Managing Challenging Conversations

Your ability to navigate conflict in challenging conversations will determine your long-term success.

Conflict as an Advantage

Whenever a large number of people are working together, conflict is inevitable. As a result, challenging conversations are an unavoidable part of business. You might encounter situations like:

  • Managing a remote employee who isn’t responsive during business hours
  • Dealing with a difficult team member who doesn’t carry his weight
  • Managing up with a boss who frequently throws urgent “fire drill” work at you
  • Responding to a colleague who throws you under the bus to protect himself
  • Catching up when your coworker forgets to keep you in the loop… again

Business results are produced by people, so your ability to work effectively together, including navigating disagreement, will determine your success. When done right, challenging situations can be an accelerator for your business success.

Conflict Avoidance Pitfalls

Man and woman in conflict, having a challenging conversation.

Most leaders think of challenging situations as “hard work” that comes with the job – something unpleasant and easy to put off. Delaying these challenging conversations, or avoiding them entirely, reduces productivity. Below are common approaches to conflict management that damage productivity.

89% Let conflicts escalate
67% Took extra measures to avoid a colleague with whom they had disagreed
24% Avoided social events with colleagues
16% Had still not resolved a conflict, which may have gotten worse over time
12% Quit their job
10% Avoided going to meetings
9% Avoided coming to work for multiple days


Mastering Challenging Conversations

When you master these simple steps, you will elevate not only your personal impact, but that of your entire team.

1. See conflict as an opportunity

Two women talking on a couch. A good setting for a challenging conversation to manage conflict.

Rather than come into the conversation nervous and bracing for conflict, approach the conversation with a sense of possibility and creativity in finding a positive path forward for you, the other person, and the company as a whole. If you are anticipating conflict, you may be the problem. Change your perspective to see the challenging conversation as an opportunity to build trust, strengthen relationships, and accelerate results, you will be more successful during the interaction.

A tactical recommendation is to be deliberate in selecting the location where you will have the conversation. If you are sitting across from each other, it’s more likely to be adversarial. Try sitting next to each other, or even better picking a neutral and relaxed location, like a coffee shop. Your physical location is a major determinant of context, and shifting context can help you approach the conversation from a collaborative perspective.

2. Get clear on your intent

Not every conversation is about the content of the work. Sometimes you are looking to build credibility or trust with the other person. Sometimes you are asking for their input to gain a broader picture of a situation. And sometimes you are seeking agreement on the best path forward. Take the time to clarify your intent, then open the conversation with the other person with what you want to accomplish in the conversation.

3. Give them the benefit of the doubt

Only 7% of your communication is the words you speak. The remainder is body language and tone of voice, which transmits your emotional state to the other person. If you come into the conversation angry, judgemental, or believing the other person is in the wrong, that will quickly be communicated to the other person, putting them on the defensive from the start. Try asking yourself a series of “what if” questions. What if the other person simply misunderstood what was expected of them? What if they had a child with a health issue diverting their attention from work? There may be many reasons for their behavior that you don’t understand. Give them the benefit of the doubt. It’s a powerful way to convey respect for the other person.

4. Be clear about the problem

Picture highlighting the importance of focusing on the problem when dealing with conflict.

When faced with a challenging conversation, it’s tempting to soften your message in an attempt to protect the other person or the relationship. Don’t beat around the bush. Obfuscation is more damaging to a relationship than clarity. Saying “that approach will require too much ongoing maintenance and won’t be sustainable,” is more powerful than “I wonder if we’re creating a sustainable process,” or “do you think we’ll be able to sustain that process in the long term?”. Find a way to communicate your concern clearly and directly, but with respect.

5. Separate fact from story

Most people intertwine the facts – the observable truth of what happened – from their story or judgment about it. For example, Joe may have missed an important meeting multiple times in the past several months. He also didn’t complete a project he was responsible for. You may be disappointed, thinking Joe is losing motivation. When you sit down to talk to Joe, start with the facts: missing meetings and project deadlines. Then you can share the conclusion you draw from the facts, including your disappointment, clearly labeled as your interpretation. There is little room for argument when you approach it this way. You should be able to agree on the facts, and you are taking ownership for the story as your interpretation.

6. Ask for their perspective

Don’t assume you have the only claim on the truth. After you have presented the facts and your story, ask the other person for their perspective. Think of this as a joint problem-solving situation, rather than a confrontation that you are trying to win. Engage the other person in the conflict management. Two people often come up with better solutions than one, so engage them in the process.

7. Make a clear request

A challenging conversation isn’t complete without a clear request for the change you want to see. Be direct and clear, not hesitant and ambiguous. Ask for what you believe is needed to resolve the situation, and check if the other person is in agreement.

8. Stay calm during conflict

Stay calm when having a challenging conversation.

Self awareness is critical during a challenging conversation. If you notice yourself getting frustrated, angry, or agitated, take a moment to regain your composure. Take a few deep breaths, or even excuse yourself for a minute. Similarly, if the other person seems activated, you can suggest a break in the conversation to let them cool down. No one thinks clearly when activated. A break is the best way to reset if you notice you, or the other person, is agitated.

Keep it Simple

This is a robust approach to challenging conversations, but in the heat of the moment, you may not remember everything. The essential ingredients to a productive conversation can be summarized if you simply remember the letter “C”.

Challenging Conversations. Stay Calm, Clear, Curious, and Compassionate.

Don’t Delay Your Challenging Conversation

Many people believe difficult conversations will damage a professional relationship. The opposite is true. When done well, challenging conversations actually strengthen the relationship. It’s an indication that you value the other person and the relationship enough that you will address the problem directly, rather than be in the 67% of people who simply avoid the other person. Treating the other person with respect and honesty builds trust, which supports your effectiveness as a leader and improves productivity.

Managing challenging conversations is a critical leadership skill. Take the time to invest in yourself and learn to manage them better. It will elevate your leadership impact, and drive improved results across your organization.

Photo credits from Unsplash: Afif Ramdhasuma, Toa Heftiba, Nathan Dumlao, ahmad gunnaivi