7 Steps to Master Difficult Conversations

Most leaders dread difficult conversations because they’re uncomfortable and unpredictable in the moment.

Even worse is what can happen after the conversation. Will it irreversibly damage the relationship with a good employee? Or will it destroy a solid connection with a colleague? Or could a tough talk with the boss hurt your career?

Difficult Conversations without Drama

That’s why difficult conversations need a double objective: Fix the issue and maintain the relationship.

“Remember that an organization is simply a network of strong, collaborative, mutually beneficial adult relationships,” says Quint Studer, author of The Busy Leader’s Handbook: How to Lead People and Places That Thrive. “The better the relationships, the better the company.”

Handled right, difficult conversations can strengthen relationships. Here’s what Studer says is the right approach.

Ask Yourself 3 Questions

Before leaders go into a tough one-on-one, they want to check intentions. Ask yourself:

• Am I being fair and consistent? Make sure you have the same rules for everyone.
• Am I focused on being right? Just because you don’t agree with what someone has said or done doesn’t mean it was wrong.
• Do I need a witness, to document the conversation or consider legal issues? If there’s any question, front-line managers want to call in HR.

Be Clear on What You Need to Say

Be ready to clearly explain:

• the problem
• how it impacts others, and
• what must change.

Use facts, statistics and documented incidents – not just observations. Stick to those points and don’t go off topic.

Schedule the Talk

When possible, schedule the difficult conversation on neutral ground to give the other person a chance to gather his or her thoughts and emotionally prepare to discuss it.

You might say, “Jared, I’d like to chat about what happened in today’s meeting on the Jones account. Can we meet tomorrow at 8 a.m. in the Beacon conference room or would you prefer a Zoom call?”

Focus on Civility, Relationship

You can cover difficult topics – such as performance, hygiene, conflict, etc. – while treating people with dignity, respect and empathy.

Start the conversation with a pledge to civility: “Our relationship is important to me and this conversation is just one moment in our time. I want to walk away with the same strong relationship we came in here with.”

Collaborate, Don’t Dictate

Your difficult conversation will be more successful if you work together to make things better. Help the employee or colleague feel ownership in the solution.

Ask questions to get a different perspective and collaborate. Try:

• What factors do you think lead to this issue?
• How do you feel about this?
• Do you have any ideas on what both of us might do differently moving forward?

Give Time, Attention

When you ask questions, let the other person gather his or her thoughts and contribute ideas. Avoid asserting your point to fill silence.

Then listen actively – focusing on what the other person says and does to relay emotions. Summarize what’s been said so you both agree to what was discussed, what needs to change and how it will be resolved.

Avoid Certain Words, Phrases

Some words and phrases only add fuel to a difficult conversation fire. You’ll want to avoid:

• Absolutes: “Clearly,” “Obviously,” “Beyond a doubt.” What to say instead: “What I’ve noticed is … ” “I’ve observed that … ”
• Exaggerations: “You always” “You never” “All the time, you … ” What to say instead: “According to our records, you were late 11 times this month.” “The customer said you didn’t return four of his calls.”
• Judgments: “You should …” “You shouldn’t …” What to say instead: “You might want to try … ” “Have you considered … ?” “One possibility is … ”
• Blames: “You make me so angry/frustrated/confused …” What to say instead: “When you do X, it makes me feel Y. Could you please not do that going forward?”