I often talk about the importance of hiring experts but I’m not suggesting you should fire all your loyal staff and start fresh. Sometimes you’ve got terrific employees already working for you. The challenge is to retrain someone who has been a Jack (or Jill)-of-all-trades to prepare him or her for a particular role that specifically meets the needs of your organization.

Assess Jack’s Skills

Often employees adapt to the role they have been given. The first step is to do a true assessment of their skills. I use a skills-based assessment tool to evaluate different skill sets of a job applicant or employee.

Right now I’m working with a founder who is in the process of turning his company over to his No. 2 employee. The founder had assumptions about his employee’s skills but as I worked with both of them, I’ve realized that actually the employee has adapted to being in the No. 2 position and is using the skills necessary for that position. He also has great skills for leading the company but hasn’t had occasion to use them. Doing an honest evaluation of the skills of a Jack-of-All-Trades helps you to know whether an employee is suited for a particular new role.

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Get specific

Be clear about the position you are trying to fill when you approach your Jack or Jill. Explain to the employee about the position, and that you are willing to put together a training program for them to take it on. Be sure to ask whether it is an area they are interested in pursuing.

Be smart about who you pursue

Even a Jack-of-All-Trades has areas where he is more skilled and interested. If you have a Jack or Jill whose strongest skill is human resources and you are looking for a CFO, that person might not be the right one to groom for that position.

Make sure that you are setting out an honest development program for your Jacks-of-All-Trades. Your staff should know that you are committed to further developing their skills to grow the business and that you will focus on their aptitudes and interests as part of this program.

Just don’t do this

Probably the worst approach to putting a Jack-of-All-Trades into a more defined role would be to make the decision rashly. Trust me, you don’t want to say: ‘Our numbers are all messed up! We need a new CFO! Bob, you’re going to be it! I’m sending you off to take some classes!’

Instead, the best way to train a Jack-of-All-Trades for a new role is to foster a culture of developing your staff into areas in which they are both interested and able.