7 Steps to Having a Difficult Conversation

Posted by Kristin Arnold on November 4, 2015

It’s never easy to initiate a difficult conversation.  You have something to say that is unpleasant or uncomfortable and/or you believe that receiver of the message will not take it well.  All in all, it’s never any fun for the sender or receiver of the information.

shutterstock_277372325BUT, you believe it must be said.

When you find yourself needing to confront someone with bad news, try these seven steps to make the conversation less difficult for you AND the receiver:


  1.  Don’t Wait Too Long.  Bad news never gets better over time.  It might get swept under the rug, but it usually festers.  Whatever the issue was, the receiver won’t know about the first instance and could be perpetuating a bad thing.  So nip it in the proverbial bud and have the difficult conversation before it escalates.
  2. Set the Stage.  Difficult conversations are best done in private.  Make sure you have thought out what you are going to say by using these steps – and make sure that you are in a cool, calm and collected mental state to have this conversation.  Ask them if you could have a minute of their time and lead them to a quiet, private place where you won’t be distracted.  You may even heighten their listening by saying, “This is not easy for me to say…..”
  3. Be Direct, Clear and Concrete.  Bring up the issue without beating around the bush.  Start with “I” statements and specific descriptions of the issue. “I noticed that three days this week (Monday, Tuesday and Wednesday), you were between 15 to 30 minutes late.”  Try not to exaggerate (“You’re always late!), be indirect (“I rely on you to come to work on time”), or speak for others (“Everyone is pissed off that you’re always late”).
  4. Separate Your Imagination from Impact.  Our imaginations powerfully interpret words, actions or appearance into a story – that may or may not be accurate.  So rather than sharing your interpretation of the events (“Evidently, you just don’t care about coming in on time”), share the impact of the behavior (“As a result of you being late three days this week, I wasn’t able to complete my work on time and had to stay late on those days”).
  5. Accept Responsibility For Your Involvement.  Rarely are we as innocent as the driven snow.  We may have had a hand in this: You weren’t clear about your expectations, you have been allowing this to go on too long, etc.  Fess up and share the possibility that you contributed to the issue. This will help support a healthy dialogue in the next step.
  6. Look for the Win-Win.  Rather than arguing about positions (“You need to be here on time” and “Traffic is always a mess”), brainstorm possibilities about how you can both have a mutually acceptable solution. Reassure them that you ARE looking for a “win-win” and then clarify what that mutual objective is (“We do great work here!”)  If there are some non-negotiables (those things that you have NO control over, now is a good time to mention it (these typically involve conversations around time and money!).  When brainstorming, just offer the possibilities vs. evaluating each and every idea.  That will just shut down the conversation!
  7. Agree on a Path Forward.  Once you have all the ideas out on the table, you’ll see some patterns or trends or maybe even one idea resonates with both of you!  Agree on how you both will proceed.  Finish the conversation on a positive note with what you will do and what they will do.  Continue to show your support to make this rather difficult conversation a non-issue!

Try these steps next time you need to confront someone or have a difficult conversation with someone on your team and contact me or comment on how it worked for you. Share the podcast with your colleagues.


Kristin Arnold is a professional meeting facilitator and international speaker who is passionate about helping leaders and their teams think things through, make better decisions and achieve sustainable results. The Extraordinary Team’s approach to building high performance teams combines consulting, coaching, training and process facilitation within the context of working real issues.

Recent Articles:

Building Team Consensus is Wise Decision

How to Make Meetings More Fun, Motivating and Interactive with a Team Huddle

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