Tough Talks: Having difficult conversations about delicate situations

May 21, 2014
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By Lori Moss

moss-lori.jpg Moss

No one relishes telling someone they aren’t pulling their weight, that they aren’t billing enough hours or aren’t winning enough cases. Those are hard conversations. Those conversations, however, typically involve issues that are black and white. You have facts and figures to back them up: Here is the company policy. You broke the policy. Here is the consequence.

What if it’s something that’s not in the employee handbook? What if you need to tell someone they aren’t dressing or behaving professionally? Those issues often fall into gray areas, leading to conversations that can be emotionally charged and uncomfortable. So, what do many lawyers do? Nothing. They hope the problem will go away.

It’s not going to go away. In fact, it’s going to fester, it’s going to affect other employees – if it hasn’t already – and it’s going to tarnish your reputation and negatively affect the firm’s bottom line.

People – regardless of the industry – avoid having tough conversations. They avoid them by trying to rationalize. Clients will tell me they haven’t had “the talk” because there just hasn’t been the right time, or the issue hasn’t affected his or her work.

I tell them to rock the boat today, because tomorrow or next week or next month, it’s going to rock the entire company. Here’s an example of an issue that was not easy to confront.

A group of employees often huddled in the break room giggling about a co-worker. He was relatively new to the firm, but already had shown he was talented, and he had good sales figures. He dressed professionally, and clients seemed to respect him. However, he was causing a stir among his co-workers because he had a tendency to – for lack of a better way of saying it – adjust himself. Not just once, but multiple times during the day. His boss noticed it, too, and wondered whether he was even conscious he was doing it. More importantly, she worried that his behavior eventually would affect his relationship with clients.

Talk about a tough conversation. But it had to be done. And, it needed to happen sooner rather than later because employees looked to the boss to deal with it.

Whether it’s talking to someone about their behavior, their dress or demeanor, here are tips to help you prepare and make the most of the difficult conversation.

Realize this isn’t just about the individual employee. It’s also about your reputation and the reputation of the firm. If you are willing to turn a blind eye on professionalism, you’ll lose respect with your employees, and you’ll also diminish the importance of professionalism within the firm.

Be a mentor. Approach conversations about professionalism as a caring mentor, someone who has the best interest of the employee at heart and who wants him to succeed.

Acknowledge it’s uncomfortable. When you set the stage, let the employee know you understand this is a delicate situation. The employee is likely to be less defensive.

Don’t get into a debate. The last thing you want is for the employee to get argumentative and defensive with comments such as “I can’t believe you’re even accusing me of not dressing professionally when there are so many bigger issues out there,” or, “Why am I being targeted when others are a lot more obnoxious in staff meetings than I am?”

Instead of a debate, you need to remind the employee that you want to help him or her improve because you value the work he or she is doing. Being more nurturing than directive will help defuse someone who feels attacked. But remember, you need to be sincere.

Don’t lecture. This needs to be a conversation between two professionals. Think of it as you giving advice to someone whom you value and care about. Consider how you’d prefer someone talk to you.

Lecture: You’ve got to stop interrupting people during client and staff meetings. It’s rude and unprofessional.

Advice: You’re so passionate about an idea that it often comes across to staff members and even clients that you’re interrupting. I know you don’t mean to be unprofessional or disrespectful, but it can be perceived that way. I bring this up because it’s an issue I’ve had to work on my whole career, and I wanted to share ways I’ve tried to overcome it.

Make it private. When scheduling the meeting, make sure it’s in a private, quiet location. No one wants to be overheard discussing issues about their professionalism or performance in public. Turn off your cell phone during the meeting, and make sure you’ve put the meeting on your calendar. Taking calls discounts the importance of the conversation and your employee isn’t going to take it as seriously. This is a serious matter that impacts your company and your employee’s career.

During the conversation, you should be able to assess – through the employee’s response and body language – whether he’s vested in his career or even vested in the firm. Depending on the issues, it may require a follow-up meeting so you can provide some additional feedback or just let the employee know you appreciate the work he or she has done to improve.•


Lori Moss is owner of Professional Presence Pro and specializes in helping law firms develop and implement professionalism standards. She will be a featured presenter at the Indiana Bar Association Solo & Small Firm Conference June 5-7. The opinions expressed are those of the author.


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  1. This is ridiculous. Most JDs not practicing law don't know squat to justify calling themselves a lawyer. Maybe they should try visiting the inside of a courtroom before they go around calling themselves lawyers. This kind of promotional BS just increases the volume of people with JDs that are underqualified thereby dragging all the rest of us down likewise.

  2. I think it is safe to say that those Hoosier's with the most confidence in the Indiana judicial system are those Hoosier's who have never had the displeasure of dealing with the Hoosier court system.

  3. I have an open CHINS case I failed a urine screen I have since got clean completed IOP classes now in after care passed home inspection my x sister in law has my children I still don't even have unsupervised when I have been clean for over 4 months my x sister wants to keep the lids for good n has my case working with her I just discovered n have proof that at one of my hearing dcs case worker stated in court to the judge that a screen was dirty which caused me not to have unsupervised this was at the beginning two weeks after my initial screen I thought the weed could have still been in my system was upset because they were suppose to check levels n see if it was going down since this was only a few weeks after initial instead they said dirty I recently requested all of my screens from redwood because I take prescriptions that will show up n I was having my doctor look at levels to verify that matched what I was prescripted because dcs case worker accused me of abuseing when I got my screens I found out that screen I took that dcs case worker stated in court to judge that caused me to not get granted unsupervised was actually negative what can I do about this this is a serious issue saying a parent failed a screen in court to judge when they didn't please advise

  4. I have a degree at law, recent MS in regulatory studies. Licensed in KS, admitted b4 S& 7th circuit, but not to Indiana bar due to political correctness. Blacklisted, nearly unemployable due to hostile state action. Big Idea: Headwinds can overcome, esp for those not within the contours of the bell curve, the Lego Movie happiness set forth above. That said, even without the blacklisting for holding ideas unacceptable to the Glorious State, I think the idea presented above that a law degree open many vistas other than being a galley slave to elitist lawyers is pretty much laughable. (Did the law professors of Indiana pay for this to be published?)

  5. Joe, you might want to do some reading on the fate of Hoosier whistleblowers before you get your expectations raised up.