How to Handle Challenging Conversations

by Gordon White

Procurement professionals regularly work with end users, particularly during procurement planning, and they often find themselves having to push back against unclear or indefensible requirements. And we all work with internal teams and colleagues, some of whom may challenge us, as well. These tough conversations are an integral part of conducting business and can make or break project success, yet few of us receive specific training or education on how to handle challenging communication.

It can be demanding, so we need tools. After 20 years as a mediator, three of my top suggestions are to:

  • cultivate a collaborative attitude,
  • bring structure to the conversation, and
  • make use of a few essential communication skills.

Collaborative Attitude

The greatest obstacle we face in dealing with others is ourselves.

Difficult communication challenges how we view and understand ourselves. When someone else is accusatory or blaming, we either have to reject what he or she says, or consider it. If we reject it out of hand, then we have stopped listening, which is never helpful. Worse, we become rigidly defensive and are more likely to be thrown off balance. I suggest that you listen carefully to the complaints or accusations of others, acknowledge to yourself where there is merit in what they say, and learn from it. Openness creates more flexibility, strength, and collaborative capacity.

Take heed if you find yourself saying, “It’s not my problem.” If you are not comfortable, or if your best performance is being hampered, it is your problem. You can continue to blame the other person (which may even be justified), but unfortunately, the more we blame, the more disempowered we become, because we can’t control others. Thankfully, what we take responsibility for, we can do something about. We can influence others positively by having more discipline over ourselves.

If another person is very challenging, chances are that he or she is not a skilled communicator. This means that you may have to do more of the communication work. You can think of it as being the mediator for both of you, while at the same time you are in the conversation. It may seem unfair for you to have to do extra work, and it probably is, but getting a good agreement or improving a working relationship may be worth some extra effort on your part – and even worth eating some humble pie.

It is of utmost importance to prepare yourself for the worst things the other person could say or do, and to develop your capacity to manage yourself emotionally. Rather than strike back or duck out of the conversation, instead, self-manage and keep your focus. You need a silent internal self-management procedure, such as telling yourself that you are being triggered – “I’m reacting strongly to what he said” – and putting attention on your physical body for a few seconds. Take a breath, feel your feet on the ground or feel the sensation, then refocus. When the going gets tough, you need to be able to pause, slow down, consider where you are in the conversation, and act intentionally.


Possessing a framework is helpful if you want to make progress in challenging conversations. Here is a four-step procedure that will add structure to your conversations:

  • Establish connection.
  • Explore new understandings.
  • Choose a focus.
  • Develop multiple options.

1) Establish connection.

You don’t have to like the other person, but you do need to form a working connection. This means a brief interchange about the conversation before you actually have the conversation. This interchange should include your intentions. Additionally, there may be context or guidelines that you want to mention. What it could sound like follows.

Intention: We have a different set of responsibilities that will always tend to bring us into disputes. For the benefit of the organization and each other, I would like to find a better way to deal with differences when they arise. What do you think of what I just said?

Context: My understanding is that we will report back to the team about what we have decided.

Guideline: I will listen to you attentively and allow you to finish what you are saying, and I would like you to do the same for me. How does that sound?

2) Explore new understandings.

You don’t have to agree in order to make progress; you do need to find new ways of seeing things. Our tendency is to unconsciously assume that we have all of the information we need in order to establish a good solution. Instead, consciously assume that you need the other person’s story about what has happened, and you need his or her ideas to solve the problem that both of you face. You could sound as follows:

How do you see it?

What is your biggest concern, and what has been most difficult for you?

I would like the opportunity to explain something to you, and I would like you to try to see it from my perspective.

What is most important to each of us at a deeper level, and why?

What additional information or assistance do we require?

3) Choose a focus.

Conflict can be messy and confusing. At some point, you need to focus on a topic on which you can make progress. Example:

For the next half hour, I would like to focus on the kind of information you supply in your requests, and how I respond to that information. How does that sound?

4) Develop multiple options.

Take some time to play with different proposals. One of the main energies that can halt progress is trying to resolve differences too quickly. In a tough conversation, be provisional. Otherwise, good ideas can be shot down before they are considered properly. You could sound as follows:

One idea is for me to provide you with a format for your requests. What would have to be considered for that to work for you?

Let’s list a few possibilities before we decide.

Remember: It’s a learning conversation in which you explore new territory, not a proving conversation in which you try to establish why you are right.

The most important outcome to achieve is a willingness on the part of the other person to continue the conversation in future as needed. If you don’t solve it all in one sitting, don’t mind. It’s more important to make a good step forward in the working relationship, because it builds your capacity to deal with any difficult situation that might come up in the future.

Communication Skills

We all have a basic human need to be understood, so we can usually make progress by demonstrating and confirming understanding. But when you say, “I understand …” or “I appreciate what you are saying …,” it is generally a good indication that you don’t understand, so notice if you hear yourself make those statements. Instead, repeat what you have heard, “You’ve said that …” Once you have summarized, there is a key follow-up question, “How well do I understand?” or “How well do I get it?” You can then have some confidence that you understand when the other person tells you that you do. But until then, assume that your understanding is limited.

In your mind, reduce the problems you have with the other person to behaviours, and then address specific behaviours, not characteristics (characteristics are often expressed as adjectives).

For example, “You have waited three days to respond to my email. That makes it difficult for me to meet the timelines you have set for this project. I am more able to comply with your request if I hear back within 24 hours.” Not: “I find you unresponsive [adjective].”

Eighty percent of your questions should be open questions that begin with “How?” or “What?” Otherwise, you are in danger of leading the other person to answers you want, rather than learning what matters to him or her.

Closed question: “Do you find that your current workload makes it more difficult to communicate with me?”

Gordon White

Principal of Gordon White Consulting

caucasian man with white hair wearing narrow black framed glassesGordon White is the principal of Gordon White Consulting in Victoria, B.C. He is a mediator and organizational development consultant who offers team development programs and negotiation training. He also teaches a course in Conflict Analysis and Management at Royal Roads University. Gordon is currently creating an online conflict management course for large organizations. He blogs regularly at You can follow him on Twitter @valueconflict, and reach him at or (250) 389-6231.

Readers are cautioned not to rely upon this article as legal advice nor as an exhaustive discussion of the topic or case.  For any particular legal problem, seek advice directly from your lawyer or in-house counsel.  All dates, contact information and website addresses were current at the time of original publication.