How to Delegate Effectively

Problem

I really would like to touch upon delegation as a manager. I feel very strongly in this area, and I frequently see people doing it in the wrong way. I encountered many pitfalls while switching my mindset to a more delegation type of leadership style and it hurts to see others fail in the same way.

When we hired my first employee at the start-up that I founded, one challenge was assigning work to this person. We were so focused on hiring that we completely forgot that we would have to come up with something for this person to do.

At the time we were literally just hiring to reduce the workload on the core founding team. Our purpose was not especially clear, and none of us had done headcount planning in the area that we were hiring in specifically. At one point, I realized that communicating the right amount of context is actually the key to effective delegation.

Actions taken

When I first hired the new person on my team, I was very idealistic in my delegation approach. Here is a broad problem. You need to solve it. Instead of a soft recommendation on the architecture, I had to let them take the reins. My approach was initially very heavy-handed. Afterward, I made a soft ramp-up plan. I would give them small tasks to test the waters on how to set up those values. Give them problems that you think would be easy for them and observe what quality of work that they produce.

Even in my current company, when I hire an engineer, they come in, and I know that they are capable of so much more. When you work with somebody new, you have to build up to that. Now, when I onboard somebody new, I almost start building out what they’re going to own long-term within the company. What is that technical area of ownership, right? You have to make it explicitly different from the rest of the team, otherwise conflict arises via shared ownership.

Ownership and being aware of what part of the puzzle that you own is a very important function. At one point, while we were trying to raise money, one engineer mentioned that they had investors that we would be able to tap into. We were like, okay, but, as an engineer, that’s probably not the best use of your time. I needed him to continue to ship and to iterate on the product itself. From their position, that would be the best way to keep investors interested in what we were doing. This principle can be difficult to remember, even for co-founders.

Lessons learned

• Some people like the concept of shared ownership, but I almost have to view shared ownership as no ownership at all. If everybody is responsible, then nobody is responsible.
• On the other extreme, some people take a micromanaging approach. This comes in the form of a manager who decides to give their report the maximum amount of context, but not the right support.
• The first few hires in a start-up will always come in and assume that, with the same context as you, they will have the same motivations as you. This may not be true. They could just be looking for an interesting job.
• All people are on training wheels. You have to slowly take them off. You should never assume that they have the same technical, team, or business context. You should learn how to set each different team up for success as a manager.