Several professionals who have had solo service businesses or small businesses have reached out to me recently for help with the entrepreneur to employee career transition. This is not surprising because the search engines think I am one of the leading experts in this space, thanks to two interviews Carol Roth did with me on years ago. (Thanks, Carol! Interview 1 and Interview 2.)

These would-be employees come to me with anxiety and self-doubt, looking for guidance. That is fine. I have mapped out the entire entrepreneur to employee process and everything that is involved on my service page. Analytical thinkers LOVE my presentation and it makes them feel comfortable and supported.

Then comes the part where they need to make the payment to begin our work together. In the past, my social proof and recommendations on LinkedIn were enough to convince people to take the plunge. Now, people seem to think they might not need the whole coaching package and want to do individual sessions because even though they may not have had a corporate job in years (or ever), they somehow think they know what will be involved – and that it will be fairly easy.

It will not be easy and they have no idea what hoop-jumping skills will be required. In short, they don’t know what they don’t know.

Is it possible? Absolutely! I have helped many entrepreneurs get corporate jobs.

Several long-time colleagues have exited the businesses they had for 14 years, 16 years, and 19 years. They left for senior manager or director positions at leading brands. At some point in this process, they called me to get the inside scoop on what was working right now.

The entrepreneur to employee job search process has all the pieces of a corporate employee to corporate employee search with some additional – and critical – pieces. Your story about why you are exiting your business needs to be buttoned up and PRACTICED. And you need several levels with slightly more detail at each if you had a big fight with your cofounder, divorced your cofounder, went broke, etc.

Mostly, you want to have your answer so short, clear, and understandable that it goes away. You can dig yourself a very big hole with this question.

The other thing you need to practice is why you are looking forward to joining a team. The person interviewing you will ask you at least once, and maybe several times, why you don’t want to start another business. They will have concerns they may not mention about whether you will fit in and be able to take direction. I urge people to tap into the real reason(s) and say it loud and proud.

It might be that you are looking forward to doing something bigger than you could do on your own. It might be that you really enjoy mentoring a big team. It might be that you are looking forward to having access to A-level talent that you couldn’t afford in your own business. It might be you are tired of being the CEO and the janitor and are looking forward to using just your best skills to benefit the organization.

Any of these can work, but you shouldn’t try to fake it. It has to come from the heart. People’s BS meters are finely tuned.

And this transition takes time, folks! Generally, at least four months, and you should plan for six. My experience has been that entrepreneurs who have never had “real jobs” don’t stick it out through the inevitable rough parts of the process. Entrepreneurs who worked in corporate previously can make the case that they know how to be successful in a corporate environment. They usually have some compelling reason for making the change and keep it front of mind.

So, if you are thinking about making the entrepreneur to employee career transition, my best advice is to hire someone to help you navigate around the potholes and setbacks. The recruiting process at most companies is stupid and broken.

However, when you hire a professional, let them do their job, follow their proven process, and trust their judgment. That is why you reached out to them in the first place.


Photo by Annie Spratt on Unsplash