I am a loyal reader of Brad Feld’s blog. He not only has thoughtful posts, but he does an incredible service to entrepreneurs with his Term Sheet series, where he explains many of the crazy terms that you can find in a Term Sheet.

Earlier today, he had a post titled When Does An Entrepreneur Need “Experienced Help”. Give it a read. I left the following comment:

From the wording of the question, I would have guessed that your friend has not had success working with entrepreneurs. The obvious clue was the judgmental “real smart ones that know when to bring [him in]“.

And his lack of success says to me that he has come into his COO/CFO roles with the wrong attitude. If I can rephrase the question as an entrepreneur with his similar wording, I may say this:

“I was interested in your thoughts on when experienced Series B executives realize they are part of an existing team and culture that needs to bring an additional perspective to the ones the entrepreneur and other executives have at the company. The real smart ones that understand know that they are bringing their experience to an existing table and are not the next great hope of the company.”

It is the very difficult job of the entrepreneur to create and the equally difficult job of the “experienced help” to come into a startup and have the entrepreneur and the rest of the team want to listen and follow. The “real smart” entrepreneurs do not roll over and the “real smart” experienced help do not expect a handover.

So how to avoid? Your advice to your friend is fine, but that may test the social interaction of the participants rather than their working style. While it does not always work, I try to set up a few business scenarios (from mundane to difficult) that we can discuss (say, how to launch a difficult product, how to turn around a difficult but loyal executive, the merits of a particular go-to-market strategy) and see how the discussion goes. Do we reach the same conclusion? Do we reach different conclusions respectfully? Does one person always give? Do we give build on top of each other or do we debate?

It is unlikely we will be friends, but we must become great business colleagues.

Bringing “professional” executives into a startup is the one of the most delicate stages of a startup’s development. I have not seen a consistently good best practice for this. If anyone else has, please share with the world.