There are a number of reasons I prefer in-office work over remote: The structure that comes with separating your work life from your home life. The stellar views of the bay from our San Francisco headquarters. And, most importantly, the ability to really get to know the teams I work with.
One of the best—and, admittedly—most difficult things about leading a company of more than 700 employees is navigating the many personalities that interact on a daily basis. I may have started my career as a software engineer, but as a CEO, I’ve grown to become much more: A mentor. A career advisor. A conflict mediator. A grief counselor. Every successful leader wears each of those hats at one time or another, and in order to pull them off, there’s one core trait you have to have: Empathy.
Most of us acknowledge that empathy is important in the workplace, but it’s not always given its due. According to Harvard Business Publishing, while 78 percent of senior leaders recognize that empathy is important, only 47 percent say their companies are effectively practicing it.
That’s because practicing real, genuine empathy—versus simply paying it lip service—isn’t always easy. Understanding how to act in a given situation requires high levels of emotional intelligence; what’s more, there are times when lending an empathetic ear isn’t enough—some form of action is also required.
Empathy may be a distinctly human trait, but interestingly, AI has emerged as a powerful tool for helping executives lead with greater compassion and understanding. Here’s how.
Bridging Communications Gaps
If there’s one common truth universal to all CEOs, it’s this: We’re busy. And when we’re busy, effective communication sometimes falls by the wayside. Emails get sent in clipped half-sentences, often without greetings or pleasantries. Requests can come across as curt. Sometimes, we don’t even bother to say “please.”
A short email can often do the trick (although you should always say “please”). But sometimes, if there’s a real issue that needs to be addressed, it has to be handled carefully.
In the past, it was easy to waste half a day staring at a tough-to-answer email, waiting for the right response to appear in a flash of inspiration. These days, that’s no longer necessary: Natural language processing models like ChatGPT can analyze the sentiment of the email you’ve received, or offer some pointers on a draft you’re thinking of sending. Is it too brusque? Too pandering? I’ve noticed that some LLMs can be a bit sycophantic unless you tell them not to be, so be sure to clearly spell out that you need clear, honest feedback.
AI can also be invaluable in bridging communication gaps for people from varying cultural backgrounds, age groups, and neurological profiles. By analyzing the language you use—whether it’s word choice, sentence structure, or tone—AI tools can flag areas that might unintentionally alienate or confuse certain audiences. This enables leaders to be more considerate of cultural nuances, generational differences, or the specific needs of neurodivergent individuals. By incorporating accessible language, clarifying potentially ambiguous phrases, or adjusting tone based on the recipient, AI can help foster a more inclusive and empathetic work environment for everyone involved.
Assessing Management Styles
The above example requires a proactive approach to cultivating empathy—in this case, workshopping a sensitive email. But AI can also help assess all sorts of interactions, from Slack conversations to presentations. In an example cited by Harvard Business review, one executive ran a meeting transcript through an AI tool, and asked it for feedback on her leadership style and how she engaged with her team. To her surprise, the analysis showed that she had a tendency to be dismissive, and cut them off mid-sentence.
But that’s where AI can shine—by highlighting hidden blind spots leaders might otherwise overlook. In some cases, it might reveal that you cut people off mid-sentence; in others, it could show you that you inadvertently favor those who speak up first.
Armed with this knowledge, you can implement small but meaningful adjustments to become a more supportive and empathetic leader. Of course, one management style won’t suit every organization, but self-awareness and a willingness to adapt are universal requirements. AI tools offer a data-driven insight into how you’re coming across, giving you an opportunity to make real-time course corrections, build trust, and ensure your style resonates with the range of individuals who make up your team.
Expanding Your Thinking
Every leader should have someone they can talk to for advice, toss around ideas with, or just offer a different perspective when times get tough.
While no tool can ever replace the advice offered by a trusted support network, what AI can do is help pose different perspectives you may not have considered. Say you’re a product manager used to talking to rooms full of engineers, designers and marketing leads. It’s a group you’re familiar with, and you share a common language. But what happens when you have to give a presentation to an audience of academics? Or sit on a panel with top-level investors who have minimal exposure to your field? Suddenly, you need to adjust your messaging and tone to engage a different audience—without diluting the essence of what you’re trying to convey.
That’s where AI can help you broaden your perspective before you ever step on stage. By simulating various audiences—or analyzing the questions and concerns likely to come from each group—AI tools can help you refine your core message and adjust your tone to resonate with people who don’t share your day-to-day context. The goal isn’t to water down your expertise; rather, it’s about highlighting the details that matter most to each audience, making the conversation more relevant. This proactive approach also helps you avoid common communication pitfalls—like using jargon that alienates listeners—and ensures you’re better prepared to address the questions or objections that might arise.
Good leaders are always trying to find ways to better connect with their teams and cultivate greater understanding throughout the organization. AI can serve as a powerful ally, bridging communication gaps and offering data-driven insights that help leaders foster a stronger, more inclusive culture.
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