ISSUE #111

A two-week absence shows exactly what you're still hanging on to...and identifies things you need to delegate.

You were promoted because you were the one who could fix anything. The outage nobody else could diagnose. The client escalation that needed someone senior and technical on the call. The project that kept slipping until you stepped in.

Years later, you're still that person. The title is bigger and so is the pile. Something lands on your desk that your team should have handled, and you tell yourself it's faster to do it yourself. It would take an hour to explain and twenty minutes to just do it. So you do it again.

That sentence is the most expensive habit in technology leadership. It's true for the twenty minutes. It's false for your career.

The leaders I coach use the same few sentences. It's faster if I do it myself. My team's already overloaded. I don't trust it'll be done right. One of them put it perfectly: the return on investment of training somebody else just wasn't worth it, so they kept doing it themselves. Years later, they were responsible for a pile of work that should never have been theirs in the first place.

I used to say every one of those sentences. I watched my own managers say them, and then I'd wonder why I was burning out.

Here's how the pattern plays out. A leader I'll call Nolan kept getting the same feedback from the executives above him: you want to be a managing director, you can't keep doing that. He'd built his reputation as the guy who gets things done, the one who jumps in and gets into the nitty-gritty. That reputation got him promoted to his current level. It was now the thing holding him back.

The cost doesn't stop with you. People grow against challenges they've faced. If they are not handed different challenges, the leader must make room to do this themselves, which means not doing what they’ve always done. When every hard problem ends up on your desk, your team never meets the difficulty that would grow them, and they adapt to being rescued.

This doesn't fix itself with time. It compounds.

Every year you stay the person who fixes everything, the organization builds more of its daily operation around you. Your team gets a little more used to waiting. Your reputation as the one who handles everything hardens. And your calendar fills with exactly the work that makes you hard to promote, because promoting you would mean somebody else has to cover it, and nobody can.

Meanwhile, the work your next role needs never makes it onto the calendar. The executive relationships. The strategy. The relationship building. The time to think about where the business is going instead of where this week's fire is. You can't build relationships with senior executives while you're doing the work two levels below them.

When I ask clients what a VP spends time on that they don't have time for today, the answers come quickly. Building relationships with other executives. Speaking at conferences. Thinking about strategy as well as delivery. One engineering leader said it straight out: I need to stop doing actual software development work.

Most of them have never written that list down. Without it, they have no reason to let go. Working harder won't create the time either. More effort at the level below only digs the groove deeper.

Here's the lens I use with clients. It's a simple delegation matrix developed by Michael Hyatt that asks two questions about every task you do: do you love it or hate it, and are you good at it or not?

Hate it and not good at it. Delegate it first. It's draining you, and you aren't even doing it well.

Hate it but very good at it. Delegate it next. This is the sneaky one. You can crank it out, so you keep it, and it stops anyone else from learning it.

Love it but not good at it yet. Pause and evaluate. If you have time, it may be worth growing into. If the deadline's tomorrow, get help. It's also a great place to develop someone on your team.

Love it and good at it. Keep it, because it gives you energy.

Now the part most people miss. Judge the boxes against the job you want, not the job you have. Writing code can be love-it-and-great-at-it for a senior engineer, and that's exactly where it belongs. If you're going for VP, it's eating the time you need for the list above.

Three questions before you sort anything:

1. Where are you going, and what are at least two reasons you want to get there?

2. What does that role spend its time on that you don't have time for today?

3. If you took two weeks off and didn't check email, what would break?

Once you know what to hand over, it sounds simple. If it were easy, there'd be a lot more great delegators in corporate America, and in my experience there aren't many.

This is where capable leaders get stuck, even after they've sorted the work.

Start with the mismatch. You think you gave someone a level four task: make the decision and tell me. They think they got a level one: do exactly as I say. So they wait for instructions, and you decide they're dragging their feet. Michael Hyatt, the leadership coach behind the matrix above, has five levels of delegation built for exactly this, and I've used his work with clients for years. Do exactly as I say. Research and report back. Give me options and your recommendation. Make the decision and tell me. Decide and go. Pick one, and say it out loud.

Then there's the handoff itself. I once ran a role play with a technology company I was coaching. The task was simple: book a meeting with a partner and write the agenda. By the end, the person taking the task said they had about a thousand questions. Who's invited? Where do the agenda items come from? How long is the meeting? Even delegating a meeting has a lot of mechanics. That's why the person taking the work should repeat it back: here's what I heard you ask for. Sometimes you've oversimplified the task. Sometimes they've made it much bigger than it is, and they're about to write a long report when all you needed was an email covering three points. A two-minute conversation fixes that. And they need to be able to say no. If they already have 25 things, where does this one sit?

After the handoff, leaders fail in two opposite directions. Some take the work back. The person struggles, the deadline gets close, and you step in and fix it. Now they've learned that if they wait long enough, you'll do it yourself. Others dump it. They throw it over the wall and say good luck. One leader I coached stepped so far back that they lost track of the work entirely. When it didn't get delivered, they were still held accountable. You can hand over the task. You still own the result. The middle is guidance: the check-ins you agreed on, good questions, helping them think it through, while the work stays theirs.

And be ready for this. When you first let go, things usually get worse before they get better. Work takes longer. Mistakes happen. That's the moment most leaders give up and take everything back. Your team will never be ready while you're still doing it. Why would they step up when you keep stepping in?

There's a quieter worry, too, and I hear it often: isn't this handing off the work nobody else wants? If all you ever pass along is the dull work, people notice, and that's a poor look for any leader. Being the leader doesn't mean you have to do all of it either. Balance it. Give people some of the good work as well, the kind that stretches them and gets them seen.

The payoff comes when you start moving people up. When someone handles a level well, move them to the next one. Level one becomes level two. Level three becomes level four. Each time they move up, you get time back, and that time goes straight into the list you wrote earlier: the executive relationships, the strategy, the things your next role needs you to develop. Delegation that never moves anyone up only rearranges the work.

The last obstacle is the one nobody likes to admit. I was once running two groups in a large organization: 15 to 20 people doing strategic technology work, and another 40 to 45 doing more tactical work. I knew the bigger group belonged somewhere else, where they'd be better taken care of. I hung on to it for too long, partly because a bigger team felt like a bigger job. That was my ego talking. When I finally did the reorg, I got pulled into international projects and presented to multiple CEOs. My one regret is that I didn't do it sooner. At a senior level, letting go can mean a whole team.

I recorded a video that walks through all seven steps: where you're going and why, what you have to stop doing, the matrix, the five levels, the handoff conversation, how to stay close without taking the work back, and how to move people up a level and move yourself up with them. It also has the full story of the group I held on to. If you're the person who still fixes everything, watch it this week.

https://www.youtube.com/watch?v=POGGk8GB9ho

Every level you grow in an organization asks you to let go of more, and it never stops. Each piece of work you keep is a piece of the bigger role you aren't doing yet.