What Should I Ask My Mentor?

photo by Maria Kostyleva (IG:masha_and_film)

There’s a moment in every mentoring relationship when the mentee sits down, smiles politely, opens their notebook... and draws a total blank.

"What am I supposed to ask you?"

That classic moment where both of you realize: this isn’t a lecture, and it’s definitely not a life coaching session. Exactly for such situations, I've collected the greatest hits of mentoring questions. Some serious, some funny, something for every taste!

🔍 Career Stuff

•  How did you get where you are today?

 (Spoiler: usually a mix of strategy, chaos, and one very kind former boss.)

• What would you do differently?

• Is it normal to feel this lost at this stage?

🧰 Skill-Building

• What should I learn next?

 (Translation: “Please make sense of this overwhelming internet.”)

• How do you actually learn new things while working full-time and trying to drink enough water?

• How do I sound smart in meetings without just repeating the last thing someone else said in a deeper voice?

🧠 Real Talk

• I’m stuck. Can I show you this mess and not get judged?

• How do you silence the voice in your head that says “you have no idea what you’re doing” — especially when it’s right?

• What do you do when your calendar is full, your brain is fried, and your cat is sitting on your laptop?

🛜 Relationships & Networking

• How do I network without sounding like a robot or like I want something?

• How do I bond with coworkers when the only thing we have in common is Jira tickets and mutual burnout?

• What’s the best way to say “That’s incorrect” in a tone that still gets me invited to lunch?

🎯 Goal Setting & Accountability

• What do I do when my 3-month plan becomes a 9-month saga with side quests?

• Is “survive Q3” an acceptable professional goal?

• How do I get back on track when I’ve fallen off the wagon, the wagon ran me over, and now I live under the wagon?

• What’s a goal-setting framework that actually works for humans, not robots, or productivity influencers, or fictional LinkedIn personas?

If you favorite question for 1-to-1 with a mentor is missing, please share it in the comments!

➡️ Chat with my 𝐀𝐈 𝐀𝐬𝐬𝐢𝐬𝐭𝐚𝐧𝐭 to learn more about my mentoring programs. And if this soulless machine doesn’t quite cover what you need, no worries. You can ask it for the link to book a trial mentoring session with me directly 😉