Most people don't decide to leave a job because of one bad day. It builds slowly. A few months of feeling slightly out of step, of doing more than you're recognised for, of wondering whether the next step is actually there or just talked about. By the time it becomes a serious conversation, most of the thinking has already happened quietly, in the background.

The trouble is, once someone gets to that point, the questions they ask tend to narrow. What's the salary. What's the title. Is it commutable. All fair questions, but none of them tell you much about whether the move is actually a good one.

I've sat across from enough people, on both sides of a move, to know that the moves which go wrong rarely go wrong because of the money. They go wrong because something fundamental about the role, the team, or the business wasn't properly understood before the offer was accepted. Here's what I'd actually want to know, if I were the one weighing it up.

About the role itself

A job spec describes what the role is meant to be, not what it actually is day to day. Ask what a typical week looks like, not in theory but in practice. Ask how the role has changed since the last person held it, and why they left. Ask what's expected in the first three months, and how that gets measured. If nobody can answer that clearly, that tells you something too.

About who you'd be working for

You're not joining a company, you're joining a manager, a team, and a way of doing things. Ask how decisions actually get made, and by whom. Ask what the manager's own reporting line looks like, and how long they've been in post. A strong team under a manager who's on their way out is a different proposition to one that's settled.

When you started, chances are you had energy, ideas, and motivation. If that drive has faded and hasn’t returned over time, it may be a cue to re-evaluate whether your role still excites or fulfils you.

About your client relationships

If you're an account handler, broker or AE, the relationships you've built haven't happened overnight, they're the result of years of consistent service. That's exactly why they're protected. Most contracts carry a restrictive covenant, typically around 12 months, that prevents you approaching or servicing those clients from a new employer until it expires. This is worth asking about directly: how a prospective employer handles that restricted period, what support looks like while you can't be client-facing with your old book, and how realistic their expectations are once the covenant does lift. Anyone who talks about your book as something you simply bring with you on day one hasn't thought it through properly.

About where it actually leads

Progression gets talked about in most interviews. It's worth pushing past the general statement and asking for a specific example, who was in a similar position two years ago, and where are they now. If nobody can point to a real example, the progression may exist on paper more than in practice.

A note on staying

None of this is an argument for leaving. Quite often, going through these questions properly with a current employer, rather than a prospective one, is what actually resolves things. If the honest answer is that the role, the team and the path forward are all genuinely sound, and it's one specific issue that's causing the frustration, that's usually fixable through a direct conversation rather than a resignation letter.