Most mentoring goes wrong in the first five minutes, and not because anybody said anything unkind.
Someone brings you a problem. You hear the problem. You start solving the problem. Twenty minutes later you have handed over a clean answer and they are thanking you, and you both leave the call feeling fine about it. Except they did not come for an answer. They came to hear their own reasoning out loud and find the hole in it, and you took the wheel before they finished the second sentence.
Or the reverse. They needed a straight answer, quickly, because a release goes out this afternoon, and you gave them a thoughtful set of questions to reflect on.
Both of you were trying. You simply never agreed on what the conversation was for.
So ask. Out loud, at the start, every time. Do you want me to help you think, or do you want me to tell you what I would do? Are you after a second opinion or a decision? Do you want me to look at this now, or after you have had another go at it yourself?
It feels almost too blunt to say. It is not. People are relieved to be asked, because most of them already know what they need and had no idea it was allowed to ask for it.
You will notice the answers change over the months, and that is the useful part. Early on people mostly want the answer. Later they want a sanity check. Later still they want you to argue with them properly, because they have made their mind up and want to see whether it survives contact with someone who is not invested in it.
Three things worth adding.
Ask again after a few months. What they needed in week one is not what they need now, and neither of you will announce the change.
Say what you can actually give. If you have fifteen minutes, offer fifteen minutes. A short honest slot beats a vague open door nobody walks through.
And when they ask for one kind of help, give that kind. If you think they are asking for the wrong thing, say that plainly rather than quietly answering a different question.
Ask first. It costs you one sentence.
– Asael Shinder
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