Hey Reader,

As a leader, how do you determine when to get better at something yourself vs hire someone better than you to do it?

I asked this yesterday on X and got a lot of good responses.

One way you can look at the question is to do a cost evaluation. Will it be cheaper to do the thing yourself or to hire someone? Sometimes it might seem cheaper to do something yourself, but when you factor in the cost of your time, and how much of it you spend learning, it’s often cheaper to hire someone.

But what if it’s something you want to get better at yourself?

I think of it as a formula:

Does this skill represent personal development I want?

If no, hire out. If yes, do it myself and learn.

For example, I have not hired a COO for ConvertKit because I don’t want to just delegate that job to someone. I want to get good at building an operating system for a company.

But with that said, I have to be careful: sometimes the thing I want to get better at isn’t necessarily the thing I should get better at. This is why it’s important to turn to other people and get feedback—especially those with more experience—because they’ll be able to point out blind spots.

While I haven’t hired a COO because it’s something I want to get good at myself, the skill I actually need to get good at is hiring people, delegating the work, and holding them accountable to the outcome.

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Have a great week!

—Nathan