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One of the benefits of being involved in several companies is you get to see a lot of individuals in action - managers, entrepreneurs, board members, technical advisors, investors, and customers. My takeaway from watching all this action can be summed up in three words: Shoot the Dinosaur.
First task: identification. Who is this dinosaur I refer to? The dinosaur is not necessarily the oldest person on your team (he may be the youngest.) The dinsoaur is simply that person on your team that places a drag on your organization by using technology or work practices from a different era (or planet).
How much time and money does the dinosaur cost a startup? Heaps. Hell, I've seen dinosaurs have the same effect on a startup as the proverbial bull in a china shop. I've seen dinosaurs bring down companies that otherwise would have flourished. I've seen dinosaurs drain the life from an entrepreneur's idea by insisting on a three year path to market when a one year path was possible.
Can a dinosaur add value? Yes, but rarely. Possible exceptions are legal and financial advice - and sometimes, human and corporate relationships. Dinosaurs with solid financial and/or legal/deal-making credentials on their resume are worth keeping around.
But operations? Development? Marketing? If you must have a dinosaur at the table, keep them as far away from that stuff as you possibly can - because what a dinosaur (particularly a dinosaur with an MBA) thinks is a solid marketing strategy for today could bankrupt your business without returning your a cent in ROI.
Is there a more humane way of dealing with a dinosaur than shooting it? In my experience, no. The dinosaur resists re-education with the same vigor as a Republican resisting socialized medicine - once a dinosaur, always a dinosaur.
Shoot the dinosaur. Kill it. Don't wait. Your business will thank you for it.