How to Master Difficult Conversations

by Dr. Robert Barner

Almost every day I hear about a professional who has posted online about walking away from job in order to escape a toxic manager or difficult work environment. I get it—no one wants to be stuck in a stressful work setting. At the same time, I can’t help thinking that a part of this recent cultural phenomena is that a lot of people haven’t been trained in how to handle difficult conversations. Instead they allow their frustrations to build until they simply give up and leave. If you are in this situation, before taking the final step of leaving your job or walking away from your boss, I would urge you to first try to have that conversation that you have been avoiding; the kind of difficult conversation where feelings run deep, and the feelings tend to get heated.

There are several steps you can take to effectively manage these types of difficult conversations. By doing so, you can learn how gain more control over your job and your career, while forging an organizational brand as a collaborative leader. If the conversation doesn’t work out you can always take the more extreme action of quitting or running to your HR office for support, but if you do you will go on record as having tried to professionally resolve the situation with your manager or co-worker.  With those caveats in mind here then are 6 guidelines for working your way through difficult situations.

Guideline 1: Keep your end objective in mind

A friend of mine works as a mediation specialist with couples who have decided to divorce but hope to do it amicably. My friend never ceases to be surprised that two people who have built a life together for many years and have amassed strong financial reserves will end up  arguing over who gets the antique tea pot that Aunt Martha left them. The simple fact is that in the heat of conflict we tend to lose sight of the big picture, causing us to dig in on small points and take actions that we later regret.

To avoid this danger you need to keep your end objective in mind, by jotting down a few bullet points describing what you want to get out of the conversation, and then bring your notes with you to the meeting. These bullet points can help anchor you in your discussion so that you don’t get sidetracked by trivial issues. At the same time, make a list of those small concessions that you are willing to make in order to achieve your end goal. If you want to convince your boss to allow you to work remotely, you might offer the compromise of setting aside time on your calendar to go into the office during the dates that important meetings are occurring. Your boss, on the other hand, might be willing to make the concession of allowing you to flex your time in the office during those days, so that you can avoid rush hour traffic.

Guideline 2: Keep your Hyde chained

I’m sure that you remember the story of Dr. Jekyll and Mr. Hyde, in which the timid and polite Dr. Jekyll experimented with a serum that transformed him into his evil counterpart. All of us have our Hyde hiding within us. We are usually at our best in managing conflicts when we are feeling relaxed, but as our stress increases Mr. Hyde pops into the scene.

If you are one of those people who has difficulty staying cool and calm in stressful situations, then consider downloading one of the more popular meditation apps such as Headspace or Calm and selecting a guided meditation exercise that works for you. Many of these exercises can be completed in less than five minutes. Taking the time to slow down your breathing and calm your mind can work wonders for you when you are sitting across from that stress-inducing person.

Another suggestion is to mentally walk through what you want to say in the situation and ask a friend to help you conduct a practice run prior to your meeting, with your friend playing the role of the other party. Encourage your friend to ask you tough questions during your practice run, so that you can rehearse remaining calm and focused. Record this session and listen to your voice, then run through the scene again until you see and hear yourself coming across as calm and focused.

Guideline 3: Pick the right time and place for the discussion

I went to my dentist yesterday for my semiannual teeth cleaning. I do this without fail, because I know from past experience the kinds of dental problems that can occur if you talk yourself out of going to your dentist for a long period of time. The same can be said about difficult work discussions. If you have a problem at work and you don’t act on it, it only festers and gets worse, until the kind of conversation that you are eventually forced to have turns out to both stressful and career-damaging.

Pick the right time and place for your discussion. If you don't, the other party will take the initiative, meaning that you may be forced into a discussion during a time when you are feeling frazzled and stressed out. Instead, close your eyes and visualize the kind of setting that would make you feel most comfortable, then make sure to use this setting to your full advantage. If you at the top of your game on Tuesday morning, then schedule your discussion for that time slot. If you feel more comfortable talking to a co-worker in your local conference room than in in their work area, then ask to have the meeting there.

One final point needs to be said here. I’m a firm believer that you should always hold your toughest discussions face-to-face. In a previous article (The Power of Face-to-face Communication) I shared research that suggests that when we communicate online instead of face-to-face, we are more likely to miss out on important social cues that help connect us to the other party. In addition, online channels tend to come across as more impersonal and transactional, so if you choose this option it might make the other party feel that you aren’t taking their concerns and feelings seriously.

Guideline 4: Create a setting that depersonalizes the issue

The worse social dynamic for staging a difficult conversation is when you are sitting across a table or desk from someone. This setting invites confrontational body language and a personalization of the issue. Statements such as “You are… (this kind of person)” or “you do… (these kinds of actions)" imply that your conflict is the direct result of the other party’s personality or underlying intentions. You can’t win by trying to convince your counterpart that they are evil, so instead try creating a setting that helps you depersonalize the issue.

As a first step, choose a meeting room where you both have privacy and feel comfortable, and where the two of you have access to a whiteboard. Instead of sitting across a table or desk from the other party, move two chairs close to the whiteboard. Invite the other person to sit with you at an angle so that you can make eye contact with each other while still keeping the focus of your attention on the whiteboard. Now hand the other person the marker and invite them to go to the whiteboard and sketch out the issue or conflict at they see it.

Something magical happens when you do this. Instead of positioning the other person as the source of your problem you are asking them for their help in outlining “the challenge” that both of you are facing. Handing the other party the marker invites them to take the lead, which will immediately make them feel like you are trying to create a space for their voice to be heard. Work with the other partner to add more detail to whatever they have sketched out on the whiteboard so that it becomes a co-constructed solution.

Guideline 5: Use the “bookend” approach to set the stage for your discussion.

Quite often the people with whom we have the most difficultly conversing are those in which our relationships are frayed and damaged. In this scenario we are more likely to walk into the situation with fantasies about what will go wrong. We prepare for war in our minds and so its war that we get. One way of overcoming this roadblock is to make use of what I call the bookend approach to difficult conversations, where you set the stage up front for the other party to listen to you, and then pause at the end of the discussion to perform a final check-in with the other party.

Your initial set-up might go something like this: “Kim, I know that you and I have been having a difficult time trying to agree on our work priorities, and that sometimes in the past those conversations have tended to get heated. I want to suggest a new approach today where we start off with me hearing you out about what’s most important to you in reaching these decisions. Later I’ll do the same."

Towards the end of the session place your other bookend. Turn to the other person and say, “I started out by mentioning that I wanted us to try a new approach today, and since this is something new for me as well, I just wanted to perform a brief gut-check with you. How did this discussion go for you today?” Asking this question lets the other party know that you care about their feelings and are doing your best to resolve your disagreement.

Guideline 6: If the stress level rises take a break

 As an experienced coach, one of the communication dynamics that I’ve frequently witnessed is that those leaders who are very strong, forceful, and results-driven tend to have a high need for closure. As a result, when they are in the middle of a difficult situation they are bound and determined to push through a tough discussion until a resolution is reached. The caveat here is that if you see the other party starting to become stressful you really need to take time to talk them back off the edge before you continue. If you don’t do this you are going to leave that person feeling damaged, and they will deeply resent being pushed into a corner as you forcefully hammer out your demands.

As an option, tell the other party that you can see that the situation is getting tense so you want to take a quick bio-break before coming back to it. When you do come back into the room, start off by backing up a bit and recapping those points on which the two of you have secured agreement. Then mention the discussion points that still need to be resolved and ask the other person if they can help you arrive at a solution. In a situation such as a tough performance review, sometimes its best to invite the other person to spend a day thinking over what the two of you have discussed before returning to the conversation. Taking this approach will help prevent everyone from getting stressed out, and generate a better solution when both of you are calm and thinking clearly.

That's about it. If you are a leader who is attempting to advance in your organization I invite you to read my book, Bootstrap: how to succeed as a leader through self-coaching, which has just been released on Amazon and Barnes & Noble. You can read advance reviews on Bootstrap on my website at rbarnercoaching.com.

Till next time!