By Joshua Menold, MBA
I’ve always described my leadership philosophy as “conservative cutting-edge,” and I usually get a puzzled look when I say it. The two words seem like they shouldn’t go together. Conservative implies caution, patience, protecting what you have. Cutting-edge implies speed, disruption, betting on what’s next. But after twenty years of building, rescuing, and scaling companies, I’ve learned that the leaders who create the most durable value are the ones who figure out how to do both at the same time.
The Problem with Being Just One
I’ve watched companies fail in both directions.
The purely conservative operator protects margins, avoids debt, keeps the same systems running for years because they work. And then one day a competitor shows up with better technology, a faster process, or a more compelling customer experience — and the conservative operator is three years behind with no way to catch up quickly. Their caution became their vulnerability.
The purely innovative operator is always chasing the next thing. New software every quarter. Constantly reorganizing. Launching initiatives before the last one has taken root. The team is exhausted, the financials are unpredictable, and nothing compounds because nothing runs long enough to mature. Their ambition became their instability.
The sweet spot — where I’ve tried to operate my entire career — is being aggressive about what you adopt but disciplined about how you adopt it.
What Conservative Cutting-Edge Looks Like in Practice
At CHE Companies, we’re deploying AI-powered workflows across a $70M+ construction platform. That’s cutting-edge — most companies our size in this industry aren’t even thinking about it yet. We’re using AI to automate meeting-to-action processing, generate daily executive pulse reports, draft company-wide communications, and build custom agent architectures that connect our CRM, field operations, and financial reporting.
But here’s the conservative part: we didn’t start by buying an enterprise AI platform and hoping it worked. We started with one workflow. We tested it. We measured whether it actually saved time or just created a new thing to manage. When it worked, we expanded. When it didn’t, we killed it without sentimentality. Every AI implementation we’ve done has had to pass the same test any capital investment would: does this create measurable value, and can we sustain it without depending on a single vendor or technology that might not exist in three years?
The same philosophy applied at Bobbitt Design Build when I led the company from 25% to over 90% paperless operations. That was a massive technology transformation for a construction firm — genuinely cutting-edge for the industry at the time. But we did it conservatively. We mapped every workflow before we selected any software. We piloted with one department before rolling out company-wide. We kept the old systems running in parallel until we were confident the new ones wouldn’t fail. The transformation took longer than it would have if we’d just ripped and replaced everything overnight, but it stuck — because the team trusted it and the processes were proven before we scaled them.
Risk Management Isn’t the Opposite of Innovation — It’s What Makes Innovation Possible
This is the insight that took me the longest to internalize, and it’s the one I’d most want to bring to any boardroom.
Most organizations treat risk management and innovation as competing priorities. The risk committee says slow down. The growth team says speed up. The CEO tries to split the difference and ends up with a watered-down version of both.
But in my experience, the best innovations come from organizations with strong risk management foundations — because those organizations can actually afford to take calculated bets. When you know your insurance structure is solid, your capital reserves are adequate, your contracts protect you, and your financial reporting gives you real-time visibility into what’s working and what isn’t, you can move faster on innovation because the downside is contained.
At CHE, I was able to launch an entirely new consumer-facing division — Cornerstone Exterior Remodeling — from scratch because the financial architecture was already in place. The capital structure was designed, the multi-state insurance and compliance framework was built, and the reporting systems could absorb a new business unit without creating chaos. The innovation was possible because the conservative foundation was already there.
Contrast that with companies I’ve advised through ITABWODI that wanted to innovate — new markets, new products, new acquisition strategies — but couldn’t because their financial house wasn’t in order. They didn’t have the reporting to know their true margins. They didn’t have the insurance structure to take on new risk. They didn’t have the capital flexibility to fund experimentation. They were stuck — not because they lacked ambition, but because they lacked the conservative infrastructure that would have made ambition safe.
The Board’s Role in Holding Both
I think this tension — between innovation and risk — is one of the most important things a board can steward. Management teams will naturally lean one direction or the other based on personality, incentive structures, and short-term pressure. The board’s job is to hold both truths simultaneously.
Is the company investing in technology and process improvement that will matter in three to five years? And is it doing so in a way that doesn’t create fragility or bet-the-company risk? Those aren’t opposing questions. They’re the same question asked from two angles.
When I evaluate a company — whether as an operator, an advisor, or a board member — I’m looking for evidence of both. Show me your innovation roadmap, and show me how you’ve stress-tested it. Show me your new market strategy, and show me the financial model behind it. Show me the cutting-edge technology you’re deploying, and show me the rollback plan if it doesn’t work.
The companies that get this balance right don’t just grow — they grow in a way that compounds. Each innovation builds on a stable foundation, which creates capacity for the next innovation, which strengthens the foundation further. It’s a flywheel, not a coin flip.
ITABWODI
My consulting firm is called ITABWODI — it stands for “Is There A Better Way Of Doing It?” That question captures the conservative cutting-edge philosophy in a single sentence. It assumes there probably is a better way. But it also demands that you actually find it and prove it before you abandon what’s working.
That’s the discipline I bring to every company I lead and every board I serve on. Be restless about improvement. Be relentless about evidence. And never confuse motion with progress.
Joshua Menold, MBA, is CEO and majority owner of The CHE Companies, a $70M+ multi-division exterior construction platform operating across NC, SC, and VA. He serves on multiple corporate and nonprofit boards and advises companies on M&A, capital structure, and operational transformation through ITABWODI, LLC.
