The questions to ask before you say yes to a new role

By the time an offer arrives, most people have already decided. The interviews went well, the title is a step up, and saying yes feels like the natural end of the story. That's exactly when it's worth slowing down.

These are the questions I ask clients to work through before they accept — whether it's an external offer or an internal move. None of them are about salary. Compensation matters, but it's the one thing everyone already thinks about.

1. Why is this role open?

Someone left, someone was promoted, or the role is new. Each answer means something different. A role that's turned over twice in two years is a different bet than a backfill for someone who was promoted internally. Ask directly: 'What happened to the person who had this job before?'

2. What does success look like at 90 days — and at a year?

If your future manager can't answer this clearly, that's information. Vague expectations now become vague performance reviews later. A good answer sounds specific: 'By day 90, you'll own the weekly business review. By the end of the year, the team should be running it without me.'

3. Who actually makes decisions here?

Every company has an org chart and a real power map, and they're rarely the same. Ask your future peers, not just your manager: 'When something important needs a decision, how does it actually get made?' You're listening for whether decisions happen in rooms you'll be in.

4. What's the team's track record on promoting from within?

You're not just taking a job; you're buying a trajectory. Ask: 'Who on this team has been promoted in the last two years, and what did their path look like?' If the answer is silence, the growth story in the interview was marketing.

5. What would make someone fail in this role?

This is the question almost nobody asks, and it's the most revealing. It surfaces the unwritten rules — the political landmines, the founder's pet peeves, the 'we say we value X but we actually reward Y.' Ask it of your manager and, if you can, of someone who'd be your peer.

6. What will I stop doing?

Every yes is a no to something else. Before you accept, write down what you're giving up: the manager who advocates for you, the domain expertise you've built, the flexibility, the commute, the team you like. Then decide — with your eyes open — that the trade is worth it.

The gut check

After the analysis, one more test: imagine it's six months in and the job is exactly what you now know it to be — the real version, not the interview version. Are you glad you took it? If the answer is a flinch, the spreadsheet won't save you.

Good decisions aren't about finding the perfect role. They're about knowing what you're actually signing up for — and choosing it anyway.