Prepare Good Questions
Eighteen easy tips to prepare good questions, so your mentor chat is useful and kind.
Prepared questions are respectful. Ask with care.
25 tips that really help
These ideas come from Radical Candor (Kim Scott), Give and Take (Adam Grant), Designing Your Life (Bill Burnett and Dave Evans), and everyday practice. Pick one tip and try it today.
Why prepare
Good questions save time and show respect. They also lead to better answers and a warmer chat.
Prepare.
Start with their story
Ask, how did you get started? People love sharing their path.
Ask it.
Ask about lessons
What helped you most, and what would you do differently? Lessons are gold.
Ask both.
Ask about your situation
Share a short challenge and ask for advice. Real problems bring real answers.
Share one.
Ask about skills to learn
What skills matter most for the next five years? Directions help.
Ask it.
Ask for books and people
Which books or people should I learn from? One answer opens many doors.
Ask it.
Ask what to do next
What would you do next in my place? A clear step helps.
Ask it.
Keep a list of five
Five good questions fit twenty minutes. Order them by importance.
Pick five.
Script: starting
How did you get started in this field? Say it with interest.
Use it.
Script: lessons
What would you do differently if you started today? Say it kindly.
Use it.
Script: next step
What would you do next in my place? Say it warmly.
Use it.
Mistake: asking things you could google
It wastes time, so do your homework.
Do homework.
Mistake: asking too many questions
Too many feel heavy, so choose well.
Choose well.
Mistake: asking only about success
Ask about mistakes too, so learn deeply.
Ask both.
Troubleshoot: when you run out of questions
Ask, what else should I know? It always works.
Use that line.
Troubleshoot: when they speak a lot
Listen and take notes. Learning comes from listening.
Listen.
Drill: write ten questions
Write ten questions and pick the best five.
Write ten.
Ask what they would do in your place
It invites honest guidance and shows trust.
Ask it.
Ask about a time they failed
Failure stories teach a lot and show trust.
Ask it.
Ask how they decide between options
You learn their thinking, not only their answers.
Ask it.
Example: the five-question page
Jo wrote five questions on one page. The meeting flowed and she took notes.
Make a page.
Example: the deep question
What would you tell yourself at my age? led to a lovely talk.
Ask it.
Troubleshoot: when they ask you the same question back
Answer honestly in a few lines and carry on.
Answer briefly.
Ask what they would do differently
This question brings honest lessons, because mistakes teach more than success and mentors often enjoy sharing them.
Ask it.
Ask for one book or person to learn from next
A single recommendation gives you a clear next step and keeps your mentor feeling useful and valued.
Ask it.
Easy things to say
When you are stuck, pick one of these. They work in many networking and career moments.
“How did you get started?”
“What helped you most?”
“What would you do differently?”
“What would you tell your younger self?”
“What should I do next?”
“Thank you for sharing.”
Your first week
One small action a day. Each day is only a little bigger than the last.
Write ten questions
Pick five
Order them
Add a goal
Practise
Ask
Listen
Further reading
- Radical Candor (Kim Scott)
- Give and Take (Adam Grant)
- Designing Your Life (Bill Burnett and Dave Evans)
The tips above are written in our own words and are general guidance. The books are suggestions for further reading.
More lessons in “Finding Mentors and Allies”
Keep going. Small steps every day make a big change.
← Previous: Ask for Twenty MinutesNext: Follow Their Advice and Report Back →
- Why Mentors Matter
- Decide What Help You Want
- Find People You Admire
- Write a Short First Message
- Ask for Twenty Minutes
- Prepare Good Questions
- Follow Their Advice and Report Back
- Give Back to Your Mentor
- Keep the Relationship Warm
- Find Peer Friends at Your Level
- Find a Sponsor Who Speaks for You
- Become a Mentor Yourself
