When a Bold Bet Turns Into a Liability

It stung more than I expected. Six months ago I would have brushed it off and jumped to the next challenge. One week you’re praised for thinking big and acting like an owner; the next, all that encouragement evaporates because a bet didn’t pay off. If you’ve been there, you know how jarring that whiplash feels.

After that, I hesitated. I started second-guessing calls that used to be instinctive. The backlash didn’t just change how others saw me—it changed how I saw myself. Suddenly, innovation felt risky, and I felt like a problem.

That’s the valuable employee paradox in action.

When Stated Values Collide—How to Align Incentives With Values

We talk a lot about “thinking big” and “acting like owners,” but the truth is, our performance systems still favor predictability and comfort. When the pressure ramps up to justify a risky decision, I’ve seen compensation caps shrink actual risk-taking—even for people who are naturally cautious enough to play it safe anyway. (Kreilkamp et al.) For a long time, I assumed that making everything clear—tradeoffs, documentation, visible prep—would protect those bets. But incentives always told a different story.

Here’s the actual test of any value. Will you stand by it when the outcome is inconvenient? Not just when things go well, but when the bold move fails, the numbers disappoint, and leaders feel exposed. Your values aren’t real until they survive inconvenience.

Imagine your operating model like a unit test suite. If your reviews and rewards penalize variance, you’re teaching the system to punish exploration. I’ve watched organizations stretch vesting periods and suddenly see a 1.1% jump in exploration; turns out, incentive design quietly governs how much variance builders are allowed to show. So, look at your last few promotions and public praise moments. Ask yourself: did those moves reward someone for clarity and courage, or just for being reliably inoffensive? My own “test suite” broke down on variance—anything noisy, anything bold, was suspect, no matter what our values deck promised.

If you want initiative to thrive, you have to align incentives with values, so impact beats appeasement every single time.

The Three Pillars to Reward—And How to Actually Do It

Let’s start with clarity. I want teams to act like owners, but for that to mean anything, everyone needs to see the standard—no guessing, no drama. “Owner-like” initiative isn’t just about saying “yes” to the hard problems. It’s about documenting the tradeoffs upfront, calling out explicit risks, and (this is the real unlock) sketching a genuine plan for learning if things go sideways. When someone ships a big swing, I expect a clear decision record: what did we know? What did we bet might be different?

I used to think asking for all this would slow things down, but now I frame it as making courage legible for everyone watching. It sets a bar you can actually see and talk about.

Then there’s courage. If you want real progress, you’ve got to reward principled dissent—especially when it lands at the least convenient moment, in front of the wrong audience, or from the person you least expect. This isn’t just about tolerating “devil’s advocate” noise. You need to build loyalty around the mission, not comfort. If you only celebrate hard truths when they’re easy, teams learn exactly how much honesty the room can handle.

Impact is where most systems trip up. Too often, we reward optics—flashy demos, smooth narratives, wins that look safe on the quarterly slide. The better test? What changed for users, what risks were surfaced and reduced, what did we actually learn, even if the thing itself missed? I learned to separate an experiment’s value from its vanity metrics—the most useful project might not boost usage, but it might illuminate something critical for the next swing.

Whatever you celebrate, calibrate it to effect: user value shipped, new insight gained, or cumulative improvement. It’s tempting to give the most praise to wins that are tidy and non-disruptive, but it’s the messy outcomes (when paired with real learning) that actually move the work forward.

You don’t anchor these pillars just by putting them in a slide deck. You have to align rewards with values—who you promote, who you praise, and who you publicly protect. If your dissenters aren’t safe, the system teaches everyone else to appease, no matter how many posters you hang about “psychological safety.” If you say “we’re like a family” but only protect people who make you feel good, you’re not leading a team. You’re running a comfort club. Incentives shape reality. What you celebrate, protect, and advance becomes the actual law of the land.

Make Courage and Impact Visible—Embed Values Into How You Reward

When it comes to promotions, standardize calibration panels to probe for principled dissent and lessons from misses—not just smooth launches. Ask people to walk through a hard call, not just a successful launch. Lately, I always ask, “Show me the tough decision you made and how you made it visible to the team.” Don’t just reward flawless execution; reward learning that comes from discomfort. This is how you make boldness and transparency mean something in your actual career ladder.

Public praise matters just as much. Make a habit to reward truth-telling, courageous bets, and productively failed experiments—especially in high-visibility settings. If you aren’t sure your rituals match your intentions, review the last three promotions or public shoutouts and audit which behaviors were recognized. I keep a simple ledger of who gets airtime and why, and whenever courage is missing, I call it out. Visibility is everything—what you praise is what people believe counts.

But the real test hits when leaders choose to reward smart risk-taking that creates real discomfort. You’ll see backlash, skepticism, and maybe some tension across the org. This is where leaders have to intervene—with explicit protection. When dissenters are targeted, step in and restate the mission: “We asked for a bold bet; the discomfort is the cost of discovery.” Normalize the risk, and bake protections into your team norms and playbooks so people know this isn’t performative.

And when supervisors offer a considered, sensitive explanation for declining a suggestion, you’re much more likely to see future voice—not silence. I’ve learned that just telling people they’re safe to dissent isn’t enough—it has to be visible, especially in the hottest moments. You want protocols so clear that even when a team is bruised, the system lets them know: your courage is still counted, your impact is still felt, and you’re not being hung out to dry. If you miss this step, you’ll see initiative drop overnight—not because people don’t care, but because they saw how vulnerable it actually is.

There’s nothing theoretical about these mechanisms—they’re what distinguish talk from actual practice. If you care about innovation, start here: encode clarity, courage, and impact into every system you control. Don’t leave it to chance, or to comfort. Make it part of the law of the land.

Safeguards for Initiative—And Why This Work Is Worth It

Another concern: isn’t this all just a license to excuse failure? No. Not if you’re rigorous about the difference between principled, well-scoped bets and reckless ones. I’ve killed ideas I loved because the tradeoffs weren’t defensible, or the plan lacked real teeth. Boldness for its own sake isn’t a virtue. What you want to reward is the discipline: clarity from the start, the courage to surface dissent, and tangible impact—including lessons learned if the outcome misses. The teams that thrive are the ones that treat misses as moments to deepen understanding, not camouflage them in a fog of process.

But I still get tripped up sometimes by old habits. Even after all this, I catch myself hesitating when it’s my turn to stake out a risky position, knowing full well how the game is played. No process fully immunizes you against that doubt. Maybe it never will.

So here’s where you come in: commit to engineering rewards for initiative—promotions, public praise, and protections—so principled initiative and uncomfortable truth-telling are recognized, not just safe wins. Do it relentlessly. If you want trust and innovation to compound, make these the behaviors your company can’t live without.