On this Veterans Day, we pause, reflect, and express our deep gratitude to the men and women who have served in our armed forces. Beyond their sacrifice, the military consistently produces some of the finest leaders in the world. They understand how to build resilient teams, operate under immense pressure, and execute missions where failure carries a profound cost.
In the corporate world, especially in enterprise technology, we frequently borrow their terminology. We discuss “deployments,” “tactical pivots,” and “strategic alignment.” We talk about building robust architectures and fortifying our digital perimeters. Yet, the most valuable lesson we can take from military leadership is not about strategy or operations, rather it is about how they view human capital, trust, and problem-solving.
As leaders in fast-paced environments like the restaurant and retail industries, we can easily get caught up in capital projects, vendor negotiations, and aggressive rollout schedules. But without the right culture, the most brilliant technological infrastructure will eventually collapse under its own weight.
This brings to mind one of my favorite leadership insights:
“Leadership is solving problems. The day soldiers stop bringing you their problems is the day you have stopped leading them. They have either lost confidence that you can help or concluded you do not care. Either case is a failure of leadership.” — General Colin Powell
When you are driving enterprise-wide technology transformations or modernizing platforms across a massive global franchise network, friction is an absolute certainty. Systems will break, integrations will fail, and operational bottlenecks will emerge regardless of how well you mapped the architecture.
The true measure of an executive leader isn’t the absence of these problems, it is whether your team feels safe and empowered to bring them to light. If the engineers, project managers, and front-line operators suddenly go silent, it rarely means your technology ecosystem is perfect. It usually means your culture is failing.
Five Principles for Leading Problem-Solvers
Cultivating this level of psychological safety requires deliberate, daily action. It demands that we dismantle the corporate “shoot the messenger” mentality and replace it with a collaborative, solution-oriented framework. To build a resilient, scalable enterprise, we must transition from merely managing systems to truly leading the people who operate them.
Here are five principles for ensuring your team never stops bringing you their problems:
- Reward the Red Flags: Make it a cultural staple to publicly thank team members who surface bad news, technical debt, or failing processes early. What gets celebrated gets repeated.
- Audit Your First Reaction: When a critical integration flaw or outage is brought to your desk, monitor your immediate response. Shift your vocabulary from “Who caused this?” to “How do we solve this and improve the system?”
- Prioritize Psychological Safety Over Vanity Metrics: A dashboard full of “green” status indicators is useless if the team is terrified to report the red ones. Never let the desire for a flawless report override the reality of the ground truth.
- Push Decisions to the Information: The people closest to the technology often know exactly how to fix it. Empower the individuals bringing you the problem to also lead the design of the solution.
- Follow Through on the Fix: If a team member takes the risk of bringing you a systemic issue and you take no action to clear the roadblock, they will quickly lose confidence in your leadership and stop speaking up entirely.
When these five principles are actively practiced, you stop being a bottleneck and start becoming a catalyst. Your team transforms from passive observers of systemic friction into active, empowered architects of enterprise success. You create an environment where surfacing a roadblock is viewed as an act of loyalty to the organization, rather than a complaint.
A Personal Reflection on Service and Speaking Up
My perspective on leadership and service is deeply rooted in my family history. This Veterans Day, I find myself reflecting on my late father, Donald Crawford. He served our country with honor, and as a veteran, he instilled in me foundational lessons about duty, integrity, and looking out for the people to your left and right.
I remember a time early in my leadership career when we were facing a significant operational failure caused by a vendor integration. The pressure from above was intense, and my initial instinct was to start pointing fingers and demanding accountability for the breakdown. My father gave me a piece of advice I carry to this day. He told me, “Leaders don’t point fingers when the mission goes sideways; they take the hit and ask their team what they need to fix it.”
He taught me that true leadership isn’t about giving orders when things are going well, it’s about shouldering responsibility and providing your team with the cover they need when things are falling apart. When I shifted my approach, absorbing the executive pressure and empowering my engineers to solve the problem without fear of retribution, the issue was resolved in record time. More importantly, that team never hesitated to bring me a problem again.
Extending Our Impact: Hanks for Our Troops
Fostering a supportive internal culture is critical, but as leaders, we must also look at how we can leverage our platforms to support the wider veteran community. That is why I am incredibly proud of my affiliation with Round It Up America (RIUA) and our partnership with the 2026 Hanks for Our Troops “(T)HANKS” campaign.
Founded by Tom Hanks, this mission-driven coffee company dedicates 100% of its net profits to organizations that support military veterans and their families. Through the RIUA integration, customers purchasing Hanks for Our Troops products at Walmart or GiveHanks.com can easily round up their purchases or add a $1, $5, or $10 donation at checkout. It is a seamless, frictionless way to fund life-changing initiatives for the men and women who have sacrificed so much for our freedoms.
Closing Thoughts
On this Veterans Day, as we reflect on the profound leadership lessons provided by our armed forces, let us challenge our own corporate cultures to be better. We spend a lot of time focusing on capital projects and vendor ecosystems, but our most critical investments are always in our people.
True leadership isn’t about having all the answers, it is about fostering a culture where the team trusts you enough to help them navigate the hardest questions. Doing that requires checking our egos at the door and shifting our focus from self-preservation to team empowerment.
📚Recommended Reading
Turn the Ship Around! A True Story of Turning Followers into Leaders by L. David Marquet
Written by a former U.S. Navy submarine commander, this is one of the definitive modern books on servant leadership and perfectly fitting for this week. Marquet writes about taking command of the worst-performing submarine in the fleet and turning it into the best by abandoning the traditional “command and control” model. He pushed psychological safety and decision-making down to the crew members who actually held the information. It is an incredibly powerful read for any executive looking to scale their operations through empowered human capital.