Some time ago, I was promoted to people manager. I wasn’t sure then (and I’m still unsure now) whether I could make the jump from individual contributor. It’s been a couple of years and I’d like to share some of what I’ve learned about delegation.

“If you want something done right, you have to do it yourself”

The first, and hardest, complication of delegation is assurance. I was promoted to the level of a principal individual contributor because of my ability to deliver.

My ability to deliver derives from the incessant voice inside of me that says “you can do better.” This is detrimental in other areas of life, but for task execution, it forces me to relentlessly work at something until the task is complete or I am forced to stop.

I am assured that my work product is sufficient because I am the one producing it.

This assurance is gone when someone else is responsible for delivering my work product. It may, and will likely, not be done to my standards. It may or may not get done on time. It may not even get done at all.

But maybe that’s alright.

After all, it’s possible that I’m too close to a problem to efficiently solve it. Maybe I’m solving the problem at the wrong time and it needs to sit for a while. Maybe the problem is only temporary, and by waiting it will disappear.

Communication Gaps

Beyond the loss of assurance, another hurdle I’ve faced is making sure the person I’m delegating to understands the task as clearly as I do. When I’m in the driver’s seat, I know every nuance of what needs to be done. But passing that knowledge on isn’t always straightforward.If I don’t explain the task well—or if I assume they already get it—there’s a risk of missteps.

The result?

Work that’s incomplete, off-target, or delayed, all because the instructions didn’t click.

The Urge to Micromanage

Then there’s the temptation to hover.

Letting go is tough when you’re used to controlling every detail. I’ve caught myself wanting to check in constantly or dictate exactly how something should be done. It’s not that I don’t trust the team—it’s that I’m wired to ensure perfection.

But this micromanaging can backfire, frustrating the person I’ve delegated to and undermining the whole point of handing off the task in the first place.

Master Delegation

So, how do I manage?

Over time, I’ve found a few strategies that help me delegate while keeping my sanity intact. Here’s what works:

1. Set Clear Expectations and Deadlines

To ease that gnawing loss of assurance, I’m learning to spell out exactly what I need.

What does “done” look like? When does it need to be finished?

By setting specific goals and timelines upfront, I give myself a safety net. I can step back knowing there’s a standard in place, and the person taking on the task has a clear roadmap. It’s not about controlling every move—it’s about aligning our understanding so I can trust the outcome.

In Jira, I try to set up brief OKRs in each task, often just one or two to ensure that whomever works on it can reference those first and take myself out of that loop.

2. Clarify Tasks with Tools and Details

For those communication gaps, I’ve started leaning on more than just a quick verbal handoff. Writing out detailed instructions, sharing examples of what I’m aiming for, and using tools like Jira to map out steps has made a huge difference. It takes extra time upfront, but it saves headaches later. The goal is to leave no room for guesswork—when they know what I mean, they can deliver what I need.

I follow up with bi-weekly checkins over Slack to see how the team is getting along and whether they are blocked anywhere.

3. Trust and Let Go (Within Limits)

To curb my micromanaging tendencies, I’ve had to practice trusting the people I delegate to. This means giving them room to own the task—letting them figure out the “how” as long as they hit the key markers I’ve set.

It’s a balancing act: I’m still there if they need guidance, but I resist the urge to hover. Not only does this free me up, but it also lets them grow, which is the bigger win.

Delivering Today

Delegation isn’t easy—it’s a shift from doing to leading. The loss of assurance, the risk of miscommunication, and the pull to micromanage are real hurdles. But with clear expectations, solid communication, and a dose of trust, it’s possible to overcome them.

I’m still learning, but I’ve seen how stepping back can lead to better results—not just for me, but for the team. Maybe that old saying about doing it yourself isn’t the full story. Sometimes, letting others take the reins is how you get it done right.