What To Do When You Don't Trust Your Teammates To Do Your Work For You?

When you become a manager at a small company, you’re usually the sort of person who Gets Things Done.

Chances are, you wear a lot of hats — if you’re a programmer, you do sysadmin and coding and triage of messy production bugs, plus maybe you also answer to the founders, and to sales. If you’re a designer, you’re probably expected to do more than just mockups and branding — you sit in on product discussions and you do user testing and you contribute to the formation of process at your company.

Your effectiveness is what makes it difficult for you to trust a new team member! How are you supposed to sit by, when New Hire Susan is likely to mess up the deployment? And how inefficient is New Hire Joe when he delivers a terrible set of mockups to the founders — mockups that you know you’ll be able to finish in an hour?

“It’s much faster to do everything right the first time,” you think, and so you override Susan and Joe and do the thing yourself. And because you are good, and because the startup has way too much work for your small team to do, you’re probably right and your work gets done faster when you do it.

A few months later, Susan and Joe calls it quits. Or they decide they’re not happy with your management style and decide they’d rather report to the founders. Or they start gaining competence, but way too slowly, and you find yourself overworked. “We need more people,” you find yourself telling the founders. “There’s just way too much work, even with Susan and Joe.”

Trusting Your Subordinates

It’s easy to say “oh, you suck because you can’t delegate well.” But this isn’t your fault! I’ve never met a new manager who started out good at delegation. Delegation is weird and strange and it is a skill that you need to develop, just like programming, design, or marketing.

It’s usually worse if you’re good at what you do, and you feel protective of it. You’ve been doing such an effective job up to now — why make everything more inefficient by giving it away?

The truth is that you know the answer to this question: you can’t do everything on your own. Building a startup is an infinite treadmill of work, way more than one person can handle. So you hire a team for you to do more together.

So how do you delegate better? How do you trust your subordinates?

The answer is to adopt a training mindset: when delegating, your job is to teach your subordinate what is expected of them. Training isn’t a separate step, divorced from delegation. Training is a key part of delegating.

Without training, delegating looks like this:

1. You pass a task to a subordinate with a half-assed explanation and a deadline, rushing off to do something else.
2. You don’t check in till the end.
3. You check the feature when your subordinate reports that it is complete, and then find out that your subordinate messed up the task, and you find yourself redoing it for them. Blahhhhhh.

With training, however, delegation now looks like this:

1. You explain the task to your subordinate. You give hands-on guidance, point out resources that they would need to accomplish their tasks, and then tell them you would come back to check in on them in a few hours.
2. You check on your subordinate’s work in regular intervals at the beginning, where it’s easier to course-correct.
3. Each time you correct their approach, you explain why. Explaining why is the feedback that enables them to improve.
4. Once you’re sure your subordinate is on the right path, you check in less often.
5. At completion of the task, you check one last time, giving feedback on what went well and what can be made better.
6. If you find that the task needs significant reworking at completion, no biggie! You ask them to redo the task. But if you’ve been checking regularly at the beginning (see step 2!) this shouldn’t happen that often.

This process of delegation immediately implies two things. The first thing is that you should delegate items with lower importance to newer hires. This gives you some buffer time for their learning — which includes course corrections and guidance. Remember: the gift at the end of this process is a more competent subordinate, one who is able to contribute to your work!

The second implication is that you should never jump in to finish a task for a subordinate! This robs them of their training, and eventually teaches them to rely on your intervention. You want to be a coach, not a micromanager.

When you see delegation as training, however, it becomes easier for you to let go of tasks. Why? Well, because if you train as part of your delegation, you can be sure that your subordinate is producing work that you find acceptable! The reward is two-fold: your subordinate grows under your management, and you get to do less of the work that you’ve passed on to them.

This allows you to have a much larger impact than if you were working on your own. It also means that your subordinate will feel happier, as they are growing under your care.

It turns out trusting subordinates isn’t as difficult as it seems. Once you see the process of delegation as an opportunity for training, you’ll quickly learn to find joy in helping other people get better — which in turn helps you.