Things I Was Completely Wrong About
Six assumptions about leadership, organizations, and human nature that didn't survive experience.
One of the unintended consequences of staying in a profession for a long time is that you eventually collect enough perspective to become suspicious of your own certainty.
When I was younger, I assumed experience worked like compound interest. Every new role, every difficult assignment, every graduate degree, and every promotion would simply add another layer of knowledge until difficult decisions became easier.
That’s not what happened.
Experience certainly added knowledge, but it also dismantled assumptions I didn’t even realize I was carrying. Looking back, the biggest inflection points in my career weren’t promotions. They were the moments when changing seats forced me to see the same problem differently.
The Army taught me one view of leadership.
Practicing anesthesia taught me another.
Becoming CEO of the AANA challenged many of those assumptions.
My time as an executive at a large healthcare company has continued to expose blind spots I didn’t know I had.
What strikes me now isn’t how much I’ve learned. It’s how many things I was convinced I understood that turned out to be incomplete.
These are six of them.
1. I Thought Expertise Was My Most Valuable Asset
Like most clinicians, I began my career believing expertise was the ultimate differentiator. Become technically excellent. Study relentlessly. Know more than everyone else. Healthcare rewards competence, and it should. Patients deserve it.
For a long time, that formula worked. Then my job changed.
Instead of worrying about clinical decisions, I found myself wrestling with questions that had very little to do with medicine:
Why do talented people leave good organizations?
Why do intelligent leaders interpret the same facts so differently?
Why do teams continue doing things that nearly everyone agrees should change?
Those aren’t technical problems. They’re people problems.
One of the biggest surprises of my career has been realizing that expertise becomes less differentiating as responsibility grows. It remains the price of admission, but it stops being the thing that separates effective leaders from ineffective ones. Judgment, trust, and the ability to build alignment among people with competing interests become the actual currency of leadership.
The Advice: If I could go back and give my younger self one piece of advice, it wouldn’t be to read another anesthesia textbook. It would be to spend as much time understanding people as I spent understanding physiology.
2. I Thought Senior Leaders Knew More Than They Did
When I accepted the CEO role at the AANA, I was convinced there would eventually be a meeting where someone handed me the real playbook. Maybe it was a three-ring binder hidden in a cabinet somewhere. Maybe it was the board retreat I hadn’t attended yet. Or perhaps there was simply a room where all the uncertainty disappeared and experienced leaders quietly agreed on the right answer.
As far as I can tell, that room doesn’t exist. If it does, nobody invited me.
What I found instead were exceptionally capable people trying to solve exceptionally complicated problems with incomplete information.
I had always assumed leadership meant having better answers. Today, I think leadership is much more about becoming comfortable making consequential decisions before all the answers exist. The variables multiply much faster than the certainty. Every decision solves one problem while introducing two new ones.
Earlier in my career, I believed more analysis always produced better decisions. I don’t anymore. Analysis is essential—but endless analysis is often just fear with better branding.
The Anesthesia Rule: One of the first lessons anesthesia teaches you is that there comes a point where you stop collecting information and start taking care of the patient. You proceed thoughtfully, you stay vigilant, and you adjust as new information becomes available.
Leadership works much the same way. Action creates information. Waiting often creates the illusion of progress. Sometimes another meeting isn’t evidence that we’re being thoughtful; it’s evidence that we’re uncomfortable deciding.
3. I Thought Organizations Wanted the Truth
One of the harder lessons I learned during my time at the AANA had very little to do with anesthesia. It had everything to do with organizations.
I walked into the role believing that if an idea was supported by evidence and clearly benefited the profession, it would eventually succeed. Reality was considerably messier. Some initiatives that seemed strategically obvious struggled to gain traction, while others moved surprisingly quickly.
Earlier in my career, I thought organizations resisted change. I don’t think that’s true anymore. Organizations change constantly—new technology, new reimbursement, new regulations, new staffing models.
What people resist is uncertainty. Change simply happens to be one of its primary delivery mechanisms.
That realization fundamentally changed how I approached leadership. Instead of asking, “How do I convince people this is the right strategy?” I started asking, “What would make this next step feel reasonable?”
Meaningful organizational change rarely happens on a Hail Mary pass. It usually looks like moving the ball five or ten yards at a time, building trust after every first down until people eventually realize they’re somewhere they never expected to be.
The Executive Disconnect: Leaders tend to think in years. Employees live in weeks.
One of the more humbling discoveries of executive leadership is that almost no one gives a shit about your grand strategy. They’re wondering whether they’ll have enough staff next week. Whether this affects their family. Whether they trust their manager. If people don’t believe the next step is safe, they won’t care much about your destination.
4. I Thought People Did What They Believed Was Right
For years, I assumed organizational conflict was mostly about values. I don’t believe that anymore.
Most people genuinely want to do the right thing. They’re also trying to preserve relationships, protect their careers, avoid unnecessary risk, and respond to whatever behaviors the organization consistently rewards.
One of the biggest shifts in my thinking came when I stopped asking, “Why would someone do that?” and started asking:
“What incentives make that decision perfectly rational from where they’re sitting?”
That single question has explained more executive behavior than almost anything else I’ve learned. People don’t simply follow values. They follow incentives. Usually both. The trick is understanding which one wins when they collide.
5. I Thought Good People Naturally Became Good Leaders
This has been one of the more painful lessons. Over the years I’ve had to remove leaders I genuinely liked. People with integrity. People who cared deeply about their teams. People I’d happily have dinner with tomorrow.
They simply weren’t effective in the role.
Earlier in my career I viewed those situations as failures. Today I see them as mismatches. Leadership is its own discipline. Being an outstanding clinician doesn’t automatically prepare someone to create accountability, navigate conflict, build alignment, or make unpopular decisions. Those skills have to be developed.
One of the hardest responsibilities of leadership is recognizing that a good person isn’t always the right person for a particular role. Those conversations never get easier.
I don’t think they should.
6. I Thought Being Right Was the Goal
Earlier in my career, I probably spent too much energy trying to win arguments. I assumed organizations changed because the best idea eventually prevailed. Experience has made me much less certain.
Organizations don’t move because one person has a brilliant strategy. They move because enough people become comfortable taking the next step.
I’ve won arguments that accomplished absolutely nothing. I’ve also compromised on ideas I cared deeply about because moving the organization ten yards ultimately mattered more than standing at midfield defending my preferred destination.
Somewhere along the way I realized leadership isn’t primarily about convincing people to believe what you believe. It’s about helping enough people become comfortable moving forward together.
That’s a much less glamorous job than I imagined. It’s also the one organizations actually need.
Conclusion
If I’ve learned anything over the last three decades, it’s that experience doesn’t simply increase your confidence. Done well, it also increases your humility.
Most growth doesn’t come from accumulating knowledge. It comes from letting go of assumptions that no longer fit reality. Replacing them isn’t an admission of failure; it’s evidence that experience is still doing its job.
I’m sure there are things in this article that I’ll disagree with ten years from now. In fact, I hope there are. Because some of the most valuable lessons in my career have begun with a realization that isn’t particularly comfortable, but has almost always been worthwhile:
I was wrong about that.
The views expressed here are my own personal views and opinions and do not reflect the views of NorthStar Anesthesia.


Well done Randy. These are all the reasons why I went the route of entrepreneurship rather than leadership. I favor cultivating the team that will win vs leading the organization that is handed down.
Sometimes it’s better to be kind than to be right.