Zendesk CLO Shana Simmons: Empathy is the new superpower for AI leaders | Tech Radar

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Zendesk CLO Shana Simmons: Empathy is the new superpower for AI leaders

Empathy, character, and cultural compliance are key to AI leadership, Zendesk CLO says

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Conversations about AI governance rarely drift toward children’s soccer games, meditation routines or the pressure of representation in corporate leadership, but then again, Zendesk Chief Legal Officer Shana Simmons isn’t your typical C-suite exec.

Opening up over breakfast at the company’s annual Relate customer conference, our conversation about AI regulation and enterprise governance quickly turned to empathy, authenticity and identity.

In an ever-changing environment in which enterprises continue to explore autonomous agents, Simmons kept returning to the same core idea: (human) culture matters more than ever. Simmons discussed the sense of how people behave when nobody is watching, how teams build trust and how companies embed responsibility into the DNA of their products long before regulators force them to.

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One of the strongest themes throughout the conversation was the idea that governance has quietly overtaken data quality as the biggest blocker to enterprise AI adoption. For an industry that’s spent years obsessing over data quality and infrastructure, that’s a major shift, and in a good direction.

That said, governance and data aren’t totally disconnected. Simmons actually framed governance as an umbrella, beneath which are multiple core pillars spanning privacy, security, AI guardrails, accountability, and of course, data.

But unlike many executives discussing governance in abstract legal language, Simmons spoke about it culturally – as something that’s deeply embedded in company culture. That means product managers, engineers and developers are expected to consider compliance too.

“Some of my product managers and engineers think they’re lawyers,” she joked. “That’s exactly what I want.”

That line was a much bigger reflection on the mood of the conversation. Simmons actively wants to break down walls between legal, technical and product teams. Instead, she wants overlap, curiosity and shared accountability.

Zendesk’s European origins during the early rise of cloud computing and privacy regulation helped create what Simmons repeatedly described as a privacy-first mindset.

The industry has entered a phase where almost every vendor can produce a flashy proof-of-concept. Far fewer can explain how those systems behave under pressure and across thousands of customers or industries.

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Simmons admitted that, during her early days, she was initially skeptical about adding more and more certifications to prove compliance. It was much clearer that she’s a believer in doing things right from the ground up – recognition can follow. For her, governance is not reactive, but rather a cultural muscle memory.

The future of work looks different, but personality isn’t going anywhere

Like many discussions at Relate this year, the conversation inevitably turned toward automation’s effects on the human workforce.

In one example, Simmons described visiting colleagues in a Manila legal team, where she discovered highly capable professionals wasting enormous amounts of time on repetitive work. Those overseas colleagues, she explained, were filled with fear that the CLO would be arriving to fire them. Rather, Simmons’ approach was to identify how she could support each and every worker to use their best skills.

That perspective has fundamentally changed how she hires. Where legal departments may once have prioritized pure productivity, Simmons now looks for two things above all else – AI literacy (which she recognized can be taught) and agency. A willingness to learn, to explore, to engage.

“Do something about it,” she said while describing employees who identify repetitive processes and build systems to solve them.

The discussion moved on to the high-output, high-value future of work. I asked a question that Shana herself had asked Simone Biles the evening before on stage at Zendesk Relate 2026.

With workers under intense pressure to deliver and today’s always-on state, I wanted to know how a CLO who leads teams of workers, supports other businesses and boards, and makes time for her own family, stays grounded.

Simmons admitted that finding balance is an ongoing process. She grounds herself by dedicating time to family, hobbies like hiking, and attending her children’s soccer games, and relies on a dual support network of peer mentorship from other general counsels and trusted family and friends.

Earlier in her career, she tried mimicking the personalities and communication styles of other executives around her. “I don’t look like what people expect a GC or a CLO to look like at a tech company,” she said.

Simmons eventually stopped viewing empathy as a weakness to be suppressed, realizing it was actually her superpower. This perspective enabled her to better understand customers, engineers, and sales teams, and build more diverse, effective teams by embracing varied communication and work styles.

Character matters when nobody important is watching, she explained in a restaurant full of customers, business leaders and passers-by, hinting at how each of them treated their servers.

When evaluating candidates, she said intelligence and qualifications are often the easy part. What she watches most closely is how people treat others they perceive as ‘less important’.

In fact, she said one of the most influential people in her hiring decisions was often her executive assistant because she observed how candidates behaved when they thought nobody senior was paying attention.

It felt like a fitting way to end a conversation about AI, because beneath all the discussion around governance frameworks, automation, regulation, and enterprise infrastructure was a much simpler recurring idea. The technology may be evolving rapidly, but leadership and jobs as a whole are still fundamentally about people and connections, and while there’s undoubtedly a big shift ahead in the world of labor, it is exactly that – a shift – and not a displacement. To really stand out in an AI-human hybrid world, this discussion made it clear that being oneself and showing very human traits, like respect and engagement, are crucial.

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With several years’ experience freelancing in tech and automotive circles, Craig’s specific interests lie in technology that is designed to better our lives, including AI and ML, productivity aids, and smart fitness. He is also passionate about cars and the decarbonisation of personal transportation. As an avid bargain-hunter, you can be sure that any deal Craig finds is top value!

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