(2022) Startup Mentorship Program: 9.5 questions to ask your mentor
Mentorship is not for everyone, since most early stage startups hate hearing opinions from experienced entrepreneurs. But sadly, because of this "closed" mindset, most startups fail (90% to be exact). In all my months of helping startups receive guided mentorship from successful founders on Sparrow, I've been fortunate enough to meet many people who're very eager to learn and scale.
And so today, I'll walk you through the basics of startup mentors, building defensible startup mentoring programs and then finally the questions you should be asking them.
If you want to get to the questions directly, just click the last title on the Table of Contents below.
Table of Contents
What is a startup mentor's job?
When should I get a startup mentor?
What is a startup mentor's job?
A startup mentor learns about your business, and provides you practical advice to overcome your real challenges. They help you differentiate short and long-term goals and help you plan your next steps to solve your deepest issues and scale your company.
It's recommended to only approach mentors from places (online/offline) that have a mentor vetting process to ensure the people showing you the ropes actually have the credentials and experience required.
Otherwise, you're better off calling your high school teacher for building a unicorn -- it doesn't make sense.
"A ‘startup’ is a company that is confused about 1. What its product is. 2. Who its customers are. 3. How to make money."
- Dave McClure, Co-founder of 500Startups
Different stages, different topics
Early stage companies
At this part of the journey, mentors will help you with business development and help get your feet wet in the startup life. Ideally, they will also teach you about go-to-market strategies that'll work for your product/service and how to successfully launch startups.
Advanced topics like optimizing growth funnels, fundraising, etc. should not be discussed at this step!
“There’s no shortage of remarkable ideas, what’s missing is the will to execute them.”
– Seth Godin, Author
Between MVP and Product-market fit
At this stage, you've validated the demand for your product and are scaling your MRR (Monthly Recurring Revenue) higher towards a number like $1000 or $10,000. Your mentoring sessions should focus around what needs to be done to find, experiment on and optimize customer acquisition channels.
Topics of mentorship can be strategic (i.e., high-level, less detailed) or be very tactical (i.e., step-by-step instructions). It's up to you to decide what level of guidance you need from your chosen mentor.
At Sparrow, I'll sit down with you to understand what challenges you need help with and then setup a call with the the advisor best fit for you.
If you want help preparing for your mentorship calls, you can use this template I made for you. It'll help you get ready before going into any meeting with someone you want to learn from, whether it's online or offline!
(Btw, if you want to join our Slack community of founders to stay accountable to your goals and discuss ideas, you may apply here.)
Scaling higher, fundraising and getting acquired
Your ARR (Annual Recurring Revenue) hit 6 figures. You and your team now have a good understanding of your customer persona. Your customers love advocating for your product naturally. And you don't push test code straight into production anymore.
Congratulations -- you've achieved product market fit.
As you scale higher towards either an acquisition or fundraising, you now need to get coached by a seasoned entrepreneur and other industry experts to take you to your next level. Some topics you're likely to discuss at this stage:
Approaching potential investors who fit your ideal persona
Learning to manage your employees to meet your growth milestones
Delegating growth initiatives across different functional teams
Finding creative avenues for business development and scaling revenue, etc.
Sparrow's startup advisors are experienced entrepreneurs who have built, scaled and sold their companies. We can help you scale through each of these 3 phases of your business.
When should I get a startup mentor?
Building on our previous section, entrepreneurship is a personal journey and different founders need support at their own time. I was fortunate enough to meet several entrepreneurs at my school before building Sparrow, but most of us grow up in places without easy access to entrepreneurship lessons.
And so I recommend over-preparing for the road ahead of you!
My personal approach is that if I think I need help with sales outreach in 50 days, I'll slowly start talking to my personal network about it from day 1. This lets me warm up to the topic and know what exact questions to ask in 50 days to my personal mentors.
Obviously this doesn't apply to all topics, but for topics like business development, don't wait for the bell to ring -- just get started with what you have and learn as you go!
To wrap this section up, if you don't know what you need to get advice on (happens a lot), try approaching successful entrepreneurs who have general experience in that area. They'll give you an idea, of what guidance to look for and where to go for it.
Then, you'll be better able to identify individuals who can help for those specific topics and then go from there. We've all been there. It's simple.
But it takes a lot of patience and a hell lot of perseverance. I don't think anyone rational should approach entrepreneurship. It's hard!
What is a mentorship program?
A mentoring program for startups is a guided initiative where you learn to tackle your specific growth challenges in a systemic way under an advisor's supervision. The added benefits of a program as opposed to having one-off phone calls with experts are:
Blindspots
You get an experienced entrepreneur's view of what skills you objectively lack today, and would need to reinforce in the future for your startup's trajectory.
Big-picture planning with your mentors
You receive a big picture plan of what you need to work on, before moving to the next step of your business. Think of it like a gantt chart personalized for your product journey.
Accountability from your mentors
You get peace of mind knowing you can run your candid questions by someone who is a few steps ahead of you and remain accountable towards your goals.
Must-know questions to ask your business mentor
Before you begin official sessions
Testing their ideas: Given what you know about my business, are there any high-level ideas you recommend I try out to scale?
Checking if there's a fit: How does your past mentoring experience make you a good fit for my exact goals?
Verifying their past mentorship: Have you previously provided guidance to other entrepreneurs with similar backgrounds like mine? What results did they achieve?
Asking about their mentorship preference: How much time commitment are you able to provide? What does a perfect mentor-mentee relationship look like to you?
During your mentorship sessions
Strategic vs. Tactical: Based on what you know about my business, do you see yourself giving me high-level strategic advice? Or are you capable of showing me step-by-step tactical processes like A/B testing my landing page, optimizing my Google Ads, etc.
Short-term vs. Long-term: How do you suggest I identify and prioritize my short-term goals form my long-term ones?
Thinking models: What mental frameworks have you used to sort through your hardest and urgent problems?
Execution tactics: Since I have these high priority items, how do you suggest I go about doing them? Is there a sequence you propose?
Self-learning: Based on my present goals and challenges, are there any online/offline handbooks you recommend I read?
Closing thoughts
I take hours to write these articles because I genuinely want to help. Our library also has templates you can use to plan for your sessions. Regardless of where you are in your startup journey, you have my best wishes!