When Sales Becomes a Toddler with Blocks
Every parent has seen the scene. A toddler sits in front of one of those brightly colored plastic toys with cut-out shapes: circle, square, triangle. The mission is obvious—match the shapes to the holes. Yet inevitably, the child decides that the triangle must fit into the square. They twist, push, and finally bang it with growing frustration. The toy, of course, remains unmoved.
In sales, many organizations do exactly the same thing. Only we wear suits, carry quarterly quotas, and call it “pipeline management.”
Forcing the Wrong Deal
Not every deal is a fit. That’s not pessimism, it’s reality. Some prospects don’t have the budget, the right use case, or the organizational will to buy what you’re selling. Yet, instead of moving on, teams cling to the fantasy:
“If we just discount a little more…”
“If we customize that feature, surely they’ll say yes…”
“If our CEO personally calls their CEO, maybe that’ll do it…”
It’s the corporate equivalent of a toddler hammering a triangle into a square hole. Entertaining to watch—if you’re not on the payroll.
Why We Fall for It
Why do perfectly rational adults persist in this madness? Three common culprits:
Pipeline Pressure
Numbers have to be made. When senior management wants forecasts, every prospect looks like a potential savior—even the hopeless ones.Emotional Investment
After months of demos, RFPs, and steak dinners, it’s hard to admit the obvious: the deal is a mirage. But sunk costs don’t make a triangle fit.The Hero Complex
There’s always the fantasy: “If I can close this impossible deal, I’ll be a legend.” Spoiler: you’ll be a cautionary tale, not a case study.
The Real Cost of Wasted Effort
When you refuse to let go of a bad-fit prospect, the damage is wider than you think:
Engineering burns weeks building bespoke features that will never scale.
Marketing is diverted into producing custom collateral for an audience of one.
Executives waste time escalating, cajoling, and negotiating with a buyer who never wanted you in the first place.
Meanwhile, the opportunities that do align—those perfect round pegs ready for your round hole—are neglected.
The Power of Saying “No”
Here’s the uncomfortable truth: one of the most strategic moves in sales is walking away.
Saying “This isn’t a fit” isn’t failure; it’s focus. It frees your team to concentrate on opportunities where your product solves a genuine problem, where value is clear, and where the buyer isn’t secretly wishing you’d leave them alone.
This is precisely why I built the 12-Vector System at Excession Events. Products today look increasingly similar, and forcing deals through brute strength isn’t a growth strategy. Winning comes from aligning with customer outcomes—business pain relief, not product features.
The Toddler Test
So here’s a thought exercise for your next pipeline review:
If you removed discounts, CEO-to-CEO calls, and endless “special” features, would this deal still make sense?
If not, congratulations—you’re the toddler with the triangle.
The good news? Toddlers eventually learn. As adults running multi-million-dollar businesses, we should too.
War-Gaming the Deal
Before you burn another week chasing a questionable opportunity, stop and run a quick war game in your head—or better yet, with your sales leadership team. Ask yourself three brutally honest questions:
Can you actually see a good reason for the client to say “yes”?
Not your reason, their reason. What’s the business pain you’re relieving? If the answer is “because our product is great,” congratulations—you’ve just described every vendor in your category.What will your competitor be saying?
Because you can bet they’ve already mapped the same business problem, and their pitch will sound eerily similar to yours. Now, imagine you’re the buyer—why would you choose them instead of you?How would you counter their statements?
Not with feature lists, but with outcomes. Features are ammunition; outcomes win wars. If you can’t articulate the client’s path to success in a way that makes your competitor irrelevant, you don’t have a strategy—you have wishful thinking.
The point of war-gaming isn’t to invent clever comebacks. It’s to expose whether the deal is fundamentally viable. If you can’t clearly see why the client would buy from you, then the brutal truth is: they almost certainly won’t. And every day you spend trying to force it is the one resource you can never replenish—time.
Final Thought
In my book Who Put That Idiot in Charge, I talk about how organizations often confuse activity with progress. Nowhere is this truer than in sales. Beating your head against deals that will never fit doesn’t make you a hero. It just makes you tired, with a sore head.
Choose alignment. Focus on outcomes. Leave the toddler games in the nursery where they belong.
Simon Dudley is a technology strategist, bestselling author (The Competitive Intelligence Playbook, The End of Certainty, Who Put That Idiot in Charge), and former senior executive at Logitech, Lifesize, and Polycom. He is the Founder & CEO of Excession Events, a consultancy that helps companies compete more effectively in a world where products look increasingly similar.
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