Hooked on Getting Lucky

"Luck is where opportunity meets preparation." - Seneca

Recruiting top leaders for your startup may seem like a game of luck. But as a first-time founder building your leadership team, you can't merely rely on chance. It's time to create your own luck with a prepared mind and a strategic approach to acquiring leadership talent.  

What's going on?

The startup space is crowded, and nabbing top leaders often feels like hitting the jackpot. “Wow, this is such a fortunate time to be in the market for talent when all these amazing people are more recruitable than ever before” is a common theme we’re hearing in 2023. However, successful founders don't win leadership talent by pure luck. They don’t sit around and wait for troubled economic waters to loosen their competitors’ grip on their best leaders. Instead of waiting for luck, great founders are always recruiting so that they are prepared for luck when it comes their way. They strategically expand their “luck surface area” by being proactive, networked, and attentive to opportunities to go in for the kill (sounds violent, but you know what we mean!) Your startup's success doesn't have to be a roll of the dice when recruiting leadership. It's an art you can master.

Why does this matter?

Building a strong leadership team is the lifeblood of your startup's growth. But sometimes, finding the right leaders can feel like a game of luck. Understanding how to engineer luck in recruitment makes the process strategic, deliberate, and successful.

Here's how you can do it:

1. Remove Anti-Luck: Don't be limited by traditional hiring methods or negative biases. Break free from restrictive thinking and actively seek unconventional talent pools.
2. Add Pro-Luck: Be ready for the perfect talent storm. Network extensively, share your vision, participate in industry events, and explore platforms beyond LinkedIn to connect with potential leaders. Be present where the talent is.
3. Apply the Luck Razor: When choosing between candidates or recruitment strategies, always choose the path with a more significant potential payoff. Focus on what aligns best with your startup's culture and goals.
4. Be Prepared: Like Serena Williams' countless hours on the court, your preparation in understanding what you need, who you need, and where to find talent is key to “getting lucky” in hiring.

By embracing the challenges of recruiting for a startup, you can significantly influence your hiring success within the constraints of the competitive market.

What do others think?

"Luck happens when you take a shot you have no business scoring. These repeated shots on goal help us build connection and share why we are so passionate about what we’re doing and the difference we’re making in the world. As an early-stage startup, it's an effective way of convincing talent way out of our league to make a bet on us."  — Varun Puri, Co-Founder at Yoodli

“Recruiting is all about the long game. Even if someone isn’t a fit right now, conversations provide valuable learnings and build connections for someday. When someday comes, I already have a network of people with whom I've cultivated a relationship, who understand what we're building and why. So many people think of recruiting reactively, but that often ends in rushed decisions. We’re trying to approach this differently by preparing for the right moment. We create our luck through intention, not haste." — George Huff, CEO at Opal

What do we think?

Building a leadership team isn't about luck — it's about preparation, strategy, and being in the right place at the right time. Founders who approach hiring with this mindset don't just stumble upon great leaders — they identify, engage, and attract them deliberately. You have the power to make your own luck in recruiting. It's all about how you play the game.

What do YOU think?

Take Action

• Evaluate your recruitment strategy and identify areas to expand your luck surface area.
• Implement pro-luck tactics like targeted networking and using modern recruiting tools.
• Apply the Luck Razor to every hiring decision, ensuring alignment with your startup's values, vision, and the problem you’re solving. When choosing between hiring two individuals, ask yourself: "Which of these two hires is more likely to increase my startup’s chances for success?" Act accordingly.
• Commit to preparation. Understand the leadership roles you're hiring for, what qualities you need and why, and where you might find the best fit.

What actions have you taken to create your own luck in recruiting? Like, share, or comment below.

This content is written for founders, startup leaders, and those who are startup curious. To receive Hooked in your inbox, subscribe to Hooked, by Madrona on Substack. Thanks to our readers for continued support and feedback!