Every day, I see first-hand how uncomfortable difficult conversations can be for many leaders and employees within our organizations.

Most times, the default mechanism when confronted with the need for a challenging conversation is to avoid them at all costs. However, the longer we hold off on having an important but difficult conversation, the greater the strain we place on that relationship. Professionally and personally, our ability to have difficult conversations is an important skill.

Have you ever avoided a difficult conversation by telling yourself that…?:

  • “It will eventually get better.”
  • “She is too emotional, I don’t want to deal with her drama.”
  • “Having this conversation may make things worse.”
  • “His high performance outweighs his poor attitude.”
  • “He is just 2-3 years away from retirement anyway.”

Confronting a problem is never easy and this is especially true for people who are conflict adverse and would do anything possible to avoid it. Amongst my colleagues I am often called upon to help navigate challenging conversations and, as a coach, part of my conversations with clients at some point or another often focus on helping them work through their fear of conflict by developing strategies to address difficult conversations confidentially.

At some point, many of us have had to deliver the dreaded line, “We need to talk.” 

This often precedes an argument rather than any conversation, so the automatic reaction for many people is to avoid the conversation altogether.

Why are some conversations so difficult that we’ll do anything to avoid them? Possibly because:

  1. We are stuck between what we feel and knowing what we really shouldn’t say.
  2. We are distracted by our internal thoughts and uncertain about what to share.
  3. There’s so much going on in the relationship with the other person that it’s confusing.

If you didn’t care on some level about your relationship with the other person, you wouldn’t struggle with this in the first place.

But avoiding the conversation allows things to build up to the boiling point. When we finally have no choice but to confront the issue, we can potentially end up damaging the relationship with the other person.

Holly Weeks, author of an article in Harvard Business Review, “Failure to Communicate,” describes a familiar “difficult conversation” scenario:

“Your stomach’s churning; you’re hyperventilating – you’re in a badly deteriorating conversation at work. Such exchanges, which run the gamut from firing subordinates to parrying verbal attacks from colleagues, are so loaded with anger, confusion, and fear that most people handle them poorly: they avoid them, clamp down, or give in. But dodging issues, appeasing difficult people, and mishandling tough encounters all carry a high price for managers and companies – in the form of damaged relationships, ruined careers, and intensified problems.”

Whenever emotions are involved, conversations get tricky. Emotions are generated in the part of the brain called the amygdala – a more primitive part of the brain. When stimulated, it calls the body into fight or flight mode. Humans are genetically hard-wired to react to emotional triggers by either fighting, freezing, or fleeing – actions which, during cavemen times, had huge survival benefits.

Are we much different now than our ancestors? Genetically, no. We still have impulses to blast someone or clam up and avoid them altogether. We are not actually hard-wired to sit down and talk it over with someone when there’s a problem.

Rebecca Knight, in an article in Harvard Business Review, gives us pointers on getting what you need from these challenging conversations while keeping relationships intact.

Change your mindset

If you’re gearing up for a conversation you’ve labeled “difficult,” you’re more likely to feel nervous and upset about it beforehand. Instead, try “framing it in a positive” way.

For example, you’re not giving negative performance feedback, you’re having a constructive conversation about development. You’re not telling your boss “no,” you’re offering up an alternate solution. A difficult conversation tends to go best when you think about it as a normal conversation.


The calmer you are, the better you can handle difficult conversations. Take regular breaks and breathe mindfully to refocus. This technique works well in the heat of the moment. If, for example, a colleague comes to you with an issue that might lead to a hard conversation, excuse yourself — get a cup of coffee or take a brief stroll — and collect your thoughts.

Plan, but don’t script

To plan what you want to say, jot down notes and key points before the conversation. Drafting a script, however, is a waste of time. Your strategy for the conversation should be flexible and contain a repertoire of possible responses. Aim for language that is simple, clear, direct, and neutral.


There are three kinds of conversations…

Fifteen years of research at the Harvard Negotiation Project has produced some interesting information about what goes on during conflict. The book, Difficult Conversations: How to Discuss What Matters Most (written by Douglas Stone, Bruce Patton, Sheila Heen and Roger Fisher) outlines three types of conversations, no matter what the subject.

In each of these types of conversations (especially difficult conversations) we make predictable missteps that can distort our thoughts and feelings.

1. The “What Happened?” conversation.

There is usually disagreement about what happened or what should happen. Stop arguing about who’s right and, instead, explore each other’s stories and try to learn something new. Don’t assume you know what the other means. Disentangle intent from impact. Abandon blame and think in terms of contributions to the solution.

2. The “Feelings” conversation.

Every difficult conversation also asks and answers questions about feelings, which are formed in response to our thoughts based on negotiable perceptions. Are they valid? Appropriate? Often feelings are not addressed directly and thus they interfere with the conversation even more.

3. The “Identity” conversation.

This is where we examine what’s at stake: What do I stand to lose or gain? What impact might this have on my career, marriage, self-esteem, our relationship? These issues determine the degree to which we feel off-centred and anxious.


Sometimes, you just need to talk it out before engaging in the difficult conversation.

This is one very important thing I help many clients with.

By talking it out before engaging in a potentially confrontational interaction, you can examine your assumptions, your emotions, and your personal identity. You can also learn to structure difficult conversations in a way that improves relationships rather than risking them.

And, through one-on-one coaching as well as top team development, I can help you uncover the root of your adversity to conflict. By identifying and understanding what it is you’re afraid of, we can work on how to approach personal conflict in the future and prepare you to lead your team with confidence.

If this sounds like exactly what you or your team needs, contact me so we can talk about the impact executive coaching can have.

Categories: Blog

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