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I know my company better than anyone. This has made sense since I founded it roughly a decade ago to provide a free fundraising platform K-12 school groups. But that doesn't mean I do everything myself there.
I can only do so much in a day – and more importantly, there are only so many capable people I have hired which will grow if given the right opportunities. Knowing when delegate it saves me from being too lean and helps my team develop valuable skills, making the organization stronger.
The founder trap can hold back great organizations and leaders
When I worked as a team lead at Weebly and Square (now Block), I often told the new engineering managers I hired that their goal was to do nothing in some ways. Think of a doctor in a hospital – if everything goes perfectly and no one is hurt, then in theory, there is nothing to do.
Imagine the opposite: a doctor who constantly needed to book appointments, sterilize instruments and prepare exam rooms. Imagine a doctor who has been doing this for six hours suddenly has to perform an operation. Do you want them to operate on you?
This is an example of founder trap. Leaders feel like they have to do everything and eventually become so burned out that they lose the ability to lead.
Delegation helps leadership focus on priority tasks and empowers other team members proactive. But every time a leader sets a meeting, creates a document, or even starts certain conversations, they take away opportunities for someone else on the team to grow.
After engineering projects, many teams have retrospectives where they ask what went right, what went wrong, and what they could have done better. I always recommend that this be done without the manager's involvement. When a manager is there, people who have feedback to share may do so without being honest because they fear it might put them in a bad light.
To have a true retrospective, you must be steadfast and honest. This can be difficult when someone signing your checks is in the room. Conversely, giving your team the power to have conversations and make decisions independently can have tremendous benefits as long as you set them up for success.
Connected: 5 delegation strategies to help you thrive 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 Shesh. 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 it was because I hadn't delegate appropriate knowledge them.
I hadn't given them enough information to decide because I assumed it was up to them. In turn, they assumed there were budget constraints because they were afraid of upsetting me.
After spending the money to do the monitoring, we actually found numerous errors that we needed to fix. I learned an important lesson that day: empowering your people to make good decisions also means giving them the knowledge they need to be properly informed.
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 cockpit. For example, if you were hiring someone to wash your car, you would 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 increase the IC's capacity to master strategies or processes. Instead of just hiring someone to wash your car, you can give them a budget so they can hire their own team to wash and detail it.
As a business leader, you can do this type of task yourself if you feel an employee isn't ready yet—but at some point, you want to give them the autonomy to make these calls themselves.
Level 3 is when you delegate wholesale and is usually for specialized types of work where your authority or experience is not as important. Let's say you're taking your car to a mechanic instead of getting it washed.
In this case, you completely trust 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 with your legal or accounting department—people you've handpicked for their expertise and trust deeply.
From delegation to relationship building
The better you are labor relations are, the more confident you can be 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. Could there be consequences if team members make different decisions than you would? Of course. But the more you practice delegating, the better your understanding 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 better as a result.
Connected: Why let people fail now so they can succeed later