Meetings can often feel like an unavoidable drag in the corporate world, but for David Singleton, the former chief technology officer at Stripe and former vice president of engineering at Google, they are a powerful opportunity if handled the right way. Appearing recently on The Peterman Pod, Singleton offered leaders two essential pieces of advice for running meetings that command attention, foster engagement, and leave participants feeling like their time was well spent.
Preparation Is Non-Negotiable
Singleton’s first point may sound simple, but he believes it is too often overlooked: leaders must prepare before stepping into the room. He admitted that even in his own career, he has sometimes been caught off guard by casual requests to “just share what’s top of mind.” The problem, he explained, is that what’s top of mind isn’t always relevant or even appropriate for the group.
“What’s on top of my mind right now is that I’m kind of hungry, and I’m not going to say that,” Singleton joked. But beneath the humor is a serious principle: people attending meetings are investing their time 15 to 20 minutes, sometimes much more listening to you. The very least a leader can do is dedicate at least 30 minutes beforehand to consider what message, updates, or context will be most valuable for that audience.
This idea echoes the practices of other high-profile business leaders. JPMorgan Chase CEO Jamie Dimon, who has famously expressed his dislike of unnecessary meetings, insists on preparation both for himself and for his employees. He reads materials in advance to ensure discussions are sharp and productive. Similarly, Jeff Bezos and his successor Andy Jassy institutionalized the practice at Amazon of writing detailed memos before meetings. Those memos, which everyone reads silently at the start, ensure that the conversation begins with shared knowledge and structure. Singleton’s advice fits right in: preparation is not optional; it is a sign of respect for the participants’ time and a way to elevate the quality of discussion.
Take a Beat Before You Answer
The second piece of wisdom Singleton offered comes from his days at Google, working under Alan Eustace, then the company’s senior vice president of engineering. Singleton recalled how Eustace had a distinctive way of handling questions during meetings. Instead of rushing into an answer, he would pause, reflect, and explain why the question mattered to the group before addressing it directly.
That pause, Singleton noted, made all the difference. It created space for those who weren’t already immersed in the issue to understand the context, which meant they could not only follow along with the answer but also learn something broader about the challenge being discussed. “I aspire to be like Alan,” Singleton admitted. “I’m certainly not that good, but I noticed that and it really stuck with me. That’s part of: Take a beat. Is it possible to take a step back and explain the context behind what you’re about to jump into?”
Singleton believes this technique does more than improve clarity. It actively keeps people engaged. If a leader answers a question in highly technical terms without framing it first, those unfamiliar with the topic will tune out almost immediately. But by pausing and situating the question in a wider context, the leader brings everyone along for the journey. It transforms a moment that could exclude most of the room into a learning opportunity for all.
Why These Lessons Matter
At their core, Singleton’s two tips are about respect for people’s time, and for their attention. Meetings may be routine, but they are one of the few moments when leaders have a captive audience. Failing to prepare or rushing into half-formed answers can squander that opportunity and leave employees disengaged. On the other hand, thoughtful preparation and deliberate communication can turn even a brief check-in into a meaningful, energizing experience.
In an era when workplace culture is under the microscope and employee engagement is harder than ever to sustain, these lessons resonate widely. Leaders who adopt Singleton’s approach are more likely to foster a culture of attentiveness, learning, and trust. After all, when people feel their time is respected and their questions are treated as valuable, they are far more likely to contribute their best ideas and energy to the work ahead.
