You Just Had a Difficult Conversation at Work. Here’s What to Do Next

Author: Dolores Bernardo

After most difficult conversations, we generally feel like, “Phew! Glad that’s over. I never want to have that conversation again.” But it’s actually really important to be able to follow up after a tough conversation. The question is: How? What specifically should you do and say to make things less awkward and to move forward, while also making sure that you’re making some progress on the points that were discussed?

For the past decade, much of my work has focused on helping leaders understand each other and collaborate effectively across functions. A lot has been written about how to have difficult conversations, but not nearly enough focus has been placed on what to do after one. From my work with executives in tech, NGOs, academia, and government, I’ve learned that the ability to follow up and build a relationship after a hard conversation matters just as much as the skill of tackling that initial difficult conversation.

Below are three key steps that can rebuild a good working relationship following a challenging conversation while also making progress on the problem at hand.

Step 1: Acknowledge that the conversation happened

We often want to “forget” or purposely avoid recognizing that a hard conversation took place with a colleague. That’s a mistake, because it leaves you powerless and also leaves your colleague guessing at how to handle the situation. My advice is: a) proactively follow up, b) acknowledge that it was a tough situation, and c) focus on the positive. There is huge value in appreciating that you were able to come together, identify and discuss a big issue, and even have the conversation in the first place. Thank your colleague for taking the time to engage in the conversation.

Consider the case of a sales director I once worked with named Richard. He’d been a rock star at his previous company, but at his first meeting presenting a sales strategy to senior management at his new job, he found his ideas rejected out of hand. He was informed that his style was totally out of sync with how the new company communicated, and he came out of the meeting feeling demoralized, with no strategy for growing sales in his region.

I urged Richard to take the reins in this situation by immediately drafting a strong thank-you email that showed that he was proactive and dedicated to getting on the same page as senior management. In the email, he acknowledged that it was a challenging conversation and then focused on the positive—the fact that they’d identified and discussed some big issues, which he was thankful to have out in the open.

Step 2: Find ways to move the conversation forward

Be proactive in showing that you’re resilient and solutions-oriented, and that you want to stay in the conversation. Even if you were only able to come to agreement about a few action steps during the difficult conversation, send a follow-up email to summarize the conversation and focus on the outcomes you both want. Why do this? Clear communication around next steps proactively moves the conversation forward. A written record also tracks any differences in perspectives, memory, or understanding, and prioritizes accuracy. Also, and importantly, new information almost always comes to light. That “new” information might actually be the true hidden sticking point that had stalled progress or created conflict in the first place. This step creates a path forward out of the conflict zone and builds a shared understanding of the issue.

In Richard’s case, I advised him to follow up with an outline of the steps that he would take, researching what had been successful in another region, and talking to his peers in Marketing, User Experience, and Product Development. He needed to get their feedback and then craft a strategy that was in-line with his new company’s values. The next time he met with senior management, he was greeted with a smile and warm handshake. He felt he had a clean slate to present his new ideas, and they were ultimately able to agree on a sales strategy for his region.

Step 3: Focus on building the long-term relationship

Remember that every interaction is just one human being talking to another. If the only interaction you have with someone is a difficult conversation, they may start avoiding you, or only associate you with difficult meetings. Instead, pay attention to building the relationship outside of the challenging conversation. This step balances both the outcome you desire on the issue at hand and the work relationship you want for the long term.

I recommend a practice called the designed alliance conversation, in which two colleagues put the past on hold and focus on how to positively shape their working relationship for the future. It includes questions like, What does success look like in this partnership? What outcomes are important to both of us? What constraints do we both have that we need to be aware of? What is important to each of us that the other might not be aware of? This gives each party a chance to be honest about how they prefer to collaborate going forward.

Team-building events like a casual dinner after work, a one-on-one walk, or sharing time at a larger off-site event can help us remember to connect as human beings. It can also be helpful to remind each other that you’re all working toward the common purpose of building a great organization and achieving the company’s mission. Emphasize the “us” in your conversations, using phrases such as “We’re all on the same team” or “We all want this initiative to succeed.” As leadership expert General Stanley McChrystal says, “It’s not enough to be great; you have to be great together.”

Actively building positive relationships after a difficult conversation isn’t easy, but it’s a muscle you can build, and it gets easier with practice. It can also give you a reputation as a go-to problem solver and collaborator—key skills for any leader.

DOLORES BERNARDO has worked for 20 years as a talent development leader, diversity and inclusion advocate, and management consultant. She currently focuses on leadership development at Airbnb. Previously, she was Head of Global Manager Development at Google, and a consultant at Accenture.