Stuck with a Problem Employee? Ask Madeleine

Dear Madeleine,

I am a 31-year-old female attorney who was recently promoted to manager of an in-house legal team for a giant global not-for-profit organization. One of my direct reports is a man who came to us after having been a partner at a highly respected firm. This is to be his last job, as he is nearing retirement.

We all thought he would bring enormous expertise to the job and add value; but, in fact, he has caused nothing but trouble. His work is shoddy on his best days—I spend far too much time reviewing and correcting it before it goes out. He makes errors that make no sense in light of his experience. He is clearly not paying attention. He leaves work early on a regular basis, which would be OK if his work was done; but he misses deadlines, which ends up as a crisis on my desk at the end of the day.

All of this would be simply annoying, but it is compounded by the fact that he is downright rude to me. He makes no effort to disguise his contempt for my age and gender.

I have made tremendous efforts to be a good manager, making tasks and standards clear, providing ample time for one-on-one meetings to review workload, etc. I would fire him—I have an entire page of documented incidents in which he failed at his task or was disrespectful or hostile to me personally—but, because of the economic squeeze of the pandemic, we are in a hiring freeze. We just don’t have the manpower to cover his work, cruddy as it is. I have gone to HR, but they are overwhelmed with layoffs and furloughs in other parts of the organization. I am at my wits’ end with this situation.

Shoddy Work Making Me Nuts


This sounds tough. I definitely used to be automatically dismissed by older men—it is a consolation of age that that kind of thing tends to fade. But that doesn’t help you right now. Right now you have a couple of separate issues, so it might help to tease them out and address them one at a time.

The first thing to tackle is the idea that, because of a hiring freeze, you are not allowed to replace an employee who can’t—or won’t—perform. That just makes no sense at all. You might think about taking the case to both your boss and HR. This is serious and will affect your team’s ability to generate required results—so I can’t believe that with enough evidence and a well-prepared argument, you wouldn’t be able to get some support to make a change.

If you absolutely cannot make that happen, you will have to get ready for a hard conversation—probably a couple of them. Start by laying out all three issues at once and setting up times to work through all three separately. My new favorite tool for hard conversations comes from Craig Weber’s work on Conversational Capacity. Craig says that to find the sweet spot in a conversation, you have to start with candor—be ready to state your position and the thinking behind it. Then, you need to practice curiosity by testing your thinking and asking questions.

You will have to decide which issue is most important and start with that. I might suggest the order of priority as competence, commitment, and attitude. The thinking behind this order is the general principle that when people do not feel equipped to do their job, they tend to lose motivation and start lashing out at others. You may see a change if you can help your employee be more successful at his job.

Competence. It seems your supposed experienced expert might be out of practice. It is fairly normal that, as people rise to executive positions, they can forget the myriad details of the job or not stay abreast of changes. That might be the case here. However, that doesn’t excuse the lack of attention to detail he is demonstrating.

Be prepared to point out several examples of errors, and then ask some questions like:

  • What is your perspective on this?
  • Can you help me understand what might be going on?
  • How do you think this situation might be addressed?
  • Is there something I can do to help?

(Questions adapted from the book Conversational Capacity by Craig Weber, pg. 97)

Be prepared to continue being curious if your employee takes a position that is different from yours. You can say something like: “I admit my perspective is different from yours; perhaps you can share what you have seen or heard that leads you to see things this way.” The more you are curious and keep him talking, the more likely you are to get to a place where he might be interested in hearing your viewpoint. But you may not be able to get a dialogue going. And if you just can’t, that’s OK. You can always default to making a simple request, such as: “please catch up on proper legal terms and double-check your documents before submitting them.”

Commitment. You can observe to your employee that he often stops work before the agreed-upon time. Make sure you have a couple of examples. If you decide to go the way of curiosity, you can ask: “is there anything in particular that is undermining your motivation or ability to hit agreed-upon deadlines?” It will be interesting to hear what he has to say. At least from that jumping off point, you might be able to renegotiate deadlines moving forward. You can also share how critical it is that he follow through with his commitments—because you also have commitments and need to be able to plan your time. The more you can stay curious and neutral, the better off you will be. Which brings us to the third issue …

Attitude. This one is tricky—and it will color the other two issues. The more you feel attacked, the harder it will be for you to stay curious and open. So anything you can do to not take your employee’s behavior personally will strengthen your position. Remember: this is not about you, no matter how cruddy it may make you feel. I suggest you ask yourself if it is truly personal. There is a good chance he is a jerk to everyone. If you find it is only you, or only women in your office, it is an example of harassment or bullying against a specific class and you really do need to take it to HR. If you are forced to keep an employee who is creating a hostile work environment, you could actually sue the organization.

Obviously you don’t want it to come to that—so start again with your observations. Then ask: “Is there something I am doing that is causing you to treat me with such contempt?” He may claim that he isn’t doing it; he may claim to be unaware of it; or he may actually be unaware of it. You can continue to practice curiosity: “Clearly we don’t agree. Let’s see what our different perspectives have to teach us about this. Can you explain in more detail how you are seeing this?”

Ultimately, if he continues to be rude and hostile, it is your right to set a boundary. But that means you have to give him specific direction on how he needs to address you. You may want to create a list of never and always statements. For example (I am making these up based on my own experience):

  • Never: smirk at me, mimic my voice, swear under your breath, or roll your eyes when I speak in meetings.
  • Always: keep to commitments you have made, be civil toward me, and tell me when I do or say something you disagree with.

In the future, you will know to start with tight supervision with new people, point out errors or inappropriate behavior the first time you see it, and then, as the new person settles in, you can loosen up. It is almost impossible to go the other direction.

It can be hard to stand up for yourself, but no one can do it for you. There is a good chance your employee is just waiting for you to draw the line and will continue to push to see just how much nonsense you are willing to put up with. Once you call him out on his bad behavior he may straighten up.

This won’t be your last problem employee. Get ready for many more to come. It gets easier. Not much easier, because you will always expect people to do their best and strive to get along with others, in other words, to be like you. Don’t let it make you bitter or cynical that many people aren’t at all like you. But do get comfortable with drawing the line.

Love, Madeleine

About the Author

Madeleine Homan Blanchard is the co-founder of The Ken Blanchard Companies’ Coaching Services team.  Since 2000, Blanchard’s 150 coaches have worked with over 16,000 individuals in more than 250 companies throughout the world. Learn more at Blanchard Coaching Services.

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