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

Date:
Mon, 25 May 2026 11:05:00 +0000

Description:
Zendesk CLO Shana Simmons says AI success hinges on a privacy-first culture and governance. Empathy, character, and agency are the traits well need in an AI-first world.

FULL STORY ======================================================================Copy link Facebook X Whatsapp Reddit Pinterest Flipboard Threads Email Share this article 0 Join the conversation Follow us Add us as a preferred source on Google Newsletter Subscribe to our newsletter Conversations about AI governance rarely drift toward childrens soccer games, meditation routines or the pressure of representation in corporate leadership, but then again, Zendesk Chief Legal Officer Shana Simmons isnt your typical C-suite exec.

Opening up over breakfast at the companys 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. Latest Videos From You may like The next AI arms race: governance as trust The AI trust advantage: How smarter security wins customer confidence How AI is reshaping compliance: Why governance still matters Governance is no longer just a legal problem 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 thats spent years obsessing over data quality and infrastructure, thats a major shift, and in a good direction.

That said, governance and data arent 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 thats 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 theyre lawyers, she joked. Thats exactly what I want. Are you a pro? Subscribe to our newsletter Sign up to the TechRadar Pro newsletter to get all the top news, opinion, features
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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.

Zendesks 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. What to read next The leadership dilemma: Governing the Agentic AI workforce How enterprises
can safely scale agentic AI How CIOs can create a strong foundation for an AI-enabled workplace

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 shes 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 isnt going anywhere Like many discussions at Relate this year, the conversation inevitably turned toward automations 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 todays 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 childrens 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 dont 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 theres 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. Follow TechRadar on Google News and add us as a preferred source to get our expert news, reviews, and opinion in your feeds.



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Link to news story: https://www.techradar.com/pro/zendesk-clo-shana-simmons-empathy-is-the-new-sup erpower-for-ai-leaders


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