Which conversation do you want to get right?

Job & internship interviews

Candidates and students preparing for an interview

Before

• Job description
• Your resume or LinkedIn PDF
• Questions you're dreading

During

Question heard: “Tell me about a time a project went wrong.”

Say: “The CRM migration: what slipped, what you changed, 30% faster after.”

Salary & deal negotiation

Anyone negotiating an offer, a raise or a contract

Before

• Your target and walk-away
• Your leverage
• Pressure you expect

During

Pressure point: “Our budget for this role is fixed at 65.”

Try: “What flexibility is there on bonus, start date or remote days?”

Mentoring sessions

Mentors in alumni, accelerator and company programs

Before

• Their goals
• Notes from last time
• Topics to watch

During

Moment to listen: “I'm not sure I'm good enough for product.”

Ask: “What evidence do you have that you'd do well?”

Account management

Account managers and CSMs running renewals, QBRs and expansions

Before

• Customer brief
• Goal for the call
• Risks you expect

During

Concern heard: “Budget's tight this year.”

Try: “What would make the renewal easier to approve?”

Sales discovery & demos

Sales reps and founders running discovery calls and demos

Before

• What you know about the prospect
• Win condition for the call
• Objections you expect

During

Objection heard: “It works fine for now.”

Try: “What would have to break for you to look at something new?”

Client discovery

Consultants, agencies and freelancers scoping projects

Before

• The brief or RFP
• What you need to leave with
• Risks you expect

During

Concern heard: “Maybe we add the events module too.”

Try: “Is that part of phase one, or a later phase?”

Support escalations

Support leads and CSMs handling escalated customers

Before

• Ticket summary
• The resolution you can offer
• Risks you expect

During

Frustration heard: “This is the second time this quarter.”

Try: “What would it take to rebuild your confidence this month?”

Managing a team

Team leads running 1:1s, feedback and team meetings

Before

• Goals for them or the team
• What's going on with them
• Topics to watch

During

Signal heard: “Just a lot on my plate right now.”

Try: “What could we take off your plate this week?”

Hiring interviews

Recruiters and hiring managers interviewing candidates

Before

• Candidate CV
• Job description
• What you're assessing

During

Probe deeper: “We kind of managed it as a team.”

Ask: “What was your part, specifically?”

Investor pitches

Founders pitching angels and VCs

Before

• Pitch deck
• Key numbers
• The investor's thesis

During

Tough question: “How big can this really get?”

Say: “12k universities in EU+US, €1.4B; start with the 900 top schools.”

User research interviews

Product managers, designers and researchers talking to users

Before

• Research goal
• Hypotheses
• Discussion guide

During

Dig deeper: “I just hacked it together in a spreadsheet.”

Ask: “What made you reach for a spreadsheet?”