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How to prepare for a 1-on-1 session

Why preparation is critical

An unprepared session is a coffee chat. Pleasant, but directionless. The expert doesn't know where you specifically need help, so they give general advice. You don't know what to ask, so you waste time on topics that don't matter.

A well-prepared session is a focused investment. The expert understands your specific challenge, and all 60 minutes go toward solving exactly that.

Before the session: what to prepare

1. Write down your specific problem in one line

Not: "I need career advice." Better: "I've been in operations for 5 years but want to move into product management. I have technical experience but have never formally led a product. I don't know if I should try within my company or look outside."

One specific line focuses the entire conversation. Send it to the expert at least a few hours before the session.

2. Make a list of 3 to 5 pointed questions

Not broad questions like "tell me your story." Specific questions like:

• "When did you know you wanted to change roles? What signal told you?"
• "Is it easier to change within a company or outside? What did you do and why?"
• "What skills from your previous role turned out to be surprisingly valuable?"

3. Prepare your situation context

Write half a page: where you are now, what you've tried before, what worked and what didn't. The expert doesn't need your entire life story, but they need to understand your context fast to save session time on general explanations.

4. Have ready where you'll take notes

Not during the session, after. While you're talking, you're distracted. Better: in the last part of the conversation, ask "Can I note down your take on X?" and write while they speak, so you don't lose the real conversation.

During the session: how to conduct it

Start with your context, not a general question

"I've spent 5 years in operations, want to move to PM, I have technical experience but have never formally led a product. Here are my main questions." That way the expert understands exactly where you are before they start advising.

Ask about specific experience, not theory

Not: "What's the best way to move into product management?" Better: "You made the change. What was your first real step? Who did you write to? How did you approach it?"

Specific stories are more useful than generic best practices.

Ask about mistakes, not just wins

"What would you do differently if you knew what you know now?" is the most valuable question in any session. Wins are nice, mistakes are educational.

Note the counterintuitive things

If the expert says something that contradicts what you believed, note it. That's gold. Experts see things non-experts miss.

After the session: how to apply what you learned

Within 24 hours, write 3 concrete actions

Not "be more proactive." Better: "1) Email Maria in the Product team for coffee. 2) Read the book they mentioned on PM. 3) Prepare for the Product Manager interview at the other company."

Assign an owner and deadline to each action

"Email Maria" = me, before Thursday. "Read the book" = me, this weekend. That way it doesn't stay floating.

If something wasn't clear, ask after

The session isn't a test. If you left confused about something, email the expert in the next few days. One pointed question after is much more useful than not asking at all.

Questions by session type

Career change session

• "When exactly did you know it was time to change?"
• "What was your first real step? Who did you contact?"
• "What made the difference in your search?"
• "What would you do differently?"

Starting your own business session

• "When did you decide it was time to leave your job?"
• "How did you validate that the idea had demand before investing time?"
• "What was your first client? How did you get them?"
• "How long before you could live off it?"

Advancing in your current role session

• "What made you a leader in your field?"
• "How did you get to that high-visibility role?"
• "What was the most expensive mistake in your career?"
• "What was the most important skill you had to develop?"

Preparation transforms a pleasant conversation into a perspective shift. It doesn't take much time, but the change in value you extract is exponential.