The offer feels right on paper. Before you sign, these five conversations will tell you whether the role is the right fit or the wrong one.
One of our most successful placements — a CTO who has since led three exits — told us the single most useful question she ever asked in an interview: “Walk me through the last time this board disagreed on a major technical decision. What happened?” The answer told her everything she needed about how decisions actually got made.
Here are five questions we coach every senior technical candidate to ask before accepting a mandate. The pattern is consistent: the better the role, the better the answers tend to be.
This isn’t about grilling the company. It’s about discovering whether the match will hold 12, 24, 36 months in.

