The first session goes like this more often than anybody admits. Somebody is assigned to you, or asks you directly, and you turn up with a plan. You are going to teach them testing, because testing is the thing you wish somebody had taught you at their age. Six weeks later you have covered a lot of ground, they are politely disengaging, and you cannot work out what went wrong.
They arrived with a different question. They usually do.
Ask it out loud in the first twenty minutes. What do you want to be able to do in six months that you cannot do now. Then wait, because the first answer is the tidy one they think you want to hear, and the real one turns up about forty seconds later, once they have decided you actually meant it.
What comes out is almost never a technology. It is that their pull requests sit for four days and they have no idea how to chase them without being a nuisance. It is that they seize up in stand up. It is that they cannot tell whether they are behind, because everyone around them sounds fluent. It is that they want to know whether this company is a dead end. Those are smaller and more awkward than a curriculum, and they are what is actually blocking the person in front of you.
Write the answer down where you can both see it. A shared note, three lines, in their words rather than your summary of them. Read it back at the start of every session, because it is the only reliable defence against the hour drifting into whatever you happen to find interesting that week.
Revisit it properly every couple of months. Goals go stale quickly early in a career. The person who wanted to stop seizing up in stand up in March genuinely wants to learn system design by July, and if you are still working from March you are teaching somebody who no longer exists.
And take the goal seriously even when it sounds too small to build a relationship around. Helping somebody get their code reviewed inside a day is not beneath you. It unblocks every other thing they will try to learn this year, and it is why they will still be talking to you in five.
– Asael Shinder
