Why Leadership, People, and Technology Must Evolve Together – An Interview with Dr. Jessica Herbert

Dr. Jessica Herbert is an executive coach and organizational strategist who develops leaders at the moments that define their organizations, promotions, new commands, restructures, and culture crises, across public safety and beyond. Drawing on nearly three decades of experience and more than 100 transformation projects across 36 states, she helps leaders align the three forces that determine whether change actually lasts, leadership, people, and technology.

In this interview, Jessica shares what stayed constant across a career spanning criminal investigations, cybersecurity, and executive coaching, what technical experts must unlearn to lead well, and the mindset shifts that help executives stay steady, and make change stick, through their highest-stakes transitions.

Dr. Jessica Herbert, PCC, Executive Coach

Your career has taken you from criminal investigations and cybersecurity to executive coaching and organizational strategy. What has stayed consistent throughout that journey?

From the outside, my path can look like a series of hard turns, criminal investigations, cybersecurity, executive coaching, organizational strategy. I don’t read it as chaos. Every role has pointed at the same thing, complex problems that only get solved when leadership, people, and technology align. What changed was where I stood in relation to those three forces. Early on, I was the doer, running investigations, then leading teams and middle management through cybersecurity work. Later, I became the owner and the strategist, guiding not only my own organization but many others through the same alignment. The constants have never moved. The intentional design of leadership, the way you empower the people around you, and the way technology is leveraged to sharpen how work actually gets done, those have been the through-line for nearly 30 years. What has evolved is our sophistication. The technology is faster, and our understanding of how to lead and motivate people is deeper than it was when I started. But the core question I’m always answering is the same one, how do you get leadership, people, and technology moving in the same direction, at the same time, toward something that lasts?

You've worked in highly technical roles yourself. What do leaders often need to unlearn when they move from being the expert to leading the organization?

The hardest jump for a high technical performer is the move into management and leadership, because it asks you to stop doing the very work you’re known for. We underestimate what that costs. You’re not just setting down a task, you’re setting down the thing you were so good at that we promoted you for it. That’s a real grief, a genuine loss, and most people are unprepared for it. The new work looks nothing like the old work, and by definition you haven’t been trained for it, so you’re suddenly not excellent at your job in the way you’re used to being. What has to be unlearned is the belief that you should be the one holding the answers to the deep technical problems. Stepping in because it’s faster for you than empowering the person now in your old seat feels like ease, but that ease is your comfort, not the organization’s benefit. When you won’t fully sit in your own chair, you leave two seats poorly filled, and that harms the whole organization. The shift is to fully release the work and find your passion in guiding it and developing the people who now do it.

You developed the DTAC methodology after leading more than 100 transformation projects. What patterns convinced you that leadership, people, and technology have to evolve together?

I think of leadership, people, and technology as three independent forces, and they rarely evolve at the same pace. Technology moves at a speed humans struggle to match. People and leadership take longer; it still takes four years to finish a degree and months to grow into a role. So the pattern isn’t that they must evolve simultaneously. It’s that an organization has to keep pushing the right levers to keep the three in balance. Picture a three-legged stool. If one leg stops growing, you don’t hire enough people, or skills wither, that leg shortens, and the stool wobbles or won’t hold you at all. Meanwhile, technology keeps stretching its leg longer and longer, throwing the whole thing off-kilter. That’s exactly what convinced me, across more than a hundred projects, the failures traced back to a neglected leg. We’re watching it happen right now with AI. Organizations assume agents can simply absorb the work of people, but what they’re really creating is a teetering stool, not enough people in the seats to balance the pressure technology is applying. You cannot stabilize on two legs, no matter which two they are. Leadership’s job is to keep investing so all three hold.

Organizations invest heavily in new technology, yet many transformation efforts still fall short. Where do you see leaders making the biggest mistake?

The biggest mistake I see is letting the cost and complexity of the technology create a myopic view of what’s actually happening in the organization. These implementations are enormous, licensing, servers, infrastructure, vendor training, procurement cycles that can run twelve, eighteen, twenty-four months. Because it demands so much money, time, and energy, leaders start to believe the technology is the whole job. “We just need to get this in.” And that blinds them to everything else the change requires. Nobody has mapped what the workflow will look like the day after go-live. No one has built internal champions and subject-matter experts to absorb the waves the new system creates. People are trained once, by a vendor, instead of being taught the tool through the institution’s own knowledge and context, which is what actually turns resistance into adoption. When a leader spends one, two, ten million dollars on technology and sets aside nothing for ongoing training, support, and development, they’ve told me plainly that they only funded one leg of the stool. Three and four years later, the system is used incorrectly, the data is a mess, and the capability they paid for was never realized, because the people were never funded from the start.

You often say that data should strengthen leadership rather than replace human connection. How can leaders use data without losing sight of the people behind it?

I’ve always said we should be data-informed, not data-driven. Data helps us understand a topic and its outcomes, and when it’s measured accurately, it should strongly inform a decision, but it should never be the only thing driving it. The trap is over-focusing on the quantitative and forgetting the qualitative. Say you’re comparing two units. Team A has ten people and produces a hundred widgets; Team B has fifteen and produces two hundred. The raw numbers say Team B is more effective. But the numbers don’t tell you that three of Team A’s people just transferred in and don’t yet know the job, so that team is actually working at a deficit. They don’t tell you about culture, about a toxic personality, about who’s understaffed or misaligned. Performance figures describe output; they don’t explain the people producing it. So the discipline for leaders is to give the data depth, to ask what’s really working and not working underneath the number. That depth usually doesn’t come from another survey or culture test. It comes from trusting your mid-level managers and the people closest to the work to tell you what’s rising, what’s falling, and why it matters.

When you're coaching an executive through a major transition, what is one mindset shift that consistently helps them become a more effective leader?

Every transition carries uncertainty, and when we’re uncertain, the brain rushes to fill the gaps. Leaders are built to think from thirty or fifty thousand feet, but the uncertainty of a transition lives down at three thousand feet. So the mind gets pulled into these short, low cycles, and that’s exactly where worry, anxiety, frustration, and self-sabotage take hold. The shift I coach is to climb back up and think ahead, to stay on the balcony. Instead of fixating on “what will this job be like when I get there,” the executive fully visualizes the future version of themselves in the role. Six weeks, six months, a year out, this is how I communicate, this is how I hold my emotions, this is my mindset. You make that future self the goalpost. Then, as the transition delivers its knowns and unknowns, its prepared and unprepared moments, you can read each one as a step toward that vision rather than a threat to it. In coaching we call it future pacing, it lets you move through today’s anxieties because tomorrow is drawn in clearer terms. Executives already know what works for them; that clarity just gets lost in the small loops. The balcony is where you lead at your strongest.

After working on more than 100 transformation projects across 36 states, what have the strongest organizations done differently to make change stick?

The strongest organizations do three things differently. First, they choose the right leader, not simply the person with the title or the one who happens to sit in the relevant department. They ask how long they need that person in the seat, and what characteristics the role truly demands, a strong communicator, someone who documents and problem-solves, who can operate autonomously and hold emotional intelligence under pressure. That champion has to carry the effort for the two to three years these transformations take, even as CEOs, mayors, or city managers change around them. Second, they structure the team intentionally across phases. The people who excel at startup, testing, and problem-solving before go-live are often not the team you need for stability and duration. Recognizing that, and bringing in external consultants for the startup phase when needed, keeps the effort from stalling. Third, they buy technology only after they clearly understand what it’s meant to fix, which existing systems it will retire, and how it fits a strategic plan that moves at the pace of the organization, not the pace of the vendor. Underneath all three is the same muscle, intention. They understand roles and behaviors, they put people in the right seats, and they rotate those seats when the work changes.

You often say that everything is possible once you find the steps and the momentum. How has that belief shaped your approach to leadership and coaching?

Leadership puts constant pressure on you to generate momentum, when sometimes what you actually need is a pause. There are other seasons where you’re the opposite, frozen, stuck in the pause, because the pressures never make it clear what the real priority is. Both ends are costly. Chase momentum too hard and you burn out; the role consumes you, becomes the only thing you think about, with no healthy way to release the stress. Freeze because you can’t see the path or everything feels on fire at once, and you’ve stopped making decisions, which is its own signal of burnout, and just as harmful to the organization, because a leader who won’t decide while everyone is looking to them does real damage. So the work isn’t choosing speed or stillness. It’s about regulating the momentum. You keep taking the steps and moving forward, but you don’t race to a hundred and fifty miles an hour, and you don’t slam on the brakes until nothing moves at all. Once you learn those regulatory practices, how to sustain a steady pace without redlining or stalling, you start to see not just what’s possible, but the pace at which it’s possible without costing you yourself along the way.

If readers could take away one lesson from your work that would help them become stronger leaders tomorrow, what would you want it to be?

If there’s one lesson I’d want a leader to carry into tomorrow, it’s this, practice honest self-reflection, the kind that makes you emotionally capable of letting go of the very expertise that earned you the position. When you release it, you open yourself to everything there still is to learn, and that is what actually builds a stronger leader. If you step into leadership clutching the traits that got you there, you’ll miss the lessons waiting on the other side, because those traits don’t serve you once you’re in the seat. A new role demands a new set of skills, and what carried you here will not carry you to the next level if you refuse to set it down. Honest self-reflection means embracing all of it, your good qualities, your difficult ones, your superpowers and your weaknesses. That’s where leaders get stronger, in the willingness to let go of things that served them well, so they can stay open and absorb what’s coming next. Do that, and you won’t wear your strengths like a badge until they exhaust you, and you won’t reach for your weaknesses as the excuse for why something didn’t happen. You’ll simply keep growing.

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