How to Hire for a Future You Can’t See

By Terri Davis

“I have no idea where I am. I can’t see. I have no sense of direction. I’m blind!”

— Gene Wilder as Wally in the comedy See No Evil, Hear No Evil (1989)

Once upon a time, the great oracle Bill Gates was quoted as saying no computer would ever need more than 640 kilobytes of memory, a limit that now fits in the metadata of a selfie. Nokia dismissed the rise of the smartphone and doubled down on their feature phones, nearly sinking the company. In 1946, film mogul Darryl Zanuck claimed television wouldn’t last because people would soon get tired of “staring at a plywood box.” And in 2007, Microsoft’s then-CEO Steve Ballmer scoffed at the iPhone, saying it had “no chance” of gaining significant market share.

Humans, even our so-called best and brightest, are remarkably bad at predicting the future. So what hope do we ordinary mortals have?

That brings me to the lofty realm of recruitment, where we hold lives and the lives of companies in our hands. What we decide shapes futures. Good moves make us heroes. Bad…well let’s just forget about those ones. Hiring top leaders is strategic, yes, but it’s also partly subjective guesswork based on our abilities to predict outcomes against the well-tailored and fresh-faced ready-to-take-on-the-job evidence in front of us. As Kenny Rodger’s said, every gambler knows the secret to surviving. We need to know how to build better hands with the cards we’re dealt.

Uncertainty is the only certainty we really have at the recruitment card table. So how can we help build the very best strategic teams for companies when we are future blind?

Leadership as Portfolio Strategy

Let’s think like an investor for a moment. When you build a portfolio, you don’t invest only in what’s safe, you invest in a mix of possibilities to create stability, strength, steady growth, and exponential upside. Some picks in the portfolio are stable. Others are riskier. Some might be outright moonshots. A good portfolio is built across risk levels, involving time horizons and market potential.

What if assembling a leadership team worked much the same way?

Instead of asking, “Who’s best equipped to run this division today?” Ask: “Which leader reflects the kind of business we might have to become?”

Instead of “What’s the safest pair of hands?”
Ask: “Where are we underweight in visionary capacity and the courage to get us there? Who can stretch us?”

By reframing hiring as future investments in the face of best-guessed blind faith, you start looking for the right bet.

Most Decisions Are Obsolete by the Time They’re Made

Here’s another truth.

Hiring against fixed assumptions is a business liability. You’re hiring leaders to solve a version of the business that’s passing like time itself. To stay ahead you need to think ahead into a future that hasn’t yet arrived and might never be.

Just like a venture capitalist writes an investment memo, your decisions on building a leadership team should reach beyond the now to articulate future needs:

What kind of future are we preparing for?
What strategic plays are we not currently built to make?
What human capabilities are missing from our bench to execute on those bets?

When you define roles in terms of your thesis about the future, you give yourself permission to hire ahead of today’s needs and understanding.

Staring Into the Face of the Future

Every future-forward executive hire can look strange in the present moment it’s made.

The armchair quarterbacks in the C-suite might muse that so-and-so seems like a mismatch. Too technical. Too entrepreneurial. Too bold. Too unconventional. Not at all like the executive she or he is replacing. They’ll possibly dig up every angle of argument against a future hire. But they don’t have your insights or prescience! You’ve been recruiting from the land of the future to fix gathering weaknesses and coming problems. As a CHRO, you hold the keys to the Time Machine, capable of knowing persons like x, y, and z are needed to tackle the variegated yet still nebulous pressures of the coming future, from evolving technologies, shifting markets, and new competitors.

To hearten you into hiring beyond convention, look at the early digital hires in retail before e-commerce went mainstream. Or the first Chief Sustainability Officer brought into extractive industries. Or more recently the trickling trend of the Chief AI Officer. At the time, they can look a little out of place. Or placed too early for the present need. That’s because they are preparations for possible futures with which we aren’t yet familiar.

Redesigning the Search Bias In Your Head

To hire like a venture strategist, you need to declutter your mind, move out all those old assumptions, and spackle and paint for a fresh new process:

Build a future thesis, not just a role spec
Every search should start with a forecast, not of the job, but of the company. Where are you heading? What disruption are you preparing for? What bets are you placing on growth, risk, or relevance?
Evaluate leaders like early-stage startups
Don’t over index on résumé shine. Index on clarity of thinking, originality of insight, and speed of learning. Treat the interview like due diligence on a founder: What hard truths do they see that you don’t? Can they articulate a unique view of your business? Stop asking default interview questions and dig deeper.
Diversify your leadership portfolio
The reality is many C-suites are overweight in operators and underweight in builders. Overweight in continuity, underweight in provocation. Future-proofing leadership isn’t about finding a safe, well-rounded individual. It’s about building a well-diversified team.
Expect misalignment as a feature
If the leader you hire fits cleanly into the current org chart, it should probably worry you; you’ve likely under-hired. You want the candidate who doesn’t quite “slot in,” but expands the slot itself, because they’re here to build something that isn’t built yet.

Don’t Just Fill the Role. Fund the Future.

Every time you hire a senior leader, you’re not just filling a vacancy, you’re allocating capital, attention, and permission against the hope this new hire will take you ably into the future.

That’s why exercising your mind to think differently about executive hires is worth the effort. It’s at first difficult to reconcile the concept that the best hire for the job might feel like a mismatch because they challenge your assumptions about what that role should be. But that’s just your past, unevolved self-thinking. The best candidates will be those who challenge the very premise of the job itself, and (hopefully) redefine what your company is capable of.

So the next time you open a search, don’t ask: “Who can run this part of the company now?”

Ask: “What kind of future are we betting on?”

Then place your wager and play your best hand.