47 Strategic Questions to Ask Your Mentor: Hit the Ground Running With Some Inspiration

I’ve been doing a lot of user testing lately and one of the most common things I’ve been hearing is, “I’m not sure what sort of strategic questions to ask my mentor!”

This post is being written to answer that question.

Hopefully, it can also offer some inspiration on talking points so that you can get the most value out of your virtual mentorship sessions.

Mentorship is valuable because you can learn from others’ stories and journeys. (see also: how mentors are different from advisors)

Be inquisitive, ask questions, try and fill in the blanks and create mental patterns from the answers you get.

Strategic questions you can ask your growth mentor

1. How do you stay positive and keep trucking when nothing seems to be working?
2. Do you have a morning (or evening) ritual that helps you be more efficient and productive?
3. How do you most effectively learn new things?
4. If you were in my position what would you recommend I do first (and why)?
5. How do you test different PPC channels? All at once and choose the best or one at a time?
6. How do you structure a sales team when you’ve got zero experience doing sales?
7. As a podcast host, how do you balance asking guests questions and putting in your own 2 cents?
8. What does a successful growth marketer’s Google Drive folder hierarchy look like in real life? (how do you organize your stuff)
9. My conversion rate is terrible and I’m not sure why. Can you look at my website and give me some feedback?
10. Is my product’s messaging clear and concise?
11. How do you decide to price your service/product?
12. How can you reposition a brand upstream after years of being a budget-friendly company?
13. How do you prioritize your marketing backlog and decide what to do first?
14. How do you balance being a parent with the stress of being a business owner?
15. I want to quit my 9-5 job and start freelancing, do you have any tips for success?
16. I just launched my new e-commerce website and am new to marketing, where should I start promoting my website to increase sales?
17. How do you design a go-to-market strategy on a super tight budget?
18. How do you build partnerships with big-name companies in complementary industries using cold email?
19. It’s easy to get users to sign up to my SaaS but they’re not reaching that “aha” moment, what would you recommend I do first?
20. I have this business idea I just can’t get out of my mind but I’m scared of failing so never start, how can I get past this mental block?
21.  I have never worked in Growth. I just joined my company’s Growth team as a designer and feel a bit overwhelmed and creatively limited. Any advice?
22. I’ve been running Facebook Ads yet have no sales. I’m stuck here and my budget is running low. Can you take a look at my Facebook business manager?
23. I’m currently working as a junior growth marketer, it’d be great to have a chat with someone who’s a bit further along in their career with more experience. What’s it like to be you?
24. We’re having some trouble setting up Mixpanel’s SDK in our React Native app, can you shed some light?
25. How do you hire your first C-level employee? What are your thoughts on giving them equity or bonus incentives?
26. What was your experience like trying to find product-market fit? Tell me the story of how you reached it!
27. I’m at a crossroads right now. I can position my startup as a premium service or a low-cost service. Can we talk through the pros and cons?
28. How do you decide what metrics to add to your KPI dashboard?
29. What are the most common pitfalls to avoid in growth marketing?
30. I’ve read books and taken courses and practiced what I could of marketing in the real world, but my results are just not really showing. Can you give me some homework? I’ll report back next week with the results!
31.  I’m starting link building and need help understanding the process and what works/doesn’t. How do you systematize link building?
32. I feel that my services are too customized and require a lot of time to serve each client. What would you recommend I do to increase standardization and decrease manual work?
33. I’m trying to put together a productized service, do you think this is a good idea in such a crowded landscape?
34. I’m tracking micro-conversions using Google Tag Manager, can you tell me if it’s set up correctly?
35. How can I get leads for calls/demos with C-level executives without being spammy and annoying?
36. I’m a technical founder (not a marketer) and am wearing way too many hats. Do you have any tips on how to stay sane?
37. We are a new agency, can we have some feedback on our client proposals?
38. I’ve created a SEO strategy centered around the creation of +100 landing pages and want to run it by someone. Can you help me validate my SEO strategy before I press “start”?
39. I’ve got a blog that’s got +50k page views per month but it makes no money. Can you help me brainstorm ideas for how to monetize it?
40. What are the best ways to interact with sign-up users from an MVP?
41. Have you paid for backlinks before? What’s the procedure/protocol for situations like this?
42. I will be attending a big startup conference soon and will even have a booth there. How can I maximize my investment and bring in new accounts for my business, meet people, make friends, and meet potential investors, advisors, and partners?
43. My SaaS does a great job of converting visitors into sign-up users, but hardly any of these users convert into paying customers. How do you come up with ideas on how to improve free trial to paid user conversion rates?
44. What’s the best way to increase followers on social media and then convert them into paying customers?
45. I’m currently bootstrapping a startup but there’s a perceivable jump between solo pushing the company forward and getting traction with investors/angels and building a team. Can you give me advice on how to successfully raise funding as a solo founder?
46. How do you know when it’s the right time to launch your product on Producthunt?
47. I’ve been scaling up my freelance consulting work for several months and I’m debating when/where/how/if I should approach the next stage of my growth. How do you scale a small freelance/consulting business scale into a full-on agency or large-scale consultancy (preferably with enterprise-level clients)?

How to maximize your value, a few tips

Here are some tips on how to get the maximum bang for your time on GrowthMentor calls.

• Ask your mentor if they’d be cool with you recording your screen with Loom – it’ll reduce your mental load of having to take notes in realtime. Just review the tape.
• Do most of the talking in the first few minutes to set the stage
• Give contextual information to help paint the picture of your current situation.
• Growth mentors will be asking you lots of questions, answer them as honest as possible.
• Be concise and focused. Small talk is fine in moderation, don’t overdo it. You’re on a call for a specific reason. Be mindful of that at all times.
• Pay attention to the words coming out of your own mouth, the best case scenario is for you to answer your own questions without the mentor having to tell you what to do.
• Come into this with realistic expectations. They’re mentors, not magicians.
• Don’t feel pressure, just relax. There’s no right/wrong way to do this. Avoid binary thinking.
• Try to form mental patterns, especially if you speak with multiple mentors. Pay attention to metadata.
• Don’t be afraid to push the boundaries of question asking. Be inquisitive. Stories are gold.
• Embrace alternative views. If you can stomach it, ask the mentors to play devil’s advocate and role play a customer filled with objections.
• Be friendly and authentic. If you’re likable, the mentors will be your biggest supporters (even after the call is over).