Hiring for a startup in the early stages sometimes requires you to go counter-intuitive. For example, take experience - it's not always a good thing.
This is not a be-young-or-die creed. It's more about the need to have a certain approach - a 'beginner's mind', which is open to new ways of doing things and is willing to find out what's needed and learn it. And while age alone is not a barrier to the open mind, ego often is.
I'm beginning to believe this approach is critical even for tactical, technical positions, though here experience in specific skills would be a definite requirement. But along with those skills, you'd need to check if the person is walking in with a 'Let's see if what I did before would work here' versus 'I've done this before, I know it all'. For example, how many of us have tried to rescue project management from the set-in-concrete opinions of 'experts'?
But what about the executive/strategic positions? Here the issue is even more pronounced as most executives have a very healthy opinion of their accomplishments. They have their own blueprints, templates and strategies on how to get things done. And these are useful, and often sought after, if they're switching from one corporation to another. They may even be helpful in established startups with stable teams, product and market. But an early stage venture is a shifting stage where you're better off polishing your improv skills and putting your well-thumbed script from past positions in the bottom drawer for a later date. For example, the VP of engineering shouldn't be surprised if there's no backup process and no sys admin to delegate it to either - he should be googling backup strategies and trying stuff like getting his comp sci major cousin to moonlight for a bit.
So how do you figure this out without some fancy psycho-savvy interviewing? Smart interviewing is important, but you can do some smart resume filtering first. Too much experience of the 'wrong' (read 'same') type is a handicap in a startup. You might have a chance if the candidate has a track record for learning/doing in different jobs and a demonstrated ability to work in places with big and small budgets (frugality, the retro startup chic), but even then you may want to go the consult-then-convert route to make sure you have a good fit - way less stressful than hire-then-fire. Startups need to be adaptive and flexible, and if you get the guy who's made a career out of driving nails with his hammer you get nothing but a pounding headache - while the one with a swiss army knife can uncork some wine, slice some cheese, open up a can of olives...
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