This is one of many biweekly columns I've ghostwritten for a B2B client specializing in trend forecasting.

So You’re Stuck in Antarctica
Crisis Leadership Lessons From a Master




Coaching difficult people is an inevitable part of leadership. It can also be an onerous task. Done well, it requires strategy, thought, self-talk, and self-assessment. It also requires a degree of vulnerability—something that many of us struggle with, particularly when we hold positions of power. This week we’re looking at various factors that play into successfully coaching problem employees.


A colleague tells us that she was recently on a call with clients for whom she’d soon be hosting a workshop. She invited the people on the call to let her know about anyone participating who might potentially be difficult: maybe they disagree with everything on general principle, or very much prefer that everything stay the same as it’s always been, or perhaps they simply poke holes in every new idea until there’s nothing left to work with.


To her surprise, the clients went silent, then giggled nervously. Finally, with some encouragement, they named names and provided details.


Get It Out of the Way Early On

“It was clear they felt they were telling tales out of school,” says our colleague. “But my team assured them that the information would not travel beyond the call, and that the reason we needed to know was so we could tailor our approach in working with each of those difficult people. We make sure to have an informal conversation with them first, one-on-one, to establish rapport, listen to what they say, notice what they don’t say, and strategize internally about how best to convey information as well as provide expected outcomes. Most of the time, it works. Sometimes it doesn’t! But it’s generally a reliable tool for us.”

Here’s why that approach works, according to Erika Andersen, founding partner of Proteus International, “a coaching, consulting, and training firm focused uniquely on supporting leaders to get ready and stay ready to meet whatever the future might bring.”  Andersen has written several articles for Forbes about coaching employees, and while those articles are a few years old, our colleague considers them evergreen inspiration for effectively leading teams and coaching difficult people. In fact, key points of her approach reflect Andersen’s 9 Ways to Deal With Difficult Employees.


Don’t get sucked into an endless vortex

Andersen writes: “…most managers get held hostage to these folks, spending a disproportionate amount of time, thought, and emotional energy on them… Here, then, are nine things that excellent managers do when confronted with a difficult employee—things that keep them from getting sucked into an endless vortex of ineffectiveness and frustration.”


  • Listen.

When an employee isn’t doing well, Andersen says, the best managers become very attentive. “They know their best shot at improving the situation lies in having the clearest possible understanding of the situation—including knowing the tough employee’s point of view.” Too often, when people are difficult we approach them having already made up our minds about them. That’s not conducive to good communication. 


  • Give clear, behavioral feedback.

Focus on what needs to be done, and on providing the employee with the information they need to be successful, rather than on your frustration. This way they feel less defensive and more empowered.  


  • Document.

Write down the key points of the situation anytime you’re faced with an employee who is causing significant problems. “Good managers know that documentation isn’t negative— it’s prudent,” writes Andersen.


  • Be consistent.

Setting expectations? Great. Now carry through on your end of that bargain. If you’re inconsistent with what you’ll accept from employees, you’re undermining your own credibility.


  • Set consequences if things don’t change.

Clarity is everything. If you see that things aren’t improving, do two things: tell the employee you believe that they can turn this around, and then tell them that if they don’t turn it around, X will happen by Y date. 


  • Work through the company’s processes.

At this stage, be sure you’re in touch with your HR department about the situation, providing all pertinent information as well as your documentation. That way you’re crossing all t’s and dotting all i’s in the event that termination becomes necessary.


  • Don’t poison the well.

It’s human to want to vent about frustrations, but be sure to avoid badmouthing the difficult employee. Per Andersen, “It creates an environment of distrust and backstabbing, it pollutes others’ perception of the person, and it makes you look weak and unprofessional. Just don’t do it.


  • Manage your self-talk.

Find a balance between thinking “This is all going to be fine” and “That jerk will never get a clue.” Ground your self-talk in accuracy, in evidence, and in fairness.


  • Be courageous.

If you find yourself faced with the task letting the person go? Do it, and do it right. “Don’t make excuses, don’t put it off, don’t make someone else do it. The best managers do the tough things impeccably,” says Andersen. 

When You Know Better, You Do Better

Aside from coaching the difficult ones, a tough thing about managing people in this day and age is simply keeping up with quickly-evolving social mores; it can seem like a full-time job all on its own. We get that. And: it’s necessary to continue to evolve as leaders if we want to continue to be successful. The keys to that are learning, growth, and a willingness to be open and vulnerable. After all, regardless of what business we’re in, we’re all in the people business.

ITIS (If Time is Short): Coaching a problem employee? Put your focus on clarity, communication, curiosity—and process.

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