The Worst Leader I Have Ever Known
By David W. | Mission Ready Father
Why you want to lead is the most important question in leadership — and most people never honestly answer it.
He was 21 years old. Freshly promoted. Impeccable uniform – every crease sharp, every button aligned, boots polished to a mirror shine. He spoke with authority. He carried himself with the confidence of someone who had earned something significant.
He had not.
That leader was me.
And what follows is the story I have never told publicly – because telling it honestly requires admitting things that most leaders spend their entire careers carefully avoiding. But Mission Ready Father was built on one promise: real experience, no highlight reel. So here it is.
Why I Actually Wanted the Rank
I joined the U.S. Army at 18 years old for reasons that had very little to do with service and very much to do with self.
I was young. Naive. Directionless in the way most 18-year-olds are. I joined because I wanted something challenging to define me – to take the raw, unformed material of who I was and shape it into something worth recognizing. The Army delivered on that – completely and without mercy. But that’s a different story.
What matters here is what happened a few years in, when I found myself eligible for promotion to Sergeant – the first real leadership rank within the Noncommissioned Officer (NCO) Corps.
I had observed remarkable NCOs during those early years. Men and women of genuine substance – experienced, capable, impactful leaders whose teams followed them not out of obligation but out of genuine respect. And watching them I made an assumption that would cost me dearly:
I knew, somewhere beneath the surface, that their credibility had been earned through experience and time. But I wanted – subconsciously, foolishly – to believe that the rank itself was the source of it. That the title carried the substance within it. That if I could just get the stripes, something would transfer.
What young adult who doesn’t yet know who they are, what they stand for, or who they want to become – wouldn’t want credibility, power, and respect? I wanted all three. And I believed promotion was the door they lived behind.
I was wrong in a way I could not yet understand.
What the Rank Actually Gave Me
I was promoted to Sergeant at 21 years old – just under three years into my Army service.
I looked the part completely. The uniform was perfect. The bearing was confident. The words came out with authority. From the outside, nothing was missing.
From the inside, everything was.
What I did not have – what no promotion ceremony can bestow and no title can manufacture – was the credibility that comes from experience, the depth that comes from failure, and the humility that comes from genuinely caring about someone other than yourself.
My words were hollow. I knew the doctrine. I could recite the right answers. But the people I was leading could hear the difference between someone speaking from conviction and someone performing it. They heard it every time I opened my mouth.
And so I compensated the only way someone without real tools ever does – with force.
I got frustrated easily. I yelled. There were moments I used ridicule to assert control – to make someone feel small enough that they wouldn’t challenge me. When soldiers pushed back or questioned my direction I responded not with explanation or confidence but with the implied threat of rank. I outrank you. Do what I say.
I used my position to benefit myself – delegating tasks I didn’t want, leaving the moment the duty day ended, missing every opportunity to learn from the experienced leaders around me because I was too busy protecting the illusion that I already was one.
I was performing leadership. And the people I was supposed to be leading could see through the performance with perfect clarity.
The only person I was fooling was myself.
The Soldier Who Told Me the Truth
About two months into wearing the rank I was correcting a soldier on something he had done wrong – or hadn’t done at all. I don’t remember the specific task. What I remember is what happened shortly after.
He pulled me aside privately.
I want to be clear about something before I describe that moment – because it matters. This was a good soldier. Disciplined. Patient. Capable. He had watched and waited for months – quietly hoping I would find my footing on my own. He had maintained his discipline far longer than most people would have. That restraint took its own kind of strength.
But every human being has a breaking point. That day, he reached his.
And here is what I respect most about how he handled it – he could have confronted me in front of the team. He had every reason to. The frustration had been building for months and the audience was right there. Instead he pulled me aside. Just the two of us. He chose to protect my dignity even in the moment he was holding me accountable.
That demonstrated more emotional control and professionalism than I had shown in months of wearing the rank above him.
In that private conversation he told me directly that neither he nor the team felt I had their back. That my actions made clear their best interests were not something I was particularly concerned with. That the trust required for a team to function simply did not exist between us.
I was stunned into silence.
His delivery crossed a professional boundary – and he knew it. But what came out in that moment was the accumulated weight of everything he had chosen not to say for months. And in the silence between his words and my response – I knew with absolute certainty that he was right. It was the most honest thing anyone had said to me since I’d put on those stripes. The dysfunction I was seeing in my team – the low morale, the lack of energy, the minimal engagement – wasn’t a reflection of them. It was a reflection of me.
I had failed to establish honesty with my team. I had never been vulnerable with them. I had given them no reason to trust me – because I had never given them anything real. Only performance.
The outcome – poor morale, dysfunction, results that fell short – was a direct consequence of the leader I had chosen to be.
I stood there, 21 years old, stripped of every illusion I had carefully constructed, staring at the truth I had been successfully avoiding for months.
That soldier’s courage – imperfect, human, born from a breaking point rather than a calm calculation – was the crack in the facade that let the light in. He could have broken me publicly. He chose to reach me privately. I have never forgotten either of those facts. And I have never stopped being grateful for both.
The Diamond Conversation
About a week or two after that private conversation – while the weight of what my soldier had said was still sitting heavily on me – my Platoon Sergeant asked me to stay behind after the duty day ended.
Staff Sergeant Louie Barlolong was serving in the Platoon Sergeant role – a position that typically belongs to a more senior NCO. Wise beyond his years. He was exactly the kind of leader I had been watching and trying to imitate without understanding what I was actually seeing.
We sat down in his office. He was calm. Unhurried. He looked at me for a moment and then asked:
“How does a diamond form?”
I was completely caught off guard. Of all the conversations I had prepared myself for – none of them started with geology.
“Over time,” I said, “deep in the earth. From coal.”
He nodded slowly. “Yes. But three things have to happen for coal to turn into a diamond. Intense heat. Pressure. And time.”
He let that sit for a moment.
Then: “What kind of leader do you want to be? A lump of coal – or a diamond?”
“A diamond,” I said immediately. “Of course.”
He nodded again. And then – calmly, professionally, and without a single word of cruelty – he recounted the previous weeks in detail. How I was managing my team. How I was leaving at the end of the duty day instead of staying with the other Sergeants. How I was interacting – or failing to interact – with the soldiers in my charge. How I was setting an example that no one should follow.
He asked me: “Based on those facts – what kind of leader have you been for your team?”
There was only one honest answer.
“A lump of coal.”
“Then here is what you need to understand,” he said. “If you want to be a diamond – there are no shortcuts. You must endure the heat. You must endure the pressure. And you must give it time. There is no other way.”
What followed was one of the most honest conversations of my life. He set clear expectations. He outlined what the path forward looked like. He told me exactly what he needed to see and exactly what he was willing to give in return.
And then he closed with something I have carried with me for 26 years:
“I believe in you. And soon – over time – you will too. And that belief will give you the confidence to lead in the most challenging times.”
The Heat. The Pressure. The Time.
What followed over the next six to twelve months was not a transformation montage – not clean, not linear, not comfortable. It was brutal feedback that hurt in the moment and was exactly what I needed. It was mistakes made in front of the people I was leading and owned publicly rather than deflected. It was staying late when I wanted to leave. It was asking questions instead of pretending to know. It was sitting with the discomfort of not being good enough yet and choosing to come back the next day anyway.
It was SSG Barlolong and the more senior Sergeants around me – men and women who had been through their own version of the coal-to-diamond process – giving me honest, consistent feedback and holding me to a standard I hadn’t yet earned the right to set for myself.
And slowly – imperceptibly at first, then undeniably – something began to shift.
Not in my uniform. Not in my bearing. Not in the words I used.
In the relationship between me and the people I was leading.
The team’s energy changed. Their engagement changed. The morale that had been so visibly absent began to return – not because I demanded it, but because I had finally stopped demanding anything and started giving something instead.
Trust. Honesty. Genuine investment in their growth and wellbeing above my own comfort and convenience.
That shift – from performing leadership to actually providing it – is the most significant professional transformation of my life. And it started in a small office with a question about geology.
Why You Want to Lead – The Question You Have to Answer Honestly
Here is the hard truth that most leadership content carefully avoids:
A significant number of people who pursue leadership roles do so for reasons that have everything to do with themselves and very little to do with the people they will lead. Research from Harvard Business Review consistently confirms that self-focused leadership motivations are among the strongest predictors of team dysfunction and turnover.
The title. The salary. The perceived status. The corner office. The feeling of being the one in charge.
None of those motivations are evil. They are deeply human – the same motivations that drove a naive 21-year-old Sergeant to pursue stripes he wasn’t ready for. But they are motivations that will eventually – inevitably – produce the same result I produced in those early months. Hollow words. Frustrated reactions. A team that can see through the performance. Morale that quietly deteriorates while the leader wonders what’s wrong with their people.
Nothing is wrong with their people. Something is wrong with the question the leader never honestly answered.
Why do you actually want to lead?
Not the answer you’d give in an interview. Not the answer that sounds right. The real answer – the one that lives underneath the polished response – is the one that determines everything about the kind of leader you will become.
If the honest answer is about what leadership gives you – the answer needs to change before the role begins.
The leaders who build remarkable teams are motivated by something that has nothing to do with themselves. They want to see their people grow. They want to be the leader someone else needed and never had. They lead because the people in front of them deserve someone who actually shows up.
That motivation – and only that motivation – produces the kind of leadership that lasts.
Before You Read the Next Section – Four Honest Questions
Put down the performance for a moment. No interview answers. No polished responses. Just you and the truth.
1. Why do you actually want this leadership role?
Not the answer you’d give your manager. The real one. The one that lives underneath the version you tell other people.
2. If the title came with no salary increase, no status, and no recognition – would you still want it?
If the answer hesitates — that hesitation is information worth examining.
3. Can you name three specific ways your team’s success matters more to you than your own comfort or convenience?
Not in theory. In practice. In the decisions you made last week.
4. If the people you lead answered these questions about you right now – what would they say?
Not what you hope they’d say. What they would actually say – honestly, privately, if there were no consequences for their answer.
There are no wrong answers here. There is only the honest answer and the answer you perform. The gap between those two things is exactly where leadership development begins.
If you want to build the complete foundation of self-leadership first — my post on leading yourself before leading others covers the full framework.
What I Would Tell My 21-Year-Old Self
If I could sit across from that young Sergeant today – the one with the perfect uniform and the hollow words – here is what I would say:
I’m proud of everything you’ve accomplished to get here. But this new chapter will be difficult. It has to be. And I need you to know that you are up to the task.
There will be moments – more than you can imagine right now – when you will want to walk away and never lead another person again. Don’t. Every leader worth their salt has felt exactly that way. You are not alone in it.
Assume best intent in the people you lead. Always.
Lead with humanity. With humility. With genuine concern for the men and women standing in front of you – not as assets to be managed but as people who have trusted you with something precious.
Shelter your team. When they fail to deliver – take the hit from your leadership. That is your job. Period.
Be honest with them. Always tactful, always professional – but always honest. They deserve the truth delivered with care, not comfortable silence delivered with kindness.
Put their needs above your own. Every day. Without exception.
Learn from every leader around you – the great ones and the terrible ones. Both have something to teach you. Neither lesson is wasted.
Check your ego at the door. Every single day. Be open to feedback, to learning, and to being wrong – especially about yourself.
It is a process. It will take time. But if you do the above – if you commit to the heat and the pressure and the time – you will build something extraordinary. Not a career. Not a title. A foundation from which the people you lead will become more than they were. And they will go on to lead others who will become more than they were.
This is how great leadership echoes into future generations.
Don’t give up on the process. The diamond is worth it.
To 1SG Louie Barlolong (Retired)
I don’t know if you’ll ever read this.
But if you do – I want you to know that I didn’t fully understand what you gave me that day until years later. Until I had led enough people, made enough mistakes, and watched enough leaders succeed and fail to finally see the full shape of what you planted in that small office.
The totality of what you did for me was not realized in the weeks and months that followed. It revealed itself slowly – through every team I led, every soldier I tried to develop, every difficult conversation I chose to have honestly rather than avoid comfortably. Through every moment I stayed late when I wanted to leave. Through every piece of hard feedback I gave because the person in front of me deserved the truth.
You were right. It took heat. It took pressure. It took time.
And you were right about one more thing.
I eventually believed in myself. Not perfectly. Not without doubt. But enough – enough to lead in the most challenging times, and to try to give others what you gave me.
Thank you, 1SG Barlolong. For seeing something in a 21-year-old lump of coal that he couldn’t yet see in himself.
The process isn’t finished. But the diamond is forming.
– David W.
Coming next: The difference between a boss and a true leader – and why the gap between those two things determines everything about the team you build.
Filed under: Leadership | Personal Development | Military | Veterans | Self-Leadership
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