Hooked on Opportunistic Hiring - Issue 20
Hire for where you are going, not for where you are.
As a founder, you are constantly stretched to balance the well-known factors of your mission, burn rate, and immediate customer needs against the lesser-known elements of new competitive threats, emerging customer opportunities, and availability of disruptive new tech. But sometimes hiring ahead of the curve can create "slack" in the system, allowing you to be more naturally agile and responsive as your encounter changes across your startup landscape.
What’s going on?
You often meet incredible leaders along your company-building journey, especially if you are always connecting and recruiting. Sometimes people make your “talent wishlist” because they are the right leader for a future point of growth. You keep these leaders in your talent arsenal so that when the time is right, you can activate them. Other times, you meet phenomenal “on the market” talent through out-of-cycle introductions that come through your VCs, employees, and your network who you want to hire, but the timing feels a bit early. Startup resources are precious. And the earlier you are in your journey, the more precious these resources are — especially cash. So, you rationalize not hiring because the risk of hiring too soon brings a great deal of heartburn. Especially right now when the name of the game is all about efficiency. Besides, you didn’t anticipate kicking off a recruiting process for another six months. The last thing you want at your startup is haphazard hiring that can lead to company bloat with B-grade talent. But we’re not talking about B-grade talent. We’re talking about the industry-shaping leaders who cause excitement and hand-wringing. The type of talent who will change the trajectory of your business.
Why does it matter?
Opportunistic hiring is a recruitment strategy that involves always being open and mindful of bringing on new talent, regardless of whether there is a specific vacancy or job role to be filled. This approach is strategic and reserved for high-demand skills or exceptional A+ talent who are truly unique. These exceptional leaders significantly elevate the bar, bringing unparalleled expertise to help you navigate the rapidly evolving landscape at your startup. When you do the math on an amazing opportunistic hire, it's worth paying several months of unexpected salary given how much incremental value they bring and business agility they unlock. All too often, recruiting delays limit business progress. The six-month hiring lead time inevitably grows, trading the cost you think you are saving for new and much bigger issues to solve. Sometimes founders wait because they prioritize holding onto things too long, missing the opportunity to scale themselves. The “I got this” approach that doesn’t quite turn out as intended. But the reality is, with business momentum, too early is rarely the reality when it comes to hiring the type of leaders we’re talking about.
What do others think?
“A senior, opportunistic hire should bring authentic diversity to your leadership team. Avoid the trap of self-replicating strengths and self-replicating weaknesses. The best reason to hire someone opportunistically is because the cohesive force they will generate in your executive team is stronger than the properties of its constituent elements. It takes time for an executive team to fully gel. If you can hire a little ahead, and pick up great talent when they come along, you give your senior team a little ‘bake time’ before things ‘get real’ for them.” - Craig McLuckie, Co-Founder and CEO at Stacklok
What do we think?
Rationalize doing it. Hiring phenomenal people ALWAYS takes longer than you think, and it will always be a competitive market to hire A+ talent. Opportunistic hiring gives you the upper edge to accelerate your business and take great talent out of the running before someone else does. Even in situations where your need is not immediate, it’s important not to spin on an illusion that there isn’t some immediate gap to fill. There always is. Great people seek these opportunities and lean into them. And, when you hire opportunistically, it sends a message. Any opportunistic hire will understand that in hiring them, you’ve not only made an early investment out of confidence for what they are bringing to the table but also for the better good of the business. The last thing they will want to do is squander the opportunity.
What do YOU think?
Take Action
Budget carefully and set aside a couple of “silver bullets” for key, opportunistic hires. Craig’s advice: Build up a positive talent “bank balance,” effectively trading some portion of cash on hand and equity pool in exchange for having versatile, engaged generalists on the ready.
Opportunistic hires have a proven track record. Craig’s advice: Over the last ten years, what percentage of the leader’s work efforts have been resoundingly successful? Stay away from people who are drawn to failure or have a pattern of leaving failure in their wake no matter how fancy their title or how well they are liked by the people around you. Hire for superpowers not the absence of weakness.
Stay accountable to bias. Craig’s advice: It’s dangerous to hire someone simply because you know them, like them, or consider them to be good people. Trust is legitimately critical but is insufficient when hiring ahead.
Always be networking. The first step in opportunistic hiring is knowing who is out there and what skills they have. Always be on the lookout for talent, even if you're not actively hiring. Attend industry events, webinars, and workshops, and utilize social media platforms like LinkedIn to connect and build your community. Remember, networking isn't only about finding someone for an immediate hiring need but also for future opportunities.
Develop a talent pipeline. Start building relationships with game-changing talent ahead of time. Cultivate and keep in touch with new talent through collaborative opportunities. Keep proven “wishlist” operators within your reach to activate. By doing this, you not only have a pool of candidates who are already familiar with you, your company, and mission, but you also have a list of go-to individuals when a need arises.
Be flexible with job descriptions and roles. Opportunistic hiring requires some flexibility in job roles and descriptions. Be ready to adapt roles to suit the individual's strengths. This may involve creating a new position for an exceptional candidate or adjusting the responsibilities of existing roles. By being open and flexible, you can close top talent who might not have been a perfect fit for a rigidly defined role but is perfect for the changing business landscape.
Set up for success. Opportunistic hiring requires having a recruitment process that's flexible enough to accommodate these sorts of hires, as well as a culture that can integrate new employees effectively, even when a specific role hasn't been created for them.
Note: These actions can help you incorporate opportunistic hiring into your recruitment strategy. However, it's important to manage this strategy carefully to avoid overstaffing and to ensure that all employees have clear roles and responsibilities.
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