Their Career Does Not Have to Look Like Yours

The quiet mistake most new mentors make is assuming the person in front of them wants your life. It is an easy mistake, because your path is the one you understand best. You know where the shortcuts were. You know which turn cost you two years. Of course you want to hand that map over. But it is a map of your terrain, not theirs. I have watched good mentors accidentally push someone toward management because management worked for them, when the person across the table lit up talking about deep technical work and went flat every time the org chart came up. I have also watched the reverse. A mentor who loved staying hands on, telling someone who was clearly born to run a team that leadership is a trap. Both were generous. Both were giving real, hard won advice. Both were answering a question nobody asked. So ask first, and ask properly. Not what do you want to be in five years, which almost nobody can answer honestly. Ask what part of last month did you enjoy most. Ask which meeting you would keep if you could delete all the others. Ask what you would do on a Tuesday with nothing on the calendar. The answers tell you far more than a stated ambition, because ambitions are usually borrowed and preferences rarely are. Then hold your own story loosely. Tell it as one data point, not as the route. I did this and it worked for me, for these specific reasons, and here is why it might not apply to you. That last clause is the whole job. Your value is not that you know where they should go. You almost never do. Your value is that you have seen more of the landscape than they have, so you can describe what is over each hill and let them choose the climb. The measure of good mentoring is not that they end up like you. It is that they end up more like themselves, faster than they would have alone. – Asael Shinder