Not only should corporate boards understand when to seize opportunities to grow their companies, they must also know “what to stop doing.” And their people remain the most critical “difference-maker.”
So says Tony DiBenedetto, board chair for Appspace, a Tampa, Florida-based company that provides a digital workplace communication, collaboration and management platform. DiBenedetto also serves on the boards for two other Tampa-based companies: A-Lign, which provides a cybersecurity compliance platform, and Trofeo, a cloud solutions company specializing in Microsoft Azure.
What are some of the most pressing topics that your boards are tackling these days?
Every board I’m part of is wrestling with the same trio: growth, AI and people. Growth isn’t just “more revenue.” It’s disciplined expansion, smart capital allocation and knowing what to stop doing. AI is on every agenda, but the real conversation is how to turn it into business value without creating chaos. And team members remain the difference-maker—how we attract, develop and retain leaders who can navigate change.
We also spend real time on succession and culture. If you don’t develop the next generation of operators, strategy won’t matter. In practical terms, we ask simple questions that cut through noise: What are the two things we must do exceedingly well this year? What should we stop? What will make customers say, that was easier?
When cybersecurity and risk come up, we frame them in terms of outcomes: protect the brand, protect the data, protect the trust. That focus shows up as governance around where we place bets, how we measure impact and how we keep the customer experience front and center. The best boards pair curiosity with discipline. They are open to new ideas and clear about what really moves the needle.
How are your boards mitigating some of their respective company’s toughest challenges?
People love to say, “It’s not personal; it’s business.” And, I say: Let’s retire that line for good. Challenges are never just financial or operational—they’re human. The best way to mitigate them is to ask better questions and stay close to the teams doing the work. You learn where the friction is and how to remove it.
I’ve also learned the value of transparency. When leaders are open about what’s working and what isn’t, people rally around solutions. That’s how you build trust and momentum, even in tough moments.
What’s new about how your boards are recruiting board members?
Diversity of thought is the differentiator. You need people with fresh experience as operators, technologists and global thinkers.
I suggest treating board recruitment as a big-thinking exercise—the same resumes from the same backgrounds won’t cut it anymore. I also look for directors who stay curious and hands-on. The days of joining a board to show up quarterly are over. The best members roll up their sleeves, ask sharp questions and help management think differently.
How do your boards keep up with the opportunities and risks of emerging technologies?
Technology is moving faster than ever, and boards can’t afford to treat it as a black box. That means spending time with product teams, talking to customers and engaging with outside experts. It also means staying grounded in business value by asking, “Does this technology solve a real problem or just create more noise?”
The boards I serve on spend a lot of time looking at how technology can make work easier, not just more digital. It’s about turning innovation into something that actually helps people move faster and stay connected.
What are your boards’ strategies to ensure their respective company remains resilient?
Resilience comes from clarity and connection. Everyone, from the boardroom to the front lines, needs to understand the company’s purpose and what success looks like. When that’s clear, you can adapt quickly to changing conditions.
I grew up a Yankees fan, and baseball shaped how I think about boards: you read the field, adjust your swing and keep stepping to the plate. There’s a line often attributed to Babe Ruth that I keep in mind—never let the fear of striking out keep you from playing the game. That’s what resilient boards do. They understand the challenge ahead of them, make the right call at the moment and move forward.
Resilient companies also communicate well. They’re disciplined about where they invest, transparent about performance and confident enough to adjust course when needed. A good board creates space for honest conversation and healthy debate, because resilience isn’t about avoiding challenges; it’s about facing them with confidence and trust.
