When Playing It Safe Is the Least Safe Thing You Can Do

I’ll be honest — I almost blew Stephen Shapiro’s book title in the intro. You’re Not Playing with a Full Deck came out as something entirely different, and Stephen, to his credit, laughed and told me he’d done the same thing. Instant credibility. We were going to get along just fine.

Stephen is an innovation expert who has worked with Nike, NASA, Microsoft, and Marriott, among others, and he has a gift for saying things that sound slightly controversial until you realize they’re just… true. Best practices are stupid. Playing it safe is the least safe thing you can do. The role of a leader isn’t to have answers.

All of it lands because he can back it up.

Safe Is the New Risky

The thing Stephen said that I keep coming back to is this: best practices are a recipe for mediocrity.

Not because they’re useless in every context, but because copying what someone else did well is by definition playing catch-up. By the time you’ve implemented someone else’s winning strategy, the game has already moved. And in a world where AI is producing the same polished, optimized, indistinguishable output for everyone who asks nicely, leaning on proven models isn’t safety — it’s a fast track to the sea of sameness.

The only real differentiator organizations have left, Stephen argues, are their people. Not their technology, not their processes, not their best-practice playbook. Their people. Which is pretty much the hill I’ve been dying on since day one, so you can imagine how that part of the conversation went.

The organizations that are going to thrive aren’t the ones doing things most efficiently. They’re the ones who have gotten clear on what they do that no one else can replicate — and then doubled down on exactly that.

The Leader’s Real Job

Here’s the other one that hit me: the role of a leader is not to have the answers. The role of a leader is to ask questions that get others to ask better questions.

We spend so much energy in leadership culture on having the answers — being decisive, being certain, projecting confidence. And Stephen’s point is that all of that answer-chasing is actually getting in the way, because most organizations are very busy solving the wrong problems.

He told a story about an airport where passengers kept complaining that baggage claim took too long. So the airport did what any reasonable organization would do — they invested in faster conveyor belts, more baggage handlers, newer technology. Got the wait time cut nearly in half. And passengers were still unhappy.

Turns out passengers were getting to baggage claim in one to three minutes. The bags were taking eight to ten. So instead of speeding up the bags further, they just moved baggage claim farther away so passengers had to walk longer to get there. Bags were waiting when they arrived. Problem solved — for almost nothing.

They’d been solving the right problem expensively when the actual solution was free. They just had to ask a different question first.

That’s what better questions do. They change which solutions become visible.

And just to tie the bow on it — Stephen made the point that this is exactly why AI prompting matters so much right now. AI will give you a thousand answers to whatever question you ask. If you’re asking the wrong question, you get a thousand irrelevant answers very efficiently. The quality of your output is only ever as good as the quality of your input. In AI, in leadership, in innovation — same principle.

A Note on Creativity vs. Innovation

These aren’t the same thing, and Stephen’s distinction is worth keeping: creativity is generative and expansive. Innovation is analytical and problem-focused. Innovation doesn’t start with an idea — it starts with a well-framed problem.

Which means if you’re leading with “here’s my idea, now let me find the problem it solves,” you’re doing it backwards. And a lot of us — coaches, entrepreneurs, leaders — are doing exactly that.

The question isn’t what’s my idea. It’s what problem actually needs solving, and am I the right person to solve it?

None of us is playing with a full deck. The ones who know that — and build teams accordingly — are the ones who end up with something worth having.


🎧 Lhttp://careerbenders.com/episode-251isten to the full conversation with Stephen Shapiro on No More Mondays

Find Stephen at theinnovationspeaker.com or grab the book at fulldeckbook.com — he designed it to be read in 90 minutes, which is either very considerate or very on-brand for a guy who talks about solving the right problems efficiently. Probably both.

from sunday scaries to scary good

It’s not your average self-help book. It’s just the one everyone’s talking about. 

“It’s wisdom every working human needs to hear.” – Anna Schardt Baker, Founder and President of Three Story Strategies, LLC

Angie Callen, PCC. MJSC

Angie Callen is a coach, speaker, and author of Scary Good: Discovering Life Beyond the Sunday Scaries. She’s spent over a decade helping people figure out who they actually are — and build a life that reflects it.

She’s a Professional Certified Coach (PCC) through the International Coaching Federation and the host of No More Mondays, a podcast about the human side of modern work.

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