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What are good questions for difficult conversations?

If you’re trying to figure out where to start, how to start and how to stay on topic in a difficult conversation, you’ve come to the right place.  At work, difficult conversation topics that are sensitive in nature will need to be handled with even more care.  Whether you’re discussing poor performance, a negative review or evaluation or conflict with a co-worker, setting the scene is important. Let’s start with choosing a location.

Where to have a difficult conversation

Realtors say, “Location, location, location!”  Believe it or not, the same is true with difficult conversations.  The environment should be comfortable and free of distractions.  In order to allow for the most honest and open conversation, privacy is also important. Both parties should feel like they can share openly and honestly so the place to host the conversation is key to setting the tone before you even begin.  

How to start a difficult conversation with an employee

Having difficult conversations with employees shouldn’t be the hardest part of your job.  Conflict resolution, building rapport and encouraging open communication is an important part of being a good leader. You can set the tone by thanking them for their time and letting them know that you are here to establish some ways that, with their help, you can help improve the situation. 
Because we know that these challenging situations can be emotionally charged, we wanted to answer the question, “What are good questions for difficult conversations?” 

Having good questions prepared to keep you on topic and phrases to redirect conversations will ensure that the outcome is mutually beneficial.

“What are your thoughts?”

“How does this make you feel?”

“What is your perspective on this?”

“What is the biggest challenge?

Phrases to Redirect:

“I’m not sure I understand enough about…but I can find out more.”

“I see where you’re coming from, but think of it this way…”

“Another way to look at it might be…”

What not to say in a difficult conversation.

There are also some things you’ll want to avoid saying in an already anxious situation.  

  • Phrases that are accusing or may exaggerate can put the other person on the defensive.  So avoid saying, “You always…” or “You never…” since chances are never or always rarely true.  Stick to the facts that you can back up.  
  • Assumptions that they agree with your perspective is not a good way to hear them out.  Stay away from “clearly” or “obviously” as they can come off as insulting.
  • Saying things like, “Have you thought of…” or “You might consider…” rather than sounding like you’re telling them what they need to do. Avoiding should phrases is best.
  • Lastly, don’t say “It’s not personal” because, while it might not be to you, it likely is to them…or at least they may feel that way in the moment. 

What to do during a difficult conversation

So far, we’ve talked about where to have a difficult situation, what to say and what not to say.  Now let’s talk about what to do during a difficult conversation.

  1. Prepare ahead of time.  Gather your thoughts on what you want to discuss and what you’d like to achieve.
  2. Select a good time and place. Choose a setting that is private, without distractions with enough time for you to discuss the issues at hand.
  3. Listen actively. Listen with the intention of hearing the other person’s perspective rather than listening just to insert your own.   
  4. Come up with a solution together.  How can you move forward from here? How can you work together?

Knowing what to say and not to say, where and how to have a difficult conversation are all keys to unlocking the tools of successful communication in the workplace.  You’ll see increased productivity and cohesiveness within your team if you are able to handle conflict with professionalism and ease. 

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