The message comes late on a Sunday. Two offers, both good, both expiring this week. A larger company with a calmer pace and a better salary. A small team building something they find exciting, for less money and more risk. Then the line that matters. Honestly, just tell me which one you would take.
It is a flattering question, and the honest answer is that you should not answer it.
Not because you have no opinion. You probably have a strong one within a minute. But your opinion is built from your life, your money, your appetite for risk and your memory of a startup that went badly in 2016. Their decision has to be built from theirs. If you choose, and it goes wrong, they lose a year and you lose their trust. If it goes well, they have learned to bring big decisions to someone else.
So help them choose, which is slower and more useful.
Start by asking what they want the next two years to give them. Not the next job, the next two years. Money for a deposit on a flat. A manager who will actually teach them. A product they can show people. Write the answers down in their words, then rank them together. Most people discover that one item is far heavier than the rest, and that the two offers look different once it is named.
Then ask the regret question. Imagine it is a year from now and you chose the startup. What went wrong? Now the other one. The fear that comes out more vividly is usually the one that matters.
Point out what they do not know yet, and how to find it out by Thursday. Who would they work with day to day? What is the startup's funding runway? Have they spoken to anybody on either team who is not doing the hiring?
If you still want to share your own view, label it clearly. Here is what I would weigh, and here is why my situation is different from yours. One opinion, offered last, after their reasoning is already on paper.
Then let them decide, and back them fully either way. Your job was never to pick the right offer. It was to make sure the choice was really theirs.
– Asael Shinder
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