When spending time with mentors becomes a waste of time

How to identify those mentors that are worth spending time with? Given that most mentors, angels or VCs are guided by a similar principle when meeting new entrepreneurs/startups, why shouldn’t you have the same approach? At the end of the day, YOUR time is the most valuable resource you own. Invest it carefully!


For the past 4 years, I’ve been truly immersed in the startup ecosystem and it all started with me being selected for the first ever Startupbootcamp organized in Europe, back in 2010. Truth be told, I wasn’t prepared for anything that followed during the 3-month business accelerator. I didn’t have the knowledge that others had or the experience that some of the entrepreneurs had at the time.

I had a lot of catching up to do and, for the most part of the program, this is what I did. While this had an immense effect on a personal level, I have to admit that from a startup point of view, it wasn’t a boost and it’s easy to see why: we weren’t ready for an accelerator. It was our technical talent manifested within a strong team that got us selected.

Since then, I’ve developed a strong entrepreneurial mindset, talked with a lot of mentors, dealt with investors and raised money, hired/fired employees, growing Appticles.com into a revenue-driven SaaS business. Basically migrating to a whole new challenge: being a CEO.

Looking back, I can honestly say that I’ve met incredible people and I’ve tried to learn as much as possible from each one of them. Even from the ones that I didn’t necessarily agree with. As a startup, we’ve participated in lots of events/competitions, meeting mentors during our 1-on-1 sessions and I have to admit — these have mostly been interesting/rich experiences.

All in all, I got to meet so many mentors that at one point it became too much to bare. When spending time with a mentor becomes a waste of time?

The following is a list that I have put together based on my personal experience:

1. Mentor doesn’t have a LinkedIn profile

I mean, really? I fail to see how this person can possibly offer valuable mentorship. Mentors usually open up their network with various introductions that your startup might benefit from. How will that even work out in this case? Maybe he’s an expert in whatever your startup is doing, but nah … it’s a long shot. This is 2015, that’s unforgiving!

2. Mentor has nothing to do with your industry

The risk here is to adventure into a discussion that adds no value for either of you. Biotech has nothing to do with Publishing, so don’t bother. Gaming has nada in common with FinTech. Your startup is about Bitcoins and in front of you stands an experienced Digital Health guy? Not going to work.

Ideally you’ve done your research to avoid this awkward moment, but if it does happen, find a way to get out of the situation: “I heard that the startup sitting at that table was looking for an experienced Digital Health mentor, let me introduce you to them.

However, there are situations when various aspects from different industries share common principles: KPIs in Gaming and SaaS have common grounds. Be prepared to lead the discussion towards that point of interest. Mentors in adjacent industries can be valuable, but you do have to do your homework, research and come up with questions/situations that challenge the mentor to identify ways of validating your assumptions. This can spark the conversation and you’ll be surely remembered when following up on e-mail the next day.

3. Mentor doesn’t take notes

From a statistical point of view, I’ve seen that the most useful mentors where the ones that had taken notes about our startup during the 1-on-1 sessions. They were organized in answering our questions, suggesting approaches to validate different assumptions and also writing down the names of the people that they could introduce us to. I love when mentors take this really seriously — diving into their purpose of actually being there: helping, guiding, connecting.

I can say that 50% of the mentors I’ve met didn’t even have a piece of paper in front of them. 90% of these conversations turned out to be just chit chat. Nothing different from just meeting a person in the street and casually asking for feedback about your startup. This is NOT mentorship, this is a waste of time … gossip. Unless you really need feedback (not guidance), in which case you’d be better out on the streets.

4. Mentor taking over the discussion

If somebody should do it, that would be you, not the mentor. And by “taking over” I mean, directing the conversation towards the right lane, not spending the entire mentoring session explaining what your startup does and allow little time for the mentor to contribute with his expertise.

The most weird 30 minutes I had with a mentor unfolded years back when I was just taking my first entrepreneurial steps, trying to absorb as much knowledge as possible. This guy, a respectable name in the startup ecosystem, started our session by saying, even before introducing ourselves, that he doesn’t understand why one would need a mobile/responsive site (this was back in 2010, when the first iPad came to market) when you have this magical function on iPhone: zoom in & out.

His aggressive attitude and my lack of experience placed me in a very defensive situation and no matter how much I was trying to explain, he was fixated on his opinion and didn’t accept any other angle of thought. A session that I was hardly waiting, eager to learn from this highly appreciated mentor, turned out to be a total fiasco.

Needless to say, that now, in 2015, responsive is the standard.

5. Mentor telling you: “This is not going to work!

“Who the hell do you think you are? Seriously, get lost!” This is a critical moment: resist the temptation of hitting the guy!

In the absence of a strong argument to accompany the above statement, these mentors qualify as experts in a very special and elitist area: being jerks. In my opinion, this is a common mistake for newbie mentors, and the sooner you put an end to it, the better. I’ve seen this being manifested mostly on narrow minded persons that believe that recent success entitles them to dictate what works and what doesn’t in this world. It’s best to stay away from these guys. They’re easy to spot: they have an opinion about everything ☺

On the other hand, “this might not work” indeed, in which case the versatile mentor will find ways to ask the right questions, challenge your assumptions and guide you towards identifying the alternatives and pivoting your startup in a better direction. That’s what a mentor does. Everything else is just noise, so mute it.

6. More than 3 mentors at once

The issue here is that one of the mentors might not be engaged into the conversation. He/she might feel left out and you don’t want that. Occasionally, what I’ve seen happening and it was hilarious from where I was standing: mentors arguing about various aspects like we weren’t even there. While this is fun to witness, it might create some unnecessary tension.

If you have to deal with more mentors at once, make sure they fit within the same topic/industry. Otherwise, it’s going to be a mess and potentially a waste of time trying to squeeze something out of anyone at the table.

7. Mentor out of obligation

He might be friends with the organizer or has sponsored the event so he’s invited to mentor the startups. It’s Saturday or Sunday and he wishes he was with his buddies having lunch at the lovely restaurant that opened a week ago. He’s doing it as an obligation and you can read that on his face.
Put him out of his misery, send him on his way.

If you find a way to engage him, that’s good for you, but bear in mind that he’s there for the wrong reasons. Do you really want him to offer you mentorship? Stick with the “guy on the street” feedback approach — this stuff is so subtle, he will be under the impression that he helped you a great deal and giving feedback is what mentoring is all about. Now he has something to talk about with his buddies at dinner (having skipped lunch).

8. Mentor with a crush

Yes, this happens surprisingly often and even our CTO has her own stories to tell ☺

You’re a female founder and at first, he (always a “he”) seems extremely helpful and you might think that this guy is “nice”. Your e-mail conversations seem to flow really well and they eventually lead to a new meeting, in town, at a coffee place near his office. You get to know him better and eventually he invites you (explicitly refers to “just” you) to a new mentoring session, at his apartment.

Just remember, some things are too nice to be true ☺

9. Entrepreneur slash Mentor slash Investor

Why do investors (either Angels or VCs) insist on calling it “mentoring” when all they do is actually scout? They say that you should ask for help and you’ll get money (eventually). Ask for money and you’ll get help. I guess that gives them enough reason to be there.

By setting everybody’s expectations, you’re not caught up by surprise when a local entrepreneur turned Angel suddenly lands at your table admitting that he doesn’t know what to do and this is his first time mentoring. Instead of a piece of paper he seems attached to a glass of wine, courtesy of the event organizers. Sure enough, you’re in for an 1-on-1 session of jibber-jabber with the entrepreneur slash mentor slash angel.

Granted, that is extreme☺.

However, the most focused discussions I ever had were in the presence of investors, aware of their purpose at the mentoring table. This isn’t a waste of time because most investors that come to these types of mentoring sessions really know their stuff and are super sharp on spending their time. Most probably, they will pick the startups to mentor instead of vice-versa.

10. Mentor not replying to your follow-ups

One thing I notice novice entrepreneurs not acknowledging is that mentors are people with their own lives (personal and professional). They agreed to meet you once, but that doesn’t mean you can harass them for the rest of their days. Treat them with the respect you’d like to receive back.

Yes, it might happen that the 1-on-1 session was valuable, but you end up not getting any reply to your follow-up. It’s a shame, really, but for some mentors this might take one, two weeks or even more. I think that a person that’s dedicated to mentoring should reply to follow-ups, no matter how late or how brief. But this is really the case when being harsh is not adequate.

Waste of time? Not necessarily, you still had the mentoring session which presumably was useful.