Having talked with quite a few people about my ideas and projects overtime i have noticed a common theme. Everybody tries to be gentle. That is ok but doen’t really help me move forward. What entrepreneurs really need is to be challenged.
I will speak for myself but i know in heart that the same principle applies to any entrepreneur. When we meet an entrepreneur we try to be polite and soft, and if we believe he is doing something wrong we choose the most indirect way to let him know.
It is in our nature to want to avoid confrontation. But in this case it is not helping anybody. Doesn’t help you, as you consumed three times the time you would need if you gave your opinion straight away. And it doesn’t help the entrepreneur as he/she is left wondering what the meaning [if any] between your words were. The result is mixed feelings and a gray area of uncertainty. In these situations an entrepreneur either chooses to ignore the feedback as noise or if he/she understood your points, he/she will try to validate it with another source or a followup call. So you both waste valuable time.
The fear of a backfire is quite valid and true. You may think: “If i tell that pumped up kid that his business model is h*******t, he will jump on me with all kinds of points why i am wrong and he is right”. That is true, yet, this kid needs that valuable lesson. If he is to fail, then be absolutely sure that he will think of that moment. And if there is a next time for that kid, he will ask WHY you believe that before anything else. Needless to say that especially applies to anyone highly involved with entrepreneurs.
Being challenging and blunt with entrepreneurs is only making them stronger and better. They may feel like trash after the discussion but it’s only in these situations that they can bounce back with a vengeance. It’s like playing squash, hit the ball hard and it will come back, hit it soft and you may need to pick it up…
Entrepreneurs are seeking validation and satisfaction from the result of their work, not what their friends, mentors of colleagues tell them. What they expect from them is valuable feedback, constant debate of their ideas, practices, style and all. If your intensions are to help somebody, it is far better to express exactly what you believe than to let him realize it by himself, possibly the hard and long way.
So give entrepreneurs what they deserve, your sincere, blunt and fast opinion about their ideas and actions.
Thanasis Polychronakis 
But are you really sure you are focusing on the right individuals?
There must be some kind of filtering process involved (when it comes to addressing individuals) if you want valid and intriguing data to be collected-harvested.
But even sometimes we lay down the wrong questions. We as humans, on times of uncertainty(which is the true nature of entrepreneurs) we tend to be emotionally driven.
So while you think you are looking for guidance you are actually seeking acceptance and confirmation which is not wrong either since entrepreneurship is all about ‘taking the leap’. To conclude id say the most important part of succeeding in your quest is to stay focused no matter the result (and this does not translate in prearranged failure in any kind of way).
Hey Harp, thanks for the comment!
I couldn’t agree with you more, actually i was thinking of posting about these issues back to back with this post but couldn’t find the time. I will however do that in the future, i will ping you then…
This post addresses to anyone that interacts with entrepreneurs, friends, experts, mentors, team, angels, VCs and all… You are absolutely right that it’s the entrepreneurs responsibility to filter and select to who he / she lends his ears to, however we constantly get exposed to comments and opinions. It is for these kind of interactions that i’d much prefer a sincere, blunt and fast opinion instead of anything else…
The point about entrepreneurs actually seeking for acceptance and confirmation couldn’t be more wise and well thought. I will quote you when i’ll write my post to how entrepreneurs should seek and take advice / guidance.
Thank you again for your comment!
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