‘How do I get better at delegating tasks?’

Off-loading work frees up time for bigger challenges so you can accomplish more. Here’s how to do that

As the space between work and not-work becomes ever more blurred, questions about how to do this thing we plug away at for 30 or 40 or 70 hours a week become all the more expansive. In Work Flow, we delve into the novel dilemmas created by the new ways we work, as well as timeless questions about ethics, gender assumptions, and toxic work situations (and how to escape them). How we work is an important component of how we live—and we’re here to help you do better at both.

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I’ve been at the same company for five years, and in that time I’ve been promoted from an entry-level position to a management role, which is great. I’m moving into a lot more conceptual and business-growth-related work, and, in addition, I’m mentoring and helping develop newer hires. 

The problem: I’m still responsible for much of the stuff I did during my first year on the job. I can almost do it in my sleep at this point, though it all takes time. I’m really struggling to get everything done. Part of me is afraid that if I delegate my old work, my company will regret promoting me, and my coworkers will resent me for passing stuff onto them. 

Everyone says delegation is a key part of leadership, but how do I even go about it? Do I need manager approval? Do I just take it upon myself to hand out the work I don’t like anymore? What if the person I delegate it to doesn’t do it right? Sometimes it feels easier to just do everything myself (at least I know it will be done right), but then I am at the office till midnight and hate myself. Can you help me delegate?

“Everyone” is correct! Delegation is a key part of leadership and a key part of business success, both micro and macro. In 2014, Gallup studied 143 CEOs from the Inc. 500 list and found that those who were good at delegating had a significantly higher growth rate for their companies, and greater revenues, than those who didn’t delegate well. They also created more jobs, and did it faster than others. This isn’t just true for those particular CEOs. Across the board, delegators have been found to get more, and better, stuff done. They’re very likely happier, too.

So let’s turn to the very first person you need to “lead” through delegation here: yourself. I’m not chastising you. You’ve been climbing the ranks for five years. I feel like the managers who hired and promoted you should have given you at least a note or two about delegation during your performance reviews and even, ideally, helped you manage taking some of the work off your plate and putting it onto someone else’s. 

But, hey, that’s not what happened, and it’s often not what happens in today’s workplaces. That’s just fine. You’re going to learn to delegate without their push in that direction. You’ve led yourself here (by doing more and more work, so your dedication is real), and you’ve led yourself to ask this question (because you know something has to give). 

Time is finite. It’s impossible to become more and more integral to the company—not just carrying out duties but really helping to lead and grow the vision of that company yourself—if you never move on from your entry-level duties. You have to cut out the stuff that’s no longer the best use of your time in order to give yourself time for the other, higher-value work. 

When someone starts in the mailroom and moves up to the corner office, they’re not still delivering the mail, right? Before you worry about resentments from your coworkers and regrets from your bosses, keep in mind that this isn’t just about you, it’s about your company and what best supports the business. 

More stats: According to a 2013 executive coaching survey from Stanford University, 35 percent of CEOs felt their delegation skills needed improvement; 37 percent said they’re working on improving those skills. (So you’re in good company.)

Here’s what you need to do to start reaping the benefits of delegation, which include more time for you to do the stuff that’s going to build both your career and your company, more trust in the workplace, a higher sense of value and empowerment for everybody, and a greater commitment to this super place you work. What could be better? (Oh, also, if you delegate, you can actually take some time off and enjoy yourself.) A win-win.

Step 1: Review your workday and duties 

Write down everything you do from the minute you step into the office (or beforehand, if you start working from home) until you turn off your computer for the night (or whatever signifies the end of your workday). Make a list! (I love lists.) Chart out a day, a week, even a month; use Google calendar to note time increments, or write this all on an old-school hanging wall calendar—whatever you need to get an essential sense of how you really spend time. 

Then designate which duties seem like they’d be good ones to delegate and which ones you definitely want to hold onto and do more of (different colored highlighters are great for this). Note anything that’s a holdover from your early days at the company as well as those you’re still doing because you think it makes it easier for everyone else. Also include duties you can do “in your sleep.” (By the way, in your sleep means you should actually be sleeping, another key to leadership success.)

Other things to consider: Are any of your duties taking an inordinate amount of time? Which ones are really important to you? Which duties align with your ultimate goals at this company? Shed anything that anyone else could do, or the ones that someone with a different skill set could complete faster. This is why there are IT and contracts departments, and so forth. There may well be a better person for the job than you.

Step 2: Ask yourself this simple question

Look at your list and focus on the stuff you’ve noted as prime delegation fodder. Ask yourself: Why haven’t you delegated this already? You may come up with several different answers, some of which you mentioned in your letter—fear of irritating your coworkers, fear of making your company think they were wrong in promoting you. 

Most people who don’t delegate are often afraid of giving up control. We know we can do the tasks so we just do. It takes too long to explain it to someone else. What if they don’t do it right? Do we become irrelevant if we stop doing the thing we’ve always done? It’s really hard to say no, or to change office dynamics or expectations. 

One 2010 study revealed two other psychological reasons why people have trouble delegating: 1) the self-enhancement effect, i.e., people think the work is better the more they’ve been involved with its production, and 2) the faith in supervision effect, i.e., people think work that’s been done under supervisor control is better than work that’s not been supervised. Both of these beliefs (along with the wrong thinking I’ve mentioned above) will lead you astray. 

If you think you’re prone to them, fight back against this tendency. You’ve got to trust yourself—and your coworkers—in order to delegate. And, as fate would have it, delegating actually builds that trust. 

Step 3: Talk to your manager 

If you’ve never addressed this at all (and it sounds like you haven’t), it’s high time you have a “state of the business union.” Hopefully you will get an assist from your boss on delegating tasks according to some of your coworkers’ skills and interests, as well as the needs and balance of the entire team. 

Explain what you’re up against workwise, and that you’re still doing work from the early days even though you’ve moved into a new managerial role yourself. Tell them that you’re eager to really pour yourself into your new duties, and that you’d like suggestions on how best to proceed with delegating. 

Are there people on the team who might be ready for the work you’re looking to hand off? Who’s best suited for which job? Which of your duties does your manager want you to keep, and why? 

Step 4: Create guidelines for the duties you’re delegating

Go back to your master list, which I hope you’ve adapted based on the conversation with your manager. Look at what you’ve decided to delegate, and to whom. Write a thorough, clear description of how to do each of those duties. Include how long they should take, specific deadlines, any resources or access someone would need to complete them, and so on. 

Basically, if you were to put this description in a bottle and send it to space, would whoever received it have a reasonable chance at following your instructions (assuming the being can read?). 

Then meet in person with the people you’ve chosen as delegates. Explain what you like about the duty, and how you get it done. Talk about how handling these tasks well are part of what led to your promotion. Express how important these tasks are to the team and to the business, and how you and your manager have selected this person specifically because of their interests, skill level, and drive. (Don’t go overboard, but it’s nice to be recognized for what you’re good at and to be told you are trusted to do more.)

If you can demonstrate these tasks in person, go for it. The more someone can learn how to do what you want them to do, the better. You’ll worry less about what happens when you hand over the reins. 

Step 5: Have faith 

Give your designated delegates room to find their own way in a process you’ve gotten so good at that you don’t need to keep doing it. If they don’t do it exactly the way you do, but their results are equally good or better, let them have that win! This is what growth is all about.

Be patient, because not everyone is perfect the first time. That’s what feedback, regular meetings, reviewing, and rejiggering (as needed) is for. You’re not leaving the company; this is part of your becoming a better mentor, manager, and yes, leader. 

Ask for updates to learn how your delegates feel about what they’re doing. Troubleshoot as needed. And enjoy going home before midnight. I hope you sleep like a baby.

Jen Doll is a journalist and the author of the memoir Save the Date: The Occasional Mortifications of a Serial Wedding Guest. Her writing has appeared in the Atlantic, Harper’s Bazaar, the New York Times, and other publications.

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