Why Leaders Who Can Properly Delegate Will Avoid This Suffocating Business Trap

I know my company better than anyone. That makes sense since I founded it roughly a decade ago to provide a free fundraising platform for K-12 school groups . But it doesn't mean I do everything there myself.

There's only so much I can do in a day — and more importantly, there are many capable people I've hired who will grow if given the right opportunities. Knowing when to delegate saves me from being too thin and helps my team develop valuable skills, making the organization stronger.

The founder's trap can trip up great organizations and leaders

When I worked as a team lead at Weebly and Square (now Block), I often told new engineering managers I hired that their goal was to do nothing in some ways. Think of a doctor in a hospital — if everything is running perfectly and nobody's hurt, then in theory, there's nothing for them to do.

Imagine the opposite: a doctor who constantly needed to book appointments, sterilize instruments and prepare exam rooms. Imagine a doctor who's been doing that for six hours suddenly having to perform surgery. Would you want them operating on you?

That's an example of the founder's trap . Leaders feel like they have to do everything and eventually become so burnt out that they lose the ability to lead.

Delegating helps leads focus on priority tasks and empowers other team members to be proactive . But every time a lead schedules a meeting, creates a doc or even starts certain conversations, they take away opportunities from someone else on the team to grow.

After engineering projects, many teams have retrospectives where they ask what went well, what went wrong, and what they could do better. I always recommend that this gets done without the manager's involvement. When a manager is there, the people who have feedback to share may do so without being honest because they're afraid it might put them in a bad light.

To have a true retrospective, you need to be unflinching and honest. This can be difficult when someone who signs your checks is in the room. Conversely, giving your team the power to have conversations and make decisions independently can have incredible benefits as long as you set them up for success.

Related: 5 Delegation Strategies To Help You Flourish With Less Stress

Your team won't grow if you don't learn to delegate properly

I remember a conversation I once had with my team at Square. We were using an expensive monitoring tool at the time to monitor the performance of our software — so expensive that the team decided to use data samples instead of monitoring everything.

When I discovered this, I asked the team why they weren't monitoring everything, and they said it was too expensive. I was upset, but then I realized that it was because I had not delegated the right knowledge to them.

I hadn't given them enough information to decide because I assumed it was above them. In turn, they assumed there were budget constraints because they were afraid of upsetting me.

Once we spent the money to do the monitoring, we actually found numerous bugs we needed to fix. I learned an important lesson that day: empowering your people to make good decisions also means providing them with the knowledge they need to be properly informed.

Related: Should I Tell My Boss About This? This is How to Balance What Your Direct Reports Do (& Don't) Need to Know

The three levels of delegation

Here's a framework I use to delegate effectively. It consists of three levels, each of which corresponds to the size and scope of the task being delegated:

Level 1 is for low-level tasks that are obviously in a person's wheelhouse. For example, if you were hiring someone to wash your car, you'd trust the person doing it to choose their own soap.

If an IC can't make these decisions alone, it's safe to say you have the wrong person in the role.

Level 2 is for decisions that grow the IC's capacity to own strategies or processes. Instead of simply hiring someone to wash your car, you might give them a budget so they could hire their own team to wash and detail it.

As a business leader, you might do this type of task yourself if you don't think an employee is ready yet — but at a certain point, you want to give them the autonomy to make these calls themselves.

Level 3 is when you delegate wholesale, and it's typically for specialized types of work where your authority or experience isn't as relevant. Let's say you're taking your car to a mechanic instead of having it washed.

In this case, you're completely trusting them to tell you what needs to be done, and all you can do is agree or disagree with the cost. As a business leader, you probably do the same thing with your legal or accounting department — people you've chosen carefully for their expertise and trust a great deal.

From delegating to relationship-building

The better your working relationships are, the more confidence you can have in delegating level 2 or 3 tasks. As things become more predictable and familiar, you can afford to let go of the reins to a greater extent.

Can this feel like giving up control? Absolutely. Can it have consequences if team members make different decisions from the ones you'd make? Of course. But the more you practice delegating, the better your sense of when and how to do it will be. Over time, this creates a culture where people feel confident and proactive — and your business will run more smoothly as a result.