When embarking on a digital transformation, it’s easy to get swept up in the enthusiasm vendors bring to the table. They offer glossy demos, confident digital transformation timelines, and an implementation roadmap that seems simple and straightforward.
But here’s the truth: those timelines are usually wrong.
Not because the software doesn’t work—but because your organization isn’t ready to move that fast. And it’s not your fault. It’s the difference between installing technology and transforming a business.
Vendors Sell Speed. Leaders Must Manage Impact.
Most software vendors have a clear incentive: close the deal, get the implementation started, and move on to the next client. That’s not necessarily a bad thing—they specialize in deploying technology, not managing your business’s internal change journey or building a realistic digital transformation timeline.
So they sell speed.
But what you need is alignment.
When a vendor says, “We can implement this in 90 days,” what they’re really saying is, “We can configure the software in 90 days if everything else is ready.”
But in most organizations, everything else isn’t ready.
You still have:
- Teams using outdated processes with tribal knowledge embedded in spreadsheets.
- Conflicting goals between departments.
- Unclear accountability for process ownership.
- Limited understanding of how the new system will actually change day-to-day work.
And until those things are addressed, even the best software will fail to deliver results.
Technology Changes Fast. People Don’t.
Software can be implemented with a checklist.
People need trust, training, and time.
One of the biggest mistakes leaders make is assuming their people will “figure it out” after go-live. They assume that since the software is intuitive or “industry standard,” adoption will happen organically.
But we’ve seen the opposite happen too often.
- Users avoid the system because they weren’t involved in its design.
- Departments revert to shadow systems because workflows no longer make sense.
- Processes break down because change communication wasn’t clear or consistent.
- Morale takes a hit because people feel unheard and overwhelmed.
And when this happens, the project goes off track—not because of the technology, but because people weren’t ready.
Organizational change management isn’t optional. It’s not a checkbox. It’s a critical driver of success. Without it, your implementation timeline is fiction.
You Can’t Outsource Your Business Knowledge
Vendors can’t build a system that works for your business if you don’t first define what “works” actually looks like.
Too many organizations try to shortcut this process. They assume the vendor will figure it out. But that’s like hiring a construction crew and expecting them to design your house without a blueprint.
You need to do the foundational work:
- Map your current state processes in detail.
- Identify pain points, inefficiencies, and exceptions.
- Define your future state vision—before anyone starts configuring software.
- Engage stakeholders across departments to validate assumptions and priorities.
If you skip these steps, you won’t be able to guide the vendor—or hold them accountable—because you haven’t clarified what you actually need.
And guess what? Most vendors won’t push back. They’ll build whatever you ask for. But if what you asked for doesn’t work for your business, that’s your problem—not theirs.
Respect the Journey: Plan for the Ripples
Digital transformation is not a one-time switch—it’s a ripple effect that touches every corner of your organization. From finance to fulfillment, HR to IT, everyone will feel the change.
Some companies will roll out changes in phased deployments. Others will take a “big bang” approach. Either way, the success of that rollout depends on how well you’ve accounted for all the ripple effects:
- Process changes: Who owns the new processes? Have they been trained?
- Reporting: Do your dashboards and metrics align with your business model?
- Integration: Will your legacy systems still function alongside the new tech?
- Data migration: Are you cleaning, validating, and mapping data properly?
- Governance: Who makes decisions when tradeoffs arise?
If you don’t plan for these impacts, they’ll hit you anyway—just later, more painfully, and more expensively.
The Timeline Illusion: Why It Always Takes Longer Than You Think
There’s a reason Third Stage is often called in to rescue projects that have gone off track.
Nine times out of ten, it’s because someone underestimated the complexity of the business—not the technology.
Think of it this way:
- Software implementation is the easy part (technically).
- Business transformation is the hard part (humanly).
When vendors pitch 3- or 6-month go-lives, they’re talking about software configuration. But true transformation requires deeper effort—redesigning operations, gaining buy-in, testing real-world scenarios, iterating on feedback, managing resistance.
And that can’t be rushed. If you try, you’ll either fail or spend more money fixing what went wrong.
The Bottom Line: You’re Not Behind—You’re Just Being Realistic
Technology will always move faster than your people. That’s not a sign of failure. It’s a sign that you understand what transformation actually means.
Organizations that take the time to build alignment, educate their teams, and clarify their processes consistently outperform those that chase the fastest timeline.
So here’s your challenge:
Don’t fall for the illusion of “quick and easy.”
Build a roadmap that’s grounded in your business—not your vendor’s pitch deck.
Ready to Build a Realistic, Digital Transformation Timeline
At Third Stage, we help organizations plan, lead, and recover digital transformation initiatives with a focus on change leadership, business alignment, and strategic execution.
If you’re starting a transformation—or stuck in one—we’re here to help you move forward smarter.
👉 Get your custom digital transformation strategy today
