Ah, delegation. You’d think telling other people what to do would come naturally. Don’t we all want to be the boss?

But, it turns out the majority of us want to make others happy.

In Gretchen Rubin’s book, The Four Tendencies: The Indispensable Personality Profiles That Reveal How to Make Your Life Better (and Other People’s Lives Better, Too), she describes what motivates people. According to her, the majority of us are Obligers — people who desire to meet outside expectations and resist inner ones. If you’re a classic Obliger like me, we find it easier to focus on making others happy over prioritizing our own happiness. For instance, I won’t just go for a run; I need an appointment to exercise – like booking a class — one where I would disappoint others and therefore, by default, myself if I didn’t attend. You can take Gretchen Rubin’s quiz here to see what type you are.

Putting aside whether you buy into the Four Tendencies, I do like how this connected to my experience and what I also see in others I mentor. I resisted delegation until I understood it truly benefited others. And then it was magic.

“Delegate more”

So, now I was a manager, and I was enjoying nurturing people’s growth and watching their careers flourish. When it came to sheer workload though, I was still doing a lot of day-to-day tasks and projects myself.

“Alana needs to set realistic expectations for what she can do…She then needs to empower others to replace her. Hiring…may be necessary to allow her to delegate more. In addition, Alana should identify…issues that need to be addressed that she does not have the bandwidth to cover and ask for help.”

During this time I was receiving seemingly contradictory feedback like I should “spend more time with each person on the…team,” but that team was rapidly growing into hundreds of employees at the time. My manager helpfully said, “this is not possible and she has to help [the feedback givers] see that.”

Deep sigh

Even now this feedback makes me rub my forehead. It was totally right, but it was incredibly difficult to change course. Why do I have trouble giving work to other people?

• I legitimately enjoyed some of the work. Mostly because I was good at those things, and I was comfortable and happy doing them. I wanted to stay in my comfort zone.
• Some of the work I didn’t enjoy. It was tedious, grunt work, but if I didn’t want to do it then why would I give it to anyone else?
• I didn’t totally trust others to do it ‘right’. I trusted my team with lots of things, but I was holding on to tasks and projects that I thought were sensitive. But the list was growing…
• And people still wanted more of me. As an Obliger, I wanted to deliver so badly. Plus I felt popular! People liked me and wanted to spend time with me. It was nice to think I was needed so much.

In the end I was missing out on higher level objectives that I should have been focusing on whilst holding on to the old work I’d already mastered. In doing so, I was actually preventing my team from taking on tasks that would challenge them. I was also obscuring the additional hiring my team needed by working overtime and doing it all. And finally I needed to start teaching people the hard truth about operating at scale; you get less 1:1 time.

Let’s go to the whiteboard

I created an exercise to help me move forward. Over the years I’ve road tested it with many team members who hit a similar “I’ve got too much work and don’t know what to do” wall. I happened to design the one below, but there are similar models out there. While you can create this in a spreadsheet or a doc, I often had people use the whiteboard while we talked.

1. List everything you’re doing. I focused on work tasks with my team members, but you could do this for your personal life as well. Important note – don’t stop when you think you hit 40 hours of work. Write it down – list it ALL: the projects you run, the meetings you have, the email clean-up time, everything.
2. Then run through and estimate how much time each item takes. This isn’t about being perfect, just guesstimate. Again, don’t stop when you hit the hypothetical 40 hours.
3. Then draw a face. Run through each item again and put either a smiling face, a frowning face, or that unimpressed, straight-line face (you can also use a plus sign, minus sign, and dash if you want to be less cute). The smiling face means you are enjoying and learning from this work. The frowning face means you are not. And the so-so face usually means that you think it’s valuable, but you don’t love it.

Sometimes I make this more complicated. I break out the way I feel about the work (do I love it?) from the value the company receives from the work (is the impact high?). It depends on the individual person’s situation. For instance, someone up for a promotion may want to stick with some highly valued work even if they don’t love it.

Then we discuss

In my case, I saw that I had a lot of work that was valued, but I didn’t love it AND I wasn’t learning from it. WHAT A PERFECT CASE FOR DELEGATION. And that got me over several humps at once.

• I could keep the work that I loved doing and that I was learning from.
• I could delegate what would help others with their careers. They could learn, and the work would be valued. This also obliged me to delegate the work; not delegating was now tantamount to hurting someone by withholding a chance to grow.
• Where the work wasn’t valued, why was anyone doing it? In some cases we would need to do it for a short period of time while we worked on a long-term solution, but it begged for solutions where no one had to manually answer that email or approve that contract.
• And I added projects where needed. In my case, I focused on a new area of strategic thinking (a topic coming up soon!) — how would I scale myself better so people didn’t feel like they needed ‘me’ all the time?

The other benefit of this exercise is that we can look at the time tasks take. We can look at total hours to make sure they’re doable. Are we well balanced between stretch, learning areas and things we can comfortably execute? And I can suggest that an employee delegate or mentor someone else on areas they are no longer learning from. I can tell them — “I know you think it’s grunt work, but it’s new for someone else and will help their growth.” And I know this from experience.

(A friend read this and reminded me about the “Give Away Legos” article — this is a good read, too!)

Now delegate

You’ll still have trust issues, so start small. Take a project with easily defined steps. Pick a team member you think will learn and benefit from the experience and has the basic skills necessary. Share what you want them to do and ask them to define milestones to check in. Step back. And evaluate.

In my experience, people often do better at the project than you would have expected. They had more time and they wanted to impress. Will you have a clunker occasionally? Someone who doesn’t do well? Of course. But don’t let them ruin delegation for you. Keep testing and building up slowly to bigger and bigger tasks.

The Forcing Function

OK, this article is already too long so let me cut to the chase. All of this really helped me, but you know what REALLY HELPED?

I got married in 2006, and I took a month-long honeymoon. Since I was going to be out of the office for so long, I delegated my entire job to my team for the very first time. When I got back, I didn’t take all the work back. I didn’t take the majority back. And everyone did fine.

“I have also seen Alana take the approach of delegating tasks more and more to her direct reports and overseeing projects now. I applaud this approach, and am certainly hearing my teammates comment about the benefits of their additional responsibilities and the added directive control they have over their projects.”

It took me more than 2 years to reach that level of trust, building up through delegating more and more over time.

I now speak of “delegation” in hushed tones, similar to how I describe the miracle of when I got my house professionally cleaned for the first time. Once you go there, you never go back.

Note: I don’t provide names or other identifiable information of who gave/provided me feedback. I also omit any confidential or sensitive information about specific work or people. I share quotations so you can experience the feedback as I did, but those examples are carefully curated. The opinions stated are my own, not those of my company.

This piece is selected from an ongoing series, chronicling my 17 years at Google and the performance feedback that has helped to shape my career. People often wonder what has motivated me to stay so long at one company. I usually tell them it’s the people and career opportunities that Google affords; it’s also the ability to level up my personal growth. I consistently ask myself: what have I learned along the way and how am I continuing to improve? As you may know, we love data at Google. In this vein, I dug back into past performance reviews and cataloged the feedback I’ve received. This has been a humbling journey, but also one where I can appreciate just how much I’ve grown over the years and help others with feedback they may be receiving today.