How to Deliver Bad News to Your Boss

4 Items That Will Make a Tough Conversation Easier

Have you ever agonized over having to deliver bad news to your boss?  The sinking feeling of having a pit in your stomach doesn’t help you want to pick up the phone to make that call. I know I’ve personally had some angst when faced with this situation.

Delivering Bad News


As a young company commander in charge of over 180 soldiers, I had a soldier get a DUI a week after another one of my soldiers tested positive for drug use.  I knew I had to call my boss, but was concerned about the phone call, as this was the second incident in a week.  My gut told me that these incidents would reflect poorly on my leadership abilities. I privately wondered if this would start me down the road of being replaced prematurely or even fired. Having the worst case scenario in my head, I sat at my desk staring at my phone.


Bad Thing Will Likely Happen Under Your Watch

It’s inevitable.  Bad things will happen while you are in charge. It doesn’t matter how good you are. Unfortunate events occur on nearly everyone’s watch.  It took me years to realize this. Once I did, I also realized that it’s not the event itself that matters as much as how you respond to the event. When bad things happen, you will need to deliver bad news.


Report Bad News ASAP

Unlike wine, bad news does not get better with time.  The opposite is true. Bad news actually gets worse with time, which means you need to deliver bad news in a timely manner.  Here are four items to keep in mind and help guide you through that dreaded conversation. Prepare for the conversation with these four items to have a better experience.


4 Items That Will Make a Tough Conversation Easier

  1. Report What You Know. This can easily be done with a 5 Ws format (Who, What, Where, When, and Why).
  2. Report What You Don’t Know. Inevitably, there will be information gaps that will require time to develop the situation. Figure out the pieces of information that you don’t know. This requires you to step back from the situation to gain perspective on the information you need, but don’t yet have.
  3. Report What You Are Doing About the Situation. Identify how you are trying to fill the information gaps and your plan of action is to work towards resolving the situation.
  4. Inform your Boss what resources or assistance you need. You may not be able to handle everything yourself. Be sure to handle items that are appropriate at your level, but also don’t be afraid to tell the boss what you need or how he or she can help you.  This requires maturity in determining what you can’t or shouldn’t do for yourself.


At the end of the day, you can’t control bad luck or nor can you always prevent unfortunate incidents.  You can, however, choose how you respond to bad news. Done correctly, you will set the example for your team on how to handle the situation. Done incorrectly and you will show your team how NOT to handle stressful situations.


Question: What tips do you have for delivering bad news?


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Photo Credit: An airman calls in a medical report while airmen prepare to evacuate a simulated patient during a tactical combat casualty care class at the New Jersey National Guard’s Joint Training and Training Development Center at Joint Base McGuire-Dix-Lakehurst, N.J., Sept. 27, 2017. Air National Guard photo by Master Sgt. Matt Hecht

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