How a good mentor can guide a startup founder

In my day-to-day work muddling in and rolling my sleeves up with startups, I end up doing a lot of mentoring. I’ve grown to understand this role better recently and find myself enjoying it more than consulting or non-exec roles. I’ve found it discipline-agnostic – whether you’re a mentor to a medical device founder or a marketing platform founder, the same principles apply but you learn yourself. 

I’ve come to appreciate that the best mentoring relationships are like the relationship between a parent and adult child. They’re characterised by genuine warmth, mutual trust and respect, underlying shared values, and open communication. They find their apotheosis in the mentee’s personal growth and transition to a new level of self-belief and confidence.

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 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 to see the potential inside themself, encourage them to look ahead and help navigate a course to 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. 11pm. He’s an absolute mess, drunk, crying. Is it cashflow problems, 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 self-removal of a tooth, but he assumes I am. An hour later and we’ve had a good chat. I feel the same endorphin rush as after closing a fund raise, exhaustion plus exhilaration and the feeling of having done a good thing. 

There has to be personal chemistry and ‘fit’ between mentor and mentee, you have to 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 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?*

John trusts me, hence the call about a collapsed relationship. He knows I care and will listen and offer objective feedback. I call myself his Business Buddy – as I do with all the folks, I find the label ‘mentor’ somewhat grandiose and uncomfortable. You need to get to know your mentee on a personal level – the stuff that makes them them. Be an active listener to truly pay attention to what your mentee is saying, instead of thinking about what you’re going to say next.  Ask open questions, and act as a sounding board. Nothing engenders trust faster than giving someone your undivided attention. Remain engaged and committed to bringing your full emotional intelligence to each meeting. It’s about listening, not speed of answers and response.


*Be open about your own vulnerabilities to create empathy.

*Avoid relationship stagnation, keep it energised.

*Be empathetic and listen carefully to what is said, and not said

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

Fiona. She had two settings: silence and shouting in frustration. She always has to have the last word, 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. But Fiona always goes for the outliers. I’m currently on Amazon ordering her a key ring in the shape of a zebra.

Many mentors think they’re ‘hoping to give them the benefit of my experience’, but 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 the mentee thinking in a different way.

The skill is to use your experience to craft questions that stimulate the mentee to think out loud. 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.


*Commence the relationship oriented on the mentee’s specific challenge, avoid open ended generalisms

*Create a schedule – but keep it loose, don’t impose a rigid or unrealistic cadence

*Show up with an open mind but be prepared to set some boundaries

3. Have an open dialogue to reframe the problem

Gerald, angel investor. How the other half live. On a zoom call with a founder to him trying to recover his previous car-crash pitch, he’s in his extremely posh study at home. Then his eight-year-old daughter comes in during the call and asks a question about the economy. 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. I tell him we’re withdrawing as there is no chemistry. It’s a strong intervention and perfectly good advice having seen the vacuum in the angel-founder engagement.

All I was trying to do is have a two-way dialogue as opposed to a discussion – in a dialogue you’re trying to create meaning not just exchanging points of view. It’s an opportunity for collaboration which takes emotional energy, empathy and smart questions. It’s about guiding someone through an obstacle they maybe blinkered on, helping them look at the problem differently. This obstacle wasn’t going to clear, so I had to help the founder see this.

Pushing back is key, not simply getting to ‘yes’ every time a mentee asks for an intervention. The airline truism is true: you have to put your own oxygen masks on first. Not what your mentee wants to hear, they want you to give them the answers. but what they need is a balanced set of options of practical solutions. Not designed to make you feel better, designed to make you think better. The quality of your questioning defines the quality of your thinking is something I instil in each of my mentee relationships.


*Your role is to help your mentee find their solution themselves

*Explain how you’ve tackled a similar challenge but highlight how conditions are different based on their situation

*Replay back the mentee’s thinking, stretch their thinking by introducing alternatives and options

4. A mentor is not a genie

If I wasn’t doing what I was doing, I’d work for the NHS. 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 see you right just like Bevan promised back in 1948. NHS workers are genies.

A mistake mentees often make is to think their mentor will be their genie, always available. 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. Also, the mentor isn’t there 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?

We tend to believe that having a mentor is about getting the best solutions to a problem on demand, a guardian angel who ensures we avoid failure by giving us the answers. That isn’t the case. It’s about helping the mentee find their right path, shaping the opportunity to think it through critically on their own.


*Solve for the long term by proving thinking tools and techniques

*Help your mentees embrace learning outcomes as growth, not just answers to problems

*Measure progress every meeting, make the mentee accountable

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

Jane. Always goes round the houses. I missed the first half of Gone Fishing thanks to a conversation that over ran. One of the hazards of mentorship is that there can be too much to discuss. Startup founders rarely have just one major challenge 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 actually tackling the practical stuff that’s coming up the next week or month. Try to keep things tied to the decisions 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 Morecambe 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 – his words! Later that day I chat with another mentee who brings his newly born daughter om the zoom: Lesanye. Pronounced Lasagne. As in Lasagne.

I have a quote from Jessa Crispin, 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 for a long time.

I talk with Mo about the various pressures 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. The present is the only time in which anything can be done, or satisfaction received.

Mo needs to see a continuity to his days. Not an accumulation, 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.


*Encourage mentees to do the work that’s in front of them

*Ensure they are reasonable in the art of the possible

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

The mentor role needn’t take an excessive amount of time, establishing firm and clear ground rules with mentees can improve efficiency. To begin, clarify what your mentee expects from the relationship, match it against your expectations, and reach consensus. You may have misapprehension as to the mentee’s long-term goals, while the mentee may have an exaggerated notion as to what services you will provide. Such misunderstandings are costly, in terms of time and tranquillity. These differences should be resolved explicitly and early in every mentoring relationship. In my experience, successful relationships are where the mentee fully understands and shares their mentor’s vision for success.

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