One of the more pernicious mistakes many less experienced entrepreneurs make is assuming that successful “big business” executives are as a rule well suited to managing smaller high impact businesses.  It’s a pernicious mistake because few things can derail an otherwise promising startup faster than putting the reins in the hands of a poorly suited, even if highly decorated, big company manager.  It is a mistake I once made at one of my own startups, and one that I have seen others make too many times.

There are several reasons big company executives – not all of them, but a lot of them – fail when they transition to the startup world.  Most are related to the notion that managing a startup typically involves making “bet the company” decisions more often (as often as daily, and seldom less often than monthly), with less information, in less time, and with less input from appropriately experienced colleagues, than managers of larger, more established businesses.  Another startup attribute that can flummox big company executives is a culture that places much more emphasis (and reward) on rapid identification of mistakes, and much less on assigning blame for them.  Finally, most big company executives come from a world where the risk reduction paradigm is based on diversification, while for most startups risk reduction is based on focusing limited resources on a very narrow front (albeit one that can change overnight: see above re “bet the company” decisions).

None of this is to say that good big business managers are as a rule not well suited to be good managers of startups.  The point, rather, is that the demands of the jobs – and thus the skill set for doing them well – are different in the two worlds.  Some folks can transition from one world to the other, some folks can’t. 

Of course, figuring out whether a particular big company manager can succeed in the startup world is the real trick.  On that score, I have yet to find a sure fire test.  In my experience, one good approach is, once a candidate has passed the blush test and knows a little bit about the opportunity at hand, to ask her “so, tell me, if you were to start tomorrow what would you do first?”  Look for an answer that focuses on action, not analysis.  Look for a “take charge” attitude: avoid, at all costs, a candidate that looks like a deer caught in the headlights.  Another good approach is to emphasize how, well, broke the company is, or will be soon, without new capital or new/accelerating revenue – and how little the company spends on support staff and services.

If my suggestions seem inadequate, well, they come from experience as an entrepreneur hiring my replacement as CEO.  He had all the right industry experience and networks, and the grey hair to go with it.  If only we had asked him what he would do on his first day at the office, we might have learned about his need for an Executive Assistant, and his passion for good HR policies – as, for example, a standard, monthly process for recognizing the birthdays of the various members of the team.  If we had, we might have avoided making a fatal mistake.