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The Value of Experimentation in Digital Transformation

Brian Kennedy

Brian Kennedy

Strategic Execution Partner · 16 September 2026 · 2 min read

Most digital transformations don't work. McKinsey's numbers have sat under 30% success for well over a decade. That's not a typo.

Here's the part that actually explains it: a separate McKinsey study found a quarter of companies say their biggest blocker isn't the tech. It's a culture that's scared to experiment.

Why "big bang" transformations flop

  • You build the whole thing before testing if anyone actually wants it
  • Getting something wrong feels like a career risk, so nobody flags it early
  • The big calls get made once, months out, by people who never touch the product
  • By the time it's obviously broken, you're too deep in to turn back

What actually works instead

  • Small bets before big ones
  • Decide what "success" looks like before you test, not after
  • Let people kill bad ideas without it being a black mark against them
  • Weeks between an idea and real feedback, not months
  • Test the two or three things that could actually sink you, first

None of this is complicated. It's just uncomfortable, which is exactly why most companies talk about it more than they do it.

Where this fits with SMART Execution

This is the Evidence phase, basically: prove it small before you bet big. Skip straight from planning to building and you're the sub-30% stat. Build in a real checkpoint and you're not.

I've watched well-funded transformations die because nobody would test the idea small first. I've also watched scrappy, "too small to matter" pilots turn into the thing that actually worked, because the evidence was allowed to change the plan.

Planning a transformation? Book a free call and let's talk about where the real risk is.

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