Ivan Kavalerov

In my journey as an entrepreneur, I’ve encountered a paradox that initially took me by surprise: my hesitation to seek mentorship from those I admire most.

I have been fortunate enough to meet and work with some truly outstanding people. Some of them were already with wealth of knowledge and decades of experience behind them, others were just at the start of their careers and at the same time already wise well beyond their years. 

Having these people in my life gave me the opportunity to have great mentors. However, as the people I want and need mentorship from are also the ones I respect and admire the most, there was a problem that I didn’t anticipate. I was hesitating to ask people to mentor me, or even after getting someone as a mentor I would hesitate to ask for their advice, out of fear that somehow me sharing my challenges and my problems would make them think less of me. 

“Fear is the mind killer”, and this kind of fear is the worst kind, as it is about insecurity and caring about others opinion. Being a startup founder one gets used to (or should get used to) not really care about what people think about them personally, as they should focus on what users and customers think about the product, first and foremost. Yet, here I was, my ambitions and desire to be seen by some of these people that I respect so much as equal still leading to me being paralysed to take action and get the most value out of these people in my network. 

Now would be a good time to say that I have solved this issue – but, probably, not yet. However, I found a way to turn this mental reaction that I have into something of a strength. 

In order to make sure that I don’t look stupid or silly in these sessions with my mentors, I focused quite a lot on making sure that I actually can ask the right question. I challenge every assumption that I have about the situation that I am struggling with, and as part of the prep to the mentor call I think through every possible workaround, action or alternative that I can take to solve the situation. In other words, I am aiming to be in these sessions as prepared as one can be, anticipating as many possible questions or suggestions as possible and thinking them through. 

This prep turned out to be one of the best things about having mentors. In many cases, I find answers that I am seeking when I am just preparing for the mentor sessions, even before I have a call with them. And the beauty of this is that this way during the session itself we get to spend a lot of time on really unique insights and ideas that I could’ve not thought of myself, which makes mentorship even more valuable for me. 

This is a known phenomenon, but it impresses me every time. As a developer, explaining your code to someone (it can even be a rubber duck near your screen!) helps you debug it. When preparing a sales pitch, roleplaying it in your head or talking to a picture of potential customers can help come up with the best words. And it is very similar in mentorship, and by the virtue of mentorship being focused on the most strategic parts of my work, the value of this “trick” is very high. 

Find a good mentor. Don’t hesitate to schedule chats with them when you are struggling with something. But make sure you really prepare for these chats as much as you can – and the preparation can be, in the end, as valuable as the rest of the mentorship experience.