EP · 011
THE SCIENTIST WHO BET HIS CAREER ON BUGS. 14 YEARS LATER, HE WAS RIGHT.
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Don't forget where you came from when you're working these big positions with these big titles. Remember where you started.
John Sherman
Former senior DoD official John Sherman on why he led with kindness and user experience at the Pentagon—and why those two things, dismissed by many as soft, turned out to be the hardest and most important things he did.
Key Takeaways
- →Kindness is a leadership strategy, not a personality trait: Sherman's framework: kindness—taken seriously and practiced consistently—produces organizational outcomes that authoritarian management cannot. It creates loyalty, candor, and discretionary effort that fear-based leadership destroys.
- →User experience matters even at the Pentagon: Sherman was an early and persistent advocate for applying UX principles to government technology—arguing that if millions of people depend on government systems, those systems should be designed for the humans who use them, not just for the engineers who build them.
- →The 'honorable' title carries a specific set of obligations: Sherman reflects on what it means to have served in a senior public role and to carry the formal title 'Honorable'—the weight of public trust it represents and the responsibility to behave consistently with it whether or not anyone is watching.
- →Leading with compassion in a bureaucracy requires courage: Government bureaucracies don't reward vulnerability or warmth as obviously as they reward authority and control. Choosing to lead with kindness in that environment is not the path of least resistance—it requires conviction and tolerance for being misunderstood.
- →How you treat people is the legacy that lasts after the work is done: In every role Sherman has held, the thing people remember most is not the policies he implemented or the systems he built—it's how he made them feel during the work. That's the legacy.
- →UX and kindness are the same idea at different scales: Sherman sees user experience design and interpersonal kindness as expressions of the same underlying principle: putting the human at the center. Whether you're designing a form or having a difficult conversation, centering the person's experience is always the right call.
- →The hardest leaders to replace are the ones who made everyone feel seen: Sherman has seen leaders who knew more, worked harder, or had more authority than he did—and been less effective because they didn't invest in making people feel genuinely valued. That investment is the differentiator.
Full Essay
We turned this conversation into a long-form essay. More context, more depth, and the moments that didn't make the edit.
Read on Substack →Q&A
Questions answered in this episode
What does user experience design have to do with government?
Everything, according to Sherman. Government systems affect hundreds of millions of people who often have no alternative—they can't use a competitor's version. Designing those systems without considering the people who use them isn't just a missed opportunity; it's a failure of public service. UX thinking is how you fix that.
What does it mean to lead with kindness in a bureaucracy?
Sherman defines it as taking the time to understand each person's situation before making decisions that affect them, being honest even when honesty is uncomfortable, and treating every interaction as an opportunity to add to someone's sense of worth rather than diminish it. In a bureaucracy, that requires deliberately counteracting institutional tendencies toward impersonality.
What is the relationship between kindness and organizational performance?
Sherman argues it's direct and measurable: teams where people feel genuinely cared for produce more, retain better, and take more productive risks. Not because kindness is a motivational tool—but because it creates psychological safety, and psychological safety is what allows people to do their best work.
How do you maintain high standards while also being kind?
By being clear that kindness doesn't mean avoiding difficult conversations—it means having them with care. You can deliver hard feedback, enforce accountability, and make unpopular decisions while still treating people with genuine respect. The two things aren't in conflict; conflating kindness with softness is the error.
What is the most important leadership lesson you learned in government?
Sherman keeps returning to this: how you treat people in the moments when you have all the power is what defines your leadership. Not the speeches, not the policies, not the strategies—but the daily, small choices about whether to see and acknowledge the humans around you.
Why did you advocate for UX at the Department of Defense?
Because people deserve systems that work for them, not systems they're forced to adapt to. Sherman found that the Pentagon had some of the smartest people in the world working on extraordinarily complex problems—and using software that made their work harder than it needed to be. That was a solvable problem.
What does it mean to carry the title 'Honorable' after leaving public service?
For Sherman, it means that the obligations of public service don't end when the role does. You carry them into every subsequent conversation, every platform you have, every time you could choose to use your access and reputation in service of something that matters. It's a lifetime commitment, not a job title.
About John Sherman
John B. Sherman is the former Principal Deputy Under Secretary of Defense for Intelligence and Security, a title that comes with the 'Honorable' designation for life. He is a longtime advocate for user experience and human-centered design in government technology—and for the proposition that kindness is a leadership strategy, not a soft skill.
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