Culture Transformation: Communicating Bad News to Executives

Summary on Culture Transformation

This episode of Coffee with Digital Trailblazers focuses on how to communicate bad news to executives in ways that are calm, constructive, and aligned with organizational culture.

Host Isaac Sacolick frames the discussion around recent outages and crises, asking when issues should be escalated, how to avoid over-escalation, and what executives actually need to hear. Guest expert and former global CHRO/board advisor emphasizes knowing your executive’s preferences, sharing updates early and often, being transparent about what is known and unknown, and always focusing communications on solutions, next steps, and long-term impact rather than drama. She and others stress managing personal anxiety, “playing cool jazz in the background,” and avoiding “Chicken Little syndrome” by classifying issues (true crises vs. bad news vs. everyday incidents), so not everything becomes a fire drill.

Additional panelists expand on practical guidelines: define clear escalation criteria (e.g., brand damage and lawsuits), decide whether you’re informing, asking for help, or seeking a decision, and never let executives hear bad news from outside your team first. They also highlight security-specific nuances, the need to lead with facts while acknowledging uncertainty, and the importance of finding the “upside” or learning opportunity in crises so organizations improve rather than just react. The episode closes with reminders to thank messengers of bad news instead of “shooting” them, and to respect that seasoned executives have heard bad news many times before and can handle it when given clear context and options

Transcript

[00:00:00] Speaker A: Bad news to executives. And we’re just going to give a few more minutes for everybody to join. I see some old friends here.

Hello Kristen. Hello Dave.

Hi Ronan. Hi Jay. Let’s see some new folks. Oh hi Roman. Roman, my wife and daughter are in your area today and tomorrow they’ve been visiting colleges up in the Chicago area.

I think they’ve been by your university, Roman.

They told me they were going by. I don’t know if that’s her, one of her top choices, but they’re out in the area looking at universities. It’s been an interesting week. They’ve been out there. I was in Las Vegas earlier this week at the workday conference.

I should have a blog post around that on Monday.

Just some of the learnings and findings I’ve had out there.

Very interesting conference and I did do a couple of posts on LinkedIn around it. So if you want like my day one and day two learnings, I did do some photos and posting around that.

But I will have a recap blog post on Monday around it.

For those of you who joined us last week we announced that the beta launch of the Star CIO Digital Trailblazer community.

A good number of you did use the coupon code and joined.

If you have not done so yet, I’m leaving that coupon code available for at least the next couple of weeks and it is a free access to the community.

So please do take advantage of it in the comments for today. If you click on the URL for this event, you can get there by going to starcio.comcoffee/next-event do click on the comments tab, scroll down, you’ll see the link which is drive.starcio.com and you will see that coupon code to join for one year free. The Star CIO Digital Trailblazer comm...

Chapters

• (00:00:00) - Good News to Executives and Bad News to
• (00:01:14) - The Star CIO Digital Trailblazer Community
• (00:02:37) - Jennifer Krevitt on CIO Network Live
• (00:03:09) - Communicating Bad News to Executives
• (00:04:28) - CDC Board Chairwoman on Bad News
• (00:05:10) - How to Tell More Senior People About the Company's Changes
• (00:09:23) - Richard Feynman on Risk Management
• (00:11:21) - Understanding the Company's culture
• (00:14:17) - Always Come prepared for a CEO Talk
• (00:17:12) - Anxious Workers: How to Deal with Chicken Little Syndrome
• (00:20:36) - CIO Network: On the Upside of a Crisis
• (00:23:58) - The Drama of the Workweek
• (00:25:17) - Culture Transformation: The Business of IT & Digital Transformation
• (00:27:37) - Communicating Bad News To Executives
• (00:31:07) - PMOs on Risk Communications
• (00:34:47) - CIO Network: When to escalate a material issue?
• (00:35:45) - 3 Golden Rules for Handling Bad News
• (00:41:49) - Crisis and the opportunity it presents
• (00:43:02) - The Need for a Healthy Culture
• (00:43:56) - Crisis and Good News
• (00:48:17) - CIO Network: The CFO's Firefighting Culture
• (00:54:02) - Senators on the Russia Investigation
• (00:54:12) - Bad News to Executives
• (00:55:09) - On the Need for More Information in Cybersecurity
• (00:56:55) - Good News or Bad News?
• (00:58:02) - Thank You for Being the Messenger
• (00:59:20) - Shaping Tomorrow: Green Tech Platforms