A Divorce Lawyer, Social Worker, And Book Editor On The Art Of Hard Conversations

Let the pros show you how to have the toughest talks.
July 4, 2022

This piece was first published in Fast Company on 04.13.18

Photo by Christina @

Everyone does “difficult conversations” differently. But no matter your approach, the challenge is the same: sorting out really touchy issues while sidestepping the risk of raw emotions–hostility, rejection, confrontation, despair–getting in the way and making things worse.

Some people’s jobs require tough conversations on a daily basis, though–people like cancer specialists, divorce lawyers, book editors, CEOs, and social workers. So I spoke with an expert in each those fields to find out how they handle it.


“Conflict resolution skills are a regular and large part of my role.” says Shelley Mattam, a Toronto-based child and family social worker. “I’ve learned a few key steps to take in advance that have significant impact on the outcome of the conversation.”

“Especially in emotional settings, the more direct the message, the less likely they are to misinterpret what you are saying.”

First, Mattam points out that it’s important to set things up properly in the first place. “Your environment sets the tone of your conversation,” she says. “Choose a place that allows the person to feel comfortable and safe to them.” Jodi Butts, CEO of Rise Asset Development, which provides financing to business owners with mental health and addiction issues, agrees. “[Setting] the right tone from the start help[s] put both of you at ease and set the stage for a more productive outcome.”


To preserve that sense of calm and security, pay attention to your body language. Mattam suggests using “open body language and a gentle voice to reduce the power imbalance,” and to “put away your phone and physically show the person that you are truly engaged.”


“Starting the conversation is almost always the hardest part,” Butts admits. So start by finding some common ground. “Open with a quick review of the points you both agree on,” she suggests.

“If your role is the reason you’re initiating the difficult conversation, it can be helpful to distance yourself from the immediate situation by grounding yourself in the framework of your role and responsibilities,” adds Butts. “You can do this by reminding them that this conversation is necessary for the organization or meet fiduciary duties,” depending on what the situation may be.

Pamela Murray, a senior editor at Penguin Random House Canada, also finds that drawing attention to what your job demands of you can help. “The way I frame the interaction is that the conversation precedes a problem that needs to be solved–if I’m initiating the conversation it’s my job to articulate the issue and move toward a next step,” she says. To do that, “I need to have an idea of what that next step might be, but also be open to suggestions from the other person.” Explaining what your role requires you to accomplish can help clear some of that common ground.


Brenda Christen is a founding partner at the family law firm of Wilson Christen LLP. “Difficult conversations in my professional world happen when separating parties want to know what might happen to them, their children, and their families,” she says.

“Often these conversations focus on many possible outcomes, some good, some not so good,” Christen explains. So a plotting a steady through-line can be useful. “Most people appreciate hearing the main message up front so that they can focus on the information that follows–instead of trying to decipher where the conversation is heading.”

“So if I’m talking to someone who is likely going to have significant financial obligations and not a lot of entitlement,” Christen continues, “I might start by saying, ‘There is not likely to be much good news in this meeting.'”

The main message might not be too comforting to some, though. But that’s no excuse for watering it down. Be unequivocal when you need to, Christen advises. “Especially in emotional settings, the more direct the message, the less likely they are to misinterpret what you are saying.”


In book publishing, says Murray, “we have to break bad news frequently–to prospective authors whose books we are unable to publish, to agents seeking a home for their client’s work, to authors whose manuscripts are not coming together as we’d hoped, or during negotiations when the point has been reached where you just can’t sweeten the pot anymore.”

“I’ve learned to take the time and space for myself after an especially harrowing conversation.”

“As with any difficult situation,” Murray explains, “I believe in approaching it candidly and directly. Sometimes you find out you’re on the same page, or your conversation may lead to some new way forward.”

It sometimes doesn’t, but candor is just as critical then as well. “Of course there are those occasions when the next step is to definitively close the door, and then it’s best to be clear, firm and kind.”


Finally, it’s important to know how you’ll close the meeting, both in terms of wrapping up the conversation and as far as the actions that have to be taken afterward.

When things get emotional, Anne Kreamer, author of It’s Always Personal: Navigating Emotion in the New Workplace, recommends acknowledging tears, not ignoring them–offer a tissue and wait patiently until the other person gathers their thoughts. A little empathy can go a long way.

All the individuals I spoke with suggested planning for the conversation to take 15 minutes more than you expect. This will prevent things from feeling rushed and may even give you a moment to collect yourself at the end. Often, there is no avoiding the impact that emotionally difficult conversations will also have on you.

I spoke to a cancer specialist who preferred not to be named in this article, but he shared that his job “takes me to the heights of human happiness when I tell someone they are cured, to the depths of human misery when I tell a patient there is [a high likelihood that] they will imminently die from their disease.”

“I’ve learned to take the time and space for myself after an especially harrowing conversation,” he said, “otherwise my own emotional responses are too extreme, and then I’m not effective to anyone.”

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