When IT roadmaps are often vendor upsell paths

David Zey Gerry Pitt

December 15, 2025

When guidance becomes direction

This series, over the next several months, is dedicated to one theme: discernment.

Technology is deeply embedded in modern business, yet the guidance leaders receive varies widely.

Some recommendations illuminate what is possible, helping organizations navigate complexity with clarity.

Others present themselves as strategy but subtly steer businesses toward predetermined upgrades and licensing commitments.

The language sounds strategic, but the structure behaves transactionally.

This first column in the series explores a pattern many organizations encounter: an IT roadmap that appears to be a long-term strategic plan but is shaped around a vendor’s product sequencing rather than the business’s operational reality.

The goal is not to criticize vendors.

Many solutions they offer are strong and valuable.

Instead, the purpose is to help leaders distinguish between plans built for alignment and plans built for advantage – because that distinction changes not only decisions, but outcomes.

And as is often the case in discernment, the clearest way to illustrate the dynamic is through a story.

How it shows up: A story of looks, sounds and feels

The meeting that moved too quickly

Imagine a business owner named Carol.

Her company is growing, her systems are showing strain and her team is balancing new demands every month.

She invites a well-regarded technology partner to present a long-term roadmap – something she hopes will give her the clarity and pacing she needs.

The partner arrives with a polished deck and a confident tone.

What it looks like: A journey mapped before it’s understood

The presentation opens with a clean, multi-year plan broken into phases labeled with strategic language such as Stabilize, Optimize and Elevate.

The visuals are clear and linear, suggesting inevitability and order.

It feels like a narrative crafted for her situation.

But as Carol studies it, she notices something subtle – each phase corresponds neatly with a specific product tier:

• The first phase requires migration into the vendor’s cloud suite.
• The second consolidates her tools into their communication platform.
• The third introduces automation available only at the premium level.

The roadmap looks strategic, but the progression feels predetermined, like a scenic hike that just happens to pass every gift shop in order.

What it sounds like: Questions with only one direction

As the conversation continues, the questions sound helpful but move only toward one destination:

• “Have you considered centralizing everything into one platform?”
• “The sooner you adopt these modules, the faster you’ll see gains.”
• “If you upgrade to this tier now, you’ll be perfectly positioned for the next step.”

What’s missing is deeper inquiry.

Carol is not being asked about workflow bottlenecks, staffing constraints or operational rhythms. 

She is being guided along a storyline where each chapter ends in a purchase.

It sounds strategic.

It behaves like a sequence.

What it feels like: A subtle tightening of options

Carol doesn’t feel anything negative: no distrust, no hesitation, no resistance.

Instead, she feels something softer but important: narrowing.

The plan feels too linear for a business that rarely moves in straight lines.

The pacing feels fast for an organization still absorbing recent change.

The options feel few, even though no one has said they are limited.

She walked in hoping for clarity.

She walks out sensing the roadmap only works one way.

That quiet awareness is where discernment begins.

The risk: When plans are built on incentives instead of needs

When a vendor roadmap is primarily shaped by product sequencing, the risk is not usually the technology itself.

Many recommended tools are legitimate solutions.

Instead, the risk emerges from misalignment between the vendor’s incentives and the business’s reality.

Misallocated investment

Budget flows toward predetermined purchases instead of toward the areas of greatest operational friction.

Critical issues – such as data quality, team capacity, workflow inconsistencies and training – go under-resourced because they do not correlate with product tiers.

Commitment without clarity

Multi-phase sequences create momentum.

Once Phase 1 is complete, Phase 2 feels natural simply because it is next, not because conditions require it.

Momentum is not strategy.

Reduced flexibility

Vendor-aligned roadmaps often lock organizations into a narrow set of choices.

Switching becomes costly, and adapting becomes difficult.

The roadmap’s structure begins to govern decisions rather than reflect them.

Overbuilt systems

Organizations sometimes adopt advanced toolsets beyond what their teams can absorb. 

Features remain unused, automation goes dormant and complexity grows faster than capability.

A false sense of progress

A formal roadmap can give the impression of transformation even when the underlying plan is not grounded in the realities of staffing, timing, culture or operational constraints.

This gap between perceived movement and real progress is one of the most expensive risks in technology planning.

What is better: A strategy that lets the business set the pace

Let’s return to Carol – this time meeting with a different advisor.

The slide deck looks similar at first glance: clear structure, multi-year view, familiar language. 

But just below the surface, the approach is completely different.

It looks like a plan built around reality

The early slides focus on:

• A candid assessment of current state
• Operational priorities ranked by impact and urgency
• Several pathways, not one
• Constraints, readiness signals and decision gates
• A distinction between necessary steps and optional enhancements

Nothing presumes a specific ecosystem.

Everything reflects the shape of Carol’s world.

It sounds like a conversation, not a funnel

This advisor asks:

• “What decisions are difficult today because of incomplete data?”
• “How quickly can your teams absorb change?”
• “Which internal capabilities do you want to build rather than outsource?”
• “What would success look like one year from now and what might get in the way?”

This is not a tour of features – it is a diagnostic conversation about the business.

It feels like space to think

Carol senses a new kind of roominess with space to weigh options, space to consider pacing, space to decide when not to move forward.

The roadmap gives her choices, not obligations.

Clarity, not compression

Direction, not directionality.

Impact: When strategy creates room to breathe

A genuine roadmap builds capability rather than dependency.

It introduces decision points between phases and moments where the business can reflect, measure and validate before moving ahead.

Each step becomes an opportunity to ensure the organization is ready, teams have absorbed the change and the outcomes justify the next investment.

The pacing is no longer dictated by product release cycles or licensing periods.

It is set by the organization’s rhythms and operational truth.

This approach helps:

• Align spending with measurable outcomes
• Reduce technology risk
• Prevent over-simplification that comes with high cost
• Strengthen internal decision-making
• Grow teams into new systems rather than being pulled through them

This is what strategy feels like when it unfolds at the pace of the business, not the vendor.

When the roadmap reveals itself: How leaders can respond

Recognizing that a vendor’s roadmap reflects the vendor’s perspective more than the business’s needs does not create conflict – it creates clarity with an understanding of what the vendor is well positioned to deliver and what they cannot provide.

Once this distinction is visible, the business can reclaim the role of strategic navigator.

Vendors may excel at implementation and support, but broad strategy requires a wider lens grounded in operational insight, budget pacing, team capability and long-term direction. 

Sometimes that strategic lens comes from internal leadership.

Other times, it is supported by a neutral technical advisor who can interpret options without being anchored to a specific product ecosystem.

Either approach restores direction to the organization itself.

This is also the moment when exploring alternatives becomes essential.

A single delivery path may be operationally efficient for the vendor, but it does not represent the full landscape of possibilities.

Looking at other approaches widens perspective and often reveals entirely different combinations of effort, cost and capability that are possibilities the original roadmap never surfaced.

Underlying all of this is a simple principle: the relationship between complexity and cost.

When a vendor proposes a path that removes all complexity for the business, the cost naturally rises, because the vendor must absorb that complexity.

When the business retains selective complexity in areas where it has strength or ownership, the cost often aligns more directly with return on investment.

With this understanding, leaders can regain control not by rejecting the vendor’s plan, but by placing it among several options and choosing the path that aligns with their organization’s readiness, resources and reality.

Discernment as a strategic advantage

When leaders discover how to distinguish between product-driven roadmaps and strategy-driven planning, the entire decision environment changes.

They invest with intention, pace decisions according to readiness and build a technology foundation that strengthens rather than drives the business.

Discernment is not skepticism.

It is clarity that enables better decisions, healthier partnerships and more sustainable progress. 

It helps ensure that technology is adopted with awareness, shaped by business context and aligned with long-term value.

Again, the purpose of this series is to illuminate patterns that help leaders make wiser choices in a complex and rapidly evolving digital landscape.