HR Feature Human Resources Management

Tough Talk

Having difficult conversations with problematic employees is never easy — but these conversations need to happen. Here are tips to get you through them.

Your law firm staff is excellent, save for one or two bad apples in the bunch. Maybe they come into the office with a bad attitude, bully their colleagues, spread lies and start trouble at every opportunity.
Kylie Ora Lobell

This kind of behavior can create a toxic environment and lead to a plethora of problems. The great employees might quit, your law firm can gain a bad reputation and productivity may suffer.

This is why you must deal with these problems instead of ignoring them. You need to do as much as you can to avoid issues in the first place, and then swiftly take care of them before they get out of control. Partners and law firm managers have various ways of dealing with harsh employee situations.

“As an office managing partner, I first assess whether the employee is being ‘tough’ because the leadership of the firm hasn’t set the person up for success,” says Joseph S. Leventhal, Office Managing Partner at Dinsmore and a board member at the Federal Bar Association. “Assuming the firm has done all that it reasonably should to make the person successful, you have to deal with tough employees head-on. And depending on the situation, tough employees may need to be asked to leave the firm because they can be like a cancer on the organization.”

It may be tempting to let a problem go “just this time,” but it can only grow bigger and bigger and eventually explode, according to Dina Lynch Eisenberg, JD, who is Legal Operations Strategist at Outsource Easier. “More employees will feel vulnerable and unsafe at work. Management must help both parties, the actor and receiver, to interact in more productive ways by providing coaching and training as well as reinforce their notion of good work behavior.”

When dealing with tough employees, you may find yourself in a difficult and uncomfortable position. You might have to make tough calls. But it is your job to protect yourself and others and ensure that your firm is performing as best as possible.

The following are ways you can safeguard your firm and guarantee that all of your workers have a pleasant environment in which they can professionally thrive.


You can avoid having problem employees on your team in the first place by taking a little more time to find the right hire. “All too often, a hiring manager will hire quickly based on a desperate or urgent need,” says Candice Pinares-Baez, a Partner at Fisher Phillips and a presenter at this year’s ALA Annual Conference & Expo. “My advice is to take your time regardless of the extenuating circumstances.”

Seth Price, Founder and Managing Partner at Price Benowitz LLP, says that at his firm, he asks a variety of people with different backgrounds and personalities to interview potential employees. He also tries to do a shadow day “to see how someone interacts during the workday, what types of questions they ask and how they behave on an interpersonal level beyond the short confines of an interview.”


Once you’ve found your new employee, you should have a 90-day probationary period to ensure that you made the right decision. During this time, Pinares-Baez says you should ensure that supervisors are working closely with the new hire to determine whether they can perform to expectations and are able to work well with the team of colleagues. “Spotting a problem employee early, addressing any issues, and making the determination to part ways early in the relationship can prevent a great deal of headache later,” she says.


Employees need feedback on an ongoing basis. By holding reviews, you can let them know their strengths and weaknesses and give them the chance to offer you feedback as well. Having open conversations helps you avoid built-up resentments from employees.

“Employee performance not only includes meeting goals or metrics, but also includes good citizenship and the ability to work well with others,” says Pinares-Baez. “Failure to do so should be addressed in the same manner as other performance deficiencies. It should be part of the employee evaluation and subject to disciplinary measures if expectations are not met in this regard.”


Your tough employee is acting up. Depending on the severity of the issue, you should decide whether it is worth firing the employee or simply giving him or her a warning. “We usually have a ‘one bite’ rule, but for serious violations, there’d be termination,” says Price.

If an employee was lying, for example, that might lead to a firing. “The warning depends on the level of severity of the lie. A white lie might just be a verbal warning, while in the case of something to deal with substance — like a client's confidences or something that is more consequential — there could be immediate termination.”

Maybe your tough employee made a mistake, but you aren’t seeing his or her perfectly acceptable reason for doing so. Before you give a warning or termination, sit your employee down to figure out what really happened.

“Don’t just assume bad intentions because there could be workplace factors at play you aren’t aware of yet,” says Einsenberg. “After gaining understanding, restate the community policy around honesty and the consequences for breaking the policy a second time. Decide how the employee needs to behave to restore lost trust. Of course, the first instance of lying may be a terminable offense.”


You may decide to fire a troubled employee, keep the warning on record or let them off because it did not turn out to be a big deal. No matter what the outcome, going forward, you need to utilize positive training and hold teambuilding activities to assure that everyone is happy, healthy and on the same page.

Price says that his firm will engage in teambuilding activities. “We try to get people outside the office to bond and get to know each other outside of the workplace in order to improve communication.”

There are other things to do aside from teambuilding, too. “There are big things that you can do to create a positive atmosphere for all your employees,” says Leventhal. “But most important is treating everyone as valuable and part of a team, thanking people for their effort and taking the time to ask how you can help them be successful in their jobs.”

Candice C. Pinares-Baez will offer further guidance on this issue in her session, “Difficult Conversations with Your Difficult Employees,” at our Annual Conference & Expo in National Harbor, May 3–6. Don’t miss out on this and other invaluable education opportunities.