There's No Future for an Organization That Can't Win

How this started

“And then I realized it. Oh, I’m too good at talking. So even with the same idea, I get the team excited about it, and that made us spend years investing in wrong ideas, and I’d be making bad calls while still thinking I was right.”

When I first came across this interview with Lee Seung-gun, the CEO of Toss (Korea’s leading fintech), I just stared at the screen for a long while. Looking back, I was that kind of leader too. He goes on: “If you don’t succeed, in the end it’s a really bad experience for the team.” And he adds: “Saying the painful but necessary thing is how a person and a company grow. It took me about five years to accept that.”

Reading these lines hit me hard. It sounded less like a successful entrepreneur’s reflection and more like an honest confession from a leader who’d been through countless failures. We tend to fall into the trap of “let’s just keep things nice.” Because we love the team, because we don’t want them to get hurt, because we don’t want to be the bad guy, we hold back the painful words. And what’s the result? The organization slowly sinks, and the people who got on the boat with us scatter, carrying nothing but the memory of failure. Time spent in an organization that never wins, no matter how warm the process felt, ends up as poison.

When I think about it, why did we gather in the first place? For social bonding? To collect a paycheck? No. We came together to achieve something, in other words, to win. But at some point we forgot about winning. We seem to have even forgotten how to define it. Watching all those nights and all that passion evaporate into the single word “failure” is a sad thing.

The paradox of the AI era

It’s the AI era. Coding has AI helping out, design mockups pour out in seconds. Data analysis no longer takes days the way it used to. The tooling has leaped forward. Productivity, in theory, should be tens of times higher. But something’s strange. Why are the essential problems organizations face the same as they were ten years ago?

Technology changes at the speed of light, but the way people work together is still stuck in stone-age inertia. Better tools don’t make organizations smarter. If anything, the convenience of better tools makes it easier to hide behind them and ignore the real flaws in communication and decision-making. Tens of thousands of Slack messages fly back and forth, but there is zero shared agreement on “where are we actually going right now?”

What it comes down to is this: the problem isn’t the tool. It’s people and systems. AI can write code for us, but it won’t define which “win” our organization absolutely has to take this quarter. That’s entirely on us. Yet instead of doing the defining work, we waste energy bringing in flashier tools and building more complicated processes.

I did the same thing. Early on, I genuinely believed adopting a new tool would solve the organization’s problems. I thought Notion would fix information sharing, Jira would make projects run cleanly. It didn’t take long to see how naive that was. Tools don’t solve problems. They just expose the hidden ones more clearly.

The trap of the leader going it alone

Let’s go back to Lee Seung-gun’s confession. The leader’s biggest enemy isn’t an external competitor. It’s their own way with words and their own conviction. When the leader speaks too well, the team stops thinking critically. When the leader’s energy runs too hot, the whole organization sprints at full speed in the wrong direction.

This isn’t a problem only at the C-level. For senior engineers and lead designers too, the moment any of them thinks “I’m right,” they’ve already walked into the trap. “I’ve worked in this field for ten years,” “Last time I succeeded with this approach” (the curse of experience covers the organization’s eyes).

I fell into that mode plenty of times during my CTO years. Thinking back makes my face burn. The one I remember most was when we were designing a new system. I was certain microservices were the right answer. One of the engineers asked, “At our current scale, do we really need to bring in MSA? Wouldn’t going monolith and moving fast be better?” I dismissed the question as a lack of technical understanding. (It’s genuinely embarrassing now.) I believed the architecture I’d designed was the answer. We invested six months building a complex system and couldn’t even properly launch a single feature the customers wanted. That engineer was right. What we needed wasn’t elegant architecture, it was fast execution.

My way with words may have gotten the team excited, but the result was leading them onto the wrong battlefield. The leader going it alone becomes the ceiling that suppresses the organization’s potential. A study of overseas startup failures keeps pointing to the same line: “When the leader becomes the primary doer or the ultimate reviewer, they inadvertently cap the organization’s potential.” The moment the leader decides everything and reviews everything, the organization’s intelligence collapses into the leader’s intelligence alone. That’s not what a winning organization looks like.

The team that only does what it’s told

The opposite case exists too. The leader has lost direction, and the team is in pure “do-only-what-you’re-told” mode. I call this the “n-people-equals-1” problem. Ten people gather, and instead of multiplying their output, the total doesn’t even add up to one person’s worth. Each person handles the ticket on their plate cleanly, but no one cares what value those tickets add up to.

As a middle manager I once hit a goal on time with my team. We built what we’d planned within the deadline, shipped it, and got the result we’d targeted. But honestly, looking back, that project contributed exactly zero to the company’s growth. The goal itself was wrong, or it was disconnected from what the market needed. And I took shelter in the relief of “I did my part.” It was a cowardly relief. That same relief never translated into any reward for the teammates who’d ground through implementing features without even knowing why, and the team’s mood was completely shattered. It was a tragedy.

If you compare this kind of organization to a sports team, it’s like one where the defenders only guard their zone and the strikers only wait for the ball to arrive. The game is won by scoring goals, but no one runs toward the goal. They just stand wherever the coach told them to stand.

“If scoring is the goal, I want to decide where to run myself.”

This isn’t arrogance. It’s a hunger for victory. A player who really wants to win reads the flow of the match, finds the open space, and moves on their own. The coach’s tactics are a guide, but the final call on the field has to belong to the player. Yet many organizations strip teammates of that judgment. A single line, “Just do what you’re told,” tramples the chance of winning.

Five years of respecting the team and failing anyway

So if you respect the team without limit and give them full autonomy, do you win? The first five years of Toss show the counter-example. Lee Seung-gun says he wanted to be a “really good CEO” early on. He was so grateful to the team that he couldn’t be tough with them, and he kept giving them more chances. The result? Five straight years of failure.

The moment the failure was confirmed, those “good experiences” instantly turned into “memories I want to delete.” The team responded coldly: “The time I worked with you is something I want to erase from my life.” It hurts, but that’s the reality. In an organization that’s gotten used to losing, “kindness” is just another word for irresponsibility.

I made a similar mistake when I was a leader. One of my teammates was running a project that kept slipping. The teammate had the skills but was struggling to set priorities. I could see it. But I held back sharp feedback because I worried about hurting the team’s mood, because the teammate looked exhausted. I said, “It’s okay, take your time.” Even when failure was clearly coming, I kept floating baseless optimism that “we’re doing great.”

Three months later the project got shut down. As that teammate left, they said this: “I wish you’d told me earlier. I didn’t know what I was doing wrong.” That’s when it hit me. The way a leader truly respects the team isn’t by making them feel good, it’s by winning together with them. Real respect sometimes requires the courage to say the painful truth.

What is winning

So what is this “win” we should be hungering for? Just hitting a revenue target? Going public? Sure, those can be metrics of winning. But the essential win is “every person in the organization feeling the win in the result.”

It isn’t simply filling in a target number. It’s the state where the product we built actually changes a customer’s life when it goes out into the world, and through that process all of us share the overwhelming sense that “we pulled it off.” That’s the real win.

Winning is addictive. An organization that’s tasted winning once moves on its own toward the next one. An organization that’s gotten used to losing, on the other hand, gets used to blaming external causes and pointing fingers at each other. Winning is the best medicine for every conflict in an organization. Winning doesn’t make every problem disappear, of course, but at least it generates the energy to solve them. Winning is the blood that runs through an organization. The way blood has to circulate for life to continue, an organization needs winning to breathe.

The real relationship between coach and player

A winning organization looks a lot like a well-trained elite sports team. Think about the head coach of a soccer team. The coach analyzes the opponent and builds tactics that play to our strengths. But once the match starts, the coach can’t run onto the field.

A player who has the ball on the field has to decide in 0.1 seconds. Pass, dribble, or shoot? If that player hesitates because they’re checking with the coach on the bench, the team will never win.

Winning teams have clear traits.

Shared goal: Every player is aligned on “we win today, no matter what.”

Role expertise: The keeper stops goals, the striker scores. They respect each other’s territory, but they help when help is needed.

Autonomy on the ground: Within the broad frame of the tactics, the player’s creative judgment is respected to the extreme.

What about our organization? Is the leader stepping onto the field and grabbing the players’ feet? Or are the players standing around in a daze, not even knowing where the ball is? A winning team moves organically without the coach’s instructions. That’s the power of a system.

What a PM is actually for

The PM (Product Manager) role matters here. Many organizations treat the PM as a “requirements messenger” or a “schedule keeper.” But in a winning organization, the PM has to be a “win designer.”

A PM isn’t someone who lists features. A PM has to prove “if we build this feature, why does it make us win?” Between technical constraints, business goals, and customer needs, a PM has to find the equation for victory.

I felt this in my bones when I took on the PM role. If the PM can’t define what winning is, the engineers and designers end up grinding through meaningless labor. A PM isn’t someone who tells the team “what to build.” A PM has to be someone who convinces the team “why we have to win this fight.” A PM’s strongest weapon isn’t data or a spec doc, it’s the conviction that they can lead the team to a win.

The courage to give things up

One thing organizations that don’t win have in common is “trying to do everything.” Everything matters, nothing can be cut. So resources scatter, and they don’t win on any battlefield.

To win, you have to know how to give things up. Focus on one goal, and you can have a clear experience of winning or losing. Mess around with several at once and fail, and you can’t even tell why you failed. You just hide behind the cowardly excuse, “we failed because we didn’t have enough resources.”

One of the most painful experiences I had was this. We were running three new projects at the same time. Headcount was limited, and I judged that all three were important. To be honest, I was afraid to decide which one to give up. (I didn’t know back then that postponing a decision is also a decision.) The result? All three fizzled out partway through. If we’d gone all-in on one, at least one would have made it, and that was the price of being greedy. That’s when I learned. You have to be able to give things up to focus, and you have to focus to win. One of the leader’s most important jobs is deciding “what we will not do.” It’s genuinely hard. But it has to be done. Giving up isn’t losing. It’s a strategic retreat for a bigger win.

The signs of an organization falling apart

An organization without winning collapses slowly, but with certainty. The signs show up in three ways.

First comes talent drain. Talented people have an uncanny nose for the smell of victory. In an organization where no win is in sight, they pack their bags first. The moment they leave, the skills and strategy leave with them. A talented person constantly asks themselves, “Can I grow in this organization?” They know instinctively that growth isn’t possible without winning. Talented people don’t follow money, they follow the experience of winning.

Second comes the leader’s isolation. With no winning, the leader’s words lose force. The team starts treating the leader’s vision as an empty shout. The leader reaches for more coercive measures, which triggers more pushback, and the loop tightens.

Third comes cultural decay. In the empty space left by a shared goal called winning, politics and cynicism move in. The mindset that “it won’t work anyway, just do it casually” takes over. Cynicism is like a cancer cell eating away at the organization.

Look at outside cases. Eighty-two percent of startups fail not because they ran out of money but because of bad management and leadership. Winning organizations are different. Georgia’s TBC Bank used OKRs to align a 1,200-person organization on one goal and became the best digital bank of 2024. In Korea, Coupang set the audacious goal of “Rocket Delivery,” measured it in real time, and seized the win. After Kakao adopted OKRs, project speed went up 1.5x, and Baemin (Korea’s top food-delivery app, run by Woowa Brothers) clarified the purpose of cross-team collaboration and built the foundation for winning. They all “defined” winning and “measured” it. OKRs or anything else, the methodology doesn’t matter. What matters is whether you’re showing the organization the direction of victory. Or whether the organization feels it’s heading in the direction of victory.

In closing

As I close this piece, I ask myself.

“Am I winning right now?”

Or, “Is the organization I belong to running toward winning?”

Winning doesn’t arrive by accident. Winning comes at the end of brutal self-honesty, the courage to take painful feedback, and the stubborn will that says “we will win, no matter what.”

There may be a counter-argument that the leader has to provide direction. That’s right. The leader has to provide direction. The point is that “direction is the leader’s, the process belongs to the team.” Pointing at the goal is on the leader; how the player breaks through with what dribble belongs to the player.

There’s no future for an organization that can’t define winning. It just repeats past failures and fades away. But if we start defining winning today, telling each other the painful but necessary words, and getting fully into one goal, the future can change. Winning is a choice. And that choice is in our hands right now.

Practices for winning, and the heart to start again

As I tried to wrap up, I figured the question “so how do we actually do it?” would come, so I’m adding a few concrete practices. These are lessons from running a company as a CEO for five years and from four years inside a CTO seat. Not theory, the kind you learn by getting cracked open on the ground.

The power of 1-on-1s

The bigger the organization gets, the further the leader drifts from the ground. The strongest tool for this is the 1-on-1. It isn’t a slot for checking task progress. It has to be the slot where you check what your teammate is worrying about, where they think the bottleneck in the organization is, and whether they’re feeling a “win” inside this organization.

I regret nothing more than how I neglected 1-on-1s in the organization I ran. I postponed them biweekly with the excuse of being busy, and they fizzled into monthly. Resentment built up among the team in that gap, and I caught it way too late. A conversation that misses its window comes back later at tens of times the cost. Conversation is the lubricant of an organization. When the lubricant runs dry, the engine burns.

Transparent information sharing

To win, everyone has to be looking at the same map. Information that only the executive team knows, context shared only among leaders, turns the team into “alienated workers.” Why we’re doing this project, what the company’s financial state actually is, what real crisis we’re facing — these have to be shared transparently. Information asymmetry breeds distrust, and distrust breaks the will to win.

Retros for failure, celebration for wins

There are plenty of organizations that blame people when things fail, but few that retro them properly. We have to record and share why we failed and what we’ll do differently next time. Equally, fully celebrating when we win matters. Small wins stack into a culture of bigger wins. Retros breed wisdom, celebration breeds energy.

Being obsessed with the customer

In the end, every win comes from the customer. Engineers and designers have to hear the customer’s voice directly. Writing code only from the doc the PM put together is just “winning by proxy.” When the maker witnesses how a single line of their code solved a customer’s problem, they experience the real win. The customer is our only North Star.

Psychological safety and a high bar

For ambitious attempts, you need psychological safety, a confidence that mistakes won’t get you punished. At the same time, a high bar has to hold. Safe with a low bar, and the organization stagnates. High bar with no safety, and the organization burns out. Balancing the two is the leader’s core capability. When you chase a high bar inside a safe environment, the best output shows up.

Ready to start over

Coming back to being someone living a private life — for what it’s worth, after running a big organization, and looking back, what’s left isn’t a flashy tech stack or a grand architecture. What’s left is just memory of “people,” “winning,” and “failure.” The colleagues I pulled all-nighters with to solve problems, the moments we shared a beer over the joy of a launch, all of that made me. There were genuinely happy moments, no question.

Even so, all those efforts failed to convert into real business value, real customer value. Eventually, I started judging people’s ability and loyalty by how long and how much they worked. Whatever value, vision, or story I tried to share, my words no longer earned their respect. The memory of that “failure” still cuts deep.

Back then I had a lot of urge to defend myself, a lot of bitterness, but now it’s time to move forward again.

I’m preparing a new beginning now. With the failures and wins of the past as compost, I’m dreaming of a “winning organization” once more. The person reading this is probably the same. We’re all people hungering for victory in our own arenas.

For the time being I’ll be focused on a two-person team with Ellie, but if I ever take responsibility again as a middle manager inside another company, I want to be responsible for an organization where autonomy in the process is guaranteed and only the result is accountable, where the direction of victory is communicated clearly to everyone, so that everyone moves toward the goal on their own.

I sincerely hope your organization, your team, and you yourself win today. As for me, I’m just going to keep showing up tomorrow and trying to define one more thing worth winning.

In the end, winning belongs to those who don’t give up.

“Winning solves everything.”

— Tiger Woods

I’m using this piece as my 2025 retrospective. For me, 2025 was a time of recovery. Maybe close to a sabbatical. There was a piece I’d written long ago and put aside. Too negative, too full of blame, the kind I couldn’t bring myself to publish. From where I stand now, I polished and re-polished it, and I’m publishing it as a piece that helps me move forward. I hope it heals you the way it healed me.

I don’t have a religion, but if there’s a god, I’d want to pray always: “Take from me my anger toward others, let me embrace and understand them, let me face my own interior, and give me the courage to take one more step forward.”