The Soft Side of Software

February 6, 2025
Volume 22, issue 6

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My Career-limiting Communication

Be thoughtful about your content. You've got a lot riding on it.

Kate Matsudaira

About 15 years ago, I sent an email that effectively ended my time at a company. Of course, I didn't realize that just then, but looking back on it now, I can easily see my mistake. I only wish I'd had the coaching on communications back then that I have now.

So, using my major email snafu as the prime example, I can now share some important lessons about communications that you may find especially useful when dealing with executives.

What did I do wrong in my message? Well, the email thread went something like this (with paraphrasing and embellishment added since I'm drawing this from memory):

In response to a weekly status update on a key project, the CEO wrote:

Why has the status changed to RED and what is the path to green?

To which I replied:

"As you know, it is really difficult to predict the exact dates software will ship. We do our best to estimate ahead of time, but sometimes there are unforeseen things that come up. In this case we were doing some testing and we came across a bug.

"This bug is really complicated because it only happens under high load, which we don't think is likely to happen in production. But we think it's occurring when two different services are both reading and writing to the same data and things get into a bad state. Since we don't understand the issue, we aren't sure about what the solution will entail but it could involve rewriting one of the services.

"Once we figure out a solution, we can set a new date and then we'll know what it will take to get to green."

While my response (eventually) answers the question, is accurate (at least from the author's point of view), and is written in a way that's accessible to most nontechnical people, it also has some serious drawbacks:

• The reader has to wade through three paragraphs to find the answer.

• The response does not instill confidence that the author will be able to solve the problem.

• The author uses phrases likely to scare an exec like: "we aren't sure" and "involve rewriting."

• The response also introduces new questions like: "If we don't think it's likely to happen in production, why do we need to fix it?"

• The response also starts by making excuses and offering explanations that probably are not of interest to the reader.

For a technology leader, it is important that each response to a question does the following:

1. Answers the question.

2. Displays confidence that the author has a plan.

3. Uses as few words as possible. (You need to be concise!)

Of course, these are just the basics. Assuming you want to land your message and build your influence, you need to strive for greatness in your communications.

Building Your Communication Skills

When I first became a leader, my communication skills were clearly in need of improvement. So, for more than 20 years now, I've read countless books and worked with many professional coaches to hone my ability to get my ideas across clearly and concisely. Gleaned from all that research, here are some of the best tips and suggestions I can offer to you.

Context is everything

Perhaps the most important tip is to be familiar with the challenges your audience faces. Before you go to an important meeting, take the time to learn and think about the challenges the other participants are addressing. What are their big concerns? What questions do they have? How do their backstories mesh with what you want to present?

Taking the time to learn about your audience and their challenges will allow you to communicate on their level. For example, if you're explaining a strategy for a product, do you need to present extensive market and customer context, or is your audience likely to already know that? Also, carefully consider how much framing your proposal will likely require helping others in the room truly understand your message. What are the risks of overdoing it? Too much explanation could end up boring your audience and losing their attention.

Putting myself in the shoes of the CEO from my original example reveals the following concerns:

• As the head of a startup, the CEO has obvious overall concerns about time-to-market and, in particular, about getting this important feature into the hands of customers.

• There also are worries about the additional costs and time required to address any problems.

• CEOs typically focus on business problems rather than technological ones and so are counting on you to bring that expertise and show them a way forward that instills confidence.

Just framing the situation from the perspective of the people you're addressing can help you quickly grasp what might be prompting a particular question and thus inform the tone your response should take in order to resonate.

The corollary to this is that you should also make sure you are clear about your message's goals. If you're uncertain about those goals, there's a good chance you won't achieve what you want. This applies to any email, presentation, or even verbal response. Be clear in your communications if your goal is to provide some elucidation on a topic, solicit feedback on a proposal, or get answers to questions that you're posing.

Being clear about your context—and your listener's context—greatly improves the chance that you'll communicate clearly.

Just answer the question (and lead with the punchline)

Whether in writing or in person, the best answer to any question from an executive comes in one of only four forms:

1. Yes.

2. No.

3. The answer (succinct, two to three words).

4. Let me follow up and get that detail.

Should you find yourself starting with an explanation, you are doing it wrong. This has been one of the hardest lessons for me, and I've had to continue working on it. This is especially true in those situations where you know you'll need to deliver an answer you don't think will be well received. In such situations, it's natural to want to lead with an explanation. All too often, however, this approach doesn't land in quite the way you expect because your assumptions about the leader's motivations may turn out to be wrong. It's always better to lead with the answer and then add an explanation only if needed or desired.

Many technologists find themselves in this situation whenever they're asked to deliver the impossible, such as: "Can you move up the launch timeline?" or "Can you accomplish the same thing with half as many people?" In these cases, the answer often is "yes" but can come with significant consequences just the same. Accordingly, it's always best to phrase your response using the "Yes, but " construction (e.g., "Yes, but we'll introduce a lot of risk in quality or expose our customers to potentially negative experiences."). This tends to land better than a hard "no" since many of the things a company leader might request are possible and yet may also take you in directions you don't want to go.

Make your communication aids work for you

Part of knowing your audience means understanding how they like to consume information. You should know, for example, if they prefer narratives (Amazon-style, long-form docs) or presentations. No matter what aids you use to make your pitch, make sure you keep your message focused and clear.

The less focused the content is, the less focused your audience will be and the more diffuse any discussion is likely to become. Potential outcomes will vary accordingly. The hazard in bringing up any topics or details you don't consider to be essential is that you're effectively inviting your audience to spend time delving into peripheral issues (and thus pushing you away from meeting your goals).

Another key point: Do not fall into the trap of reading your content. Whether you have a narrative to deliver or are presenting slides, prepare your key messages in advance and hone your speaking points to make sure they're clear.

Also remember that, in most cases, data trumps all. You should be able to instantly cite any important numbers or facts that bolster your message and also be prepared to point out references if necessary. If you use visualizations, spend time thinking through how you can add as much information to the image as possible. (You can always refer to Edward Tufte's books on data visualization if you need a framework.) And look for opportunities to leverage size, colors, and annotations to help tell your story.

Bottom line: Be thoughtful about how you present your content. Whether in email, documents, or slides, use punchy visuals (bold, italics, bullets, etc.) to make content easier to digest with your most important points clearly highlighted. Make sure that data, charts, and photos are unambiguously labeled, with any caveats noted. In general, steer away from pie charts, averages, and percentages (unless you've considered the alternatives and are convinced these are the best mechanisms available to you). That's because, as popular as these devices might be, they often manage to tell only part of the story and miss opportunities to highlight the relative size of datasets, outliers, or trends over time.

A bit of preparation can go a long way. Every opportunity for you to present is a chance for you to shine. Just remember that relationships are like filmstrips: Every time you interact with someone, it creates another frame in the filmstrip they already have for you. The more interactions there are, the more they'll "know" you. But if you have only a limited number of opportunities—as is likely with a top executive—you'll really need to make every moment count.

Kate Matsudaira is VP of technology for SoFi's Money (checking and savings), credit card, Invest, insurance, At Work, and partnerships. Previously she was a VP at Splunk, where she was responsible for the Observability product suite. She has also worked as an executive at Google and helped build several successful startups that were acquired by eBay, O'Reilly Media, and Limelight. She started her career as a software engineer and lead at Microsoft and Amazon. She is a keynote speaker and published author, and has been honored with recognitions such as the NCWIT Symons Innovator Award. She lives in Issaquah, Washington (outside of Seattle), with her husband, Garrett; three boys; and three dogs.

Originally published in Queue vol. 22, no. 6—
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