Sport is Embracing Risk, while Business is Avoiding it...Why?

We love borrowing metaphors from sport. Leaders are coaches. Sales teams are athletes. Strategy is a game of execution under pressure, and we all use "playbooks." Most of the time, those comparisons work.

But right now, something unusual is happening. Sport and business are moving in opposite directions when it comes to risk—and the reason has less to do with data or performance, and more to do with morality.

In elite sport, risk is being reclaimed. In modern business, risk has been quietly moralized, and marginalized.

And once risk becomes a moral issue, behavior changes fast.

Sport Is Relearning How to Take Risk

Watch high-level sport today and the pattern is unmistakable. Tennis players go for winners on shots that used to be defensive. Golfers chase distance even when it costs accuracy. (Golf teaching has changed from focusing the young on “getting it in the fairway’” and then teaching distance, to “rip it as hard as you can”,” and then teaching control). Football coaches go for it on fourth down at rates that would once have triggered outrage. Quarterbacks attempt throws that would have been benched ten years ago. This isn’t recklessness. It’s recalibration.

Sport has adopted a different viewpoint that says playing “safe” doesn’t eliminate risk—it just limits upside. Analytics didn’t make athletes bolder; they made the cost of caution visible. Losing slowly, politely, and defensibly turned out to be worse than failing decisively, and fast.

Mistakes are still punished. But not taking the shot is now seen as the bigger error.

Business, Meanwhile, Is Doing the Opposite

In business, especially inside large organizations, risk is no longer something you take. It’s something you manage, mitigate, transfer, duck, or avoid.

At first glance, that sounds sensible. Who would argue against prudence? But beneath the language shift is a deeper change: risk has been moralized. Risk is no longer treated as an inevitable condition of decision-making. It is treated as promising personal failure.

What It Means to Moralize Risk

Something carries moral weight when it becomes a signal about character, not just competence.

In a moralized environment:

• Good outcomes imply good judgment and good people

• Bad outcomes imply flawed judgment—or worse, flawed people

Crucially, the presence of risk itself becomes suspect, even before outcomes are known.

After a failed decision, organizations rarely ask - “Was this a reasonable judgment given what was known at the time?” They ask: “Why wasn’t this risk mitigated?”

That question assumes the risk should not have existed. Which quietly reframes uncertainty not as an unavoidable reality, but as a preventable lapse. This is how risk shifts from being a technical variable to a moral one. People willing to take on risk begin to be perceived as reckless, disorganized, selfish, thoughtless - morally questionable at best.

When Exposure Becomes a Character Test

Once risk is moralized, decision-makers are judged less on the quality of their reasoning and more on the visibility of their exposure. You can make a thoughtful, well-reasoned decision and still be seen as irresponsible if it introduces risk that later becomes visible. Conversely, you can avoid making any meaningful decision at all and still be viewed (wrongly) as prudent.

In this world:

• Prudence becomes virtue

• Caution becomes considerate and  professional

• Courage starts to look like recklessness

Not because the decision was bad—but because being associated with risk itself is bad.

Modern organizations don’t lack intelligence. They lack courage. They lack sponsorship. Sponsoring an initiative now means carrying moral liability.

How Rational People Adapt

Faced with this incentive structure, people adapt intelligently.

They learn that:

• Delay is safer than decisiveness

• Consensus is safer than ownership

• Process is safer than judgment

• “We aligned as a group” is safer than “I decided”

Committees grow. Reviews multiply. Governance expands. Each layer adds reassurance—and removes clarity. What looks like diligence often functions as insulation. This isn’t cowardice (maybe). It’s survival.

When mistakes are treated as ethical failures rather than contextual judgments exercised under uncertainty, the rational move is to minimize personal exposure—not to maximize outcomes.

Why Sport Can Take Risk and Business Can’t

The difference between sport and business isn’t appetite for risk. It’s how failure is interpreted. In sport:

• Failure is expected – failure and success are accepted as two sides to the same coin

• Accountability is immediate and explicit

• Yesterday’s mistake doesn’t permanently disqualify tomorrow’s decision

A quarterback who throws an interception is allowed to throw again.

In business:

• Failure is retrospective and forensic

• Context evaporates

• Decisions are judged with information that did not exist at the time (look at how we judge our historical predecessors by critiquing their actions and tearing down their statues, refusing to allow for the context of their time.)

A buyer who sponsors a failed initiative may never sponsor another. So buyers behave exactly as the system teaches them to.

No Decision as a Moral Safe Harbor

This is the uncomfortable truth behind modern buying behavior:

“No decision” is no longer a failure mode. It is a risk strategy. Doing nothing preserves reputations. It avoids scrutiny. It allows attention to drift. Inaction rarely carries moral weight (it should). Action does.

So deals stall without objection. Transformations linger in review. Opportunities die quietly in committee. From the outside, this looks like indecision. From the inside, it feels like professionalism.

The Real Divergence

Sport has accepted that avoiding risk does not eliminate it—it guarantees mediocrity.

Business, by contrast, has convinced itself that risk can be engineered away through process and governance. The result isn’t better decisions. It’s fewer decisions.

Until organizations relearn how to carry risk—rather than merely managing it—business will continue move (despite popular claims in the media) in the opposite direction of sport: slower, safer, and increasingly unable to take the shots required to win.

In a world where deciding itself has become the riskiest act of all, choosing not to choose will remain the safest moral position available.

Confronting Risk Without Sounding Like a Jerk

The Comfortable Fiction We’re All Operating Inside

Most humans avoid uncomfortable situations. “Don’t ask the question if you don’t want to hear the answer” exists for a reason. We spend large parts of our lives not asking difficult questions while still thinking of ourselves as principled and decisive. The big cans we kick down the road—death, illness, taxes—are obvious. In business, we do the same thing just more politely, while retaining plausible deniability!

Modern B2B runs on numbers that describe motion, not meaning. Activity metrics feel objective, safe, and defensible. Pipelines preserve optimism even when the underlying story is poor. We’re  managing optics, not reality.

Won't Read it? Too Long? Listen Instead

Fear Isn’t the Problem — Avoidance Is

Fear and discomfort are normal and rational. As Bill Paxton says in Edge of Tomorrow, “there is no courage without fear.” Modern buyers feel exposed, and risk today isn’t just about making a wrong decision—it’s about being seen as the person who sponsored it.

That pressure has intensified thanks to success conditioning, social media, and the explosion of available information (which is available to all and is perpetually growing.)  Silence and delay are usually protective behaviors, not disinterest. Inaction is often the most rational move available.

Why “Building Relationships” Became the Great Escape Hatch

When sellers avoid difficult conversations, they often hide behind “I’m building the relationship.” There’s an old John Cleese training video where a buyer spends time with a friendly salesperson they never buy from—safe, pleasant, and informative—while buying instead from a competitor they find irritating but effective. Most of us have been that friendly salesperson at some point.

The myth rests on confusing familiarity with trust. Politeness gets mistaken for progress. CRM systems quietly reinforce this fiction by rewarding logged interactions rather than meaningful movement.

People don’t buy because they like you—though they rarely buy from someone they actively dislike. Neutral beats needy, pushy or arrogant. Buyers act when uncertainty becomes unsafe.

The Clumsy Way to Confront Reality (And Why It Backfires)

Once a seller decides to confront risk or discomfort, the danger isn’t that they do it—it’s how. Ideas like Challenger were well-founded but widely misapplied. Only firms with deep institutional authority—McKinsey and the like—can directly challenge how a business is run without resistance. The rest of us need to tread more carefully.

Leading with blunt truths, data dumps, or forced urgency usually backfires. Sounding superior, impatient, or performative turns “challenging” into confrontation. I’ve crossed that line myself—recently being described as “combative.” When sellers think they’re being bold, buyers often experience threat.

The Real Skill: Holding Uncomfortable Conversations with Care

Confronting fear doesn’t mean indulging it. Pitching disaster if a buyer doesn’t choose you is a reliable way to get rejected. The differentiator is nuance. It’s not whether you raise risk—it’s how.

Tone matters more than content. Shared exploration beats diagnosis. Curiosity helps, but curiosity without perspective quickly becomes exhausting. Back in sales a few years ago I had to tolerate a partner salesperson who took this idea too literally. In fact, me and some of my colleagues would bet on the over and under as to how many times he’d actually use the word “curious.” 

Buyers don’t want to repeatedly explain their business. With AI they rightly expect sellers to arrive informed. Handled clumsily, perspective becomes FUD. Handled well, it helps buyers confront fear safely.

What This Looks Like in Practice

Helping someone confront hesitation requires restraint. Sellers often fall into extremes: over-optimistic “rainbows” selling or doom-laden scare tactics. Both miss the point.

A more effective approach starts with trade-offs—before the buyer asks. Acknowledge what might not work. Raise where others have struggled or failed. Doing this early lowers defensiveness and preserves dignity. You’re not removing agency; you’re protecting it.

Why This Runs Against Modern Sales Orthodoxy

Sales training optimizes for persuasion. Tools optimize for tracking, not thinking. Sellers are taught to reduce friction, not surface it. The result is a flood of rational information that explains activity but avoids why people hesitate.

Friction already exists in the buyer’s mind—they just haven’t voiced it. If sellers don’t surface it, buyers don’t move, and sellers don’t know why.

Reframing the Seller’s Role

The modern seller’s job isn’t to make buyers feel good—it’s to make them feel clear. We’ve moved from the information age to the interpretation age. That requires sense-making, not more data.

The idea of the seller as guide isn’t new, but trust isn’t built by subtly steering buyers toward your solution. It’s built by helping them confront risk—including the risk of doing nothing. AI helps here, not by replacing selling, but by revealing connections and trade-offs that are subtle and hidden in the wealth if information that buyers get buried with. When clarity emerges, selling still matters—but good deals, with buyers having more comfort and clarity, begin to close themselves.

A Word of Warning

Demographics matter. Many decision-makers today are nearing the end of their careers. “Sun-setters” are less inclined to change anything. With them, assume “no decision” is the default outcome.

This is where candor matters. If you see real opportunity and compulsion, be prepared to escalate sooner rather than later. Helping someone confront risk sometimes means confronting and challenging who is best positioned to decide.

Modern B2B doesn’t fail because sellers lack information or effort. It fails because we’ve built systems that reward comfort over clarity. The hardest conversations aren’t risky because they’re confrontational — they’re risky because they’re honest.

New Thinking for a New Year

It's that time of year again. You know, when we get reflective. Think about what we achieved (and didn't) in the previous year. You'll see people shouting from the roof tops on what a great year they had, and how they're mapping out their recipe for success in 2026.

To avoid all that ('cos who cares - right?) here's what we're thinking (maybe also "who cares!") about B2B selling in these changing times of AI's threat and promise. Why does this matter? Well, maybe it does and maybe it doesn't but if you/as you contemplate the impact of AI in selling and maybe consider using some of the ideas and tools that are out there, the least you should do is go under the surface. See what these tools are based on (if anything.) See if there's a hint of new or original thinking that under pins these tools. Here's ours!

Modern B2B Sales Is Built on a Fiction - (And Shadow Exists Because We’ve All Been Playing Along)

Modern B2B sales rests on a comforting lie: that buying is rational, linear, and controllable if we just apply the right framework hard enough. Identify needs. Quantify value. Overcome objections. Close.

We repeat this like an incantation—while simultaneously admitting that humans make decisions emotionally, irrationally, and defensively. Somehow, both ideas are allowed to coexist without anyone calling time. It’s a bit like acknowledging gravity exists, then continuing to design airplanes as if it doesn’t.

Shadow exists because this contradiction finally became impossible to ignore.

TLDR? Go to the web page, move down a bit and watch the video!

Where this thinking came from (and why it no longer works)

Traditional sales thinking was forged in a very specific historical moment: when sellers controlled information and buyers depended on them for access to it. Complexity could be simplified into stages, checklists, and CRM math. Progress could be measured by movement. Authority belonged to the seller.

There was an implicit barter system at play. Sellers were able to say: “Prove you’re serious, and I’ll share information. Stop looking serious, and I’ll withdraw my effort.”

That world is gone.

Today, buyers have unlimited information and almost no clarity. They don’t lack data—they drown in it. They research obsessively, delay endlessly, and default to doing nothing. Not because they’re unconvinced, but because deciding feels personally risky, politically dangerous, and professionally irreversible.

Meanwhile, sellers cling harder than ever to systems that promise certainty and control—precisely because outcomes feel less controllable than they used to.

“No Decision” didn’t suddenly appear as a competitor. It was quietly promoted to the top of the leaderboard while everyone was busy optimizing dashboards.

* The best, most recent example of sales thinking that’s out of date and misapplied is the Sales Methodology called MEDDIC. MEDDIC is really a “deal inspection” and qualification model. Just like RevOps thinking it was built by and for the largest companies and only works for them. Just because Salesforce use it, doesn’t mean it will work for you, in fact that’s a good reason NOT to use it!

The baggage we’re still carrying (and pretending isn’t there)

Modern sales carry a lot of unchallenged assumptions that should have expired years ago:

• That buyers are logical actors who just need better information

• That confidence comes from certainty, not from managing uncertainty (there is a difference)

• That objections are problems to defeat rather than risks to acknowledge

• That progress is the same as movement through (arbitrary) stages

• That more activity, data, and tooling can compensate for human hesitation

We also quietly deny a few truths that make everyone uncomfortable:

• Buyers often don’t know what they want—but feel they’re not allowed to admit it, and showing any hesitation or lack of supreme confidence has become fatal in the corporate world

• Decisions often decay under scrutiny rather than improve

• “Consensus” is frequently avoidance dressed up as alignment

• Leadership has been replaced by “risk mitigation,” and doing nothing is often treated as the best form of risk mitigation.

We say we understand these things. Our behavior suggests otherwise.

What’s actually changed—and what hasn’t

What’s changed is obvious:

• Buyers don’t need sellers for information

• Decisions involve more people (spread the risk), more exposure (everything’s visible), and more perceived personal downside (ego challenging)

• Risk is more visible, reputational, and asymmetric

What hasn’t changed—but is constantly misunderstood:

• People still decide emotionally and heuristically, not analytically

• Loss and regret loom far larger than upside (roughly 7x, if you believe Daniel Kahneman—and you should)

• Trust is built through safety, credibility, and intent—not persuasion

• Insight comes from pattern recognition, not individual brilliance

• Progress happens in small, low-risk steps—not bold commitments (but we lack the patience being constantly pressurized by the investors)

In short: the human parts of buying never changed. We just kept trying to engineer them out of the equation!

The real problem sales has been avoiding

Unsuccessful sellers become the victims of structured failure - because we’ve designed selling around deal mechanics, not decision dynamics.

We’ve optimized pipelines while ignoring confidence. We’ve automated activity while misunderstanding momentum. We’ve treated hesitation as resistance instead of self-protection.

And when outcomes disappoint, we do the most predictable thing possible: add more process, more tools, more numbers, more pressure.

That usually works about as well as shouting instructions at someone who’s already nervous (you know, like your Dad used to!)

The thinking Shadow is built on

Shadow isn’t another sales “method,” and it definitely isn’t AI pretending to be a motivational speaker. It’s built on different premises:

Selling is not about moving buyers forward. It’s about helping them feel safe starting.

That sounds softer than it is. In practice, it’s far more demanding.

Shadow is designed around how decisions form, stall, wobble, and survive—not how we wish they did. That means focusing on:

• Decision dynamics, not deal stages

• Reducing perceived risk before increasing conviction (recognizing trade offs and risks, for instance)

• Creating movement without pressure (recognition of the power of loss aversion)

• Helping buyers think, not persuading them to agree

• Supporting confidence before, during, and after decisions

Instead of teaching sellers to sound smarter, Shadow reminds them how to be (and sound) more human. Instead of optimizing activity, it focuses on meaningful progress. Instead of pretending buying is logical, it designs for the fact that it isn’t.

Why this matters now

AI didn’t create these problems—it exposed them. When AI is layered on top of flawed assumptions, all you get is faster nonsense (that might sound cleverer, but is still nonsense) . Shadow exists because using AI responsibly in sales requires confronting the uncomfortable realities we’ve been ignoring for decades.

We stop shaming hesitation. We stop confusing motion with momentum. We stop pretending confidence can be forced. We recognize the meaning and importance of trust.

We design selling around humans—because humans are the hard part and always have been.

Everything else is just software.