Leadership + teams + the space between
Mark Twain allegedly said it best:
"It's not what you don't know that gets you into trouble. It's what you know for certain that just ain't so."
Nobody puts that quote on a motivational poster about digital transformation, and they should.
The leaders I see struggling most right now with transformations (digital or otherwise) aren't the ones who don't understand technology but the ones who understand their business so well, who have been so right for so long about how it works, that the idea of doing it differently feels less like an opportunity and more like an accusation.
The "way we've always done it" is usually the sediment of a hundred good decisions made over years by people who built something that's achieved success. That context deserves respect. It also cannot be the reason an organization stays exactly where it is while everything around it moves.
Working with a senior leadership team earlier this week, I was reminded that what we know for certain looks completely different depending on where we're standing.
The people closest to a decision understood it because they made it based on hundreds of inputs they received.
What became clear is that being close to a decision and being equipped to carry it forward are two entirely different things, and the distance between them rarely gets the attention it deserves.
Most leaders are taught to share the why behind a decision, which is important. What matters just as much, and happens far less often, is sharing how the decision was made, even at a very high level, this conversation is useful. The reasoning that was weighed, the options that were considered and set aside, the risk that was accepted deliberately rather than by accident. This is especially useful for a new leadership team coming together.
When the people responsible for translating a decision understand the thinking behind it, not just the conclusion, they develop something that no implementation plan can give them. They develop the judgement to make the next decision themselves, with confidence, without needing to bring it back up the chain.
When certainty stays at the top and the thinking behind it doesn't travel, the rest of the organization is left to execute on conclusions without the context that made them make sense.
With that in mind, digital transformation has been a hot topic in a lot of the rooms I've been in lately, so I'd like to invite you, collectively, into one room I'm fortunate enough to help curate.
Scott Snowden, John Pehler, Rob Manne and I are in the final month of preparation for the Digital Momentum Summit in Toronto on June 2, based around one central question: how can forward-looking businesses create sustainable digital transformation without feeling like the ground is crumbling beneath them?
The day is built on proven strategies, real-world implementation stories, and an honest look at when, why and how the decisions were made to move toward digital transformation plus the ecosystems and conditions that made those transformations actually stick rather than stall.
I'm thrilled to speak with Derek Johnson, COO of Welke, to bring one of those stories in person. As a family business operating since 1985, navigating what it genuinely means to modernize without dismantling what took decades to build. The kind of story that sticks with you because it sounds a little like yours.
Come learn from Derek and many other speakers going through the process of digital transformation on June 2nd, walk away with learnings, tactics and tools you can use. Better yet, bring your team so you're all learning together... it'll make implementation that much easier!
As a thank you for being a loyal reader, please use code VENNED at registration to get your ticket. Full details at dxmomentum.com.
Don't be the subject of a 100-year-old Mark Twain quote. See you on June 2,
Kendra
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