My mentoring advice to startup founders: do the work that is in front of you

During lockdown I was ‘zoom mentoring’ a number of startup founders, focusing on them as a person, not their startup ventures, which were paused. 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.

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 themselves, encouraging them to look ahead and help navigating 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.

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

1. Ensure there is personal chemistry and empathy

John calls me. It’s 2.30am. 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 replacing a car battery or laying a parquet floor, but he assumes I am. An hour later and we’ve had a good chat. I feel the same weird endorphin rush as after closing a fund raise, 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 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 very quickly shorthand explanations will do, and they can immediately dive in and understand the primary challenges. Questions to ask include: can this person give actionable advice? Have they said something straight away that makes me stop and think?

To stand out as a mentor, you really have to get to know your mentee on a personal level – the stuff that makes them them. Be an active listener, making a conscious effort to truly pay attention to what and how they say things, 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 and intellectual horsepower to each meeting.

Takeaways:

  • Be open about your own mistakes and vulnerabilities
  • Avoid relationship droop, keep the exchanges energised
  • Don’t give homework, focus on execution progress

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

Fiona. She has 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 says maybe, and spouts a metric-tonne of moaning. She never slows down or pauses. I’m currently on Amazon ordering her a key ring in the shape of a zebra.

Many mentors think they’re ‘going to give them the benefit of my experience’, when actually, that isn’t necessarily what the other person needs, or wants. Effective mentors speak for less than 20% of the time. The key is to say just enough to get the other person thinking.

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.

Takeaways:

  • Kick off relationships around distinct problems or challenges
  • Create a schedule – but keep it loose, don’t impose a rigid or unrealistic cadence
  • Show up prepared with questions

3. Have an open dialogue to reframe the problem

Gerald, angel investor. On a zoom call, trying to recover a car-crash pitch for a mentee. How the other half live. 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’s no emotional fit. What have I said? It’s perfectly good advice.

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 for collaboration which takes emotional energy, empathy and asking tough questions. Helping someone through an obstacle is about helping them look at the problem differently.

What I do is change perceptions and get mentees to tell themselves a different story. This reframes their mindset as to what they perceive to be possible. Every problem, every dilemma, every dead end we find ourselves facing appears unsolvable inside a particular point of view. Enlarging the box, and problems take a different dimension, potential new opportunities appear.

It’s also important to create rhythm, routine and boundaries. Rhythm and routine are essential to keeping us alert. Boundaries are key too. The airline truism suddenly becomes very real: we have to put our own oxygen masks on first. I will be of no help to anyone else if I burn out.

Good advice is priceless. Not what you want to hear, but what you need to hear, practical based on possibility. Not designed to make you feel better, designed to make you think better. The quality of your questioning defines the quality of your thinking. With Gerald, I never lost the Raiders of the Lost Ark image. Indiana Jones I’m not.

Takeaways:

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 dong 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 see you on the road from cradle to grave just like Bevan promised back in 1948. NHS workers are genies.

A mistake mentees often make is to think the mentor will be always available for them, seeking immediate gratification. 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?

Also don’t set the mentor up as a role model or simply pump them for answers in the path of the development of the relationship. 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. 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. Mentoring is about helping the mentee find the right path, shaping the opportunity to think it through critically on their own.

Takeaways:

  • 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. Some ninety minutes later and I’ve missed the first half of ‘Hamilton’ thanks to a conversation that over ran and didn’t have the faintest clue what was going on in the second half. Debriefing with wife afterward, 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 startup 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 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 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.

Takeaways:

  • 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

Michael 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. Michael tells me he has a baby called Sayton (pronounced Satan, as in King of the Underworld). Later that day I chat with another mentee who brings his newly born daughter onto the zoom: Lesanye. Pronounced Lasagne. As in Lasagne.

I read a quote from Jessa Crispin, founder of Bookslut.com and it’s 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, and the way I continue to work too.

I talk with Michael about the various enemies of doing our work. I say Make your work ‘happy work’. For me, happy work is best done when we take our long-term plans somewhat lightly and work from moment to moment. It is our daily bread that we are encouraged to ask for. 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.

Takeaways:

  • 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

So that’s my mentoring experience, which highlights our top three leadership tools:

  • Our ears: listen, listen some more, and then some more
  • Our eyes: look for any dissonance between what is said and what you see
  • Our mouth: speak to acknowledge, then clarify, then inspire

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