Delivering Bad News to Those Who Deserve It

“It’s not the difficult conversations that bite you the hardest,” I told the manager. “It’s the ones you put off until too late.”

I listened to the manager’s reasons and told him, “Here are the risks you take. You dread telling ‘Robert’ what and how he needs to improve because he lashes out at you and remains sullen for days after you’ve counseled him. You finally draft a written reprimand, but before you deliver it, Robert voices a safety concern in front of others. Now your reprimand seems seem retaliatory—and Robert’s an employee who feels justified in reporting his grievance to a regulatory agency.”

man in pink dress shirt
Photo by Andrea Piacquadio on

“You’ve told me ‘Caitlin’ spends more time talking with coworkers than working. She makes lots of errors. You keep hoping she’ll improve, but she doesn’t. You’re deciding whether to fire her when she announces her pregnancy. Now, whatever you decide seems like pregnancy discrimination to the Human Rights Commission.”

yelling formal man watching news on laptop
Photo by Andrea Piacquadio on

The manager argued with me. “Won’t the regulatory agency see the date at the top of the reprimand and realize I wrote it before Robert raised the safety issue?”

“Sure, except you didn’t give the reprimand to Robert until after he voiced his concern.”

“In my defense,” the manager says, “Caitlin’s a popular employee. When I discipline her, she complains to her coworkers, who think I’m unreasonable.”

“You act as if that’s a reason. It sounds like an excuse, and one that tells me you need to build stronger relationships with your other employees. Have the conversation before it’s too late. Besides, if Caitlin doesn’t know what she needs to fix, her performance won’t improve.”

If you’re a manager who puts off delivering bad news to employees that need it, here’s what you need to know and do:

Delay can cost you.

Managers often pay a steep price when they delay “bad news” discussions. Besides the above costs—that the discussion when they hold it may seem retaliatory or discriminatory—employees often sense when a manager plans to confront them and make pre-emptive strikes. Or, as in the example of Caitlin, employees don’t fix  problems they don’t see. You’ll find more examples of the retaliation problems that result from delay in “Allergic to Discipline,” “Retaliation Landmine” p. 103-106; “When You Supervise a Grouch,” p. 98 to 109 in Solutions: 411: Workplace Answers; 911: Revelations for Workplace Challenges and Firefights,

Start well

Plan an effective start and remain in control of your emotions. Before you sit down with the other person, commit to truth as your compass and respect as your rudder. Both steer you toward success.

If you’re vibrating with frustration, set your emotions to the side.

When you begin the discussion, make it clear you seek a good outcome, with words such as, “I’d like us to have a productive conversation.” You’ll find more suggestions for how to accomplish this in “The Most Effective Way to Start a Conflict Discussion”, Navigating Conflict: Tools for Difficult Conversations (p. 77-81),


If you want someone to change behavior, provide them with specific examples. Saying “be more pleasant and respectful with upset customers” doesn’t give an employee the direction they need to make changes, particularly if they’re not a naturally pleasant person. If you say, “When dealing with an upset customer, listen without interrupting and when the customer finishes, say, ‘I’m sorry this happened, let’s find a way to fix things for you,’” you provide specific guidance that shows the employee you want them to succeed. You’ll find more information on how to change an employee’s problem behavior in “Pressing Reset,” p. 95-104, Managing for Accountability,


Any employee can tune you out when you talk “at” them. In addition to presenting clear, improvement-oriented information, you also need to listen to what the employee says.

If your employee doesn’t talk, ask open-ended questions such as “Can you tell me how you see this situation?” Not only do you benefit from understanding your employee’s rationale but listening shows respect.


Bad news discussions require two documents. Prior to the conversation, prepare a document outlining your “talking points” and use it to stay on track in the discussion.

Following the discussion, provide your employee with a dated memo that documents what the employee needs to fix. In this document, state how and when you intend to follow-up to note improvement, or to discuss the consequences if improvement doesn’t happen.

Do you put off delivering bad news to employees that need it? Don’t risk the price delay might cost you. Instead, plan an effective start, outline specific expectations, listen, and document.

© 2023 Lynne Curry

One thought on “Delivering Bad News to Those Who Deserve It

  1. Delay produces more difficulties, not fewer! Amen to that. There are some great examples here, and they all show that there can be legal repercussions if the employee who the boss finally reprimands or tells about their poor performance the timing may be such that the complaint can be correlated with another event such as pregnancy or a safety warning and then discrimination may be claimed by the employee. The tips on how to prepare for the difficult conversation with the employee are great ones.

Leave a Reply

Your email address will not be published. Required fields are marked *