Mastering Difficult Conversations: Earn the Trust of Those Around You


Whether you’re giving bad news to a CEO, firing a subordinate, pushing back on a peer perspective or defending your position from aggressive challenges, having difficult conversations is part of being a leader. While these conversations aren’t always enjoyable, the appropriate mindset, clarity and preparation can make you highly effective in achieving your desired result and, at the same time, enhance your standing as a leader.

Get the facts.

It’s important to always make sure you have the relevant facts. Finding out in the course of the conversation that your facts are wrong makes an already difficult conversation worse—plus you instantly lose credibility and probably damage the relationship. Before the conversation, do your homework. Look for objective facts, talk to people with different perspectives on the issue, and consider alternative explanations. If you know that your facts are incomplete, acknowledge that at the start of the conversation and invite the other person to fill in the gaps before you launch into making your points.

Clarify your intentions.

In preparing for a difficult conversation, it’s important to think about your goals and determine the ideal outcome that would achieve those goals. The following exercise removes much of the emotion and focuses on what you’re trying to accomplish.

For example, if a colleague consistently undermines you in leadership meetings and you want it to stop, you should approach your conversation differently depending on whether you want to strengthen your relationship or simply want the disrespectful behavior to end. Consider the example below—neither goal is inherently right or wrong, but being clear on the outcome you want will lead you to engage in very different behaviors:

Goal: Build a relationship to stop bad behavior

Goal: Push back on bad behavior


What do I want for me?

Build a stronger relationship with her so that she no longer undermines me in meetings. If she has a problem, she will bring it to me directly.

Explain and firmly ask her to stop her bad behavior immediately.

What do I want for the other person?

To achieve self -awareness and empathy. I want her to see my side, understand the impact of her actions and stop undermining me because she respects me as a peer.

To take this as a warning. I want her to know that I will not put up with this anymore and if she doesn’t stop, I will take action.

What do I want for the relationship?

I would like us to be good colleagues, respectful of one another and mutually supportive.

I want her to respect me so that she no longer undermines me.

What do I want for other stakeholders?

The other members of the leadership team should know that we are all pulling in the same direction and that we can have honest and constructive disagreements to get to the best decisions.

I want them to know that I am good at what I do and will not be pushed around.

What would a successful outcome look like?

My colleague will understand why I find her comments undermining and why that is not good for us or for the leadership team. She and I will agree on different ways that she can disagree with me on substance without undermining my authority.  Our relationship will be stronger because we will have had an honest conversation about a difficult topic.

My colleague will understand that I will not tolerate bad behavior and that I can hit back hard if I need to.

Get to neutral emotional ground.

If you are seeking to enhance your relationship with the other person, the way you deliver your message is just as important as the message itself. Pay attention to your choice of words.  Separate the problem from the person. Avoid beginning sentences with “you” and start them instead with “I” instead, framing the issue in terms of the impact on you rather than judgment of the other person’s behavior. Set a respectful tone for the conversation by staying calm and listening actively to the other person. Even if you believe they are wrong, giving them a chance to be heard will greatly enhance the likelihood of reaching a positive outcome and will earn their respect for you as a leader. Acknowledge your role in the problem too and avoid casting yourself as a victim and the other person as a villain.

Communicate with generosity, respect, integrity and truth.

If you’ve done your homework, you have the facts but you do not know the other person’s motives. Assume good intentions until proven otherwise. Assume as well that the other person wants to solve the problem as much as you do.

Be hard on problems but kind to people.

While it’s important to be tough on problems, you can simultaneously be kind. Being kind does not mean you give people a pass—only that you note their mistake and solicit their ideas for fixing it rather than dwelling on the fact that they made a mistake. This will ultimately produce trust and a desire to fix the problems at hand.

Difficult conversations are a necessary part of leadership. Avoiding them has a cost to everyone involved—and can lead to underperforming employees, a lack of transparency, or worse, a culture of disrespect. As a leader, you need to master the art of difficult conversations to make them work for you and to earn the trust and respect of those around you.


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