10 best practices to select a startup mentor

Martijn Rutten
5 min read

The general view of an entrepreneur goes something like this: you have a revolutionary idea and are confident enough to pursue it despite the whole world telling you you’ll never make it. Along with that comes the general thought that true entrepreneurs do everything by themselves. They are so smart they can do everything better, right?

Well, no. Although the job of a founder is still pretty lonesome, common sense prevails. You should ask for help. Founders that surround them with a network of experienced entrepreneurs can avoid many of the common startup pitfalls and greatly increase their chances of success.

So you should get a mentor. Preferably a whole bunch of them, for every step of the way.

In any startup scene, there is an abundance of mentors or coaches swarming around the young entrepreneurs in the hope that some of their energy and marketing hype will rub off on them. Many of these once were a middle-manager at a large corporation and all too often were forced to make a living as consultant after an internal reorg.

For a consultant, there is hardly any better marketing and easy money than to get a paid board-seat at a high-profile startup.

But yes, you should get a mentor. How to make sure your mentor actually helps you to move your startup forward? Here are my 10 rules:

1. Never use a mentor that has never ran his own startup as a founder or CEO

This is an absolute must. Well, unless the mentor is for a specific topic such as patent law. Seriously, that middle-manager may know a lot about management, but have no clue about startup dynamics. You are a startup, i.e., a flexible organization in search of a scalable business model where cash is king. That does not rhyme with big-company politics. Ideally, your mentor is an active CEO of a startup that is a step ahead of yours.

2. Take the advice with a grain of salt.

In the agile software development, managers are denoted as “chickens”, and the developers as “pigs”. As a result managers are not allowed to talk in the daily standup meetings. Why not? Chickens are only involved in the process of making food, but pigs are committed. Your mentor is a chicken, but you face the butcher if things go haywire. Listen carefully to the advice, but always make up your own mind.

3. Is the mentor brutally honest?

You want to hear any doubt or stupidity from your side asap. You simply cannot afford to continue in the wrong path. Mentor’s should take off the velvet gloves to make sure you execute that necessary pivot well before you run out of cash.

4. Does she/he tell you what to do in the first meeting?

This typically happens with ex-CEOs with a big CV and corresponding ego. They have seen it all, and will instantly tell you what they did that was oh so successful, and therefore you should do the same. Say thank you, and leave. A good mentor knows how to listen, understand your story, and only then give you their feedback so you can steer your own path.

5. Watch out for the Halo effect

Much of our thinking about company performance is shaped by the halo effect. When a company is growing and profitable, we tend to infer that it has a brilliant strategy, a visionary CEO, motivated people, and a vibrant culture. When performance falters, we’re quick to say the strategy was misguided, the CEO became arrogant, the people were complacent, and the culture stodgy.

Investors have a tendency to get fooled by this one. A CEO that sold his company for lots of money is deemed to be your best advisor. True, if the CEO knows how to listen, and the domain of his company exactly matches with yours. you may be in for a treat. But all too often his success was in a different domain with vastly different dynamics. And maybe he just got lucky once? Beware of the Halo effect (and read the book).

6. Be wary of board-seat junkies

Board-seat junkies go for the easy money and prestige. If they ask you to get them on your board, you probably shouldn’t. A good board member typically is too busy running his/her own company, and will be reluctant to accept the responsibility at first.

7. Check your references

Realize that a mentor is not much different from a hire. Don’t let their CV fool you. Can the mentor listen? Does she respond quickly when you call them at night? Did he do his homework? Can he deal with your investors and stakeholders without burning bridges? Call up other startups he or she advised.

8. Check the expiration date of their network

Know that an ex-employee has no more power in that organization. A startup CEO that got acquired by, say Google, has little power at Google after he/she left. Contacts go stale very fast as organizations reorganize. And while you’re at it, check how the former company regards the mentor. You don’t want to inherit your mentor’s bad rep.

9. Cherish their failures

A bankruptcy is a much stronger learning than a walk in the park. You may get much more out of a mentor that failed and learned his/her lesson than a successful CEO that never had to fight. But do check if they are able to admit past mistakes and learn.

10. Don’t break the bank, but also don’t pay peanuts to get a monkey

A good mentor will do this out of personal interest in you and your story, not for the money. But if there is nothing in it for them, it is hard to ask for commitment. A good mentor will ask for a compensation, but only as a gesture of you being serious.

That’s it. My 10 rules for selecting a mentor, coach, board member, or hey, investment partner for that matter. What are your experiences?

Tags: Mentor Team

About Martijn Rutten

Fractional CTO & technology entrepreneur with a long history in challenging software projects. Former CTO of scale-up Insify, changing the insurance space for SMEs. Former CTO of fintech scale-up Othera, deep in the world of securitized digital assets. Coached many tech startups and corporate innovation teams at HighTechXL. Co-founded Vector Fabrics on parallelization of embedded software. PhD in hardware/software co-design at Philips Research & NXP Semiconductors. More about me.