What to Ask a Startup Mentor in Your First Call

A 30-minute mentor call has a meta-trap: you will spend 20 minutes explaining your business and leave with 10 minutes of advice. Worse, those 10 minutes will be generic because the mentor did not have time to understand the specifics.

The fix is structural. You send a short brief in advance, walk in with three pre-chosen questions, and use the hour like an interview you are running.

Send a one-page brief before the call

Paste this into the booking note or DM:

• *One sentence:* what we do and who we serve.
• *One sentence:* where we are — revenue, users, team size, runway.
• *The decision we are weighing.* Two sentences.
• *The 2–3 options we have considered* and what we think the trade-off is.
• *Three questions I want to ask.* Ordered by priority.

Mentors who get this brief walk into the call sharper. The call starts at minute 20 instead of minute 0.

Good questions to ask

• *"What would you do differently if you were starting this company today?"* Pulls the mentor into reflection instead of advice-giving mode.
• *"Who is the person I most need to meet in the next 90 days, and why?"* Networking ask, disguised as a substance question.
• *"What signal would tell you this isn't working?"* Pre-empts sunk-cost bias in your own decision-making.
• *"If you had to bet on one of these three options, which and why?"* Forces a specific opinion instead of "it depends".
• *"What is the most common mistake founders at our stage make that they can't see?"* Asks for something they would not have volunteered.

Questions to skip

• *"What do you think of my idea?"* — too vague, will produce polite platitudes.
• *"How did you get started?"* — kind, but it is their story, not your strategy.
• *"What are the top 3 things every founder should know?"* — generic answer, guaranteed.
• Anything you could have Googled.

In the last 5 minutes

1. Recap what you heard in one paragraph. "If I summarise what you just said — X, Y, Z." Confirm or correct.
2. Ask for one specific action before the next call: an intro, a read, a number to hit.
3. Ask whether to follow up after. If yes, ask when.

After the call

Send a thank-you message the next day with what you decided. Mentors who hear back become real advisors. Mentors who hear nothing forget you.