5 Tips for Navigating Difficult Conversations

Our work, our relationships, and our lives succeed or fail one conversation at a time.

Susan Scott

In this era of digital communication, it’s easy to overlook, ignore and avoid the relationships in our lives that need work. If you’ve ever sent an email when you should have picked up the phone, purposely dodged someone’s cubicle, or sat fuming in silence during a frustrating meeting… you’re not alone.

Sometimes we avoid difficult conversations because we don’t know what to say or we’re afraid of what we’ll hear in return. Other times, we convince ourselves that we don’t have the time to deal with it or we don’t want to hurt others' feelings. Or, we may simply lack the courage to confront the issue directly.

Having difficult conversations is hard work. But avoiding them for too long is hard too. Avoidance can lead to frustration, anger, exhaustion, and even depression. If you’re in this situation, consider the time and energy being drained every time you think about the issue. List the benefits you’ll realize if your relationship with this person improves. Then, take a step forward.

1. Prepare your content

Start with your goal. What do you want to get out of the conversation? It should never be about being hurtful or ‘winning’ an argument. If that’s your objective, quit while you’re ahead. A productive goal could be around developing a better understanding, getting past a roadblock, resolving a specific issue, and/or moving forward productively with a specific activity or objective. State your goal in clear terms that are specific to your situation.

Next, write down what you want to say and organize it into key points. It’s best to keep the information limited. No one likes having a laundry list of issues thrown at them. Prioritize your list and plan on focusing on no more than 2-3 of the most important issues.

The person you’re talking to may need help understanding the issue so have a few examples in your back pocket. Also, be prepared to discuss the impact – on you, your team, the project, or the company. Your concerns will carry more weight if you can clearly explain why it’s important.

Make sure you can describe the issue in ways the person you’re speaking with will find compelling. Remember that everyone is asking WIIFM (What’s In It For Me). Think about what motivates them and how they want to be perceived. How will their own goals be helped by improving their relationship with you? Weave this information into what you want to say.

2. Practice

Do a role play or two. Ask friends to be objective and offer honest feedback on how you can improve what you’re saying. Keep in mind that being prepared does not mean memorizing a script. Trying to remember exact words could add to your nervousness and it doesn’t allow for the natural ebb and flow of conversations.

3. Prepare yourself

Start with how you’re thinking about the conversation. Labeling it as ‘difficult’ means you’re anticipating problems which will add to your jitters. Think about it as having a constructive conversation to move forward; an opportunity to develop new ideas, hear a different perspective, or identify alternatives. Anything to reset your thinking in a positive direction.

Before the meeting, take steps to calm and center yourself. Take a walk, have a cup of tea, focus on your breathing, and take the time to collect your thoughts.

4. Deliver. Stop. Ask. Listen.

It’s often good to start by acknowledging the discomfort for you both. Stating that you know this might not be an easy conversation shows empathy and can be the start of a productive dialogue. Also, be aware of your tone of voice. It’s often said that 10% of conflict is about the issue and 90% is about the tone of voice. Work to remain calm, patient and interested.

Explain that you’d like a chance to voice your concerns and then you'd like to hear the other person’s perspective. They will be less likely to interrupt if they know their turn is coming. Once you’ve finished explaining your key points, pause. Stop. Give them time to absorb what you said. Silence can be hard but is often needed to show respect for their feelings.

Ask for their perspective. Express a genuine interest in hearing their side of the story. Only by hearing one another out can you accomplish the goal you set in Step 1. While the other person talks it’s important to listen with an open mind. Work towards finding common ground and determine your mutual goals.

Take ownership for your piece of the problem. You will have more credibility and influence in this situation if you acknowledge your role in creating or perpetuating it.

5. Develop next steps

Make a commitment. Find something you can commit to that will improve the relationship, even if it’s only a small step. Encourage them to do the same. One possible commitment is to discuss issues with one another on a timely basis in the future, should they continue to come up.

Be patient. Unless the issue is simple, you may not fully resolve it in the first conversation. Even if you can’t reach any other commitment, resolve to continue the dialogue and schedule a second meeting for a specific date.

Remember… the relationship won’t fix itself and it may get worse unless you step in. And what’s the worst that can happen? That you crash and burn? That you’re rejected? Rejection would show that you tried which is an easier pill to swallow than knowing in your heart of hearts that you lacked the courage to even give it a shot. And who knows... you may be planting seeds that will bear fruit in t he future!