Having Difficult Conversations

Being an administrator in the public education system has meant that I’ve had a few conversations with people where the content was difficult for me to share and, in most cases, even more difficult for the other person to hear.

Some examples …

  • PT conversationMeeting with a student who has not achieved to their potential;
  • Conversing with parents about their child’s struggles;
  • Debriefing with a staff member who was not successful in an interview;
  • Sharing the tragic news of a student or staff member who has died.  Unfortunately, I’ve had to do this a few times in my career.

Everyone has to deliver difficult news at some point.  Certain professions do so more regularly than others — Trauma Surgeons, Oncologists and First Responders come to mind.  But educators also deal with bad news on a regular basis.

train derailment

One Never Intends to Derail Progress – Delivering Bad News Has the Potential to Increase that Risk

Learning how best to deliver the bad news is actually more important than the news itself.

Do it well and you provide the conditions that help maintain relationships that are critical to building success.  Deliver the news poorly and you risk derailing progress in the workplace.

My experience has taught me that there are some guidelines that can help deliver bad news ‘better’:

#1 – Is There a Better Time to Share the Information?


Is There a Better Time?

It isn’t always possible to delay the sharing of upsetting news but it’s worth considering as an option — not to simply avoid giving the information, but figuring out if sharing it within a different context might be better.

Some advice I’ve heard before is to try to avoid Fridays as well as first thing in the day as both can be problematic.  Giving the bad news on Friday doesn’t allow for an easy ‘check-in’ the next day at work.  And the beginning of a day means that the person then needs to process it all day long at work.

#2 –  Be Direct & Be Factual — Get to the Point

Peanuts Lucy

Just the Facts

Get to the point fairly quickly.  Beating around the bush becomes obvious and only increases anxiety levels.

Yes, you need to make sure that you frame the news properly, but I’ve found that it is more important to provide time after delivering the news than to spend endless amounts of time at the beginning trying to prepare the person for it.

State the facts as objectively as possible and as close to the beginning of your conversation as seems reasonable.  People are already feeling anxious and your delaying the inevitable can make it almost unbearable.

#3 – Show Compassion


Compassion and Patience

Compassion is always a great idea.  Being sympathetic to the situation is critical — expressing thoughtfulness, gentleness and kindness is always appropriate.

Offer your opinion only if requested.  Opinions and Compassion are NOT the same thing.  Don’t share parallel experiences that you’ve had (the other person typically doesn’t want to hear about your troubles at this time) or what you’d do in this situation (you likely don’t understand the complete picture so offering a solution is unwise).

#4 – Ensure that you Have Enough Time 

Don’t rush them out the door.  You need to provide the other person with processing time.  They may choose to leave right away, but I’ve found that many people tend to stay awhile to process the information in front of you.  Don’t rush.  Make sure that you’ve set enough time aside.

#5 – Anticipate Next Steps

Be proactive in your planning.  Yes, you need to plan for the actual sharing of the information, but you also need to anticipate potential next steps.

Will they require time away from their job?  Do you need to provide coverage for them? What about extra support for them when they leave your office or room?

And most importantly …

#6 – Don’t Wear Their Anger Personally

Remember, it’s not about YOU.  The person you are talking with may become upset.  They may even yell at you.  not meDon’t wear their anger or their emotion, but continue to show compassion and support for their situation.  This will not only help them to move forward, but also allow them to see you as someone to support them as they transition to next steps.


Be the Person who is Prepared, Compassionate and Calm

compassionWhile we don’t look forward to the time when we need to deliver bad news, knowing some things that can make the delivery of the news a bit better will help everyone — especially the person who will be receiving it.


6 thoughts on “Having Difficult Conversations

  1. Great post Dave, and such helpful information. I’ve learned a great deal from you over the years, and I still am even though you moved on!

    Thanks so much,


    Sent from my iPhone

    Liked by 1 person

  2. You are a master at the art of difficult conversations – thank you for the tips! May I add one more? Self-care is often not a priority for administrators and it needs to be. This means taking time to do that workout or walk, spend quality time with loved ones, and put down that phone and step away from the email. We need to care and have compassion for ourselves as well. 🙂


  3. HI Dave:
    I’ve enjoyed reading your posts, and like to offer something in return.
    This comment has nothing to do with your post this month, but occurred to me because of your title, ‘The Power of Why’.
    I thought you might be interested to know that the power of Why is a component of the Toyoda Production System that has transformed manufacturing and other processes over the last 40 years.

    The idea is when something undesirable happens, ask Why at least 5 times, to get to the root of the problem. As teachers, we may not be able to do much about the actual root of some problems (eg. income inequality), but others, like loneliness might be something we can influence. Here’s a brief post on the idea.


    • Hi Ray, Thanks for writing to me. The power of the word WHY lies in it’s ability to seek understanding. And once we have understanding we are much more able to find the appropriate solution. I appreciate your comments and your link to the Toyota website — it was a short yet interesting read. Hope that you are well.



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