Nobody Gets Fired
A few years ago we lost a deal we should have won, and the loss taught me more than any of the wins that year. (It was quite a few years ago back when I used to run sales for a younger sheepCRM. My ineptitude as a salesman might of course be the real reason, but let's not allow that to ruin the premise of this essay.)
The organisation was a good fit. We had done the work: a demonstration tuned to exactly their renewal structure, a migration plan, references from two similar bodies, a price that undercut the incumbent by a meaningful margin. On every axis a reasonable person would weigh, we were the better choice, and I could show it on a single page (I did show it on a single page!). They chose the incumbent anyway - larger, older, more expensive, and by any feature-level reading, worse. When I asked the person who had championed us what had happened, she was honest with me. "Nobody," she said, "was going to get into trouble for staying with them."
I filed that away as a disappointment. It took me a while, and some reading well outside the software shelf, to understand that it was not a disappointment. It was the whole game, stated plainly, by someone kind enough to say it out loud.
🎯 You are answering the wrong question
The mistake I was making is the one almost every founder makes, and Rory Sutherland names it precisely in Alchemy. We assume the buyer is trying to make the best decision. Often they are not. They are trying to make the decision they will not be blamed for, and those are not the same thing.
"The desire to make good decisions and the urge not to get fired or blamed," Sutherland writes, "may at first seem to be similar motivations, but they are, in fact, never quite the same thing, and may sometimes be diametrically different." This is the truth hiding inside the oldest cliché in enterprise selling. "No one ever got fired for buying IBM" was never IBM's slogan, but it became, in Sutherland's phrase, "the most valuable marketing mantra in existence" - because it does not describe the product at all. It describes the buyer's exposure. IBM's genuine pitch to a nervous purchaser was never "we are the best." It was "if you choose us and it goes wrong, that is not your fault; if you choose the clever upstart and it goes wrong, that is entirely your fault."
Once you see this, a second, more painful line from the same book lands. "The fatal issue," Sutherland writes, "is that logic always gets you to exactly the same place as your competitors." My single beautiful page of reasons was not a differentiator. It was table stakes. Any competent competitor could produce an equally logical page pointing the other way, and the buyer knew it. Logic is symmetric. It does not break ties. It just proves that everybody in the room is a plausible choice, which is the last thing a challenger wants to establish, because plausibility is exactly the ground on which the safe incumbent wins.
🧾 The tax you did not know you were paying
So if not logic, what decides? Jonah Berger, in Catalyst, gives the mechanism a name, and it is the single most useful idea I have taken from a business book in years.
"The more ambiguity there is around a product, service, or idea," Berger writes, "the less valuable that thing becomes." Note what that sentence does not say. It does not say the product is less valuable. It says it becomes less valuable, in the buyer's hands, purely as a function of their uncertainty about it. Your software could be objectively superior and still be worth less to the person deciding, because they are pricing in the risk that they are wrong about it.
And uncertainty does something worse than discount you. It freezes the buyer entirely. "Uncertainty acts like a pause button," Berger writes. "Stopping action and freezing things where they are. So, while uncertainty is great for the status quo, it is terrible for changing minds." This is the part I had completely misread. I thought I was competing against the incumbent. I was not. Most of the time I was competing against the buyer doing nothing at all - staying paused, renewing by default, because the pause felt free and the switch felt like exposure. The incumbent did not have to beat me. It only had to keep the buyer uncertain enough to keep waiting.
🔓 The job is not persuasion, it is de-risking
The reframe that follows from this changes what you actually do on a Tuesday. Berger's whole argument in Catalyst is that we get change backwards. We ask what would convince someone to move, and we pile on reasons, features, discounts - more pushing. The better question, he says, is the opposite one: "Why hasn't that person changed already? What is blocking them?" You do not win by adding weight to your side of the scale. You win by removing the thing holding the buyer in place, and for a challenger that thing is almost always doubt.
Which turns the entire job from persuasion into de-risking. One lever is to make standing still visibly expensive. Berger calls the buyer's attachment to the current arrangement endowment, and the counter is to "surface the costs of inaction and help people realise that doing nothing is not as costless as it seems." The safe choice only looks safe because its costs are hidden and deferred - the slow data decay, the workaround everyone has stopped noticing, the report that quietly stopped being trusted. Your job is not to attack the incumbent. It is to put a number and a date on the cost of the pause, so that "wait another year" stops reading as the free option it is pretending to be.
🪟 The window, not the trial
The other lever is the one every instinct points you toward and most people reach for too soon. Once you accept that the buyer is pricing risk rather than features, the obvious move is to lower that risk by letting them try before they commit. Run a pilot. Give them a parallel fortnight. Prove it in the small before you ask for the whole. It feels like generosity, and for years it was the move I reached for.
It is often a mistake. A trial is not a demonstration; it is a project - usually a long, distracted, half-resourced one, running alongside the buyer's real job for weeks. Bent Flyvbjerg, who has spent a career studying why big projects fail, gives you the reason in one image. "Think of the duration of a project as an open window," he writes in How Big Things Get Done. "The longer the duration, the more open the window. The more open the window, the more opportunity for something to crash through and cause trouble, including a big, bad black swan." A trial holds that window open on purpose. Every week it runs is another week in which a bad import, a confused user, an ordinary piece of bad luck can crash through and hand the nervous buyer exactly the story they were afraid of. Trials do not always de-risk the deal. Sometimes they are the thing that loses it.
And even when nothing goes wrong, a trial rarely does the job people hope. It has the quality of a fire drill: everyone knows it is not the real thing, so nobody quite behaves as they would if it were. The data that matters does not get migrated, the awkward edge cases do not get tried, the team gives it the attention you give a rehearsal. Worse, most trials begin with no agreed picture of what a good result would even look like - no success criteria, no decision resting on the outcome - so they drift into a superficial kick of the tyres, a second look at a product the buyer has already seen. That is the quiet tell: a trial that only confirms what a good demonstration should already have shown is not reducing uncertainty at all. It is deferring the decision while the window stays open.
Because the buyer's fear was never really your product. It was the transition - the migration, the onboarding, the fortnight where the old thing and the new thing both half-work. That is where the black swans live, and that is what "nobody got fired for staying" is quietly buying: not a better system, but the absence of a dangerous crossing. Which tells you where the real lever is. You do not reduce the risk of a crossing by extending it into a trial. You reduce it by making it short.
So the offer that beats the incumbent is not "try it first." It is "you will barely feel the switch." Fast migration, short onboarding, delivered in small self-contained parcels - one membership type, one dataset, one workflow - each opening for hours or even minutes, not weeks and months, and closing cleanly before the next begins. Flyvbjerg calls it modularity, and it is the opposite of the big-bang cutover the buyer is dreading. Small things, done quickly, repeated. The window never gets wide enough for a black swan to fit through.
This is where his own maxim earns a place in a sales conversation: think slow, act fast. Let the buyer take all the time they want to decide - leaning on a nervous person only triggers the retreat we come to in a moment. But once they commit, deliver fast. The safe incumbent offers slowness at both ends: a slow, comfortable non-decision and, if you ever left, a slow, frightening exit. You offer the inverse, and the inverse is more honest - a careful decision followed by a crossing so quick there is barely time for anything to go wrong.
There is a blunter truth underneath all of this. "Watch your downside," Flyvbjerg writes. "Risk can kill you or your project. No upside can compensate for that." The nervous buyer is not being irrational. They are being correct. No feature compensates for a migration that takes their operations down for a week. So stop trying to argue them out of their caution. Honour it. Shrink the thing they are right to fear until it is small enough to say yes to. Speed, in the end, is not a growth tactic. It is respect for the buyer's downside - and it is the one form of proof the big, safe, slow incumbent structurally cannot offer.
🃏 The moves that feel wrong and work anyway
Here is where the behavioural reading turns genuinely counterintuitive, because the most effective moves are the ones every instinct tells you to avoid.
The first is to volunteer your own weakness. Sutherland cites Robert Cialdini's finding that admitting a downside, at the point of closing, actually increases persuasive power. "Yes, it is expensive, but you will soon find it is worth it" is strangely more convincing than an unbroken wall of strengths - because naming the flaw lets the buyer file it and move past it, rather than lying awake wondering what you are hiding. A challenger's honesty about its own limits is not a concession. It is a de-risking device, because the buyer's deepest fear is not that you are imperfect. It is that you are imperfect in a way you have not told them about.
The second is to stop pushing when you feel resistance, not to push harder. Berger's name for the reflex is reactance: "when pushed, people push back." The nervous buyer, leaned on, does not move toward you. They retreat toward the incumbent, because retreat feels like regaining control. The catalyst, he writes, "allows for agency and encourages people to convince themselves" - a menu rather than a mandate, a question rather than a claim. In a sales conversation this is almost physically hard to do, and it is nearly always right.
And the third is the one I now believe most: that a problem, handled well, is worth more than no problem at all. Sutherland notes the finding that a customer whose complaint you resolve at your own expense becomes more loyal than one who never had the fault - because, as he puts it, "solving a problem for a customer at your own expense is a good way of signalling your commitment to a future relationship." The incumbent's stability offers the buyer the absence of problems. It cannot offer proof of how you behave when one arrives, and for a wary buyer that proof is the more valuable thing. It is one of the few kinds of trust you cannot fake and the big safe vendor cannot demonstrate.
🐑 The challenger's chair
I think about all of this constantly, because at sheepCRM the challenger's chair is the only chair we have ever sat in. Our buyers are membership organisations and charities, and they are, for entirely rational reasons, close to the most risk-averse purchasers in the economy. The person choosing is often a new CEO, or a single hard-pressed membership manager. Their data is their entire relationship with their members. If a migration goes wrong, the cost is not a line in a budget - it is a furious annual general meeting and their own name attached to the decision. The uncertainty tax on a small vendor, in that room, is enormous, and no amount of my beautiful single page reduces it by a penny.
What reduces it is everything the behavioural reading points at, and almost nothing the feature comparison points at. A full migration of one workflow before the whole org commits. A candid account of what we are not good at, offered before they ask. The renewal that we made painless when it broke, three years ago, for the organisation now giving us the reference. This is the same argument I made about buyers' fear in The Non-Anxious CTO, seen from the seller's side of the table: the anxiety in the room is real, it is the actual thing being priced, and pretending it is a rational feature debate is how challengers lose deals they deserved to win. Fifteen years of building this company, which I wrote about in Fifteen Years of sheepCRM, has mostly been an education in this one point.
🧭 Where this leaves the better product
None of this is a licence to have the worse product. A fast migration only de-risks the deal if you can actually deliver it fast; admitting a weakness only works if the weakness is survivable; de-risking a purchase you then botch is the fastest way to prove the nervous buyer right. The product still has to be good. The behavioural reading is not a substitute for building the better thing. It is the correction to the belief that building the better thing is sufficient - the belief that costs founders more deals than any competitor ever does.
Because the buyer is not lying to you when they nod along with your logic and then renew with the incumbent. They are answering a question you were not asking. You were pitching which choice is best. They were deciding which choice they can defend on Monday. Until you have made the answer to the second question point at you - by shrinking the doubt, surfacing the cost of standing still, and proving how you behave when something breaks - the better product does not even get to compete. It just gets to be the plausible upstart nobody got fired for turning down.
Make your product the safe choice, not merely the right one. The right one was never the thing being bought.
If you're weighing a change like this, the whole point of the piece is that the crossing is the risk - so the work is to shrink it. That is what I do at Croftsware: help organisations make software change and transformation small enough to survive. And if you run a membership body or charity, where the migration is exactly what has kept you on a system you have outgrown, that is the problem sheepCRM was built for - a fast, low-drama crossing by design.
James Webster is the founder of sheepCRM and director of Croftsware. The ideas here are drawn from Rory Sutherland's Alchemy, Jonah Berger's Catalyst, and Bent Flyvbjerg's How Big Things Get Done, three books that belong on every founder's shelf and almost never make it onto a sales-training slide.