The Now Factor
Why the most successful leaders live in the present
One of the first questions I ask a founder, after hearing how they built their business, is one of the simplest.
“What are you most excited about right now?”
The answer tells me more than the story that came before it.
Every founder has a story. It almost always begins with a willingness to take risks, a few painful mistakes, and the determination to keep going when most people would have stopped. Those experiences build resilience, instinct, and real wisdom.
But they can also become invisible anchors.
The Anchor Nobody Names
I was working with a founder whose business had plateaued. Revenue was flat, not declining, just not moving. The team was capable. The brand had earned genuine respect in the market. From the outside, everything looked fine.
What I found, when I started digging, was that the strategies that had driven the company’s early growth had quietly become the company’s identity. The founder wasn’t running the same playbook because it was still the right one. He was running it because it had worked, and questioning it felt like questioning everything that had made him successful.
This is what I mean by an invisible anchor. Not a mistake someone made. A success that was solidified in the past and not updated to the present.
In a recent piece I wrote about why smart, successful people stay stuck, the finding was straightforward: smart people don’t stay stuck because they don’t know what to do. They stay stuck because they don’t do what they already know. The same applies to companies. Most plateaus aren’t caused by a lack of good ideas. They’re caused by an unwillingness to question the ideas that produced the last great result.
There’s a screenwriting rule called “kill your darlings.” It means the work you’re most attached to, the scenes you toiled over, the structure you’re proudest of, sometimes those are exactly what needs to go because they’re no longer serving the story.
Blockbuster understood its business better than almost anyone. At its peak, the company had more than 9,000 stores, brand recognition that required no explanation, and a distribution network most competitors would have spent decades trying to build. When Netflix approached them about a partnership in 2000, Blockbuster passed. From inside the company, the decision probably made sense. They were doing well. Netflix was a niche player with a mail-order model. Why trade what’s working for something unproven?
They filed for bankruptcy ten years later.
What made Blockbuster a cautionary story wasn’t a single bad decision. It was the accumulation of reasonable decisions made inside a worldview that had stopped evolving. The business environment shifted. The company kept executing the strategy that had always worked. By the time the gap became obvious, closing it was no longer an option.
Kodak invented the first digital camera in 1975. The engineer who built it described management’s initial reaction: “That’s cute, but don’t tell anyone about it.” They held the technology and chose to protect the film business instead. When the market moved anyway, they had nothing left to protect.
These aren’t stories about companies that failed because they stopped caring or stopped working hard. They’re stories about companies that kept doing what made them successful while the world quietly reorganized itself around something different. The strategy that built yesterday’s company became the assumption that blocked tomorrow’s growth. Most of the time, nobody inside even noticed the transition was happening. They were too busy executing.
The Stories Organizations Tell
In an article I wrote called Mind Games, I explored the stories we tell ourselves inside our own heads. Organizations do the same thing.
“Our customers only care about price.”
“No one can do this the way we do.”
“This is how we’ve always done it.”
Those stories begin as explanations, become beliefs, become culture, and eventually become barriers that no one inside the organization even notices anymore.
Once a company decides what it is, every decision gets filtered through that identity, including decisions about what to question and what to leave alone.
When a company reaches a plateau, the problem is usually diagnosed as a sales issue, a marketing issue, a recruiting issue. Those may all be real. But in my experience, they’re symptoms. The actual problem is usually one layer deeper: the assumptions driving those decisions have gone unquestioned for too long.
Assumptions don’t announce themselves. That’s what makes them hard to see from inside the system.
What a Mirror Actually Shows
Every leader has blind spots. Not because they’re incapable, but because success naturally reinforces certain ways of thinking. The longer you’ve been successful, the easier it is to mistake familiarity for certainty.
The most useful question an outside perspective can ask isn’t “what’s wrong.” It’s the question no one inside the organization is asking, usually because the answer would require changing something that worked before.
One of the first questions I raise in any consulting engagement is the one that almost never gets asked from inside a business: What should we stop doing?
Not what should we add. Not where should we invest more. What should we stop. Before you add anything, this question should be answered.
That question is harder than it sounds when things are going reasonably well. There’s no obvious pressure to ask it. Which is precisely when it matters most.
The leaders who consistently make good decisions through changing markets are usually the ones who’ve built some mechanism for this, whether through a trusted outside perspective, a board member who isn’t afraid to disagree, or the discipline to seek out honest disagreement before acting on a plan they’ve already written.
The Chill Factor
In an earlier piece, I wrote about what I called The Chill Factor. The calmest leaders usually make the best decisions. Not because they’re indifferent to outcomes, but because staying present long enough to see reality clearly, rather than reacting emotionally to yesterday’s victories or yesterday’s fears.
That calm makes a specific kind of conversation possible. The kind where a founder can say: this approach worked before, and it may not be what we need now. The kind where a leadership team can question a belief they’ve held for years without anyone feeling personally attacked by the question.
Calm isn’t the absence of urgency. It’s the ability to hold urgency without letting it collapse your perspective.
The Question Worth Starting With
The companies that continue growing past every natural plateau aren’t the ones spending the most energy on what made them successful. They’re the ones still asking honest questions about what’s actually happening now.
What has changed in our market that we haven’t caught up with? What are our customers telling us that we haven’t been willing to hear?
Before your next leadership meeting, try one question: If we were starting this company today, what would we build differently?
That question is uncomfortable for a reason. The discomfort is usually pointing at something real.
The leaders who stay in the present don’t use the past as evidence that they already know the answer. They use it as information for asking a better question.