How to Deliver Bad (and Good!) News in Writing

**Originally published at YFS Magazine

In what seems like a lifetime ago, being a first-time CTO, I had a lot of big ideas. I was determined to break a bunch of eggs and make a glorious splash in my first ninety days. After spending a month talking to everybody on my team, I made a list of some things I wanted to change. The first I thing I wanted to accomplish was for my leadership team to embrace the values that I believed in. For the sake of completeness, here are the values I use as a leader:

1. Leaders empower their teams to make decisions versus making it themselves.

2. Leaders don’t shy away from hard problems.

3. Leaders are emotionally intelligent.

4. Leaders are T-shaped; they have depth in one or multiple areas, but they don’t hesitate to jump into unknown areas.

5. Leaders are comfortable with ambiguity.

6. Leaders act like owners. Nothing is beneath them.

7. Leaders have a very flexible growth-oriented mindset. They believe that when presented with a seemingly insurmountable task, all they need to do is learn new skills that will allow them to complete that task.

8. Leaders never shy away from conflicts.

9. Leaders understand the mechanics of how the company makes money.

10. Leaders recruit and retain the best.

So, I wrote a quick email to my leadership team with a couple of lines about realigning the team to start using the new set of values and listed out the values themselves. I followed that up with a live Zoom meeting, in which I was determined to make a soaring speech that would end with tears and applause.

As it turned out, my presentation was a disaster. After I ended my spiel, I waited for the applause, but I only received blank stares. About twenty seconds of uncomfortable silence passed before one of the directors piped up and reluctantly asked me, “So . . . what do you want us to do?”

I had recorded that meeting and watched the recording that night. It was terrible. My delivery was weak and my monologue was filled with pointless filler words like “so,” “like,” “yeah,” and so on. Most significantly, I didn’t explain the “why.” Why do I want the leadership team to adopt a new set of values? Why do I think these new values will help? How do we enforce these new values? Are these values just for leaders, or should they be pushed down to the teams as well?

I spent the next few days writing a document that explained the “why” in detail. I added narratives to each value and explained them in detail. I went into how I came up with the

value, why the value was important, how to use it daily, and what positive changes leaders could expect once they embraced the new value. Once I was done, I sent the document over for a preread to my leadership team and then pulled them all together for a discussion about the new values rather than a speech.

The Intent Behind Communicating

If you look at any job description for managers, invariably you will see “excellent communication” as a required skill. Sometimes it will say “excellent written and verbal skills,” other times it will say “experience communicating to executives,” or “experience communicating to technical and nontechnical audiences alike.”

What I have found is that excellent communication skills in the context of managers is not so much about whether your audience understands the words, but about understanding the emotion behind those words. How do you want the audience to feel after they read your email? How do you want your team to feel after you talk to them? How do you want your stakeholders to feel after you deliver the status to them? While grammatically correct sentences do matter, expressing the appropriate emotion for the situation is what effective communication is all about.

So how do you effectively communicate emotions?

Verbal versus Written Communication

Most people assume that the spoken word is the easiest way to transmit emotion. It is, in fact, the most commonly used approach. However, after spending multiple decades listening to multiple

leaders, I have come to the conclusion that most people are only good at verbal communication for very short bursts of time.

This is why I believe managers and leaders need to learn how to write and write well. In my opinion, a well-written document beats a verbal explanation, and learning how to write effectively will eventually make you a better speaker and overall better communicator.

How to Write Well

One word: narratives. Narratives are the best way to convey complex thought with emotion. PowerPoint decks have decimated our collective ability to write narratives. Bullet points encourage what I call sound-bite thinking.

The sound bite completely fails in providing any details to the reader, including failing to answer the most important question: So what? The narrative on the other hand explains the “so what?” and more to the reader without requiring a voiceover from the author.

Here is an example of bad news delivered in a sound-bite versus narrative format:

Sound bite—Project X’s release has slipped to next week, and because of that Project Y’s kickoff is delayed, as well.

Narrative—The X team discovered a late-breaking release blocker today (mm/dd/yyyy). The team worked over the weekend to fix the bug, but given the severity of the bug (a link to the bug report), they decided to spend a few more days testing to make sure all edge cases are tested. New release date for Project X is mm/dd/yyyy. This will affect the kickoff of Project Y that was scheduled for this week. The new kickoff date for Project Y is mm/dd/yyyy. We could kick off Project Y earlier if we split resources between Project X and Project Y, but we don’t recommend that because the team believes (insert evidence here). Project X is a bigger customer priority than Project Y and splitting resources could further delay Project X’s delivery. If leadership disagrees with the decision of swarming on Project X, please contact us.

The sound-bite update will generate a thousand questions. The narrative will generate no further questions. The narrative projects the right emotions to its readers—a sense of urgency from the team, thoughtful decision-making, and a strong point of view of what should be done next.

So how does one write excellent narratives?

Good writing is clear and concise. Great writing evokes emotion in the hearts of the reader.

As Stephen King, one of my favorite writers, says, “If you want to be a writer, you must do two things above all others: read a lot and write a lot.”

***

Mahesh Guruswamy is a seasoned product development executive who has been in the software development space for over twenty years and has managed teams of varying sizes for over a decade. He is currently the chief product and technology officer at Kickstarter. Before that, he ran product development teams at Mosaic, Kajabi, and Smartsheet. Mahesh caught the writing bug from his favorite author, Stephen King. He started out writing short stories and eventually discovered that long-form writing was a great medium to share information with product development teams, resulting in his book How to Deliver Bad News and Get Away with It: A Manager's Guide Greenleaf Book Group (January 14, 2025). Mahesh is passionate about mentoring others, especially folks who are interested in becoming a people manager and newer managers who are just getting going. Learn more at maheshguruswamy.