One of the things I have always loved about start ups is that smart, ambitious, courageous people can reach high and take on a job bigger than they have ever had before…unless you are the CEO.

This seems rather ironic. On the one hand, we have all heard the numbers from recruiters about how many open CEO searches there are at any one time. No one kids themselves that we have high quality, experienced CEO’s to fill all those roles. And yet Boards don’t often seem to set up an environment where a “rookie” CEO has a real opportunity to grow into the job.

Some Board members don’t believe in backing first time CEO’s. As one of my VC client’s said openly, “We don’t have time to develop leaders.” Others say they are willing to go with a first-timer (if the deal is good enough and competitive enough), and some are even up-front enough to say “we are giving you a chance, but if you don’t cut it we — or the next round investors — have to find the right guy”

Unfortunately, this sets up an uncomfortable situation from the beginning, with the CEO feeling like he is on borrowed time. He may be reluctant to ask for help, or to enlist coaching and mentoring resources — afraid that to admit he doesn’t know something is to reinforce the VC belief that he “isn’t the guy”. So you have a guy who hasn’t done it before, who may not ever have seen it done well before, pretending he knows exactly what to do (and defending himself mightily if he fails).

So…how do we solve this dilemma? The responsibility may be on the CEO-wannabe to ensure that he engages in an ongoing conversation that is open and constructive. He should be prepared to present the Board with his own self-assessment, listing those areas where he is less experienced and identifying resources to help him. He (or she) should set up a structure so that concrete conversations happen on a regular basis about CEO performance, and that objective data is gathered. (Frequently, using a 360-degree process and tool, such as that listed on this blog, can help facilitate the conversation). The CEO should be willing to ask for and accept (and utilize) feedback from not only the Board but from other resources.

As for Board members…have the hard conversation early. Rather than remaining mute out of fear of losing the deal, earn the entrepreneur’s trust by openly discussing your expectations. Provide the entrepreneur with an honest assessment of where he or she falls short, and be prepared to share resources he or she can use to grow. Work with the entrepreneur to agree upon a process for ongoing assessment, using an objective tool or party to facilitate the discussion.

A few year’s ago the SF Chronicle ran the results of an informal survey they did of companies in the Bay Area, comparing their ultimate success against whether they still had their founders involved. They found that the companies who retained their founder in some role were ultimately more successful. What that means for investors is that they need to work harder to set up an evaluation process for the CEO that will enable the company to retain the talented founders. What it means for potential CEO’s is that they need to accept that the best way for them to help the company be successful may be to move out of the CEO role at some point. The key for both is knowing when, and how, to best make that decision.