Debra Zabloudil headshot

A Planner’s Guide to Delivering a Difficult Message

Whether you are telling your board a project went over budget or advising a team member to behave, having a difficult conversation is an important skill to master.

Debra Zabloudil, CAE, FACHE, president and CEO of The Learning Studio, Inc., does not like to call communicating sensitive information a “soft skill.” She says, “Too often, not mastering the art of difficult conversations can be a “CLM”—career-limiting move.”

Zabloudil calls effective communication “an antibiotic” for problems and the more value-driven the problem, the harder it is to have the conversation. For example, if you stay late at night until the job is done but your coworker leaves at 4:30 on the dot every day, reconciling the two approaches is going to be tricky.

Zabloudil recounts one difficult conversation she had to have when she found out two team members out on the road had been spotted dancing in the fountain at Copley Square in Boston after a few too many cocktails.

So, whether you are dealing with fountain dancers or a project over budget, here are her tips for delivering the bad news.

The formula is: Audience + Message + Medium + Training

Consider whom it is you have to have the difficult discussion with. Whether you are talking to your board about a budget or taking a coworker aside to tell them to stay out of public water features when they are on the job, it is important to be respectful when delivering bad news. You can be more informal with a team member than someone on the board, but if you want the person receiving the news to take it seriously, then be serious when delivering it.

Have supporting data. If you go to the board have the figures to show you did your due diligence on the issue and leave them with charts or other data to prove it. Bring enough data to show the problem is real, but not too much that it is overwhelming.

Show up with a plan B. Don’t use what she calls the “throwing a dead cat on the table approach” because then all you have is a dead cat on the table.  Go in with a plan to mitigate the situation, for example explain you need more marketing for an event where registration is low, or tell them you need another month to see if things turn around but if not you need to shut down the project. Walk in with a solution. If the difficult conversation is about a subordinate’s work ethic or performance, focus on the good things first. Zabloudil suggests saying, “We noticed you did X to improve workflow,” and then tell them the area that needs work. Make sure the message is delivered in a timely fashion. If you wait too long to talk to an employee he or she is unlikely to be able to improve before the department is affected; if you don’t tell the board you need more money for marketing as soon as you see a problem with registration, you won’t have time to turn the event around.

It is always better to deliver a sensitive message face to face. If you can’t meet in person use Zoom or Skype or some other method where facial expression and body language will show their reactions. Don’t assume that because the sensitive topic affects you that you are the only person who can have the conversation. If you have a history with the person, or you think that you are not the right person for the job, have a coworker or someone in HR take over. Email is not the medium for difficult discussions, although it is a great way to follow up afterwards. Follow up is important because when people are emotional memory may not be accurate. Instead of remembering the good things about job performance they may only remember the bad things. Send an email detailing what you discussed and the steps that were agreed on to address it. 

If you can get training then do. It’s not just people from human resources who have to have the difficult conversations, and it is an important skill to have. Think about it: If you burned a bridge every time you switched vendors, your company would suffer.

Steps for a Difficult Meeting

Begin with good news.

Provide reasons for the bad news, e.g., registration numbers are down because of a problem at the location.

Use data to demonstrate the bad news, but not so much data you overwhelm the participants.

Be aware of your demeanor, now is not the time to be defensive or focus on blame. 

Offer a compromise or alternative if you can.

Close with action steps, and focus on the future.

Invitation to a Difficult Conversation
Zabloudil says sometimes triggering the difficult conversation can be the hardest part, but remember that ambushing the person will not help the discussion go more smoothly. Here are some sample messages to send to set up the meeting.

“I have something I’d like to discuss with you that I think will help us work together more effectively. 

“I’d like to talk about ______ with you, but first I’d like to get your point of view.”

“I’d like to see if we can reach a better understanding about ________. I really want to hear your feelings about this and share my perspective as well.”


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