A blog reader who I know and have worked with in the past asked me the following question:
I was interested in your thoughts on when entrepreneurs realize they need experienced help and have taken the company as far as they can, when they let go, when they stay too long and the real smart ones that know when to bring someone like me in early and work with me instead of fighting against me.
This friend has been the number two guy in several companies. In each case, he was brought in by the entrepreneur as the CFO or the COO. In the situations I’m aware of, he was initially welcomed by the entrepreneur (who – in each case – was the CEO and had an autocratic style), but – after a while, started to have real difficulty working with the entrepreneur, especially as the company outgrew the entrepreneur’s experience base.
As I pondered this question, which would require an entire book to really address it, I realized there was a parallel issue in all the situations I was aware of. My friend is an extremely capable medium stage executive. He’s not a raw startup guy, but he knows what to do from 50 to 1,000 people. In each case that I’m aware of, the entrepreneur “brought him in” to help “get the company to the next level” (where have you heard that before.) However, the entrepreneur / CEO didn’t really cede control and - when my friend started to put his mark on the company, a very predictable friction occurred.
While I think this kind of relationship is possible, it’s critical that the entrepreneur and the new executive agree on roles and rules of engagement up front. I think the biggest problem is that during the recruiting process, both sides are selling the other side on their desire to work together and their ultimately flexibility. Since the entrepreneur is looking to hire and the executive is looking for a job, there’s a fundamental conflict in their motivations and the honest, difficult, confrontational stuff doesn’t come out - until later.
My simple advice to my friend – once you get past the “selling part” of the process and have a real offer on the table from the entrepreneur, go out to dinner (or better yet – get on a plane and go somewhere together for the weekend) and have the real conversation about what life is going to be like. See if you can get the issues out on the table before you accept the job. If you can, listen carefully, engage, and see where you go. If you can’t, you just learned something huge.
Predictably, the same information applies when an entrepreneur is considering a new investor – VC or otherwise.
Posted in: QACOMMENTS (2)
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
Excellent comments You Mon - I assumed that was part of the "interview" process, but it's crucial to reinforce how important that is.
, June 21, 2006 10:34 AM
Thanks for signing in, . Now you can comment. (sign out)
(If you haven't left a comment here before, you may need to be approved by the site owner before your comment will appear. Until then, it won't appear on the entry. Thanks for waiting.)