5 Strategies To Prepare For A Difficult Conversation At Work

Before saying these four dreaded words to a colleague: “We need to talk,” here’s how to make a tough confrontation go smoothly.

5 Strategies To Prepare For A Difficult Conversation At Work
[Photo: Flickr user marty hadding]

You’ve got a tough conversation coming up. Maybe you’re giving a negative performance review, or maybe you need to deal with a personality clash that’s upsetting the whole office.


You know you need to think through this conversation beforehand, but inadequate attention is not the problem. You can’t stop thinking about this conversation. The problem is that the way you’re thinking may not be helpful.

“We always tend to go to the worst-case scenario,” says Marcia Reynolds, an organizational psychologist and author of The Discomfort Zone: How Leaders Turn Difficult Conversations Into Breakthroughs. “It’s sort of a protective device our brain has.”

“The leader sets the emotional tone,” she says, and if you go in apprehensive, “you’re setting up a scenario that this is going to be awful.” Here’s a better approach.

1. Focus On The Other Person

Instead of thinking about what you want, ask: “What is it that would be most useful for them?” says Reynolds. “A lot of times we know the impact of our behavior. We just don’t know how to change it.”

Approach the conversation from the perspective of how you can help the person get better results from team members, or at least not have everyone in the office cringe when he or she comes to a meeting.


2. Think Through Your Opening

How you begin the conversation matters a great deal, but don’t fall back on the feedback sandwich: compliment-criticism-compliment.

“Please don’t ever do that,” Reynolds says. “You sound so insincere. Better to get down to here’s what it is I want to help you with.”

3. Practice Out Loud Beforehand

“When we practice in our heads, it’s not the same,” Reynolds says. “You have to practice out loud so your brain can actually hear you speaking.”

You don’t want to flinch when you say something difficult. Practice in your car during your commute until the words come easy.

4. Call A Peer For Help

Even if you need to keep the details confidential, you can role play scenarios with another manager who’s been through this before. This can help you think through objections that might come up.


Sometimes people do get defensive during difficult conversations, and practicing responses will boost your confidence that you can stay calm.

5. Don’t Fear Emotions

Ultimately, difficult conversations can become turning points in a person’s career journey. “You will make them uncomfortable, and that’s good,” says Reynolds.

Strong emotions drive lessons deeper into our brains than when we just receive straightforward information. Approaching a difficult conversation with this mindset increases the chances that everyone emerges stronger on the other side.

About the author

Laura Vanderkam is the author of several time management and productivity books, including I Know How She Does It: How Successful Women Make the Most of Their Time (Portfolio, June 9, 2015), What the Most Successful People Do Before Breakfast (Portfolio, 2013), and 168 Hours: You Have More Time Than You Think (Portfolio, 2010). She blogs at