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How to Have Difficult Conversations

“Can I see you in my office?”

The work equivalent of “we need to talk,” this one sentence has the power to unleash a tornado of emotions.

In the best-case scenario, you’re a leader who has many conversations with all your team members: the congratulatory, the difficult, check-ins, etc. Conversations are happening every day—it’s what you do. So rather than summoning someone to your office, you’re more likely to say: “Let’s chat about this.”

Worst case? Your office is akin to the principal’s office, and when employees are summoned, everyone knows why. And they’d rather eat dirt then take a seat on that chair facing your desk.

Chances are you’re a leader somewhere in between unbelievably amazing and despicably awful, and you’re looking for some support to get those difficult, but essential, conversations rolling off your tongue with a little more ease.


What’s the next line?

Some conversations are best held in private, and The Difficult Conversation is one such occasion. You’ve issued the invitation, and undoubtedly there is some uneasy anticipation on the other side.

Initiating difficult conversations can be as nerve-wracking as being on the receiving end. And sometimes, even more so. You’ve thought about the conversation, planned how it might go, considered your responses…over and over…and it still doesn’t get comfortable.  And here’s the thing: it won’t be comfortable. You need to learn to sit in uncomfortable.

We frequently equate difficult with negative but it’s not always the case. A difficult conversation can be positive, helpful, re-affirming. As leaders, we develop people through difficult conversations. And, if handled well, as recipients we learn from difficult conversations.  Reframing “bad or difficult” to “problem solving” is a useful shift to get the conversation started.


It’s not you, it’s me.

Wrong. This is about the employee, and shifting focus to yourself for this conversation is going to set things awry from your first words. Be clear in identifying what this conversation is about, and keep the employee front and centre. Engage the team member to hear “uh-oh, problem, but let’s work it out” and not “NOW what’s his problem?”

Instead of: “I want to talk about Situation A…”

Turn the perspective around: “Let’s look at Situation A, and what might be helpful for you to move it forward…”


What’s your problem?

If you’re embarking on a difficult conversation, then technically, you’re out to solve a problem. To prepare for the conversation, you need to name that problem. Identify the precise information which you need the employee to hear and to understand—don’t be tempted to spin or minimize the information. Create a key message to deliver early in the conversation, operating on the premise that most people retain very little of a conversation.

Here’s an example:

“This is the problem <<succinctly state the facts>>. This is what we need to achieve <<state the goal>>. Help me understand your perspective and how I can help, so we can solve it.”


Choose the best time to meet.

Sorry. There is no “best time.” If a conversation is likely to be difficult, there will always be a reason to put it off: birthday, sick pet, bad hair day… Take the deep breath and go. As a leader, you can still acknowledge the challenging process, and share it: “This might be a hard conversation, but we’re going to push through together. I’m committed to working through this with you.”


Leaders have difficult conversations to support teams and individuals. Great leaders have all the conversations.


Tips from Smart Savvy Leaders:

Catherine Ducharme

Be concrete. Be clear. Be compassionate. Be affirming. It’s beneficial during the conversation to acknowledge the other person’s feelings: “I understand your frustration...”  “I hear your concern...”  “I know you want to do right by the team.”

Use these conversations to help your team members move forward, and to transform over time. The intent is never to cut people down, or criticize in an unconstructive way. People should leave the conversation feeling optimistic.


Peter Reek

You’re the leader, and your team needs to know with certainty that you’re just as prepared to deal with the tough stuff, as to share kudos or facilitate a brainstorming session.

Reframe the conversation (in your mind) from being a difficult one to being a growth opportunity (for both sides). View each conversation as a natural outflow of doing business and growing a high-functioning team. When you view your role as facilitating growth and increased awareness / understanding, great things can happen.

Stop yourself from predicting outcomes and projecting motives. Be ready for contingency planning and steering conversation in the needed direction, but refrain from assuming you have a solid handle on the mindset of your team member. This will ensure you refrain from attaching motives that may not exist.

Listen to understand as opposed to listening to respond. Don’t fret about what you’re going to say next, you’re not reciting lines, you’re interacting with another human being and opening the door for a meaningful conversation.

Be direct, call a spade a spade, don’t downplay the need for the behaviour change. You may be the one who helps them identify a blind spot and save them from ongoing career challenges. And, there is always the possibility, they will do the same for you.


Peter Reek is founder and president; Catherine Ducharme is a recruiter and leadership development facilitator and trainer with Smart, Savvy + Associates. We find high-calibre marketing, communications, creative and sales professionals with proven track records and in-demand skills for companies who need them, across the Pacific Northwest and in Toronto.

Smart, Savvy + Associates also provide leadership and training development programs for workplace programs, corporate retreats and individual growth opportunities. Contact Peter or Catherine to discuss your organization’s training needs.


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