One Skill That Will Save Your Next Digital Transformation: Ask Better Questions
I’ve been around enough technology rollouts to know the feeling in the pit of your stomach when things start to unravel. The project kicks off with high hopes, the vendor promises the moon and the executives declare it “mission critical.”
But then reality sets in.
The tech doesn’t perform as promised. Adoption lags. Workarounds pile up. And the field reverts to spreadsheets, sticky notes and side texts. Six months later, the software is collecting dust and the team is back to square one.
If I’m being honest, I’ve lived this story more times than I care to admit, both inside construction companies and as part of the technology vendors trying to serve them. But the hard truth is this: most of those failures weren’t caused by bad software.
They were caused by bad questions.
The Harsh Truth on Digital Transformation Failure
The statistics are sobering. Around 70% of digital transformation initiatives fail to meet their intended objectives (McKinsey, Enate). In fact, some studies paint an even bleaker picture in that 84% fail completely (WWT) while 88% of business transformations fall short of their original ambitions (Bain & Company).
In construction specifically, the gap between promise and reality is especially wide. New BIM platforms, predictive analytics or project management systems get piloted with great fanfare but end up abandoned or half-used. Often though, the problem isn’t that the technology doesn’t work. It’s that the evaluation process was rushed, shallow or handled by the wrong people.
An Underrated Skill: Asking Good Questions
I’m big into podcasts and recently I caught a really good one by Craig Groeschel. On one episode of his leadership podcast, Craig dropped a truth bomb that applies perfectly here:
“The one who talks the most learns the least.”
Leaders often feel pressure to have the answers, but Craig flips the script. The most effective leaders don’t succeed because they know more, they succeed because they learn more. And they learn more by asking better questions.
He calls it full-contact, immersive listening. Not just nodding politely and waiting for your turn to speak but leaning in, being fully present and refusing to rush to the solution. The longer you’ve been leading, the harder this becomes. Experience can trick you into thinking you’ve heard it all before and real leadership requires curiosity.
But there’s more. Craig goes on to explain that the most valuable insights rarely come from the first question. The first answer is usually surface level. The second is expected. But the third? That’s when the truth comes out. That’s when people finally trust you enough to tell you what’s really going on.
And here’s his challenge: you can’t get Level Three learning with Level One questions. If all you ask are shallow, checklist-style questions, you’ll get shallow answers. But if you press deeper, you uncover insights that change outcomes.
This isn’t just a leadership lesson. It’s a digital transformation survival strategy.
Applying Better Questions to Tech Evaluation
When I look back on the digital transformations that worked versus the ones that failed, there’s one common thread: the conversations that got deeper ended up driving change. The ones that stayed shallow died in the field.
Here’s what that looks like in practice through my key takeaways from Craig:
To Get Better Answers, Ask Better Questions
I once sat through a tech evaluation where the team proudly checked boxes on a feature sheet. “Does it integrate with scheduling?” Check. “Does it handle submittals?” Check. Two months later, the software was deployed and six years later it still wasn’t adopted. Why? Because no one had asked the right questions.
The better questions would have been: How does this platform connect to our scheduling tool? How does it adapt as we grow into new project types? What workflows will it simplify and for whom?
Feature checklists tell you what software can do. Better questions reveal what it can change. Great tech conversations aren’t about capabilities, they’re about outcomes.
Full Contact Immersive Listening
Some of the best tech insights we ever got didn’t come from a glossy demo. They came from dusty boots and hard hats. I’ll never forget shadowing a superintendent who, halfway through explaining his daily routine, muttered: “Half my day is wasted chasing down which app to use.” That didn’t show up in a requirements document. That came from listening in the field as frustrations spilled out in real time.
Leaders evaluating new platforms can’t afford to sit in isolation. Ride-alongs, jobsite visits and one-on-one listening sessions reveal truths that no sales deck ever will.
You learn more in an hour on-site than a month of polished vendor pitches.
The More You Do, the Harder This Gets
Here’s the uncomfortable truth: the longer you’ve been around digital transformations, the more likely you are to think you already know the answers (me too). An executive walks into a room, hears two minutes of complaints and finishes the objection for the team. That mindset kills transformation.
The leaders who succeed approach evaluations with beginner’s humility. They ask as if they don’t know, even when they think they do. They’re curious enough to probe deeper, patient enough to listen longer and humble enough to admit they might be wrong.
In construction, experience is a strength. But in digital transformation, assuming you’ve “seen it all” can blind you to what’s really needed today.
The Gold is in Question Three
As Craig said, surface-level questions get surface-level answers. I once watched a project engineer get asked, “Do you like the current system?” He shrugged and said, “Not really.” End of conversation. How do you dig deeper? Like this:
Q1: Do you like the current system?
Q2: Why not?
Q3: What does that frustration actually cost you in lost time, missed data or workarounds?
That third question is where the real gold hides. It turns a complaint into a measurable problem. And measurable problems are solvable.
You Won’t Get Level Three Learning with Level One Questions
Too many evaluators stop at Level One questions: “Can it log change orders?” Sure, most systems can. That’s the shallow end.
Level Two digs a little deeper: “How fast can we process them?” That’s efficiency, but it still isn’t transformation.
Level Three is where the real insight lies: “How does this platform help us prevent the root causes of change orders in the first place?” Now we’re not just processing problems faster, we’re eliminating them before they start.
That’s the difference between adding software and leading transformation.
You Can Beat the Statistic
Here’s your challenge: don’t let your next digital transformation be a statistic. Instead of rolling out another tool, start with better questions. Listen. Ask and ask again. Make sure the tech serves the team and not the other way around.
You’ve got the edge now. You’ve seen the numbers. You know the gaps. So, let’s build a new norm: one where transformations succeed because we asked the right way, led the right way and listened the right way.
Get to your third question today and let that be the spark that makes the next project the one that finally sticks.
Construction is cool, tell your friends!