5 Strategies for Managing Unmanageable Employees

Photo by Austin Distel on Unsplash

As an entrepreneur, you’ll encounter your share of employees. During the hiring process, you’ll do your best to select candidates with solid experience, a great attitude, and references that support their abilities to perform in a work environment. Unfortunately, even the best candidates in the interview process can have quirks that make them difficult to work with in day-to-day operations.

Not all working difficulties are worth firing a candidate over. For example, you might have a fantastic programmer who always gets his work done on time and doesn’t mind getting paid less than his contemporaries, but is sometimes difficult and flat-out refuses certain requests to cooperate.

Absolute submission isn’t a prerequisite for a healthy working relationship — in fact, some resistance is good and can help you understand differences in perspectives. But unmanageable employees make it difficult to keep your team productive while retaining the image of a leader and the integrity of your original direction.

If you find yourself in such a situation, try one of these five strategies:

1. Set firm, written expectations. Be clear in the early stages of your relationship that there are some things that aren’t negotiable. Setting expectations in advance of any issues ensures there is no surprise or confusion when those expectations are enforced. For example, upon hiring, you can make sure your employees know that working from home is okay, but only after giving 24 hours’ notice to an immediate supervisor. If an employee rejects this policy by declaring work-from-home days the morning of a workday, remind him/her that this firm policy was made clear up front. Generally, a warning is a prudent first course of action, but if violations are repeated, termination may be necessary.

2. Prioritize your requests. This is a professional version of “picking your battles.” If you know your employee is going to resist at least some of your requests or directions, be clear about which ones are necessary and which ones are open to discussion. For example, if you call for a meeting with your difficult employee with the intention to ensure his work toward an upcoming deadline, address a punctuality problem, and request a meeting attendance, the deadline issue is undoubtedly the most pressing. You can offer leniency in the less important areas, telling your employee he can skip the next meeting and have some flexibility in his arrival time, as long as he doesn’t miss the deadline. Doing so shows that you’re willing to compromise on minor issues, but your overall vision must take absolute priority.

3. Find alternatives. There are some items in your business that are black and white — for example, if you meet this upcoming deadline, your client will be happy, and if you miss it, your client will leave. Therefore, meeting the deadline is necessary. The way you achieve these ends is more of a gray area; you may ask your employees to come in early each day in a week to ensure this deadline gets met, but your unmanageable employees might resist. Instead of forcing the non-morning people to comply with your requests, remind them that the deadline is firm and ask them for an alternative solution to ensure it gets met.

4. Document improvement plans. If your employee challenges every request or is otherwise impossible to manage in any meaningful way, document her known issues and mutually create an improvement plan. For example, you can work with the employee to come up with a 90-day plan with four main necessary improvements to her behavior and performance. Once these 90 days are up, meet again and go over the improvement points. If she has improved, your problems are solved. If she has not improved, you have clear grounds for termination.

5. Use peer pressure. If the rest of your team is perfectly manageable and easy to work with, use them as examples to help your problem employee assimilate. For example, if three of your best employees comply with a new policy and see a spike in performance, reward them publicly with a free lunch or something similar. Eventually, your difficult employee will learn that complying with management yields positive results, and will naturally come closer to the cultural standards your company has set.

Some employees are simply easier to manage than others, and some hard-to-manage employees are worth the extra effort. If you choose to keep a more challenging employee on your team for the long haul, all it takes is a shift in perspective and a little extra patience to make things work. If you’re still having trouble after employing these mitigation strategies, it’s probably time to find a new candidate.

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

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