How 'Problem' Employees Can Teach You More Than 'Easy' Employees How can the word "problem" be a good thing? Here, a small business owner with 15 years of personnel management under her belt shares how the hard-to-manage team members are actually the ones who make you a better leader.

By Emily Reynolds Bergh

Key Takeaways

  • Running a successful business requires attention to your staff as much as to your services.
  • Solving HR problems is more empowering and enlightening than never facing challenges in the first place.
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I don't know about you, but "over" is the most-used prefix in my lexicon these days. More often than not, I'm overworked, overwhelmed, overtired and overextended. So why would I, or any of my fellow entrepreneurs, invite more complications into our work environments? Why would we keep on "problem" employees when we don't necessarily have to?

For me, the answer is straightforward: I learn far more from staffers who are, uh, "difficult" than from those who aren't. And the longer I'm the boss at my own PR firm, the more I realize that it's the learning that I find fulfilling; it's the learning that keeps me going and growing.

Related: How to Manage These 6 Different Workplace Personality Types

Solution-based staff supervision

Before I explain what I mean by a "problem" employee, I want to clarify that I don't mean someone truly troublesome — someone dishonest, lazy, unreliable or mean-spirited. I'm not running a daycare, after all. I have enough kids of my own to raise and discipline. No, I mean that the talent is there (or at least budding talent), and the commitment and passion for the job are there, but they're just a handful to manage. So you have to find ways to handle them that work for both of you. Here are some examples that come to mind.

Case study #1: The needy employee. Chelsey was young and relatively inexperienced, but she was sharp and upbeat, and she won me over with her hunger to excel. The problem was, she couldn't seem to make the slightest move without running it by me. A bit of hand-holding is expected when training a newcomer, but I didn't have time for babysitting.

So I assigned her a mentor on my staff who would guide her through her various job functions with a series of task-based lessons. The goal was to develop her skill set and, in the process, her self-confidence. The trick was limiting the time the mentor would devote to Chelsey. They had one-hour sessions on Tuesday and Thursday afternoons, and beyond that, Chelsey couldn't come to her mentor with questions or doubts — she had to wait until their next session and, in the meantime, do the best she could on her own.

Within three months, Chelsey was working far more independently, not to mention effectively. I learned from Chelsey, now an account manager for a swanky advertising agency, that team members need coaching, not coddling. If you need your people to grow up a little, treat them like adults.

Related: Do You Need a 'Babysitter' for Your Business?

Case study #2: The overstepper. Jeremy was a dynamo. When we met, he promised me he could secure media placements like no other, and he'd rest at nothing to be the best publicity manager I'd ever seen. He didn't disappoint, and when he moved away and moved on, it was a sad day in my office.

But what I wasn't sad to see go were the constant calls, texts, and emails I'd get from him round the clock, even on weekends, holidays and vacations; he was go, go, go, and it was exhausting me. He just didn't seem to have any boundaries, so I realized I had to create some of my own.

Rather than singling Jeremy out, I devised an employee handbook that included an "After-Hours Decorum" section, in which I mapped out what working hours were expected of my team and what circumstances warranted interruptions around those hours. Everyone signed their agreement, and whenever Jeremy overstepped again after that, I'd playfully remind him of company policy with a cute little note and emoji. It took a few weeks to redirect his habits, but after that, we were wonderfully in step!

Case study #3: "Miss Independent." I'll never forget Jess — her fierce determination, pluck and resourcefulness. But from the day I took her on, her unspoken message was clear: "I prefer to work alone." The problem was that my team doesn't run like that: we must collaborate at all turns to attend to each aspect of a client's contract adequately.

Jess didn't like to view herself as a link in a chain, though; she wanted to be a self-contained clasp. She'd pass on materials to a client before I'd review them. She'd email a press release to a media outlet without prior approval. She'd inform our webmaster that a blog was ready to be posted when it hadn't been proofread. Nuh-uh. Not on my watch.

So I brainstormed with my editorial manager to produce a workflow pipeline. We held a group meeting to review the flowchart, and I clarified that adhering to it wasn't voluntary. Given Jess's stalwart work ethic, she readily understood that she now had to follow protocol like everyone else, so she fell in line without much resistance. Jess taught me that it's great to have a strong-willed filly in your stable, but when it's your business, your corral, you still have a right to tame a wild horse and train them to trot with the rest of the herd.

Related: 5 Tips to Make Managing Employees Less Stressful for Everyone

Case study #4: The headache. Nathan was so funny. He brought levity to our meetings and perspective when things got stressful in the office. But oh my, that guy gave me a headache! Every single time he came to me, it was to profess a problem and then painstakingly detail all the circumstances.

I relied on his expertise in his role and admired what a willing learner on the job he was, so after popping one too many ibuprofen after his last complain-a-thon with me, inspiration struck: teach Nathan how to solve his own problems instead of solving them for him. So I turned my idea into a bit of a professional development unit, giving Nathan the express assignment to start sending me emails presenting the issue briefly and then listing at least three ways he'd address the problem if he were in charge.

Since he loved earning gold stars and enjoyed sharing his considerable knowledge, my experiment succeeded. Before I knew it, Nathan was sending me messages containing options A, B and C — and all I had to do was reply with a multiple-choice answer! Not only did I reduce the number of fires that crossed my desk, but it led my employee to learn how to put out his own fires.

So the next time you're dealing with a team member who's a little more challenging than cooperative, ask yourself where the learning is and what you can do to advance their professionalism while also benefiting your profession. The easy, breezy, steady employees make my business run smoother, but the more difficult staffers have taught me to be a better leader by making tough decisions.

Emily Reynolds Bergh

Entrepreneur Leadership Network® Contributor

Founder at R Public Relations Firm

Emily Reynolds Bergh — vintage-shoe hoarder, cycling junkie, & lover of pink drinks — is a marketing & PR pro with 15+ years of experience under her belt. Now the founder & owner of the award-winning R Public Relations based in New York, she’s been featured in numerous publications & podcasts.

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