What Makes a Good Mentor, and Why Most Aren’t

What Makes a Good Mentor, and Why Most Aren’t

Over the past few years, “mentor” has become one of the most worn-out words in the startup world. You see it on websites, in investor decks, on LinkedIn, in accelerator programmes. Nearly every startup has a page of smiling faces under the heading “Our Mentors”. And nearly every founder who is honest with you will admit, after the second drink, that most of them never got much out of it.

I have been advising many startups for a few years now, so this topic concerns me directly and I cannot pretend to look at it from the outside. That is exactly why I want to be tough on it. A good mentor can save a company years. A bad one eats your time, gives you false confidence and sometimes nudges you toward wrong decisions with an air of authority.

Why most “mentors” are not really mentors

Let me start with what does not work. Some patterns repeat so often you could almost tick them off a list:

  • They give generic advice. “Focus on the customer.” “Execution matters more than the idea.” “Keep going.” All true, all useless. Advice that fits every company helps none of them.
  • They talk about themselves. You arrive with your problem and leave an hour later knowing everything about their career.
  • They have never built or run a business. They were consultants, corporate managers, lecturers. There is a huge gap between knowing how things should work and having signed the payroll in a month when there was no money in the account.
  • They have nothing at stake. If their advice is bad, they lose nothing. You do.
  • They collect titles. They appear as “mentor” or “advisor” on the websites of dozens of startups. Nobody can genuinely help that many companies at once. It is a logo collection, not a job.
  • They vanish after the photo. They show up at demo day, pose for a picture, hit like, and you do not see them again until the next event.

What a good mentor actually does

A good mentor asks questions before giving answers. The first minutes with you are not a monologue but an interrogation. What are your numbers? Who pays? Why do customers leave? What have you already tried? Only once they understand your situation, not a generic one, do they tell you what they think.

They have relevant experience, failures included. A mentor with only success stories does not impress me. My most useful lessons came from the bad moments. In 2009, in the middle of the financial crisis, I was forced to sell my majority stake in MarketOnline, Mediadot and Azerty (Romanian online businesses I owned at the time), because the alternative was bankruptcy. I regretted it for a long time. But since then I know exactly what a founder negotiating with his back against the wall looks like, and you do not learn that from books. I wrote more about it in what I learned from 20 years of entrepreneurship.

They tell you uncomfortable truths. That your product is not as good as you think. That your co-founder is not pulling his weight. That your price is too low. That you should shut down a business line you have spent two years on. A mentor who only cheers you on is a fan, not a mentor.

They open doors. One phone call to the right person can be worth a month of work. A good mentor puts their own name on the line when they introduce you to a client, an investor or a partner, and only does it when they believe you are ready. That is also a test: if six months in they have never once offered to introduce you to anyone, ask yourself why.

They are there when things go wrong. Anyone is available for coffee to celebrate a funding round. A real mentor is the one you call on a Sunday night when your biggest client has just walked away or when cash covers only two more months. And they pick up.

Skin in the game: why it matters that they have something to lose

Here is an opinion I fully own. I believe the best mentor is someone who gains from your success and loses from your failure. That is why I work for equity, not for fees: no hourly rate, no retainer, no fixed fee, just a stake in the company. If I do not deliver results, I do not get paid. Simple and honest.

I am not saying every mentor should ask for shares. There are generous people who help for nothing in return, and they are precious. But when someone has a real stake, the quality of their attention changes. They stop giving advice out of politeness. They give it as if it were their own money, because, to a degree, it is.

Mentor, advisor, coach, investor: not the same thing

A lot of confusion comes from throwing all these roles into one bag. In short, this is how I see them:

  • A mentor helps you grow as a founder. The relationship is long-term, more personal and often informal.
  • An advisor helps the company in a specific area: strategy, marketing, fundraising, entering a market. Usually a formal role and, ideally, with equity.
  • A coach works on your personal behaviour and performance. They do not need to know your industry; they need to ask good questions and hold you accountable.
  • An investor puts in money and expects a return. They can also be a mentor, but do not forget their interests are not always identical to yours, especially on valuation, dilution or an exit.

How to choose a mentor, and how to test them

Do not pick a mentor for their fame or for the number of logos on their profile. Pick them for how relevant they are to the problem you have right now. A few simple tests:

  • Check what they have built. Not what they have taught, what they have built. Have they run a company? Been through a crisis? Hired and fired people?
  • Bring a real problem to the first meeting. Watch whether they ask questions or jump straight to answers. Watch whether they talk about you or about themselves.
  • See how they react when they disagree with you. If they tell you what you want to hear, you have learned what you needed to know.
  • Ask other founders they have worked with. Not the ones in the website photo, but the ones from a year or two ago. Did they stay involved? Did they actually help?
  • Start small. A limited project over a few months, before you give them an official title or shares.

How to be a good mentee

In fairness, here is the other half of the truth: plenty of founders complain about their mentors, but they are not great mentees either. It works both ways.

Come prepared. With up-to-date numbers, a clearly framed problem and what you have already tried. An hour lost on small talk is an hour in which nobody learned anything. I once wrote that one prepared person is worth ten unprepared ones, and it applies perfectly here.

Act on the advice. You do not have to follow all of it, but if you keep ignoring what you are told, why keep asking?

Report back. Tell your mentor what you did with their advice and how it turned out. It is the only way they can calibrate their help and, frankly, the only thing that keeps them motivated. Nothing kills a mentoring relationship faster than silence after a good conversation.

Instead of a conclusion

A good mentor is rare. Worth searching for patiently, testing without embarrassment and treating with respect once you have found one. And if your startup page lists ten “mentors” and none of them has returned your call in the past three months, maybe it is time for a clean-up.

What about you? Have you had a mentor who changed your trajectory, or just nice photos on the website?