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.

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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.