Help Me Understand…

How Great Leaders Use Questions to Build Trust, Uncover Risk, and Improve Decisions

After two back-to-back weeks of board meetings, I found myself reflecting on the train ride from New York back to Philadelphia. A few observations came to mind.

People want to be engaged.
When board members ask thoughtful questions, it energizes the room. It signals that the work matters and that leadership is paying attention.

Recognition matters.
Not empty praise, but authentic acknowledgment of meaningful results. Genuine recognition reinforces the behaviors and outcomes organizations want to repeat.

Boards bring perspective.
Because board members aren’t running the business day to day, they can often see patterns, risks, and opportunities through a different lens. Their greatest value isn’t having all the answers, it’s offering perspectives management may not yet have considered.

Tone matters as much as the question.
People don’t just want to be heard; they want to feel respected. Curiosity creates dialogue. Condescension shuts it down. Some of the best conversation starters I’ve heard are:

  • “Help me understand…”
  • “I may be missing something…”
  • “Walk me through your thinking…”
  • “What are we seeing…”
  • “What would make us change our minds…?”
  • “Where do you have the lowest confidence?”
  • “How is the team doing?”

Those simple phrases demonstrate both emotional intelligence and humility.

Be willing to share your failures.
Board members aren’t omniscient despite what some may think. We all learn through successes and mistakes. I’ve always found it more valuable when a board member shares where something didn’t work, what they learned, and how that experience shaped better decisions. That’s wisdom, and wisdom is one of the board’s greatest responsibilities.

It’s not enough to report on today’s weather. Great board members help management think through what might be coming next, why it may happen, and how to prepare for it.

Trust is built between meetings.
The board members I’ve valued most throughout my career are those who invest in establishing relationships outside the quarterly meeting cadence. They get to know the team. They ask questions. They stay engaged.

That trust becomes invaluable when the business inevitably hits turbulence.

No company wins forever. Even exceptional businesses eventually face market shifts, competitive pressure, or unexpected disruption. The strength of the board-management relationship is often tested most during those moments, not during the good quarters.

One final thought for management teams:

Know your business’s motion.
Know how the key drivers interact. When one variable changes, what typically happens next? That’s different from having all the answers. It’s understanding the dynamics of your business well enough to explain its expected behavior while remaining open to new information.

I call that controlled confidence…speaking with conviction while remaining intellectually curious. Confidence comes from experience. Experience grows through continuous learning.

And finally…

Be yourself.

It’s remarkable how often people change their personalities in boardrooms and executive meetings. Authentic confidence builds credibility. Manufactured confidence usually creates doubt.

People don’t expect perfection. They expect honesty, preparation, accountability, and a willingness to learn.

Those qualities earn trust with your team, your board, and ultimately, your customers.

To Merge, or Not to Merge

Recent mergers within the payments industry have many wondering what’s next. In reading several blog posts, news publications, and LinkedIn articles, I see industry professionals scratching their heads and asking “what’s to gain from these mergers?”

Companies acquire or merge for 3 primary reasons – to gain market share, acquire talent, or round out a product gap – this includes technology. I suspect that the recent mergers have been driven by pressure from within the industry to achieve size and greater scale – hence share. The market share play becomes the focus of mergers when the other two reasons are lacking from the equation.

Imagine if two Pharma companies that both produced ibuprofen merged, what would they gain other than greater share? However, if one of those companies produced a ground breaking Alzheimer’s medication you now have a new entity that is potentially more valuable given its broader reach and product offering. So the question to be answered is what specific gaps and gains will be addressed by these recent combinations. And here’s a hint….the answer can’t be “operational efficiencies” which is simply code for saying the plan is based upon squeezing cost out of the business to drive short-term financial results.

Let’s also not forget the #1 reason for combo failures – cultural misalignment. Synergies that look great on paper still must be executed by human beings…those same human beings that have been living with, and in, specific cultural norms for a period of time. People often underestimate what’s required to combine companies – to combine cultures. What if the U.S. and Mexico were suddenly merged together into one country?  Just because it works on paper doesn’t mean it will actually take hold…heck we struggled to figure out NAFTA let alone something grander. Cultural differences are too significant to underestimate.

This will not be the last combination. Corporate decisions tend to revert back to our childhood days of playing musical chairs…no one wants to be left standing without a seat. Unfortunately these mergers are not addressing the key problems the payments industry is facing – a dynamic buyer, global sellers, legacy technology, and infrastructure dilemmas. How these four things can be best brought together is the idea, or solution, the market requires. These transactions clear the path for smaller, more nimble players to answer this question and disrupt what has been an industry slow to change and innovate. In the end, the buyer holds the most powerful vote to determine what is most valued.  My belief is they will continue to vote for more choices for easier and secure ways to make their purchases.  This vote will be given to those agile enough to listen to the need and place the creation of a new customer experience as the #1 priority, versus clinging to the belief that bigger is better.

Talent and Innovation

Everyone says they want to innovate. Every company talks innovation. We’re now seeing innovation as a core value for many companies. But are they really innovating?

Innovation is about talent. In the absence of talent there can’t be innovation. The first step to innovation is recognizing the two types of talent required to be innovative.

The first type of talent required to innovate is visionary talent. This is the talent, skill, or competency to see things others cannot see, or are unwilling to accept. Visionary talent is often related to first-movers. Many of the products and services we use on a daily basis started first with a vision. A mobile phone, a smart watch, wireless headphones (or ear buds), technology in the cloud versus a mainframe. These inventions, or innovations, required visionary talent. How do you spot visionary talent? Individuals that possess an insatiable appetite for learning, dreaming, and pondering not what is, but what could be.

The second type of talent required for true innovation is technical talent. This is the talent that is required to bring the vision to life. Think of Steve Wozniak to Steve Jobs. Technical talent tied to visionary talent. Or Charlie Munger to Warren Buffett. Technical talent is what enables our ability to bring dreams into our daily reality.

In 1899, Charles Duell, then Commissioner of the U.S. Patent Office, said, “Everything that can be invented, has already been invented.” While I personally don’t believe this to be true, let’s for a moment assume it is. If this were to be true, then arguably technical talent would be far more valuable than visionary talent. Why? Because the focus would be on incremental improvements of things that already exist. However, this raises a thought provoking question. What’s invention versus innovation.

In 1849, Italian inventor Antonio Meucci, invented the telephone. It wasn’t until 1876 that Alexander Graham Bell won the first U.S. patent for the device. Fast forward to 1973 when the first phone call was made on a Motorola mobile phone. Was the mobile phone an invention or simply an improvement on something already invented? Remember, it was 50 years after the phone was invented that Duell said everything that could be invented already had been invented.

Regardless, visionary talent and technical talent combined are required to innovate. Combining the creator of dreams with the builder of those dreams allows us to improve our lives in meaningful ways.

What’s your talent pool like? Who are your visionaries and who are your techies? How often do you review your organization for these two types of talent? Your answers to these questions will be the proof point for whether you are building and living an innovation culture.