Startup Founders: Are You Too Assertive, Or Not Enough?

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Startup Founders: Are You Too Assertive, Or Not Enough?


I came across an article recently titled “Researchers Uncover Best Bosses’ Success Secret”.  I was hoping to find some revealing insight about what makes great bosses.  Unfortunately, I really didn’t glean that from the article.


Basically, the point the article makes is that the most successful bosses tend to find a good balance between being too assertive (and possibly aggressive) and being too nice.  I found this particular revelation to be less than satisfying.  Seems overly obvious that like with many things, balance is key and the optimal value rarely lies at either extreme.


I thought a bit about this and began to wonder how this balance might be found within startup founders.  I talk to startup founders all the time, both successful and not-so-successful.  Is there a particular leaning one way or the other?  Is there a pattern?  I’m not sure.


Here are some of the thoughts/ideas I had.  Feel free to push-back or make counter-arguments.


  1. Startups that have raised venture funding seem to me to be more assertive, on average, than those that haven’t.  This doesn’t surprise me too much.  I’m guessing that VCs, like other people, gravitate towards others that are like them.  VCs are a relatively assertive bunch so it would not surprise me if they were more likely to fund similarly assertive entrepreneurs.  Further, the entire process of VC-fund raising seems to favor the assertive.


  1. Startups that are bootstrapped may exhibit the opposite characteristic (particularly software startups).  In order to recruit a talented software team, founders of bootstrapped startups have to offer something other than high cash compensation and monetary rewards.  One of those things might just be that they’re easier to get along with and fun to be around.  Think about it:  If you were a software developer looking to take a big stake in an early-stage software startup and work for a below-market salary, are you more likely to pick an uber-assertive (or aggressive) founder or one that is more laid-back?  I’d pick the laid-back one.  Similarly, if the company is venture-backed, it can afford to pay competitive salaries and hence hold people accountable.


Clearly, I’m painting in broad strokes here and am dancing a fine line towards stereotypes, but I like to think in stark contrasts sometimes, as it helps identify patterns that are sometimes useful.


What do you think?  Are there any patterns you’ve seen when it comes to degree of assertiveness in startup founders?  Which way do you lean?  Do you think this helps you or hurts you?


Posted by Dharmesh Shah on Mon, Feb 05, 2007


Assertiveness is not the opposite of nice, and thus, they're not endpoints on a continuum. I think it's possible to be assertive as well as nice; I guess that's called persuasion.

posted on Monday, February 05, 2007 at 10:33 AM by David Duey

I'd definitely agree with you about #1 since assertiveness can be linked to confidence. I don't believe I'd want to fund a group who was willing to give into every suggestion/challenge that I threw at them. You don't want somebody completely hard-headed, but you do want people who believe in their ideas. For #2, I'm not sure that I quite agree. Some non-assertive owners are just laid back and very open to suggestions. Others just have no sense of direction, and their product kind of floats from idea to idea.

posted on Monday, February 05, 2007 at 1:18 PM by Chris Campbell

I question #2. if someone is taking a big stake in an early-stage start-up and working for below-market salary, wouldn't they be most interested in the founder being someone who is likely to succeed? Equity is just so much paper if the start-up fails, and there is not much point in exchanging current income for equity if you are not banking on success. That is not to say that success is tied to being an aggressive boss. There are many management styles, both good and bad, and being assertive does not mean being difficult. Some of the best leaders in my experience are those who know what they want and don't comprimise their goals. However, the difficult part, which most people never really master, is getting others on board with your goals. An assertive leader can choose to inspire or bully their team, but inspiration is far more likely to succeed in the long term.

posted on Monday, February 05, 2007 at 2:20 PM by Vince Frisina

I agree with your points. Can we be honest here? Most people who are extremely (or even moderately/fairly) assertive are not as fun to be around as those who are pushovers. (then again, that could just be me) Whenever you get two assertive people together they usually butt heads. One will have to stand down or they will have to come to an agreement. Things are tense and not as much fun this way, I've found. But you're right -- it does take assertiveness to build a successful startup. The biggest problem is founders believe everyone has the same 100% zeal and optimism about their startup as they do. When you have 40-100% of the company, and your employee has .0001% to 3% (as is usually the case), and where not there when you sat around with buddies & decided to start the co., then why should they? (unless you are already like a YouTube just before its about to get bought, etc -- rarely the case early on) Just my $02, from both sides of the fence.

posted on Monday, February 05, 2007 at 3:31 PM by Shanti Braford; On Web Apps

A laid back boss in a startup ? I wouldn't want to join that company at all. In my opinion assertiveness almost always equals to passion and commitment. And of all companies startups do need assertive bosses.

posted on Monday, February 05, 2007 at 7:49 PM by Website Developers

Assertiveness + Ready for Risk = startup.....
I think the person who is going to startup something somewhere in his mind,planning is assertive.just whts the problem is one can get or see that assertiveness......again one thing is that person who is assertive is always ahead of sometimes people around him keep joking..that what exactly he is thinking of.I know i am going out of track..but this is the common thing i found....I am writing here all these things because...someone who is coming here..may have started or may want to start i suggest dont think of anyone and just start according to ideas in your mind....dont give up to negative forces around you...and keep going....because i strongly you are reading are ahead of world..ahead of time...and want to do something...just start...!!!!


posted on Tuesday, February 06, 2007 at 12:06 AM by UdayRaje Patil

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