Recruitment Sales & Discovery Questions

Warm the conversation up and set a collaborative tone before you start qualifying.

• Thanks for taking the time — how’s your week going?
• What made you open to a conversation with us?
• Before we dive in — is there anything specific you wanted to get out of this call?
• How much do you already know about us and what we do?

Understand where they are now and what’s pushing them to look. Push and pull factors drive every decision later.

• Walk me through your current role — what does a typical week look like?
• What are the pain points at your current employer?
• What’s changed recently that’s made you open to moving?
• If you could change one thing about your current job, what would it be?
• What do you like about where you are now? What would you want to keep in your next role?
• Is there anything that could realistically fix the situation where you are?
• How long have you been thinking about making a move?

Get to the real reasons they’d move — not the polite ones.

• What are you optimizing for in your next role?
• What’s most important to you in your next move — and what’s second?
• What would your ideal role look like day to day?
• What kind of problems do you want to be working on?
• What kind of team environment do you thrive in?
• What would make you turn down an offer, even if the money was right?
• Rank these for me: compensation, growth, mission, flexibility, team, tech.
• Are there any other factors important to you that we haven’t covered?

Check alignment between where they want to go and what you can offer.

• Where do you want to be in 2–3 years?
• What does progression look like for you — management, deep IC, founding your own thing?
• What skills do you want to develop next?
• What’s the most ambitious thing you want to achieve in your career?
• Is there anything about an early-stage environment that worries you?
• What would need to be true about a company for you to commit for the long term?

Know exactly what you’re competing against — processes, offers and timelines.

• How active is your search right now — passive, or interviewing elsewhere?
• What other companies or processes are you in at the moment?
• What stage are those at — first calls, finals, offers?
• Are you holding any offers right now?
• How do those opportunities compare to this one?
• If you received two offers at the same time, how would you decide between them?
• Have you applied anywhere else that hasn’t come back to you yet?
• Is there a dream company you’re waiting on?

Pin down when they’ll decide and who’s involved in the decision.

• What’s your timeline for making a decision?
• What’s your notice period?
• When would you ideally want to start a new role?
• What’s your process for making a decision like this? What steps do you go through?
• Who else is involved in this decision — partner, family, anyone else?
• Are the important people in your life onboard with a potential move?
• Would relocation, remote or hybrid working affect your decision?
• Is there anything that could delay or accelerate your timeline?

Surface expectations early and honestly — no surprises at offer stage.

• What are your compensation expectations?
• What are you earning currently — base, bonus and equity?
• How did you arrive at that number?
• Is there any flexibility on that figure for the right opportunity?
• How do you weigh base salary versus equity?
• What does equity mean to you — how do you think about its value?
• Are there benefits that really matter to you — healthcare, pension, parental leave?
• Is there a number below which you simply wouldn’t move?
• Are there any unvested shares, bonuses or sign-on amounts you’d be walking away from?

Confirm they genuinely understand and want this role — not just any new job.

• Based on what you know so far, how do you see yourself contributing here?
• What excites you most about this role specifically?
• What concerns or hesitations do you have about the role or the company?
• Do you fully understand the responsibilities, growth plans and expectations?
• Is there anything about the role that’s unclear or that you’d like more detail on?
• Who else on the team would you like to meet before making a decision?
• What information could I give you that would help you feel confident?

Discovery doesn’t stop after the first call — keep probing throughout the process.

• What’s your biggest hesitation about this opportunity?
• Has anything changed in your situation since we last spoke?
• Is there anything worrying you that you haven’t mentioned yet?
• What would stop you from accepting an offer from us?
• Is there anything we could be flexible on that would address that concern?
• What questions have you been asked elsewhere that I haven’t asked you?
• If you were to decline, what do you think the most likely reason would be?

Test commitment before you ever put an offer on the table.

• Suppose we could meet the conditions we’ve discussed — would you accept?
• On a scale of 1–10, how likely are you to accept if we offer what we’ve discussed?
• What would get you to a 10?
• If we made you an offer this week, what would you do?
• Would you be prepared to drop your other processes if we met these terms?
• Can you give me your word that if we meet the conditions discussed, you’ll resign and start on the agreed date?
• Is your decision contingent on anything happening elsewhere?
• What’s left to figure out before you’d be ready to say yes?

Confirm the exact terms and get the verbal yes before the written offer goes out.

• Before we put this in writing — base, bonus and equity as discussed — do you accept?
• Is there anything in this offer you’d want changed?
• Are we competitive against the other options you’re considering?
• When can you verbally commit? I’ll have the written offer to you within 24 hours.
• Are you waiting on any other offer before deciding?
• What start date works for you?
• Is there anyone you need to speak to before signing?

Most counter-offers arrive between resignation and start date. Prepare them now.

• When you hand in your notice, do you expect a counter-offer?
• What’s the norm at your company — do they typically counter?
• What would you do if they matched or beat our offer?
• Is there really anything your current employer could offer that would solve the reasons you’re leaving?
• Have you been counter-offered before? What happened?
• How will you handle the resignation conversation? Have you thought about what you’ll say?
• What will you tell them if they ask what it would take to keep you?

The deal isn’t done at signature — keep selling until day one.

• How are you feeling about everything now it’s signed?
• How did the resignation go? How did they react?
• Would you like to meet the team socially before you start — dinner, drinks, an event?
• Is there anything you’d like to read or learn before day one?
• Any concerns creeping in now it’s real?
• What can we do to make your first week great?