By Lisa Goldenthal, Top 15 Executive Coach & Creator of The BOSS Method™
Rolling out new technology is a lot like starting a diet in December.
The excitement is real. The commitment? Questionable.
At first, everyone’s nodding on the kickoff call like, Yes, this is the future!
By week three, half the team’s whispering, Can’t we just go back to Excel?
I’ve seen this in billion-dollar companies and fast-scaling startups alike. The biggest failure point isn’t bugs, funding, or talent.
It’s forgetting that humans run the tech — not the other way around.
👉 According to McKinsey, 70% of digital transformations fail — not because of poor technology, but because of people factors like fear, unclear communication, and lack of trust.
If you want your 2025 rollout to finish strong and set you up to dominate 2026, start here:
1️⃣ Focusing Only on Features, Not Feelings
Tech doesn’t fail because of bugs. It fails because of brains.
People don’t fear new tools — they fear looking incompetent using them.
💡 Pro Tip: Launch the “why” before the “how.”
Simon Sinek said it best — people don’t buy what you do, they buy why you do it.
2️⃣ Assuming Everyone Learns at the Same Pace
Treating everyone like a tech pro is like giving everyone the same weights at the gym. Someone’s going to pull a muscle.
💡 Pro Tip: Create tiered learning paths. Pair fast adopters with slower learners. Make curiosity the team currency.
3️⃣ Skipping Early Wins
Waiting for Phase 3 to celebrate? By then, your team’s emotionally checked out.
💡 Pro Tip: Celebrate micro-wins in week one — even if it’s just, “We logged in successfully!”
4️⃣ Ignoring Feedback Loops
Silence isn’t satisfaction. It’s disengagement.
💡 Pro Tip: After each rollout phase, ask:
What’s working?
What’s confusing?
What’s missing?
5️⃣ Overloading Teams With Too Many Tools
Adding five platforms in one year? Congrats — you’ve just built chaos at scale.
💡 Pro Tip: Limit major changes to three at a time. Simplify before you optimize.
6️⃣ Underestimating Cultural Resistance
Peter Drucker said it best: Culture eats strategy for breakfast.
And it chews up your tech rollouts for lunch.
💡 Pro Tip: Build a culture of experimentation before you introduce innovation.
7️⃣ Forgetting to Model the Behavior
If the CEO doesn’t use it, no one will.
💡 Pro Tip: Publicly model the behavior. Lead with action.
8️⃣ Not Aligning Tech to Tangible Goals
If your people can’t see how this connects to revenue or retention, they won’t care.
💡 Pro Tip: Tie every tool to a clear outcome. Clarity fuels adoption.
9️⃣ Punishing Mistakes Instead of Rewarding Experimentation
If trying something new gets you punished, no one experiments again.
💡 Pro Tip: Celebrate bravery over perfection. Progress requires permission to fail.
🔟 Overlooking Communication
“The single biggest problem in communication is the illusion that it has taken place.” — George Bernard Shaw
💡 Pro Tip: Over-communicate success stories, progress, and appreciation. Transparency builds momentum.
THE GOLDEN THREAD
Technology doesn’t fail because of bugs.
It fails because of brains, culture, and communication.
Change isn’t about forcing adoption — it’s about building confidence.
And when your people feel safe to learn, they’ll surprise you with how fast they grow.
🚀 Question for You: Are you managing technology — or leading transformation?
🔥WANT TO GO DEEPER?
Want to make your team fearless through change?
Reply with “FEARLESS” or DM me on LinkedIn, and I’ll send you my private Leadership Energy Loop™ — the system I use to help CEOs turn chaos into confidence and transformation into traction.
Let’s finish 2025 strong — and start 2026 unstoppable.
— Lisa
#Leadership #ChangeManagement #HighPerformanceTeams #EmotionalIntelligence #DigitalTransformation #BOSSMethod #CategoryOfOne