How to get the best results from hiring a former entrepreneur.

I have been an entrepreneur for 8 years and in the corporate world for about 6. At some point, had the privilege of being an Executive Coach. I had great learning opportunities in engaging former entrepreneurs as well as being engaged as one. So, here are some lessons that would help you, as a business owner, or a board member, to get the best out of engaging an ex-entrepreneur, into a full time role.

  1. Give a role that requires ‘change’ or ‘top-down’ perspective. Roles that require managing, Business As Usual (BAU) or a department, may not get the best out of him. You could make him responsible for driving performance, change, innovation, employee engagement or a turnaround, transformation, scale-up, or a start-up. Even, if he is going to manage a key department, it could be with a mandate to bring about ‘change’ with agreed performance criteria. You may also transition him through various departments, before ultimately giving him a role that uses his top-down perspective.
  2. Bring out his natural sense of ownership on the job. Its very different when he is an actual owner in his business and when he is in employment. Its important to communicate mutual expectations. Link his contribution to the company’s goals and set performance measurement benchmarks. Figure out what authority/resources/tools may be required, to accomplish his goals. This will help, invoke a sense of ownership which, he is so used to working with.
  3. Find out why he wants to get into a full time employment. You may or may not want to broach this topic, but avoid making a presumption on whether or not he was successful in business. For all you know, he could have made a conscious choice to wind-up a money making business, that no longer served his vision or no longer gave him joy. Even if his business did not sustain, he has likely learnt important lessons that may help your company avoid costly mistakes.
  4. Are you worried about lack of domain knowledge in your sector ? If he has been a smart businessman, he will pick up the sector knowledge before you realise. Typically, an employee who has spent 10-15 years in a sector, may be considered fit for a strategic role. But you may not, look at an entrepreneur with the same lenses. If he is diligent, he would figure out the missing links and capture the domain knowledge while working towards the goals. So if he has the leadership skills, and has spent years in other sectors, you may still consider him for a senior role. He is likely to come in with a fresh perspective, and you may discover some old assumptions that may no longer be true.
  5. Position him in the hierarchy, closer to the ownership, board, or the CEO. However, if you must have him lower down the hierarchy, let the expected reporting manager take full ownership and accountability for the results. In any case, keep an open channel with him, with a dotted line reporting to the top.
  6. Once hired, place your trust, empower and make accountable for results. Position him through the organisational structure with a balance of authority and responsibility. Absence of empowerment, may affect his ability to bring out the best from the people. You can always make changes or discontinue the engagement, but its best to give a fair opportunity.
  7. Engage him with clarity about his future plans. Don’t presume that he is transition, waiting for another business opportunity. If you are going to hire him with this thought at the back of your mind, you may not empower him adequately which is necessary to get the desired results. Its best to talk this over in the beginning and get some meeting of minds and mutual assurances.

Engaging former entrepreneurs comes with its own risks. However, if you are able to strike a win-win, it may propel your business towards excellence and instil the much needed ‘intrapreneurial’ work culture that you have been striving to bring into your organization.


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