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9 Questions To Ask Yourself When Finding a Mentor

Our flagship Mentor Program is designed to help Founders grow their customer base, secure funding, access vital subject expertise & commercialise at scale.

So, you’ve decided to find yourself a mentor. Smart move. You’ll be happy to know that 70% of startups that receive mentoring are still going strong after 5 years. That’s double the rate compared to those that don’t.

The big question is: how do you find a good mentor? Someone who is committed towards helping you to become better at what you do.

The fact is that if we take a look at history, mentoring has been around for centuries. This ancient tool is not to be underestimated as an extremely valuable way of growing your skills, network and knowledge with the help of a high performing leader who’s been around the traps.

We spoke to Stephenson Mansell Group, our partner in Stone & Chalk’s flagship Mentor Program, and asked them what founders should be looking for in a mentor. Here’s what they said:


  1. Are they accomplished in the area that is relevant to me? Choosing a mentor who has deep experience and success in your field can equip you with invaluable resources to help you accelerate at scale and keep moving forward. Barbara Sharp, CEO & Co-Founder of Pax Republic, says, “I have to pinch myself when I think about the access to the real smarts that the S&C mentor program has given me. I mean, company directors, banking executives with 30 year careers, people who have done deals that I dream about. The startup dream is so much more do-able when you have such a rich resource as a sounding board.”
  2. Do you relate to and trust them? This is perhaps the most important question to ask yourself, as a mentor will provide input in helping make decisions that can have a major impact on your business and your life.
  3. Do they carry a mentor mindset? A true mentor embodies a mindset motivated by the desire to selflessly help their mentee succeed and achieve their goals without competing agendas.
  4. Can they provide the right balance of both challenge and support? A good mentor is prepared to ask the tough questions and challenge you, as well as providing you with a safety net of support.
  5. Are they a good listener? Whilst a large part of a mentor’s role is to share their knowledge and insights, mentoring is not all about them doing the talking. A good mentor should actively listen and give you their full and undivided attention, ensuring they seek to empathise with you.
  6. Do they ask good questions? Good questions will: challenge your thinking; provide insight; deepen your understanding; and allow you to see things from a different perspective.
  7. Are they well connected? One measure of success is having a highly developed network. A good mentor will be able to introduce you to any relevant contacts who they believe can inspire and assist you further. One of our program mentees, Nigel Lovell, Founder of OpenSparkz, has a great example of this. He remembers the day “one of my mentors burst through the door unannounced blurting that she had found somebody to invest in the business!” Additionally, Dmitri Muntean, Managing Director of Payshield, explains that,"The mentor program consists of mentors who have been in the industry for decades and who have access to all possible connections. It provides invaluable help.”
  8. Do they realistically have the required time and energy for me? Mentorship is most effective when mentors have enough time and energy, and the right level of commitment to work with you. Be sure there is an understanding before pairing up about how often you will meet and what the expectation is around what they can provide as a mentor.
  9. Can they read me and the situation? Being a Founder of a startup can present massive challenges and come with a lot of pressure. That’s why it’s critical that your mentor understands who you are as a person and is able to identify the difference between normal levels of stress and signs of burnout. This will enable them to advise you on steps required to help manage your stress or they can refer you to someone who can.

The opportunity to be matched with highly qualified, experienced and committed mentors is certainly a significant benefit of being a Founder within Stone & Chalk.

As Anne Moore, Founder of PlanDo, puts it, “Founders tend to have attributes like resilience and being able create a long-term vision, however these traits alone are not sufficient to grow and scale a business. There are a swathe of technical skills needed, and this comes with mentoring from expert individuals that have these skills, which can be translated into gaining insight into both how you see yourself, as well as how the market will see you.”

We hope these insights help you solidify some great mentor matches that will equip you to navigate the startup journey as smoothly as possible.

If you are a S&C resident and would like to be considered for Stone & Chalk’s Mentor Program, reach out to Annie via If this article has inspired you to consider becoming a mentor, please apply here.

9 April 2019

Filed under: mentors, thought leader


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