By Ray Ramos

History is filled with cautionary tales. Not just of tyrants and generals who fell from grace, but of leaders undone by smaller, quieter failures—ones that rarely make headlines but still erode trust, corrode teams, and cripple organizations from the inside out.

We tend to study the big collapses: Caesar declaring himself emperor for life, Nero fiddling while Rome burned, MacArthur defying civilian authority. These are dramatic examples, easy to gawk at like slow-motion train wrecks. But they’re not the ones I want to write about.This isn’t a piece from the Green Notebook. It’s from the Red one—the one where we record what not to do. Not the blatant power grabs or public implosions, but the subtle sins of leadership. The small drafts of poison subtly poisoning the well until it’s too late to recover, and the damage is done. These mistakes are less salacious than the news headlines, but they can still be just as damaging and are often more prevalent. They quietly infect organizations every day, normalize poor behavior, and embed themselves in the guise of “that’s how it’s always been done.” The subtlety of these mistakes can be easy to miss, so it takes deliberate study to ensure you can avoid them.

It’s been 30 minutes, but it feels like three hours. You’re at your first major military conference—AUSA, SOF Week, one of those high-stakes, high-vis events. You’re a young field grade officer representing your unit’s initiatives, tasked with building relationships, shaping future joint ventures, and tracking down the right people to help integrate some game-changing technology. 

As you float from handshake to handshake, trying to strike that impossible balance between confident and humble, visionary and grounded, you cling to your second bottle of water—not because you’re thirsty, but because your hands need something to do.

Eventually, nature wins. You make a break for the restroom, relieved for the pause. After finishing up, you step to the mirror, wash your hands, and—for the 57th time—fuss with your hair. That’s when you see it: a billboard-sized piece of spinach wedged between your front teeth. It practically winks at you.

In that moment, the panic sets in. The realization dawns:

Was that spinach there the whole time? Why didn’t anyone say anything? How could they just… let me?
Answer: They were being nice. Not kind.

This is the trap many leaders fall into. We avoid discomfort in the name of politeness. We confuse protecting someone’s feelings with protecting their future. But real leadership demands more than being nice—it demands being kind enough to tell the truth, especially when it’s uncomfortable.

Giving feedback is one of the hardest, most important responsibilities of leadership. Setting the goal is easy. Steering the ship—correcting its course in real time—is where the real work begins. Whether it’s guiding daily operations or conducting formal performance counseling, feedback is the rudder.

Some leaders wield feedback like a flamethrower, scorching subordinates in front of their peers. Others avoid it entirely, cloaking their silence in monk-like patience. Neither approach serves the individual or the team, but the more common sin is the latter—silence.

In Ultralearning, Scott Young outlines three types of feedback:

In the military, we tend to rely heavily on the first two. Corrective feedback requires time, effort, and vulnerability. But it’s the kind that builds competence, confidence, and commitment. It’s an investment in your people—and in the future of the organization.

And here’s the catch: we often give the most attention to our lowest performers. That makes sense in a zero-defect culture like the military, where removing someone from a role is difficult and documentation-heavy. But in the process, our top performers get ignored.

I’ve made this mistake. I poured time into struggling teammates and overlooked the high-flyers. But your best performers need feedback too—especially when they might be better than you were in the same job.  So how do we provide them proper feedback?

Here’s what I’ve learned:

In his 2011 TED Talk, GEN(R) Stanley McChrystal said, “Leaders can let you fail and yet not let you be a failure.”  That’s the essence of good feedback. It’s not about control—it’s about care. It’s not about perfection—it’s about development. Feedback is how we keep people learning, aligned, and capable of doing more than they believed possible.

We’ve all seen it. A big dog spots a squirrel sprinting up a tree through the window—ears perk, tail thrashes, paws scramble, coffee spills, toddlers topple. Total chaos, all because of one small twitch.

This is the image that comes to mind when a senior leader casually floats an idea in a meeting. Not an order. Not even a directive. Just a thought. But because of their position, the room reacts. Suddenly, the staff is spinning up slides, drafting white papers, prepping briefs. The “tail” of the organization is wagging hard—and the boss has already moved on, wondering what’s for lunch.

Don’t get me wrong: leaders should have good ideas. They’ve often been selected for their creativity, insight, and ability to drive action. But the mistake isn’t in having the idea, but the in how it’s delivered.

A mentor once told me, “Don’t voice your opinion first—ask for everyone else’s.” That advice gets more important the higher you go. The more rank you carry, the more weight your words have—even when you’re just thinking out loud.

If you speak first, you risk shutting down better ideas before they surface—especially from the quietest or most junior person in the room. And if you’re not clear, your offhand comment may be mistaken for marching orders.

Yes, there’s a time for direct orders. When bullets are flying, clarity beats consensus. But most of leadership happens outside those moments. And in those spaces, you have to coax, not command. You must speak with intent—or stay quiet long enough to let someone else step forward.

In Good to Great, Jim Collins describes Level 5 leaders as those who create enduring success—even in their absence. Great leaders build systems, not spotlights. They deliberately develop rooms where others can speak, and organizations that move with clarity—not chaos. So the next time your eye twitches with a bright idea, make sure the tail only wags with deliberate intention.

We’re all products of our environment. That’s not new. What is new is the of that environment.

It’s no longer just the five people we spend the most time with. It’s our email inbox, our Spotify playlists, our favorite podcasts, the ads we scroll past, the audiobooks we consume, the news cycles we binge, and the algorithms, dripping in dopamine, that know us better than we know ourselves. Our environment has multiplied—and it’s shaping us, whether we notice or not.

But here’s the good news: if we’re mindful, we can shape it in return. We can be of growth—personally and organizationally.

This principle is often lost on leaders who confuse declaring culture with designing it. Especially in the military, we’ve all seen the incoming commander who shows up with a bang: a rousing speech, a stack of command philosophies, and a perfectly worded vision statement.

I’ve done it myself. It’s not wrong—but it’s often out of sequence.  These documents describe an end state. They articulate what we want to be. But they don’t create the conditions to become that thing.

You can’t just say, “I want to be jacked and tan,” and expect it to happen. You have to build the habits, the schedule, the gym access, and the motivation. The same goes for an organization. Culture doesn’t emerge because you put it on a poster. It emerges from architecture—daily routines, resource allocation, decision-making norms, and micro-behaviors.

A billboard says who we are.  An architect builds systems that prove it.

Are you leading a special operations unit that claims to produce the world’s most capable warriors? Then make sure your environment supports that claim: carve out protected time to train physically and mentally, bring in expert coaches, invest in recovery resources, and enforce standards that reflect the warrior ethos.

Are you running a five-star hospitality brand known for going the extra mile? Then build policies that empower employees to do just that. Give them permission to replace a lost child’s toy without asking, to send a condolence card without approval, to make things right before the customer even knows something’s wrong. And don’t just do it for your customers—do it for your people.  They deserve the same treatment because as the architect you live your values through action not billboards.

That’s architecture.

Claiming to be a servant leader is easy. But unless your daily practices support that claim—training your people, giving real feedback, keeping your door open, and investing in their growth—it’s just another billboard.

Leadership isn’t declared. It’s designed.

I’ve made each of these mistakes. I’ve stayed silent when someone needed honest feedback, thinking I was being nice when I should’ve been kind. I’ve floated a stray thought that kicked off a full-blown staff scramble—all because I didn’t speak with clarity or intent. And I’ve slapped a vision on the wall without laying the bricks beneath it—just another billboard with no architecture behind it.

These aren’t just things I’ve observed in others—they’re lessons inked in the margins of my own red notebook, written in hindsight, frustration, and more than a little self-deprecating humor. But that’s the work of leadership. You don’t arrive polished. You build, stumble, adjust—and if you’re doing it right, you share what you’ve learned along the way.

So here’s my ask:
If you’ve got a red notebook of your own—filled with lessons learned the hard way—I’d love to read a page.  What mistake shaped you? What do you wish you’d known earlier?

And if you’ve had the unfortunate pleasure of serving with me, above me, or under me… feel free to contribute. I’m listening.

Drop a comment. Share a story. Pass it on.

LTC Ray Ramos is a U.S. Army Special Forces officer currently serving as a USAREC Battalion Commander.  He has served on the Joint Staff,  Army Staff,  Special Operations Joint Task Force,  7th Special Forces Group (Airborne), 75th Ranger Regiment, and 82nd Airborne Division. In that time, he deployed to Iraq, Afghanistan, and Central America.  He holds a Master’s Degree in Global and International Studies from the University of Kansas and a Bachelor’s of Science Degree from the United States Military Academy.