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Why Leaders Who Act on Fleeting Opportunities Win

I’ve learned that some opportunities don’t wait for ideal conditions; they test your readiness. Leadership advantage increasingly belongs to those who can recognize and act on fleeting opportunity signals. These moments rarely arrive with perfect timing or full clarity, yet they often shape the trajectory of our work, our companies, and sometimes our industry.

Last Friday, one of those moments appeared for me.


I was sitting in a dentist’s office in St. George, Utah, catching up on LinkedIn between appointments, when a post from Andrew Ng flashed onto my screen. Ng, the founder of DeepLearning.AI and widely regarded as one of the top pioneers in the field for his unmatched blend of scaling deep learning and educating millions, was hosting an intimate gathering in Mountain View that very evening on AI-powered recruiting and the future of talent acquisition.


No long announcement. No generous registration window. Just a flicker of opportunity aimed at those alert enough to notice and bold enough to act.


For many leaders, inconvenience is where the story would end. But here’s something I’ve learned after decades in executive search, behavioral assessment, and now AI-driven talent innovation: Game-changing opportunities rarely feel convenient. They feel urgent.

And the window to act is often measured in hours, not days.


I sensed immediately that I needed to be in that room. Not because it fit my schedule (it didn’t),  but because it aligned perfectly with the future of work, the future of recruiting, and the AI-powered tools I’ve been building and advocating for. So I acted.


I rewrote my resume on the spot with the help of Claude. Submitted the application. Received confirmation. I pivoted my travel plans, drove two hours to Las Vegas, caught a flight to SFO, rented a car, and arrived early at Fenwick & West’s offices to claim a good seat.

And because I acted, something remarkable happened.


During the Q&A, I shared a perspective on career signals: the “green shoots” that signal growth trajectories and the “browning leaves” that indicate stagnation. I spoke about validated heuristics, economic framing, and how AI systems can (and must) be designed to interpret the deeper story in a career journey.


Ng leaned forward, looked directly at me, and said: "Would you stay after and talk with me and my team? What you're saying is exactly what we need. And would you be willing to work longer-term to help build something for the industry?"


That moment (the invitation, the alignment, the possibility) would never have existed had I hesitated.


That’s when it struck me: In leadership, the cost of hesitation is often invisible, but it is staggering.


The future doesn’t announce itself. It flickers. The leaders who advance are the ones who move while the signal is still glowing.


Yet acting decisively is only possible if you’ve trained your perception. Before leaders can move fast, they must learn to detect the early signs of opportunity: the subtle cues that signal potential long before the rest of the world notices.


Detecting Signals


Leaders Train To See Opportunity Signals

Most people imagine opportunity as a spotlight. In reality, it’s closer to a weak signal on a radar screen. Something you notice only if you’re tuned to the right frequency. For CEOs and senior leaders, that means developing:

  • Pattern recognition for emerging trends

  • Sensitivity to alignment between opportunities and long-term strategy

  • Awareness of when a moment feels disproportionately important


When I saw Ng’s post, I knew instantly it wasn’t just another event. It was a convergence of everything I’ve been building toward: AI-enabled recruiting, disruption in talent markets, and the broader consequences of technological acceleration.


And yet the signal was subtle. No one would have blamed me for ignoring it.

Leadership often begins with the ability to detect what others overlook.


The Vulnerability Paradox

Some of the most meaningful leadership decisions come wrapped in discomfort.

To attend the event, I had to confront several forms of vulnerability:

  • Logistical vulnerability: I was hours away, with no flight booked.

  • Professional vulnerability: I could have been rejected.

  • Reputational vulnerability: What if I arrived and added no value?

  • Personal vulnerability: What if I simply wasn’t ready?


This is the paradox: The moments that move our careers forward rarely feel safe. They feel like a risk, because they are one.


But risk is not recklessness. Risk is awareness paired with action.


Speed As a Leadership Skill

I have worked with CEOs for decades. The strongest ones are not just intelligent; they are decisive. They know how to collapse the space between insight and action.

Speed today is more than a competitive advantage; it’s a leadership competency. Here’s what moving fast looked like for me on Friday:

  • Using AI (Claude) to instantly reformat my resume

  • Writing a tailored cover letter in minutes

  • Submitting my application while still sitting in the dentist’s office

  • Rebuilding my travel plan on the fly

  • Arriving early to maximize strategic engagement


You cannot predict outcomes, but you can control your readiness to accelerate when the moment calls for it.


Serendipity Creates Leverage

I’ve said for years that “room selection” is an underrated executive skill. Be in the rooms where the future is being shaped, and your ability to contribute multiplies.

That night in Mountain View was the perfect example of why:

  • Ng’s team was testing new ideas in real time

  • They were hungry for practitioner insight

  • The attendees were deeply invested in the topic

  • The Q&A became a moment of live industry shaping


My contribution wasn’t planned but because I was present, prepared, and positioned well, the opportunity to influence emerged naturally.


Movement Over Certainty

Nassim Taleb defines “antifragile” systems as those that grow stronger through volatility. Leaders grow stronger the same way.


Experiences like Friday night that entailed rapid decisions, high stakes, and immediate adaptation reinforce resilience, sharpen instincts, and expand strategic horizons.


Playing it safe builds predictability. Taking informed action builds capability. Especially now, as AI restructures entire industries, leaders must learn to:

  • Move with incomplete information

  • Engage with experimental systems

  • Collaborate with emerging innovators

  • Operate confidently in ambiguity


If you wait until an opportunity is fully formed, it’s already gone.


A Closing Challenge

Opportunities are increasingly perishable. AI accelerates cycles. Markets shift faster. Talent landscapes reconfigure overnight. And innovation windows open and close before some leaders have even scheduled their first meeting about them.


Last Friday, I chased a firefly moment and it led to conversations, relationships, and potential future collaboration I could never have predicted.


Your opportunities will look different. But they will flicker just the same.

So I’ll leave you with this question: When was the last time you sensed a signal that was faint, inconvenient, uncertain, and yet you chased it anyway?


To learn more about the event and our specific conversation, click here to view the recap on LinkedIn.


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