This is the third article of a three-part series.

Welcome to Part 3 in our series on best practices for leading multiple functions. With the majority of companies having fewer than 100 employees, most employees are asked to do a variety of different tasks.

We have looked at this from the individual contributor and manager perspectives. In this article, we will expose one of the greatest challenges this type of work environment faces and a simple strategy to overcome it.


Oddly enough, even though an employee may be handling multiple functions, he can become defensive and protective of his territory. In many cases, this shows itself as an unwillingness to share information, implement new practices or incorporate a new company direction.

This is particularly evident in employees who have a long tenure at a growing organization. Many lose their sense of urgency and/or their excitement for new initiatives. This type of employee has seen it all before and his lack of excitement can hamper progress, become toxic and undermine leadership.

While it is true that most leaders wait too long to fire people, it is understandable why this is so often the case in small companies — particularly with this type of employee. It is difficult to fire someone handling multiple functions and even more challenging if he has been doing it for a while.

At best, everything is in his head. At worst, everything is in a pile of papers scattered about his work area ... and in his head. Further, leaders often feel a sense of loyalty to these seasoned employees.


A best-practice, proactive move is to document processes as you go. Make it a rigorous practice that is built into the core systems of the company. "Write it down" should be a mantra, and there should be a template that is known and shared by all for creating SOPs and checklists with a noted method and place for storing them. It should be evaluated and re-evaluated regularly, and discussing it should be a brief part of regular meetings and a natural part of daily operations.

In reality, if that did not happen at the start, then everyone is playing catch up. The organization ends up with a bunch of employees with valuable institutional knowledge that everyone regards as job security. Silos are formed, issues silently brew because no one is talking about them (or knows to ask or tell someone about them), and the next crisis is just an unexpected employee absence away.

So what do you do? As one of my clients loved saying, you build the plane while you are flying it. And the best place to start is with the most challenging employee.

Next steps

First, understand why those entrenched employees seem to be so difficult: They have been through a lot of change. In fact, they have been in a constant state of change since they were hired.

Once you understand that these employees can change and have changed they are likely just a bit tired of it and feeling underappreciated you can start to work with them. How? Go back to the basics: Acknowledge what they do, ask their opinion, listen to what they tell you and start finding ways to work with them instead of around them.

Barriers will come down, silos will dissolve, teamwork will begin to bloom, and problems will start to get resolved. Be patient and write down your new processes. It is likely that this difficult employee will become the greatest advocate (and if not, then you can fire him).