Should you consider hiring someone who has many years of contractor experience to be an employee?
This one is more of a yellow flag than a red one. It can work, but you should understand the risks.
Long-time contractors are typically specialists with depth in their niche. Hired guns. Snipers. Delivering specifics on time and with precision.
However, when you transition them to employees, the landscape shifts. You’re need team members who are invested and show up every day with curiosity and conviction. Your contractor ace swimmers may flounder on dry land.
Employees need a different skill set. They require breadth. Versatility is their secret weapon. They juggle tasks, pivot quickly, adapt to new roles. Their playground is vast. Their utility, manifold. They care. You want them to care.
A contractor turned employee might struggle to broaden their horizon and to invest the way you need them to. The singular focus that once was a strength may now be a constraint. Plus, they’re used to filling a role for time period, and then moving on.
Hiring a long-time contractor as an employee is an exercise in balance. It’s about finding that sweet spot where a contractor’s laser-focused expertise and an employee’s diverse skill set intersect. It’s also about finding someone who’s willing to invest — in the mission, the team, and themselves.
So, look before you leap. Transitioning a contractor to an employee might sound like a logical move, but it’s not always the winning move. Beware.
