There is an old saying in enterprise technology: "Nobody ever got fired for buying IBM."

It may be one of the most successful pieces of marketing psychology ever created. Not because it tells us anything about IBM's technology, but because it tells us something uncomfortable about the people buying it.

On paper, enterprise buyers are supposed to be rational. They have procurement frameworks, vendor scorecards, technical evaluations, weighted criteria and spreadsheets designed to remove emotion from decision-making.

Yet somewhere behind those spreadsheets is a human being with a career, a reputation and a perfectly reasonable desire not to be remembered as the person who made a disastrous decision.

Rory Sutherland's thinking on behavioural economics offers an interesting perspective here. What if the buyer isn't necessarily trying to make the best decision? What if they're trying to make the most defensible one?

Those are two very different things.

The hidden job of a B2B purchase

Imagine two software vendors. One is a global technology company with decades of history and a product that meets 80% of the requirements. The other is an unfamiliar challenger offering better functionality, faster implementation and a 30% lower price.

The challenger should win, at least according to the spreadsheet. But what happens if the implementation fails?

If the established vendor fails, the buyer can explain that they selected a recognised company, followed the evaluation process and made a decision many other enterprises would have made. If the challenger fails, the conversation may take a different direction: "Who recommended these people?"

Suddenly, the issue isn't technology. It's personal judgement.

The potential reward for choosing an unconventional vendor may be modest, while the consequences of getting it wrong could be enormous. This is the asymmetry challenger brands often misunderstand. Organisations celebrate innovation, but the people making purchasing decisions may bear a disproportionate share of the consequences when innovation fails.

The buyer isn't necessarily buying the best technology. They're also buying protection against being wrong.

Why better products don't always win

Most challenger brands respond to this problem by producing more evidence of superiority. More features, better benchmarks, detailed comparisons and elaborate presentations explaining why their technology outperforms established competitors.

But what if the buyer already believes their product is better?

Imagine a CIO saying, "Your technology looks impressive, but we're not sure you're the right partner for an organisation of our size." The sales team hears a technical objection and schedules another demonstration. Yet the CIO may actually be asking something entirely different: "Can I put my reputation behind this company?"

No additional feature can automatically answer that question.

Established brands benefit from familiarity. Their names carry years of accumulated recognition, perceived stability and institutional acceptance. Buyers use that familiarity as a shortcut when evaluating uncertainty. It doesn't necessarily make the product better, but it can make the decision feel safer.

The challenger thinks it's competing against another product. In reality, it's also competing against the comfort of choosing something familiar.

Costly signalling: why some marketing claims matter more than others

Behavioural economics offers a useful idea called costly signalling. A signal becomes more credible when producing it requires meaningful effort, commitment or accountability, especially when it would be difficult for an unsuitable provider to imitate.

Consider the phrase "enterprise-grade." Almost every software company uses it. A startup with ten employees can make the claim just as easily as a multinational technology company. Because saying it costs virtually nothing, it provides little evidence of capability.

Now consider a vendor saying, "Here is a customer in your industry who has been running our platform for three years. Their CIO is willing to speak with you."

That's different.

A referenceable customer, independently verified outcomes, meaningful service guarantees and a willingness to accept contractual accountability are harder to replicate than impressive adjectives.

This is where challenger brands should reconsider their marketing priorities. A serious case study may be more valuable than another thousand advertising impressions. An independent technical assessment may establish more credibility than a polished brand film. A customer who is willing to answer difficult questions can be more persuasive than a dozen sales presentations.

The distinction isn't between expensive and inexpensive marketing. It's between marketing that looks impressive and evidence that actually reduces uncertainty.

People trust people who have already taken the risk

Here's another interesting aspect of enterprise buying. The buyer doesn't always need to trust you immediately. They may need someone they already trust to trust you.

A CIO may value another CIO's experience. A CFO may take reassurance from a finance leader who has solved a similar problem. A bank may find another regulated financial institution's experience more relevant than a generic customer testimonial.

I call this borrowed confidence.

The buyer hasn't experienced your product personally, but someone whose judgement they respect already has. Their experience makes your proposition easier to believe and your recommendation easier to defend.

This becomes even more important in complex buying committees. A CIO worries about security and integration, a CFO about financial exposure, procurement about vendor stability, and the business leader about operational results. They're evaluating the same product, but each is trying to avoid a different failure.

Good B2B marketing understands these differences. It doesn't simply repeat the same product benefits to everyone. It provides the particular evidence each stakeholder needs to feel comfortable supporting the decision.

Stop trying to be the better gamble

Challenger brands love calling themselves disruptive. They celebrate breaking conventions, challenging market leaders and doing things differently. That language sounds exciting to founders and investors, but it may sound rather less attractive to someone responsible for a multimillion-dollar implementation.

The buyer doesn't necessarily want to join your revolution. They want their business problem solved without creating another one.

So don't stop demonstrating innovation or proving technical superiority. Instead, make those advantages easier to trust. Show where your technology has worked, introduce credible customer references, explain implementation risks, provide independent validation and make accountability visible.

Above all, help buyers explain their decision to people who weren't present during your presentation. Because many enterprise deals aren't lost in the product demonstration. They're lost afterwards, when someone in the steering committee asks, "Why are we choosing this company?"

The famous IBM saying survives because it captures a fundamental truth about human behaviour. People don't simply optimise for the best outcome. They also seek to avoid regret, embarrassment and personal consequences.

For challenger brands, that means the real competition isn't always the incumbent's technology. It's the perceived safety of choosing it.

The incumbent sells familiarity. The challenger must sell confidence.

Your marketing challenge isn't simply to convince buyers that you're better. It's to make them comfortable putting their reputation behind you.

Because in B2B, the best product may win the evaluation. But the most defensible decision often wins the contract.