Tech is evolving faster than we can blink—bigger phones, smarter homes, AI everywhere. It’s an integral part of many of our lives, just as much as it seemingly runs them.
And it's even more true for businesses. According to a recent study...
A staggering 95% of small business owners in the U.S. report using at least one type of technology platform in the running of their business. At the same time, 87% of them report that tech/data are the "backbone of operations" and have helped their businesses operate more efficiently. (And that's just small businesses.)
The World Is Changing (Fast)... Is Your Leadership Keeping Up?
As broader organizations brace (and build) bigger and better tech, rapid transformation seems inevitable. Only the best and most versatile leaders can navigate the complexities of this shift and drive the future forward.
In fact, tech, product, and engineering teams will lead this very charge. A Hunt Club market survey revealed that these departments are where leaders expect to see the most change in the next year—whether it’s through budget increases, structural shifts, or growing headcounts to support the transformation(s) ahead.
The mandate has never been clearer, and to succeed, organizations must know how to evaluate and assess their current and future leadership, ensuring no gaps exist that could potentially derail these critical efforts. Without strong, future-focused leaders, critical talent gaps could derail your 2025 transformation goals before they even begin. So it’s time to assess your leadership bench—and act fast.
One CTO Has Seen It All
To gain a deeper understanding of the leadership it takes to drive successful transformation, we spoke with John J. Higginson, a seasoned CTO with a wealth of experience across industries and company stages. Having served as CPTO of Groupon, CTO at Enova, CPTO at Florist Transworld Delivery, CTO at Applied Systems, and CTO at Chief, Higginson has seen it all—from scaling startups to leading established enterprises through pivotal moments of change.
He shares his insights on what it takes to lead in today’s fast-paced tech landscape, key ways to assess if you have the right leaders, and the methods to leverage when your leadership is resistant to driving transformation/change.
John J. Higginson |
3 Ways To Assess If You Have the Right Tech Leadership For Transformation
Never underestimate the power of assessment. Many leaders and organizations get caught up in the relentless drive for growth and can sometimes forget to take a step back and assess what's really happening beneath the surface. As Higginson tells us, "One of the skills I've honed over the years is being able to drop into a situation (e.g., new team, new industry) and quickly assess what's going on. It's helped me in M&A situations, it's helped me figure out how to salvage troubled projects, and it's helped me figure out how to make teams better."
Here are five key ways to assess your current tech leadership in that same way. Look for any gaps in leadership and take action where needed to ensure your organization is poised for success:
1. Start From the Top — Evaluate the CTO's Own Evolution
"It's funny, when I started people thought of the CTO as just the person who made the computer run. This mysterious job was separate from everything else. Over time, the role has become much more customer-, market-, and people-focused. A future-ready CTO is one that has evolved with the times, and no longer just the person who 'made the computer run.'"
What might this actually look like?
For customers and the market, the CTO is expected to be open and conversant in what the expectations are, to be part of sales discussions, and to be in the details of requirements. "In fact, CTOs are often also Chief Product Officers," says Higginson.
From a people standpoint, the biggest change has been the shift from CTOs being mainly concerned about picking the right technologies to being able to find the best people and build the test team to leverage those technologies.
TLDR? CTOs have shifted from being the technical expert to being the "head coach" who makes the most of a team of technical experts.
2. Always Check For Curiosity
"Technology always changes, so being curious, and having an open mind is vital," says Higginson. "That's especially true of growing teams where the job description is pretty dynamic. My first engineering job in a startup was a coder, but also a systems administrator.... a creator of training documentation.... and migrating data from other systems. The list goes on."
Curiosity fuels this adaptability, enabling individuals and teams to stay ahead of change and continuously learn new skills. It’s this mindset that empowers leaders and teams to thrive in an environment where the only constant is evolution itself.
3. Ask Yourself: "Will they open their doors for me? Solve a problem with me?"
True collaboration, while many of us think of it as a mere tablestake quality, is becoming harder and harder to find. It's helpful to put this nebulous trait under the microscope and ask a few key questions to really determine one's collaborative spirit. For example...
- Will they actively share their expertise and resources when you ask for help?
- Will they listen to your ideas with an open mind, even if they differ from their own?
- Will they work alongside you to find a solution, even if it requires extra effort or stepping out of their comfort zone (or job scope)?
"Collaboration is essential because no technology role is a solitary act," Higginson shares. "Everyone has to work within the team to build great products. You need people who can debate and find their way to the best answers. You need people who genuinely enjoy solving problems together."
Resistant to Change? Wrong Leadership? How To Help Solve This in 3 Ways
1. Leverage the Power of Storytelling
"Having worked in some industries like Insurance and Banking that are notoriously change-averse, I've developed a few approaches. The first is storytelling," says Higginson. "You need to explain the way of the technology, what it means to the people who will use it or the customers they support. What the future could look like."
Everyone loves a good story. By framing the conversation in a way that connects with people's lived experiences and aspirations, storytelling helps create a shared vision, making change feel less intimidating and more like an opportunity for growth.
2. Get Tangible To Gain the Buy-In
Tangibility. The importance of this cannot be overstated.
When you present tangible, relatable examples of how technology and necessary change can directly impact processes, products, or people, it becomes easier for stakeholders to visualize the benefits and actively contribute to it. Concrete results from similar implementations or case studies help demystify abstract concepts, making the potential transformation feel achievable and real.
"Build some early versions, some prototypes that show the promise of the technology. Most people need something tangible to embrace something new, to understand," says Higginson.
3. Choose Your Fighter Find Your Champions
"The last thing is to find champions. It's one thing as a leader for you to say something is good or useful. But it's incredibly powerful when peers say it — it helps change minds and creates a sense of a shared journey."
Higginson purports that when influential voices from within the ranks support change, it not only boosts morale but also builds a collective momentum that makes the journey toward change more cohesive, impactful, and well, a success.
John J. Higginson Out Of Office⚖️ How I would describe my leadership style in one fell swoop: Autonomy coupled with accountability.I don't micromanage people. I want to hire smart people that can run their area of the team. But we agree on outcomes and I hold them absolutely accountable for those results. From a personal standpoint, I like to debate things, hear different points of view. And I have a healthy sense of humor (lots and lots of "dad jokes") which hopefully makes work a bit more fun. 🥃 The tech/AI innovation I wish existed is: I really want a personal robot to do things like dishes, laundry, maybe make me an old-fashioned. 🛸 A fictional character I'd want on my tech/product team is: Lt. Uhura from the original Star Trek series. No matter what the alien language or technology, she could make sure people communicated. ❄️ The next destination on my travel bucket list is: Stretch goal: Space, just the ISS would be cool. On earth: Antarctica. 📓 The personal habit that contributes most to my success is: I take notes throughout the day and then review them at night. It's to help remember things I need to do but I also find it gives me a broader perspective on if I'm spending my time and energy on the right things. |
Build Future-Ready Teams With Support From Industry Experts Like John J. Higginson
John J. Higginson is the Chief Technology Officer at Curriculum Associates and a diverse technology leader in the Hunt Club ExpertAccess Program, which puts first-string operators in your back pocket for all things talent, so you can hire better, smarter, and faster.