by Reta Coburn

Let’s face it, we’ve all been there… a situation where we have to deal with conflict, or a difficult topic. Regardless of whether you are a person who tends to avoid these conversations, or one who jumps in and addresses the issue immediately, it is wise to take a little time to prepare to ensure the best outcome.

How to approach and have difficult conversations or work through conflict is a topic that repeatedly comes up in my coaching conversations. In fact, it is one of the top five issues that plague individuals. What’s more, it’s not unique to any particular level of individual in the organization or type of role for that matter – everyone has to navigate these conversations in their workplace and at home. Perhaps this topic resonated for you because you’re facing one at the moment.

Since it is such a common issue, and avoiding the problem only serves to make the situation more difficult, you can benefit from learning some strategies to help you address the problem and work toward an appropriate resolution. 

If you have the opportunity to take some time before a difficult conversation, some investment in planning for it will strengthen the outcome. However, sometimes you are caught in the moment and don’t have the time to strategize first. Either way, here are some practical and easy to implement next steps that may offer support.

What Outcome Do I Want?

The first thing I usually ask a coaching client after they explain the challenge they need to work through with someone is “what is the outcome that you want from the conversation?”

“To begin with the end in mind means to start with a clear understanding of your destination. It means to know where you’re going so that you better understand where you are now and so that the steps you take are always in the right direction.”

— Stephen R. Covey

Depending on the issue, it may be helpful to explore the outcomes that you want to achieve in two steps. 

  • The first step looks at the issue that has arisen and is prompting the conversation. It is the behavior we want to stop (or start), resolution that is needed on a problem, action required on something pressing, etc. 
  • The second step is uncovering any other desired outcomes that could be more foundational in nature, such as sustainability around the changes, better communication going forward and leaving the relationship intact or better afterward.

Are You Looking at the Situation Through Others’ Perspectives?

It can be beneficial to use perspective taking strategies, like zooming out, to prepare for navigating a difficult conversation. Taking a bird’s eye view and asking yourself open ended questions about the other person’s standpoint such as:

  • What might be important to this person on this issue?
  • Why might they be taking that approach to this problem? 
  • Are there factors or information they have/don’t have that might be shaping their position on this? 

A pause for this contemplation allows us to consider other possibilities and determine how to best approach the conversation and use our influence to guide toward a positive outcome. Influence is a key skill, and one of the emotional intelligence competencies. Daniel Goleman describes influence as the ability to have a positive impact on others, to persuade or convince them to gain their support. 

Some questions you might ask yourself to help you work toward achieving alignment as you prepare are:

  • Where do we share common views or goals in this situation?
  • What are some objections that the individual will have with my position?
  • How can my approach support them or how might they react to these points? 

The ultimate goal is to facilitate a dialogue and guide it toward your ideal outcome or adapt in the moment to new information and reach an alternative conclusion that you’re satisfied with.

Are You Challenging Your Assumptions?

As you’re zooming out, also challenge yourself on your assumptions. You may be feeling that the other person is being selfish, only thinking about how their team looks in this situation. But if you choose to give yourself space to consider that there may be other possibilities, perhaps there are other things at play? Consider the possibilities and keep your assumptions in check:

  • Maybe their team had some recent setbacks and missed a critical deadline so they feel under elevated pressure to deliver.
  • Perhaps they have lost key people on their team and are struggling.
  • Possibly they are facing setbacks in their personal life and are simply not able to put their best foot forward. 

Instead of allowing our thoughts to get away from us with assumptions, try interrupting those thoughts and give the other person the benefit of good intentions. Moving ourselves from being closed off or rigid to open or even empathic can support a richer dialogue and healthier exchange that keeps the relationship intact. 

Remember that Words Matter

Do you remember a time where you phrased something in a particular way or chose select words that you wished you could have a do-over for? That is a resounding yes for most of us. We have used words or phrases in the heat of the moment that didn’t land well and took the conversation off course. To the extent you can, putting advance thought into how you frame points or questions that you want to raise can serve you well. It may free you from struggling in the moment to find the ‘right words’ and create more space to listen and focus on the exchange you’re having. 

A few examples might help illustrate why words matter. 

  • Prelude phrases like “with all due respect” can be perceived as I am about to say something that you’re not going to like. 
  • Responding to a point or argument with “I disagree and …” may inadvertently heighten tensions. You can still be heard by simply raising your rebuttal without first putting your stake in the ground. Or you might say, “My perspective on that is different. The experience I had with that was …” or “I’m not sure I understand where you’re coming from. Can you share with me how you got to that place?” 
  • Be thoughtful in your use of the word “why” in questioning. Why questions can feel interrogating for some people and inadvertently put them on the defensive. “Why did you do it that way?” as an example might be received as critical versus approaching it differently with:
    • Can you share how you evaluated the options to get there?
    • Tell me more about how you approached that.
    • What types of risks did you identify in your analysis?

You get to the same result but reframing your why question in this manner will invite the other person to explain and educate instead of moving into defense territory. You might find it helpful to jot down a few bullets on how you’d like to frame certain points you are going to raise or how you might respond, anticipating challenges that you expect to hear.

Setting the Table, So to Speak

I have had many clients who struggle to initiate the conversation. What are the right words to open with and how do I convey my concerns when I know I will face a strong reaction? This worry becomes an obstacle for them, time slips away and then it is too late. Other clients are naturally comfortable charging ahead with these conversations or have already built their competence in candor and are at ease through routine practice. 

For those of you who struggle, this structure of ‘setting the table’ can support you as you build competence or if you’re naturally a processor it may simply be a tool that you onboard to create space for yourself to prepare. In either case, I would ask you how you could ‘set the table’ for the conversation. Here are some examples of how that could sound:

  • That was a good conversation. I can see that we’re not fully aligned yet so I am going to look at our calendars and carve some time out for us to explore this more.
  • You shared a viewpoint at the meeting this morning about my region’s performance that l would like to understand better. Can we connect tomorrow on it after the client site visit?
  • I can see how important this is to you and feel like we need to dialogue more on this once I can reflect on the points you raised. Would it be okay for us to revisit tomorrow?

There are many ways to create the space you might need so hopefully these examples serve as inspiration for you to land on language that feels right for you.

How Do You Want to Show Up? (Intentionality)

Lastly, let’s shift and focus inward for a few moments. You’ve thought about the outcomes that you want to achieve from the conversation so now I would typically invite clients to think about setting their intention or, as we often say in coaching, how they want to ‘show up’. 

If you envision the conversation watching yourself from a balcony, what do you want to see? Clients would have very different responses to that question, saying things like they want to: 

  • Put the other person at ease
  • Be confident
  • Create understanding 
  • Promote unity
  • Be curious; facilitate discovery
  • End in a better place than they started
  • Bring positivity, and more

Understand here that in initiating the conversation, you are creating the situation that the other person is responding to so your intentionality can make all of the difference.

One bigger picture question that I invite you to consider is what culture do you aspire to create in respect of candor within your team? Candor is an important ingredient to building trust so as you continue with your journey of having challenging and healthy conversations, perhaps you can also think bigger picture about how candor can strengthen relationships, increase engagement and accelerate your team’s performance. How can you embrace and normalize candor within your interactions and build it as a core competency within your team? 

Sometimes the situations we face in our organizations are just so big and multi-faceted it is difficult to take a step back and remove ourselves from the situation so we can figure out the best next steps. If you feel that you could benefit from an outside view, we would love to connect with you. Contact us at or call us at 970-279-3330 for a no obligation, free consult and learn how we can help you develop strategies to help you and your organization move forward successfully.