How to have tough conversations: 8 tips

All leaders have to deliver tough news sometimes
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It’s never comfortable to be on either side of a difficult conversation. However, being able to have a tough talk or deliver unwelcome news – telling someone they’re not getting that raise, intervening when a direct report’s behavior is off base, reviewing the performance of a team member whose work is falling short – is a core skill that all IT leaders or managers must master.

When it’s time to address an issue with an employee, peer, or business partner, people tend to make one of two mistakes, says Cheri Torres, a business leadership coach and author of "Conversations Worth Having." They put it off, which often exacerbates the situation, or they shoot from the hip, which can lead to a less effective conversation, hurt feelings, or worse.

[ Can't find a good work-life balance? Read also: Blended, not balanced: 8 ways to reclaim sanity at work and home. ] 

Having difficult discussions may never be a welcome task, but there are ways to make this a core competency and ensure that these conversations are as productive and painless as possible. Consider these 8 strategies:

1. Make sure good news outweighs bad

“For every one time you must give constructive feedback, you want to have 10 or more interactions that involve positive feedback.”

“For every one time you must give constructive feedback, you want to have 10 or more interactions that involve positive feedback,” says Beth Linderbaum, managing consultant at workforce development firm Right Management. “Managers who build a strong relationship based on trust and transparency will have the best foundation for delivering tough messages.”

2. Never wing it

“Even if you are an experienced leader or manager, take the time to really prepare ahead for the conversation,” says Elizabeth Freedman, principal at Bates Communications. “Think through what you are going to say and also prepare for what they might say and questions they may ask.”

3. Exercise empathy

“Being criticized raises our fear of rejection, not being good enough to belong. Receiving critical feedback can trigger our own fear of being rejected,” says Torres. “The more fear, the less access we have for connecting and working things out together.”

Before having the conversations, consider the other person’s side. What might be inhibiting their performance? What might help? “Find out if there are outside influences that are impacting someone’s performance and behavior,” advises Tony Daniello, director of infrastructure services at Computer Design & Integration.

4. Avoid the "feedback sandwich"

You know the formula where you give a compliment, provide constructive criticism, and then give another compliment? It doesn’t work. “If every conversation starts that way, the individual will always think there is something negative approaching whenever you give them a compliment or positive reinforcement,” Daniello says.

Linderbaum advises suggests replacing this approach with a “consistent and authentic rapport with your direct reports where you can share your observations about their performance, hear their insights, and work together to develop a plan forward.”

5. Flip the script

“Flip the focus from what is wrong to the outcome you want.”

Difficult conversations can be an opportunity for learning and growth, says David O’Hara, president of IT management and consulting firm Improving, but that’s more likely to happen when the conversation is framed in a positive way. “Flip the focus from what is wrong to the outcome you want,” advises Torres.

For example, a talk about how an employee’s behavior is putting people off becomes a discussion about why good relations between team members are important. “Your work is falling short” can be repositioned to “What needs to happen for you to excel.” Bad news about the promotion evolves into a conversation about how to better position for the next opportunity.

Stephanie Overby is an award-winning reporter and editor with more than twenty years of professional journalism experience. For the last decade, her work has focused on the intersection of business and technology. She lives in Boston, Mass.


These are some excellent tips and I believe that exercising empathy is extremely important. Before you meet face-to-face, take the time to sincerely consider the other side of the story. I have been relying on this post to prepare for a difficult conversation at work --> []. But some of these tips have given me a new perspective on difficult conversations. Thanks for sharing.