How Do You Have Tough Conversations at Work?

Note: It’s never comfortable to be on either side of an awkward 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 managers must master. Enjoy. (Previous installments of all of my blogs can be found on my website at

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. 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 fear of being rejected,” says Cheri Torres, a business leadership coach. “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.

Beth Linderbaum, a management consultant, 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

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 positively. “Flip the focus from what is wrong to the outcome you want,” advises Torres.

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

6. Be specific

“Conversations need to be direct, regular, and honest,” says Giancarlo Di Vece, president of software development provider Unosquare. “Sugar-coating feedback does nothing for the company nor the underperforming employee.” Particularly within the technology group, those receiving feedback or information on their performance will respond better to detailed input supported by data. That may include concrete examples of behavior, specific instances where the behavior showed up, or times and places it occurred.

“As a leader, you need to evaluate and ensure you have done your due diligence in advance of the conversation,” Freedman says. “Pull your examples together. Gather perspectives from others who have seen this behavior if that is needed to ensure you can provide clarity.”

Also, be as honest and forthcoming as possible. When a leader or manager offers only partial feedback or fails to give the full reason for something, this “reduces the likelihood of their being able to address the problem,” says Freedman.

7.  Replace "but" with "and"

Being thoughtful about language goes a long way toward having a constructive conversation. Instead of saying “You had great visual aids, but you could have given your audience more time for questions” try “You had great visual aids, and next time you might think about adding more time for audience question.”

“The word ‘but’ erases everything that comes before it and can put people on the defensive,” says Linderbaum. “The tweak may seem small but the impact it will have on how the receiver interprets the feedback and how it makes them feel makes a powerful difference.”

8. Offer remedies – and hope

It’s important to give the other party a remediation plan. Daniello always has a “get well” plan in mind for employees that may include additional training or mentoring sessions, for example. “Layout a clearly defined path forward to address the feedback, including timing, milestones, and measures of success,” says Freedman. “This is particularly important if it is in the context of someone not getting a promotion.”

Giving the other person hope – that a raise is still an option, that they can continue to progress in the function – is helpful. Never end the conversation on a negative note, warns Daniello. But avoid giving false hope, Freedman says, as that “can damage both the employee and the leader’s reputation.”