Say What You Hate To Say: 5 Ways to Tackle Uncomfortable Conversations

As a manager, you sometimes have to say things you hate to say.

You likely dread the conversation — and try to put it off.

Turns out, you aren’t alone. Many people put off uncomfortable conversations for as long as six months, a Crucial Learning study found, going so far as to:

• Avoid the other person at all costs (50%)
• Dance around the awkward topic when they speak to the person (37%)
• Consider quitting their job or taking a different job (37%), or
• Quit their job (11%).

Chats to Avoid

But really, who doesn’t want to avoid these touchy subjects — those that cause the most trepidation, according to research from Fractl:

• Negotiating a raise
• Addressing a difficult personality
• Lack of accountability
• Apologizing for a mistake, and
• Addressing a lack of clear direction.

Of course, these conversations are never that clear-cut. They’re usually more about everyday annoying workplace issues.

Sure, asking for a raise is cut and dried. But, “addressing a difficult personality” is often about having to tell Janice she can’t be such a witch to colleagues. Or a “lack-of-accountability conversation” is really about telling Bob he smells and needs to shower and use deodorant every day. And that “lack-of-clear-direction chat” is usually just a rehashing of Sam’s string of failures.

Hate To Say It, But …

So you have to say things you hate to say.

“Scary conversations are crucial conversations,” says Joseph Grenny, a social scientist and coauthor of Crucial Conversations. “In these moments, most people run the other way because experience tells them the other person will be angry or defensive. And yet, our research shows the select few who know how to speak up candidly and respectfully — no matter the scary topic — can solve problems while also preserving relationships.”

Fortunately, there are ways to hit the topic head-on, keep everyone comfortable, and most importantly, get the issue resolved.

Here are five tactics to navigate uncomfortable conversations in the workplace:

1. Face Up

Uncomfortable conversations would seemingly be so much more comfortable if you didn’t have to look at each other. But that’s not as effective as a face-to-face conversation.

Either meet privately in a neutral space — not your office — or via video if it’s a remote employee. Don’t hide behind a phone or blank monitor.

2. Be Curious

Some conversations are uncomfortable for just you because the employee or colleague has no idea he or she is doing something wrong or weird. They have no shame or recourse — at first, at least.

So assume the best of others when you need to address touchy issues. Be a curious colleague, rather than a frustrated boss.

One way: Use tentative language when you address the issue: “I’m not sure you realize you …” “I’m not sure you intend this …” “You might not be aware of …”

3. Stick to the Facts

Considering the person on the other side may not even know he or she is about to embark on an awkward conversation, share facts, not conclusions. Reason: Your conclusions could be completely wrong and create a tense situation.

For instance, if you say, “You always talk over others in our meetings because you think your opinion is the only one,” the figurative fists will go up. Instead, say, “In the last two meetings, you interrupted me twice and spoke over Greg until he retracted his suggestion.”

4. Get Feedback

Once you’ve laid out what you see as the problem, let the other person give his or her point of view on the behavior.

Invite it. Ask something like, “What’s your take on this situation?”

5. Work Together on the Solution

Once you have the situation out and in the open — and are hopefully beyond the most uncomfortable parts — treat the conversation like a two-person problem-solving mission.

The book, Powerful Conversations by Phil Harkins, gives one of the best frameworks we’ve ever seen. Try this:

• What’s Up: We covered this above. By now, you should’ve told your side of the situation and asked the other person how they see it.
• What’s So: With facts from both sides, you can more likely remove any emotional charge from the conversation. Explore the impact on each of you, the team and the larger organization.
• What’s Possible: Give your possible solutions or alternatives, and ask the other person for the same.
• Let’s Go: Commit on both sides to taking action with accountability included.