6 ways to kick off a difficult conversation

Stop avoiding tough conversations. Use these icebreakers to diffuse stress and have more productive one-on-ones
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When you need to deliver bad news, just initiating the conversation can be fear-inducing. You might avoid the other person or delay the conversation for days – tactics that only make the problem at hand worse and deepen your anxiety about the whole thing.

As uncomfortable as it can be, tackling issues head-on with authority and confidence is a skill leaders must possess. And a good opening line can set the tone for a more productive conversation and put both parties at ease.

[ What does your vocabulary say about you? Read also: 8 powerful phrases of emotionally intelligent leaders. ]

We asked leaders for the exact words they use when bringing up difficult topics with others at work. If you struggle with this leadership issue, try out these helpful phrases and tactics.

1. Have a code word

No need to come up with something new and clever every time you need to have a difficult conversation, says Katie Horgan, co-founder and VP of operations of GivingAssistant.org. Have a go-to standard phrase instead, she suggests.

“Everyone on the team knows that the phrase ‘give you feedback’ is the signal for accepting feedback and simply listening.”

“We use ‘Would you be okay if I gave you some feedback?’ or ‘I’d like to give you some feedback. Is now a good time?’ as a way to introduce direct, constructive feedback to each other,” says Horgan. “Everyone on the team knows that the phrase ‘give you feedback’ is the signal for accepting feedback and simply listening. They are only requested to say ‘thank you’ at the end, nothing more is expected. Of course, they can open up more dialogue if they choose to. By having a standard signal phrase, it lets people know what kind of a conversation to expect. This is beneficial for all of us in starting tough conversations.”

2. Start with “Thanks”

Never underestimate the impact of kindness and appreciation.

“Open with ‘Thank you,’” says John Crossman, CEO of Crossman & Company. “Thank them for their service, hard work, previous successes, etc. It must be sincere. I like starting the conversation this way because it frames the meeting with positive, sincere affirmation. Then move into the tough subject. When you move into the tough part, be straight, clear, and kind.”

3. Share the power

“It’s better to prepare someone in advance than to hope a clever icebreaker is going to ease the way into a difficult conversation,” says Adam Cole, co-director of Grant Park Academy of the Arts. “Gentle, honest, and simple are the best ways to communicate that a difficult conversation is necessary. In addition, to ease the feeling of powerlessness or to minimize the other person feeling like a victim, it’s helpful to offer them some kind of power over the conversation, or at least a choice.”

Cole puts it this way: “You might say: ‘I want to have a conversation about your performance at work and I’m looking for a time where we can talk uninterrupted for a while. Could you please let me know when your schedule is free for this?’ The tone of this request sets the person up for the importance of the talk while reassuring them that their input is important and that they will be listened to.”

4. Lean on a classic

The classics are classic for a reason – they work, says Stacy Caprio, founder of Accelerated Growth Marketing.

“I’ve found the classic phrase, ‘Do you want the good news or the bad news first?’ delivered with a smile and laugh to be a good icebreaker for tough conversations,” says Caprio. “Everyone knows the phrase and that it means there will be good and bad news coming, which softens the blow when the bad news does come because they’re already expecting it. It’s also a way to deliver a bit of good news along with the bad.”

5. Make working together the goal

Giving bad news or pointing out a problem is often so painful because we care about the relationship with the other person – and how that relationship will hold up after everything is said. Stay focused on the work you can do together, says Akiva Goldstein, CEO and solutions architect for Onsite In 60.

This phrase leads to a joint effort and no finger pointing.

“For existing clientele, I sometimes have to say, ‘As much as I enjoy giving you good news, I need your help with an issue so we can resolve it together,’” says Goldstein. “I have done this for old servers needing to be replaced, when a project was running over budget, when an ISP was going to be late with an Internet install for a new office, and several other times when I’ve had to initiate a tough conversation. Maybe it helps clients remember the times I was able to share good news, or maybe it’s because I’m asking for their assistance – either way, this phrase leads to a joint effort and no finger pointing.”

6. Stick to a script

If you really struggle in this department, or if you tend to get stage fright and forget everything you know the moment the meeting begins, it might be helpful to stick to a script.

Carol Lempert, a professional actress turned executive coach, helps business professionals increase their executive presence by learning the skills actors use to have great stage presence. She proposes the following script leaders can use to ease into any tough conversation:

  • Start with a statement of mutual purpose. For example:
    • “I know that doing work that it intellectually rigorous is important to you. It’s important to me too.”
    • “One thing I’ve always admired about you is X. I know that’s important to you, and it’s important to me too.”
  • Follow with a statement that shows that you know that the person means well. For example:
    • “I don’t think it was your intention to…”
    • “You might be surprised to hear that…”
  • Follow with an example of the behavior.
  • Follow with a question. For example:
    • “What’s your experience of what happened?”

[ Want to get even better at this skill? Download 4 things to do before a tough conversation. ]

Carla Rudder is a community manager and program manager for The Enterprisers Project. She enjoys bringing new authors into the community and helping them craft articles that showcase their voice and deliver novel, actionable insights for readers.  


Very useful. Thanks