Two Doors, Every Leader Chooses One

Two Doors. Every Leader Chooses One.

May 27, 20264 min read

We've got plenty of titles and org charts. What we're short on is people who actually want to lead.


I ask this question a lot. What does it take to be a good leader? And it's not just me — I hear it from others too, people who are struggling to get answers, get things done, get their teams to actually work together. It keeps coming up because the answer should be simple. And yet here we are.

Nobody is perfect. Your title, your level, your position — none of that makes you automatically right or automatically better than the people around you. But it does come with responsibility. Real responsibility. And the way I see it, once you step into a leadership role you've got two paths in front of you.

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I've seen both. I've seen the mix of both. But what gets me every single time is watching leaders who are getting paid serious money to do a job — and they can't find the emotional maturity to resolve a difference of opinion. They can't sit across from someone and disagree like an adult. That's wild to me.

"No."

Let me tell you about something that happened to me.

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ay one thing, do another

We've all been there. You watch a leader sit in a meeting, nod along, say all the right things about open dialogue and courageous conversations — and then the moment someone actually has one, that person finds themselves on the outside looking in. Suddenly there's a problem with their attitude or their fit or their approach.

"When I see a leader 'report' an employee from another team, that's the professional equivalent of running to tell mommy when your feelings got hurt."

Why say one thing in public and something completely different behind closed doors? How do you get to a C-level role and not genuinely care about the outcome of the company? And part of that outcome is partnering with people. Actually partnering — not performing partnership while undermining it privately.

When people see that behavior at the top, they learn fast. They stop speaking up. They go along. They figure out who's safe to agree with and they play the game. Now you've got an organization full of people who know what's broken and won't say a word about it because the last person who did became an example.

The people who do speak up? They become the scapegoats. The ones who don't fit in. Suddenly there's a reason to question their work, their judgment, their commitment. It's easier to remove them than to hear what they're saying.

You can't afford not to invest in your people

I know the excuse. We don't have time, we have deliverables, the business is suffering. But your business is suffering partly because of this exact thing.

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Not every person on your team is the right person for where the company needs to go in two years. That's just reality. Sometimes you need architects, sometimes you need executors, sometimes you need to make things leaner. The team that works for you now might not be the right team later. That's okay. But the answer isn't to silently judge and then quietly discard.

The answer is to give people real feedback. Give them a path forward. Invest in them. And when you genuinely can't make it work, help them transition out with some dignity and bring in the right talent. What happens instead is people get comfortable, no one challenges them, no one shows them what's next — and then one day they're just gone, replaced, and no one learns anything from it.

That's not strategy. That's avoidance dressed up as management.

So why would you choose to burn it down?

Honest answer? A lot of people in leadership roles aren't qualified for them. They got there through technical skill or politics or just being around long enough. Not because they have the emotional intelligence or the genuine interest in other people that leadership actually requires. And once they're in the seat, it's easier to protect the position than to grow into it.

So they play cover-your-ass. They surround themselves with people who won't push back. They manage up and ignore what's happening below them. And the team — the people doing the actual work — keeps showing up anyway. Not because they're inspired. Because they need the job. Because the paycheck is worth the pain. Because they're still hoping something changes.

That's not loyalty. That's survival. And if that's what's keeping your operation going, you've already lost — you just haven't seen it on a dashboard yet.


Look — this isn't complicated. You either build people or you use them. You either say the same thing in the room that you say in the hallway, or you don't. You either have the courage to hear something that challenges you and engage with it, or you turn around and say "No."

Two doors. You're going to walk through one of them. Your team already knows which one you picked. The question is whether you do.


The leaders who get this right aren't special. They just decided — over and over — that building something mattered more than protecting their seat. And they held the door open for the people behind them.

Rich is a seasoned business executive adept at merging business strategy with technological innovation. With a background in business consulting, startups, and product development, he understands how technology drives sustainable growth. His experience across various industries allows him to effectively integrate business insights and problem-solving skills. Rich has led strategic re-engineering efforts to reduce costs, optimize services, and establish robust governance at companies like Salesforce, Dell Technologies, and Accenture. He excels in streamlining operations and leveraging processes, people, technology, and culture to propel growth.

Rich Nazzaro

Rich is a seasoned business executive adept at merging business strategy with technological innovation. With a background in business consulting, startups, and product development, he understands how technology drives sustainable growth. His experience across various industries allows him to effectively integrate business insights and problem-solving skills. Rich has led strategic re-engineering efforts to reduce costs, optimize services, and establish robust governance at companies like Salesforce, Dell Technologies, and Accenture. He excels in streamlining operations and leveraging processes, people, technology, and culture to propel growth.

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