you help yourself and your delegatees to success. 

–– Mathias

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