The Coffee That Is Still an Interview: Informal Meetings With CEOs and Chairs

“It is just a chat. No need to prepare.”

Senior candidates hear this often. A CEO wants to meet for coffee. A chair suggests a quick catch-up. A board member invites you to lunch before the formal process starts.

It may feel casual. But in senior hiring, informal meetings are often where the real decision is made. The CEO or chair is forming a view of you: whether they like you, trust you and can see you in the role.

Many strong candidates lose roles in these meetings because they treat them as social. This article covers why informal meetings matter, what they assess, how to prepare without looking scripted, questions to ask, mistakes and following up.

Why informal meetings matter more than they seem

In formal interviews, candidates are prepared and careful. In informal meetings, they relax. That is exactly why decision-makers use them.

Informal meetings let a CEO or chair see:

• How you think in an open conversation

• How you treat people, including waiters and assistants

• Whether you listen as well as talk

• Whether you are genuinely interested in the business

• Whether they would enjoy working with you

These impressions often outweigh a strong formal interview.

What they are really assessing

Chemistry. Would they enjoy working with you every week?

Judgement. Do your views on the business make sense?

Curiosity. Do you ask good questions?

Discretion. Do you talk about your current employer appropriately?

Fit. Would you fit the culture, the board and the team?

Commitment. Do you really want this role?

Preparing without looking scripted

Prepare as you would for a formal interview, but present it conversationally.

• Research the business. Read the annual report, recent news and the CEO’s or chair’s public comments.

• Know your story. Have your key achievements ready, but share them naturally.

• Prepare questions. Three or four thoughtful ones.

• Know your reason. Be clear on why this role interests you.

Do not bring a presentation or folder unless asked. Keep it relaxed but informed.

Questions to ask

Good questions show interest and judgement:

• What do you see as the biggest opportunity for the business in the next few years?

• What would success look like in this role after the first year?

• How would you describe the culture of the leadership team?

• What made you decide to look for someone now?

• What do you enjoy most about working here?

Listen carefully to the answers. Follow up naturally.

Mistakes that cost people the role

• Treating it as social only. Talking about holidays and sport for an hour with no substance.

• Talking too much. Not letting the CEO or chair speak.

• Being negative about your current employer. It raises concerns about discretion.

• Sharing confidential information. About your current business or clients.

• Seeming unsure about the role. Senior decision-makers want people who want the job.

• Poor manners. How you treat others matters.

• Drinking too much at lunch or dinner. Keep it light.

Talking about your current role

You will likely be asked about your current role and why you are open to a move. Be positive and discreet.

“I have enjoyed the role and we have achieved a lot, including the refinancing and the system change. I am now looking for a bigger challenge, ideally in a growing business where I can be more involved in strategy.”

Avoid criticism and confidential details. See why do you want this role.

When it happens before the formal process

Sometimes a CEO or chair meets you before a role is formally advertised. This is a chance to shape the role and become the preferred candidate. Show genuine interest and good ideas. Be clear that you would welcome a formal conversation.

Following up

Send a short thank-you note within a day. Mention one point from the conversation that you found interesting. Keep it brief and professional.

See thank-you emails after an executive interview.

How search consultants see informal meetings

When I was in executive search, I often heard clients say, “I liked them in the interview, but the coffee did not go well.” Or the reverse. Informal meetings regularly changed the outcome. I always told candidates: treat every meeting as part of the interview, however casual it feels.

Video calls count too

Informal meetings increasingly happen by video. The same rules apply. Check your background, sound and lighting. Look at the camera. Keep the conversation natural.

Your profile

Your LinkedIn profile is often checked before an informal meeting. Make sure it is current and matches your resume. See LinkedIn for executives.

A quick self-check

Before your next informal meeting, write down three questions you want to ask and one sentence on why the role interests you. That is enough preparation to make the meeting count.

What to wear and where to sit

Dress one step below a formal interview, unless you know the person well. For a coffee with a chair, smart business without a tie is usually right. When in doubt, ask the search consultant.

Arrive a few minutes early. If you choose the spot, pick somewhere quiet enough to talk without raising your voice. Offer to pay, but do not argue if they insist.

When the search consultant is in the room

Sometimes the search consultant joins the meeting. Treat them as part of the conversation, not a spectator. Brief them beforehand on what you want to get across, and ask them afterwards how it went. Their read on the room is often more honest than the CEO’s polite goodbye.

Signs it went well

You will rarely get a clear answer at the end. But there are signals:

• The meeting ran longer than planned

• They talked about the future as if you were part of it

• They mentioned other people they want you to meet

• They shared things they would not tell an outsider

If you saw two or more of these, the meeting probably helped your case.

Signs it did not

• They kept checking the time

• The conversation stayed on small talk

• They did not ask about your experience or ideas

If that happens, ask the search consultant for feedback. Sometimes the timing was simply wrong. Sometimes there is something you can fix before the next meeting.

A second informal meeting

If you are invited back for another coffee or a dinner with other directors, the stakes are higher, not lower. The decision-maker wants others to see what they saw. Prepare again, with fresh questions based on what you learnt the first time.

Keeping confidential searches confidential

Informal meetings often happen in public places. Think about who might see you. If you are a sitting CFO meeting a competitor’s chair, a busy cafe near either office is a poor choice. Suggest a quieter venue, a private room or a video call.

Keep your phone face down and your notes out of sight. Do not mention the meeting to colleagues, and do not post anything that hints at it. Discretion in how you meet is part of what they are judging.

Your next step

Treat your next coffee or lunch with a CEO or chair as an interview. Prepare your story, your questions and your reason for wanting the role.

If you want help preparing for senior conversations, my executive interview preparation helps senior leaders prepare for formal and informal meetings.

If you have a meeting coming up, book a complimentary Clarity Session.