Crucial Skills®

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6 Steps to Approaching Challenging Conversations (Guide)

Think of a time when you needed to have a challenging conversation with someone at work, but kept putting it off. Almost everyone has been in this position before, and it’s a deeply uncomfortable one.

Why don’t we tackle challenging conversations with our bosses, colleagues, and direct reports?

Fear is the main reason. We might fear:

  • Their reaction
  • Consequences
  • Being wrong
  • Hurting their feelings
  • Not knowing how to approach it
  • Previous bad experiences
  • Making things worse

As a result of this fear, we often shut our eyes to the conflict and hope it goes away on its own. Unfortunately, this is rarely the outcome.

To approach challenging conversations, you need to prepare as if you were taking a road trip. The longer and more difficult the journey, the more things you would check before starting out. Even on a local trip, you’d check that your tires aren’t flat and that you have enough fuel.

In the same way, you should never walk into a challenging conversation without some level of preparation.

How to plan for a challenging conversation.

These are the questions you’ll need to consider before embarking on a challenging conversation at work:

  • Where are we starting from?
  • Where are we going?
  • Where can we get next time we meet?
  • Which obstacles could get in the way?
  • What driving style should you use?
  • How will you know you’ve arrived?

As you think through these questions, it will help to talk out your answers with a coach or other trusted person, or to journal them. Externalizing your thoughts in this way will help provide clarity and bring out new insights.

Step 1. Where are we starting from?

To start, get clear on the issue you’re trying to address.

  • Why is it so important to you?
  • Why is it so important to them?
  • What do you value, and what do they value, in this situation?




Start from a better place.

Crucially, before you begin the challenging conversation, ask yourself if you—or they—are already in conflict? (Hint: if you are tending to only think about the outcome you want, it could be that you’re already in conflict.)

If that’s the case, try washing out your filter or cleansing your lens. We refer to this as ‘Recasting the Past’ to help get a clearer, more objective view of the picture.  You might ask yourself:

  • What might they do that will frustrate you?
  • How could you view their behavior differently?
  • What might be their positive intent?
  • Might there be an underlying cause of their behavior?
  • How might they view their own behavior?
  • How could you react differently?

For example, Fred was having difficulty with one of his colleagues. He often experienced him as aggressive, especially in team meetings. Fred’s typical response was his own version of abrasiveness. It was only when Fred looked at his colleague in a new way, or ‘cleansed the lens,’ that he realised his colleague usually behaved with aggression when he was feeling insecure. Fred then chose not to respond with his version of abrasiveness, but with empathy and support.

As much as you may want to try to change the other person’s behavior, in reality, you only have the ability to change your response to them.


Step 2. Where are we going?

The next step is reflecting on what each of you wants to achieve—not just your own goals. And there’s more to it than just the two of you: most challenging conversations at work have implications for the team, your relationship, and the issue itself.

What are you willing to compromise on?

If both of you remain rigid, you’re probably not going to make any headway. Keep in mind that you can only change your own behavior, and figure out where you’re willing to make compromises and any areas where you’re not.

Think through which one would you’d be willing to compromise:

  • What they want
  • What I want
  • The issue
  • The impact on the team
  • My relationship with them


Step 3. Where can we get next time we meet?

Once you’ve made the decision to face a challenging conversation you’ve been avoiding for a long time, it’s tempting to think you’re going to solve everything in one sitting. Unfortunately, it may take a few discussions to unravel the conflict and reach an understanding.

When you’re realistic with your objectives, you’re less likely to get frustrated and heated when things aren’t getting resolved as quickly as you’d hoped.

Step 4. Which obstacles could get in the way?

Be proactive about potential roadblocks that may cause either of you to become more embroiled in conflict. These are some things that could get in the way:

  • Lack of clarity about your purpose
  • Unrealistic expectations of yourself or others
  • Expectations not being met
  • Distractions and diversions
  • Misinterpretation of behavior: yours or theirs

Another obstacle to success is what we refer to as overdone strengths: a quality that works for you when you’re at your best, but works against you in the wrong context. Your Overdone Strengths may come out to play if you allow yourself to enter the conversation already in conflict or if you allow something to send you into conflict during the conversation. If you’d like, you can learn more about the Core Strengths philosophy on strengths here.

Think about how you’ll address each of these obstacles if they arise.

After several coaching sessions, Eric decided he needed to take a different approach with a direct report who he’d been struggling to manage for some time. He found the person very difficult, even arrogant and obstructive in previous conversations. So, he decided to approach the next conversation in a more supportive way by demonstrating tolerance and trust. Eric would still need to be persuasive but in a different way. Armed with this new approach, Eric headed down the corridor to meet his direct report. Halfway there, he remembered how difficult the last meeting had been and metaphorically ‘dropped’ his supportive, trusting, and tolerant approach on the floor and left them behind. Instead, he entered the room ‘carrying’ abrasive, stubborn, and rigid. Needless to say, the meeting didn’t go well.

Step 5. What driving style should you use?

This next consideration is all about the other person. To get on the same page during the challenging conversation, it’s important to understand their values and strengths so you can adjust your communication style accordingly. This is what we call Relationship Intelligence (RQ).

If Fred, the abrasive colleague in the above example, is motivated by results, frame your conversation around the positive results you two can achieve if you work together.

Step into his shoes and focus on delivering your message in a way that will resonate with him—including things he might find frustrating about your behavior.

Be yourself with more skill.

The key to successful challenging conversations at work is authenticity. As you shift your approach to communicate better with the other person, you’re not changing yourself. You’re being yourself with more skill. 

Step 6. How will you know when you’ve arrived?

What’s the definition of success after a challenging conversation? A good measure is trust. When you feel at odds with someone, you often doubt their intent, even if you know them well.  When you trust someone, you understand what they’re saying, even if they don’t communicate it well.

Challenging conversations don’t have to be so… challenging.

If you or others at your organization would benefit from learning the skills to master challenging conversations at work, Core Strengths can help. We offer conflict management solutions that empower people to resolve their conflicts and prevent new ones.

Download Our Guide to Approaching Challenging Conversations