How having a mentor helps startup founders see the light at the end of the tunnel

Over recent years I’ve seen many startup founders embrace mentoring as a means of developing themselves. This has enhanced their leadership skills and accelerated growth of their venture, thus building a more sustainable organisation. I’ve long been an advocate of mentoring, and this blog shares a few of my thoughts as to how to build an effective mentor-mentee relationship.

The word mentor emerged from Homer’s epic poem The Odyssey. Mentor was a friend of Odysseus, King of Ithaca. When the king went to war, Mentor became a friend and advisor to the king’s son Telemachus. I’ve learned a lot from mentors who were instrumental in shaping me.

Mentoring isn’t just about telling someone what to do, rather it’s all about helping them work things out for themselves and to see their own potential, encourage them to look ahead and help navigate their destination, with a gentle, nurturing push in the right direction.

A mentor typically has some relevant experience they draw on to help the mentee. Not to say I would do this but to basically say, Okay, let’s look at this question, or What do you think about that? They basically use their wisdom to help somebody else develop wisdom of their own. There’s a good case made for mentoring at certain points in our startup journey.

So, let me share some of my recent experience, with lessons and takeaways from my mentoring clients, as to what shapes an effective mentor-mentee relationship. The names have been changed by the way!

1. Ensure there is personal chemistry, empathy – and speed mentoring doesn’t work

John calls me. He’s an absolute mess, drunk, crying. Is it cashflow problems again, lost a key customer? I ask. No. He’s just split up with his girlfriend. I’m no better trained to counsel him than I would be to talk him through laying a parquet floor, but an hour later and we’ve had a good chat. I feel the same weird endorphin rush as after helping a startup hire a new member of staff, exhaustion plus exhilaration and the vague feeling of having done a good thing – like some of you may do after running a 10k for charity.

There has to be personal chemistry between mentor and mentee, you must invest in the relationship with your mentee as a person. And speed mentoring doesn’t work. For mentors, the fit can be assessed by asking: can I clearly be helpful to this potential mentee? can this person be completely open and honest with me? Are they willing to provide deep context about their problems and vulnerabilities?

Mentees should choose someone who is close enough to their industry so that shorthand explanations will do, and they can immediately dive in and understand the primary challenges and goals. Questions to ask include: can this person give actionable advice? Have they told me something in the first meeting that I’ve been able to apply right away?

To stand out as a mentor, be an active listener, making a conscious effort to truly pay attention to what your mentee is saying, instead of thinking about what you’re going to say next. Nothing engenders trust faster than giving someone your undivided attention. Remain engaged and committed to bringing your full emotional intelligence and intellectual horsepower to each meeting.


·      Be open about your own mistakes and vulnerabilities.

·      Avoid relationship droop, keep the exchanges energised.

·      Don’t give homework, focus on execution.

2. Don’t assume anything – set expectations together at the outset

Fiona. She had two settings: silence and shouting. She always has to have the last word. And it’s a loud one too. I tell her if you hear hooves clip-clopping outside your bedroom door, it could be a zebra. But when you take a look, it will almost certainly turn out to be a horse. She just wants me to be her personal Google-meets-Wikipedia to solve her problems. I’m currently on Amazon ordering her a key ring in the shape of a zebra. Humour is the bedrock of our relationship.

Many mentees think their mentor is ‘going to give me the benefit of their experience and solve my problems’, when actually, that isn’t necessarily what the mentee needs. Effective mentors speak for less than 20% of the time. The key is to say just enough to get their mentee thinking.

The skill is to use your experience to craft questions that stimulate the mentee to think out loud. With Fiona I try to get her to press pause. But be careful with those questions. If you know where the conversation is going this is not a mentoring exchange, a predictable sense of direction doesn’t stimulate reflection. Part of this is setting the tone, style, structure and approach to the relationship and expectations early.


·      Kick off relationships around distinct problems or challenges.

·      Create a schedule – but keep it loose

·      Show up prepared with questions.

3. Have an open dialogue to reframe the problem

Gerald, angel investor. How the other half live. On a zoom call, trying to recover a car-crash pitch for a mentee. He’s sat in his extremely posh study at home. Then his extremely posh eight-year-old daughter comes in during the call and asks a question about the economy. Before he answers he asks her a question. Do you know what the economy is darling? Sure, she replies, it’s the part of the plane that’s terrible. You can see how revolutions start. He looks like the Nazi at the end of Raiders of the Lost Ark. I tell him we’re withdrawing, there is no relationship chemistry here. He agrees and thanks me for my candid approach. What have I said? It’s an honest statement.

All I really try to do is have a good, two-way dialogue as opposed to a discussion, trying to create some new meaning not just exchanging points of view. It’s an opportunity to share emotional energy, empathy, and transparent questions. Helping someone through an obstacle is about helping them look at the problem through a different lens.

Good advice is not what you want to hear, but what you need to hear, practical based designed not to make you feel better, but to make you think better. The quality of your questioning defines the quality of your thinking.


I always try to follow this meeting progression:

  • Mentee explains challenge they’re facing.
  • Mentor explains how they’ve tackled a similar challenge.
  • Mentee explains how conditions might be different based on their situation.
  • Mentor suggests what to replicate from her experience based on her mentee’s specific context.

4. Don’t let your mentee treat you like a genie

If wasn’t doing what I was doing, I’d work for the NHS. Who doesn’t love the NHS, apart from Matt Hancock? It’s unlike any other national asset, no one talks in fond tones about the Bank of England. The NHS does an amazing thing for us all. They delivered you when you were born and one day they’ll zip you up in a bag, but until then they’ll do everything that medial science allows to help from cradle to grave just like Bevan promised back in 1948.

A mistake mentees often make is to think the mentor will be always available for them, sometimes just to chat, or seeking immediate gratification on demand. I’ve got a problem my mentor could solve, so I’ll call her now. The mentor isn’t there to be at the beck and call to sort your problems. Your mentor is there to help you work things through yourself. In fact, when you bring an issue to the mentor, first thing she might say is, so tell me about your thinking about this issue so far?

Also don’t set the mentor up as a role model. What’s important is to say I want to be myself, but there are things that I can learn from them, which will be useful for me, and I’m just going to focus on those particular things.

We tend to believe that having a mentor is about having a guardian angel who ensures we avoid failure. That isn’t the case. Mentoring is about helping the mentee find the right path, shaping the opportunity to think it through critically on their own terms.


·      Solve for the long term.

·      Help your mentees embrace failure as growth.

·      Measure progress every meeting.

5. Don’t boil the ocean every meeting – focus on your mentee’s blind spots

Jane. Always goes round the houses. I missed the first half of Hamilton thanks to a conversation that over ran and didn’t really manage well for the final thirty minutes. Debriefing with my wife afterwards, watching the first half didn’t seem to have helped her understand it either.

One of the hazards of mentorship is that there can be far too much to discuss. Very few startups have one major challenge or problem on their plate. It can be tempting to unpack everything that’s going on, but this will only limit how deep your conversation can go on the issues that matter most.

Be intentional about picking the key questions you really want to solve in a session. Try not to veer into big, conceptual thinking, it’s easy for your time to run out without tackling the practical stuff that’s coming up the next week or month. Try to keep things tied to the decisions that need to get made, or solutions that need to be found by unpacking blind spots.

To achieve this, I ask questions like Why is that important? instead of straight up saying something is or isn’t. This gives mentees the prompt they need to develop their own insights.


·      Be honest and transparent.

·      Celebrate their achievements, convey belief in ability and potential.

·      Avoid a meeting agenda that is too jam-packed.

6. Provide an underlying philosophy: do the work that is in front of you

Mo from The Bay Area calls. At last, someone from San Francisco, this is my entry point to Silicon Valley! No, he’s from the Colwyn Bay area. It’s a shame our child protection duties don’t extend to vetoing some of the terrible names my clients saddle their babies with. Mo tells me he has a baby called Sayton (pronounced Satan, as in King of the Underworld).

I give Mo a quote from Jessica Crispin, founder of and it has stuck with me: I just do the work that is in front of me. I don’t know if she’d still say she works that way but it’s the way I’ve worked all these years.

I talk with Mo about the various enemies of doing our work. One of them for him is frustration, he does not have the time to finish everything he wants to get done in time. For me,  work is best done when we take our long-term plans somewhat lightly and work from moment to moment within these plans – 90-day sprints. It is our daily bread that we are encouraged to ask for but it has to move the needle. The present is the only time in which anything can be done, or satisfaction received.

What I really crave, more than anything, is a continuity to my days. Not an accumulation, the sense that they’re adding up to anything, just a continuity, the sense that one day leads into another leads into another and on and on, that they make some kind of chain of progress. I did yesterday’s work yesterday. I’m doing today’s work today. I’ll do tomorrow’s work tomorrow.


·      Do the work that’s in front of you.

·      All good things must begin sometime.

·      Avoid fluff and grandstanding, there are jobs to be done.

Mentoring provides increased confidence and higher self-awareness for mentees; the mentoring process exposes new ideas and revelatory ways of thinking or problem solving. As Isaac Newton said, If I have seen further, it is by standing on the shoulders of giants. Show me a successful individual and I’ll show you someone who had real positive influences in his or her life – a good mentor.

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