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

Written By: Dharmesh Shah February 5, 2007

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?


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