Unlock the Power Play: How Embracing Risk Can Catapult You to Industry Domination—Are You Ready to Flip the Script?

A few years ago, I was working with a CMO at a mid-sized SaaS company. He was a smart guy, really experienced and had been in the industry for over two decades. But he was stuck. Not because he lacked capability or drive, but because every strategic conversation he had started the same way: “What are our competitors doing?”

That’s a reasonable question. It’s also, I’d argue, the wrong one to lead with.

When your starting point is what everyone else is doing, you’re explicitly agreeing to play in their category, by their rules. You’re studying their moves and trying to execute a slightly better version of a game they already own. You end up fighting for margins in a commoditized space. You’ll probably get decent results. Decent, but not great.

The leaders who actually shift markets don’t start with their competition. They start with a different question entirely: What do we believe is true that nobody is acting on yet?

Why “safe” strategy isn’t actually safe

I want to push back on something a lot of leadership teams treat as conventional wisdom, which is that conservative strategy reduces risk. It doesn’t reduce risk. It just trades one type of risk for another.

When you optimize for predictability, you’re essentially betting that the rules of your market won’t change. That’s a bet most leaders don’t even realize they’re making, and in most industries right now, it’s a bad one.

Safe strategy produces average outcomes in a stable environment. But stable environments don’t stay stable for long. The companies that get caught flat-footed aren’t usually the ones that took wild swings, but the ones that refined their existing approach for so long that by the time the market shifted, they’d lost the muscle to respond.

I’ve seen this repeatedly when companies try to out-optimize the competition rather than rewriting the rules entirely. Think about the shift happening right now from traditional search engines to AI-driven discovery. The brands trying to squeeze a few more drops out of legacy SEO are fighting a losing battle. The ones creating massive value are the ones defining entirely new categories, like Answer Engine Optimization (AEO) or Generative Engine Optimization (GEO). They aren’t doing the old thing slightly better; they are forcing the market to adopt a completely new methodology. 

What calculated risk actually looks like in practice

Here’s where I think a lot of leaders get tripped up. They hear “take more risks” and interpret it as either a pep talk or a license for chaos.

Calculated risk is a process. Before you can design a new category, you need a real hypothesis — not a feeling, but an actual stated belief about a massive shift that the market hasn’t priced in yet. Your experiments are tests to see if the market is ready to adopt your new vocabulary. 

Then you run the smallest version of it that can actually produce signal. The goal is cheap, fast and reversible. Set your success metric before you start, not after. Post-hoc rationalization is how organizations convince themselves that failed experiments actually worked, which is worse than admitting they didn’t.

And when something isn’t working, kill it. This is genuinely hard if you’re the one who championed the idea, which is why I’d encourage any leader running experiments to write a pre-mortem before launch. Agree in advance on what the data would have to say for you to walk away. It doesn’t eliminate the emotional pull, but it gives you something to point to other than your gut.

The culture problem nobody talks about

Most teams aren’t short on unconventional ideas, they just don’t have the confidence or reason to voice them.

If the unspoken rule in your organization is that failed experiments carry personal cost, people will stop proposing them. Rationally. It’s the smart move for the individual, even when it’s terrible for the company. And the worst part is it usually doesn’t happen through any explicit policy, but through accumulated signals: whose ideas get shot down, who gets credit when something works and how leadership talks about the things that didn’t.

The practical implication for you as a leader is this: You have to go first. As a leader, talk publicly about something you tried that didn’t work — not in a polished, lesson-wrapped way where the failure gets redeemed by a tidy takeaway. Just plainly and openly. It signals to your team that your organization is different from what they assumed, and that signal is hard to fake and impossible to mandate.

The leaders I’ve seen make the biggest strategic moves weren’t necessarily smarter or better resourced than their peers. They were simply more willing to be wrong out loud.

The question that separates category leaders from market followers

There’s a framing shift that I come back to over and over in the work I do with leadership teams. Market followers ask: How do we respond to where things are going? Market makers ask: What would the market look like if we built it the way it should work?

Those two questions lead you to completely different places. The first keeps your ceiling set by whoever is ahead of you. The second removes the ceiling.

Now, this requires conviction before you have proof. You’ll have to commit to a direction before you can point to data that validates it, and there will be people in the room who think you’re being reckless. But the alternative is waiting for enough consensus to move, which guarantees you remain a commodity. You don’t want to be the best in the world at an old game; you want to be the only one playing the new game. 

The market doesn’t reward the careful organization fighting for a slice of the pie. It disproportionately rewards the one who baked a new one. Start taking the risks that get you there.

A few years ago, I was working with a CMO at a mid-sized SaaS company. He was a smart guy, really experienced and had been in the industry for over two decades. But he was stuck. Not because he lacked capability or drive, but because every strategic conversation he had started the same way: “What are our competitors doing?”

That’s a reasonable question. It’s also, I’d argue, the wrong one to lead with.

When your starting point is what everyone else is doing, you’re explicitly agreeing to play in their category, by their rules. You’re studying their moves and trying to execute a slightly better version of a game they already own. You end up fighting for margins in a commoditized space. You’ll probably get decent results. Decent, but not great.