What to look for in a startup mentor
Finding the right mentor for your startup is one of the most important decisions you’ll make as a founder. It will impact the entire trajectory of growth – both personally and professionally.
Many founders are aware of the need for mentorship, but few realise that choosing the right mentor requires more than just seeking out successful people with lots of money.
We’ve seen countless founders stumble because they didn’t know what to look for in a mentor. They found someone who was accomplished but distant, or someone too eager but lacking experience.
And mentorship isn’t a one-size-fits-all deal. The mentor you need when your company is pre-revenue won’t be the same person who guides you when you’re scaling globally.
We sat down with Stephenson Mansell Group – a world-class executive development firm – and they've revealed the nine questions founders should be asking themselves when evaluating a mentor.
1. Are they accomplished in the area that is relevant to me?
This might seem obvious, but it’s often overlooked. Many founders gravitate towards well-known names, figures who are visibly successful, but that doesn’t necessarily mean they are the right fit for you. The mentor needs to have real experience in the domain where you face challenges. For example, if you’re a tech founder, having a mentor with a strong track record in healthcare might be helpful, but only if they have also scaled tech startups.
Barbara Sharp, CEO and Co-Founder of Pax Republic, speaks highly of her experience with Stone & Chalk’s mentor program: “I have to pinch myself when I think about the access to the real smarts that the program has given me. Company directors, banking executives with 30-year careers, people who have done deals that I dream about. The startup dream is so much more doable when you have such a rich resource as a sounding board.”
What Barbara’s talking about isn’t just access to success, but access to relevant success. Her mentors had experience in areas directly applicable to her challenges, giving her actionable insights and advice.
2. Do I relate to and trust them?
Mentorship is deeply personal. You can’t be vulnerable with someone you don’t trust, and vulnerability is key to mentorship. You’ll need to expose your business’s weaknesses, your fears, and sometimes your insecurities as a founder. If you can’t do that, you’re wasting the opportunity.
This trust isn’t built overnight, but you can usually tell early on whether you relate to someone’s style of communication and their approach to problem-solving. More than just being experienced, your mentor should be someone you can imagine yourself working with in both the best and worst of times.
3. Do they have a mentor mindset?
There’s a difference between a successful entrepreneur and a great mentor. Not everyone who is successful in business knows how to help others succeed. A true mentor is selfless. They want you to achieve your goals without an agenda of their own. If you sense that your mentor is looking for something in return—whether it’s equity in your company or something else—it might be a red flag.
The best mentors are in it for your growth, not theirs. They don’t need validation from mentoring you, nor are they expecting you to be the next unicorn just to enhance their reputation. They are there to guide you, not to manage or micromanage your journey.
4. Can they provide the right balance between challenge and support?
Mentors must walk a fine line between being a cheerleader and a challenger. You don’t want someone who simply praises everything you do. You need someone who can ask the hard questions and push you to think differently. But equally, you need a mentor who can provide support when things get tough.
A good mentor knows when to challenge you and when to offer a listening ear. They’re not afraid to tell you when your idea doesn’t make sense, but they do so in a way that encourages learning and growth, not defeat.
5. Are they a good listener?
It’s easy to think of a mentor as someone who simply imparts wisdom. But the reality is, a good mentor listens more than they speak. They should listen carefully to your challenges, your aspirations, and your fears, so that their advice is tailored to your specific situation.
Founders often feel like they have to explain everything—after all, no one knows your business as well as you do. But a great mentor will make you feel heard and understood, which will allow them to offer advice that’s not just relevant, but also timely and actionable.
6. Do they ask good questions?
Good questions are the bedrock of effective mentorship. A mentor who asks thoughtful, probing questions is far more valuable than one who simply provides answers. Good questions make you stop and think, forcing you to consider angles you hadn’t before.
A mentor who asks good questions isn’t just guiding you; they’re teaching you how to think. They help you develop the critical thinking skills that will be essential as your company grows. Look for someone who challenges your assumptions, not someone who merely confirms them.
7. Are they well connected?
The old adage “It’s not what you know, but who you know” often holds true in the startup world. A mentor with an extensive network can open doors for you that would otherwise remain closed. They can introduce you to potential investors, partners, and even customers.
Nigel Lovell, Founder of OpenSparkz, shares a story from his experience with Stone & Chalk: “One of my mentors burst through the door, blurting that she had found somebody to invest in the business!” It’s that kind of unexpected but critical support that comes from a mentor who is well-connected and genuinely invested in your success.
8. Do they realistically have the time and energy for me?
The most brilliant mentor in the world is useless if they don’t have the time or energy to dedicate to you. Make sure your mentor has the bandwidth to be fully engaged.
This doesn’t mean they need to be available 24/7, but there should be a clear understanding of how often you’ll meet and what the expectations are in terms of communication and support.
It’s important to set these boundaries early on to avoid disappointment later. Make sure both parties are clear about what the mentorship will look like in practice.
9. Can they read me and the situation?
Startup life is intense. It’s filled with pressure, uncertainty, and long hours. A mentor needs to be able to read between the lines. They should be able to tell when you’re stressed, overwhelmed, or even burnt out, and they should know how to respond.
Good mentors don’t just focus on the business; they care about the founder as a person. They recognise that mental health is crucial to long-term success, and they’re able to provide guidance that keeps you healthy, not just profitable.
Final thoughts
Finding the right mentor is more art than science. It’s about finding someone whose experience aligns with your needs, but it’s also about chemistry, trust, and communication.
When you find the right mentor, they become a partner in your journey—someone who helps you navigate the ups and downs of startup life with wisdom and insight.
Keep these questions in mind, and you’ll be well on your way to forming a relationship that accelerates both your personal and professional growth.
