Copy of What Got You Here Might Be What’s Holding You Back (TPL Insights #283)

By Rob Andrews

Why senior leaders must unlearn, rethink, and rewire to lead in a world that refuses to sit still.

Let’s be blunt: “That’s how we’ve always done it” is not a leadership strategy. It’s a resignation letter in disguise. There’s a dangerous phrase I hear often in boardrooms:

“That’s how we’ve always done it.”

It’s usually followed by one of its equally outdated cousins:

“This model’s worked for decades.”

“I trust my gut.”

“If it ain’t broke…”

Except it is broke. And we all know it. Because if you’re honest with yourself, things don’t feel like they used to. The same strategies that once drove growth are now stalling out. The “sure bets” are missing the mark. And you’re starting to see cracks in the armor, but your inner voice keeps telling you to double down.

When Charles Butt began his transformation of H-E-B in 1987, he hired a very expensive consultant who told him in no uncertain terms: “Charles, if you’re going to be successful in transforming your company, you have to transform yourself first. By that, I mean you’re going to have to let all of your old success models go. You’re going to have to learn to think without limitations, to accomplish things most leaders in your position would tell you are impossible.” You know what happened next. H-E-B went from sleepy little regional grocery chain to perhaps the best supermarket chain in the world.

H-E-B is literally doing what “experts” like Michael Porter, the famous Harvard strategist, said was impossible. Porter, for example, says that we must choose one of three possible strategies: price leader, differentiator, or niche operator. Charles chose to think without limitation, beat Wal-Mart pricing by 300 basis points, and deliver a superior customer experience. The H-E-B brand is now so powerful that when the company opened its first store in the Dallas-Fort Worth metroplex, there were people lined up hours before opening, waiting to get in.

Let me ask you: What if your experience is no longer your biggest asset, but your biggest liability?

The Trap of Cognitive Ease

Nobel laureate Daniel Kahneman wrote in Thinking, Fast and Slow that humans are wired to choose mental ease over effort. We favor intuition over analysis, habit over reflection. The more familiar something feels, the “truer” it seems, even if it’s completely wrong (Kahneman, 2011).

That’s a scary realization when you apply it to executive leadership. Because the higher you climb, the more isolated you become. And the easier it is to mistake comfort for competence.

Kahneman called this phenomenon “cognitive ease.” I call it executive autopilot.

And in today’s world, autopilot crashes companies.

Experience ≠ Accuracy

In Think Again, organizational psychologist Adam Grant (2021) puts it plainly: “The people most likely to overestimate their abilities are the least competent.”

Ouch.

But here’s the kicker: The more experience we have, the harder it is to unlearn. Our expertise becomes armor. Our certainty, a crutch. We stop asking questions. We stop listening. We stop growing. And slowly—without even realizing it—we become irrelevant.

The Market Does Not Care About Your Legacy

Look around.

Blockbuster knew everything about video.

Kodak knew everything about cameras.

BlackBerry knew everything about secure mobile communication.

Every one of them was full of smart, experienced people who didn’t want to rethink the game.

And every one of them got steamrolled by the future. Harvard professor Rosabeth Moss Kanter famously said, “Everything looks like a failure in the middle.” That’s true. But it’s only a failure if you refuse to adjust.

The Cost of Certainty

Research from McKinsey shows that fewer than 25% of corporate transformations succeed. The #1 reason? Leaders refuse to change their minds. They cling to outdated models, legacy org charts, and playbooks that worked in a different economy, with a different workforce, and different expectations (McKinsey & Company, 2023).

As Grant (2021) put it: “The best leaders are not the ones who have all the answers. They are the ones who know how to ask better questions.”

Let that sink in. Questions, not answers. Learning, not lecturing. Adaptation, not arrogance.

Leading in Complexity Requires a Different Mind

In The Fifth Discipline, Peter Senge (1990) warned that many leaders “see the world in fragments” and then try to “fix the pieces.” That approach worked in the industrial age—but today, everything is interconnected.

Your business is not a machine—it’s a living system. And systems require different thinking.

They require systems thinking.

You cannot “optimize operations” in one division while ignoring cultural rot in another. You cannot “drive shareholder value” while bleeding out employee trust. You cannot solve adaptive problems with technical solutions.

Your Org Is Watching You

Here’s something your team will never say out loud: They’re watching what you prioritize. They see what you dismiss. They know when you’re stuck in old patterns, even if you don’t.

When you fail to question yourself, you give your people permission to do the same. That’s how mediocrity becomes systemic. That’s how “good enough” becomes a ceiling. That’s how once-great companies stall—and sometimes implode.

In An Everyone Culture, Kegan and Lahey (2016) argue that organizations built for continuous earning—at every level—outperform those that prize control, hierarchy, or status quo. The healthiest cultures are not built on certainty. They are built on humility, curiosity, and the discipline to challenge assumptions.

So What Now?

If you’re a CEO, a board member, or a senior exec reading this and feeling a little heat: good. That means you’re paying attention. It also means you still care enough to grow. So let me offer a few provocations:

Audit your own thinking.

Not just your calendar. Not just your P&L. Ask yourself: What are the core beliefs driving my leadership—and are they still valid?

Kill your sacred cows.

If something “has always worked,” it’s probably overdue for a rethink. Look at what your org reveres. Then start asking why.

Hire the people who challenge you.

If your leadership team agrees with you on everything, one of you is unnecessary. Diversity of thought is not optional; it’s your insurance policy against blind spots.

Learn faster than the world changes.

Read. Reflect. Engage people younger, bolder, and weirder than you. The leaders who win today are not just decisive, they’re deeply curious.

Build organizations that rethink as a reflex.

Make it safe to challenge assumptions. Celebrate intelligent failure. Reward humility. Teach your teams how to think, not just what to do.

References:

Grant, A. (2021). *Think again: The power of knowing what you don’t know*. Viking. https://doi.org/10.1002/emt.30838

Kahneman, D. (2011). *Thinking, fast and slow*. Farrar, Straus and Giroux. https://doi.org/10.1007/s00362-013-0533-y

Kegan, R., & Lahey, L. L. (2016). *An everyone culture: Becoming a deliberately developmental organization*. Harvard Business Review Press. Retrieved from https://ssir.org/books/excerpts/entry/becoming_a_deliberately_developmental_organization

Moss Kanter, R. (2003). *Leadership for change*. Harvard Business School Publishing.

McKinsey & Company. (2023, April 26). The state of organizations 2023: Ten shifts transforming organizations*. Retrieved from https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/the-state-of-organizations-2023

Senge, P. M. (1990). *The Fifth Discipline: The art and practice of the learning organization*. Currency/Doubleday. https://doi.org/10.1002/pfi.4170300510

Warmest,

Rob Andrews

Chairman & Chief Executive Officer

Celebrating 28 years of Executive Search, Leadership Advisory, and Interim Executive Excellence

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