Why Do Businesses Struggle with Change

If Fridays feel like the only day you can breathe, you’re not alone. That tiny window of “fix-it time” is where most real improvements are born. My personal sweet spot is Saturday 7:30–9:30 a.m.—free work, no pings, just scratching the itch that moves the business forward.

Today’s itch: why do businesses suck so much at change?

We like to pretend it’s a coin flip. Spoiler: it kind of is. In one study, roughly half of initiatives were failures, a third were successes, and the rest landed in “meh.” Said differently, you’re often staking livelihoods on a bet with Vegas odds. And we still do it—because envy is persuasive. An exec skis with a buddy who “won” on SAP, flies home, and green-lights eight figures. Months later, Finance smiles for the ribbon cutting…then quietly keeps using spreadsheets. The shiny platform becomes a very expensive monthly ledger.

Part of the trap is accounting cosmetics. If it’s CapEx, we can stretch the pain over years. If it’s OpEx, we swallow it now. When the program misses, the asset turns “impaired,” and everyone pretends nine figures of value is still sitting there. On paper, anyway. In practice, you’ve bought change fatigue, not capability.

Then we repeat the pattern with the next shiny thing—AI this time. We replace “Press 1 for a human” with “Did you say…potato salad?” and call it a transformation. Customers roll their eyes. Employees get whiplash. Your organizational “immune system” goes autoimmune—overreacting to every new change because the last ten left scars.

Here’s the deeper issue: most teams don’t know what game they’re playing. Basketball teams don’t tackle because the rules are clear and the hoop is obvious. But in most companies, we launch changes without a crisp definition of the game, field, and scoreboard. People hedge. They run micro-mutinies, small experiments in resistance to see what happens if they miss curfew. If nothing happens, the “new way” becomes optional.

We also refuse to look at cohorts. Cities still bid for the Olympics, even though nearly every one blows the budget. Remodelers still trust the lowball kitchen estimate, even though the local average says otherwise. Businesses do the same with change: “We’re different.” Sure. But your variance from the cohort is rarely as big as your confidence suggests.

So what actually helps?

1. Name the game in plain English. What problem are we solving? For whom? How will we know it worked? Keep it so clear your most cynical stakeholder can repeat it without notes.

2. Start where the work lives. Don’t buy a continent-sized system for a village-sized problem. Go to the floor. Watch the handoffs. Fix the “two-minute annoyances” that shred adoption long before you touch architecture.

3. Price the soft stuff like it’s hard. Communication, training, stakeholder interviews—these are not “nice-to-haves.” Treat them as first-class deliverables with time, owners, and acceptance criteria. The hours are visible. Make the value visible too: fewer escalations, faster cycle time, cleaner close.

4. Use cohorts to set honest guardrails. If similar companies overshoot by 30%, assume you will too. Plan for the drywall surprise. You’ll either be right or pleasantly under budget.

5. Protect energy like a budget line. Change fatigue compounds. Sequence initiatives. Close loops loudly—what shipped, what didn’t, what we learned, and what we’re stopping. Nothing restores trust faster than a visible stop.

If you’re working on long, messy artifacts (SOWs, release notes, playbooks), try a “table-of-contents first” workflow in your AI tools: feed the transcript or notes, generate a TOC, and confirm section-by-section before expanding. You’ll trade shallow summaries for structured depth and keep everyone aligned as you go.

In the end, change doesn’t fail because people hate new things. It fails because we make the goal fuzzy, the path noisy, and the feedback invisible. Clear the fog, and the coin starts landing your way a lot more often.

Process Debt Truth: Most change fails not from bad ideas, but from unclear games, if people can’t see the hoop, they won’t take the shot.