Before You Change Your Tech Stack: A Field Guide for Leaders

By Katie Burkhart, Emma Davis, Bob Harvey, and Mike Zucker

Introduction

If you’ve ever been in a meeting where someone says, “We need a new tool for that,” you’re not alone.

Businesses often turn to new technology as a shortcut to better performance. But more often than not, the problem isn’t the tool. It’s unclear processes, misaligned goals, or the hope that software can solve what strategy has not.

Four leaders in four different fields — marketing, sales, operations, and strategy — came together to share what they’ve learned from guiding organizations through the messy business of choosing, implementing, and measuring technology. What follows is a practical guide to rethinking your tech stack, and doing it for the right reasons.

Step 1: Identify the Real Need

Don’t mistake discomfort for a tech problem.

Many companies change their tech stack not because they’re ready to grow, but because they’re frustrated — with a clunky process, outdated tools, or inconsistent results. But as Mike puts it, “Technology ≠ transformation.”

Operational issues almost always start with people and process. If you can’t clearly map how a workflow functions, where it breaks down, or what outcomes it’s meant to achieve, no amount of automation will fix it. In fact, layering new tech on top of weak foundations can make things worse and add confusion, not clarity.

Katie reframes the question entirely:

“Organizations asking, ‘Should we change our tech stack?’ are starting in the wrong place. Instead ask, ‘What do we do? What could be done better and what does “better” look like?’ and then, ‘Are different tools the most effective way to get there? If so, why?’”

Emma adds that the best signal for change isn’t frustration — it’s readiness.

“You’re ready for a change when you have clear processes in place and are ready to scale them — beware the hope that paying for a tool will buy functional process.”

If you’re paying for a platform and can’t articulate the problem it solves or the value it adds, that’s a sign something’s off. But it might not mean you need new software; it might mean you need better clarity about your operations.

Ask yourself:

• Can we define the problem this tool is meant to solve in one sentence?

• Do we have the process documented and owned?

• Would optimizing that process, rather than changing tools, fix 80% of our pain?

Step 2: Evaluate Tech Stack Options Through the Right Lens

A tool should fit your problem, not your wish list.

Once you’ve clarified the need, resist the urge to chase features. Katie cautions that “more features doesn’t mean better – in fact, it often just means overwhelm.” Instead, look for flexibility: something that fits your current state but can evolve with you as you grow.

For Emma, accessibility and usability are non-negotiable.

“We’re a small organization. I don’t want to pay for admins to run my tools for me. I want software my team can figure out and solid support when we need it.”

Cost matters too, not as the only criterion, but as a test of realism. “If you’re gambling your entire margin on a piece of software to solve your problems,” she says, “you need to go back to the drawing board.”

Mike takes a systems approach. He evaluates whether the underlying problem could be solved through process redesign before adding more tech.

His checklist includes:

• Can existing tools be better configured?

• Is this scalable and compatible with our current ecosystem?

• What is the total cost of ownership, including integration, training, and support?

• Does the vendor have a track record of keeping the product updated and improving it over time, or will it be outdated before we finish implementation?

Meanwhile, Bob encourages teams to stay strategic.

“In sales, AI is rewriting how we sell. But the winners don’t chase tools; they use strategy → objectives → tactics as a loop. If a tool doesn’t serve the strategy or advance your objectives, it’s just noise.”

A simple but powerful method is Emma’s evaluation matrix:

The goal isn’t to find the shiniest tool. It’s to find the one that best supports your specific goals, processes, and people.

Step 3: Secure Buy-In and Align Stakeholders

People, not platforms, determine success.

Even the right tool will fail if the wrong people are excluded.

Mike has learned that adoption resistance often starts at the top:

“Too many initiatives are driven by what someone overheard at a conference rather than by internal discovery. When executives bypass input from real users, they create systems that don’t fit the work.”

He advocates for early engagement of key influencers and end users, not just during rollout but during the discovery process itself.

Emma agrees and adds a critical point about incentives:

“If the people critical to implementation aren’t the ones who benefit from the tool, you need to make it worth their while to participate. Show how it helps them, directly or indirectly.”

That alignment work pays dividends later when the project hits friction. The CFO cares about cost efficiency; the marketing team cares about usability; IT cares about security. Everyone needs a clear connection to the “why.”

Katie recommends making trade-offs transparent:

“Show your work. Let people see what was prioritized and why. When people see how their feedback shaped the decision, even if their preferred tool wasn’t chosen, they’re more likely to support the outcome.”

Bob brings it down to a frontline truth:

“Salespeople adopt when they see WIFM — What’s In It For Me. Show them how the tool helps them win more deals, close faster, or reduce friction, and you’ll see adoption soar.”

Alignment doesn’t happen by accident. It’s designed, communicated, and reinforced.

Step 4: Implement Without Chaos

Map the process before turning the switch.

Most implementation failures aren’t technical; they’re human. Teams underestimate the disruption, skip proper onboarding, or assume everyone will “figure it out.”

Mike emphasizes mapping the future-state process before any rollout:

“Define roles, handoffs, and data flows first. Make sure people understand what will change and why.”

Emma adds that teams need protected time to explore the tool together:

“Don’t just give people logins and say, ‘good luck.’ Hold a workshop where the team can poke around, review resources, and ask questions together. Learning is faster  and stickier when it’s shared.”

Bob stresses the importance of a champion — a respected peer who models the right behavior, answers questions, and removes friction.

Implementation should never be an afterthought. It’s where strategy meets reality.

Step 5: Measure What Matters

Define success before you start, not after.

Too often, teams declare victory once the new tool is live. But adoption isn’t success; outcomes are.

Mike: “You can’t measure improvement without a baseline. Establish what success looks like before implementation, whether that’s reduced error rates, faster onboarding, or higher productivity.”

Emma: “Tie it back to your original goal. If you implemented a CRM, has your close rate improved? If it’s a project management tool, are fewer tasks slipping through the cracks? If it’s about employee pain points, do they actually feel things have improved?”

Bob: “Measure what matters: execution metrics like cycle time, forecast accuracy, or rep productivity. Review them regularly, and use the data to reinforce impact.”

Katie: “Sometimes, you don’t know until you try. Set rules for when to pause or abandon implementation. That prevents sunk-cost thinking from keeping you trapped in a tool that doesn’t deliver.”

The point of measurement isn’t to prove you made the right call, but to ensure you’re getting closer to the outcomes you defined at the start.

Lessons Learned

Across every discipline, a few truths emerge:

• If the process is unclear, tech accelerates the chaos. – Mike

• Start simple, stay focused, and appoint a clear owner. – Emma

• Tools don’t fix weak strategy; they amplify it. – Bob

• Ask better questions before buying what you think is a magic wand. – Katie

Technology is a multiplier. It magnifies whatever you already have — good or bad. If your processes are strong, your people aligned, and your goals clear, the right tools can help you scale faster and smarter. But if those foundations are shaky, even the best software will only make the cracks show sooner.

Conclusion

Changing your tech stack is one of the most expensive and visible decisions a business can make. But it’s rarely about the tech itself.

The smartest leaders treat technology as an enabler, not a savior. They start with clarity of purpose, align people early, design the process before implementation, and measure what matters most.

Before you buy, pause and ask:

• "Why are we really considering upgrading our tech?"

• "Are we improving our ability to do the work and deliver value, or just increasing the noise?"

• "Are we fixing a problem, or just upgrading our chaos?"

Contributors

The authors are members of the Greater Providence Trusted Advisor Group, a mutually chosen group of experts with a shared passion for helping businesses thrive by providing best-in-class services and support.

Emma Davis — CEO, Working Planet Marketing Group A data-driven marketing leader who believes clear processes, measurable impact, and a healthy dose of pragmatism beat “shiny object” decisions every time.

Find Emma here: workingplanet.com | linkedin.com/in/emmapdavis

Mike Zucker — Managing Partner at BizNav Partners and Fractional Executive  A systems-minded operator with decades of experience turning chaos into clarity. Motto: “Process before platform.”

Find Mike here: linkedin.com/in/mzucker36

Bob Harvey — Fractional Sr. VP Sales, Sales XcelerationSpecializes in building agile, AI-ready sales organizations. Focused on measurable revenue outcomes and the people who drive them.

Find Bob here: salesxceleration.com | linkedin.com/in/bob-harvey-233b0b6

Katie Burkhart — Founder and Lead Strategic Facilitator of Point:Value Known for helping companies ask better upstream questions and build tools that serve strategy — not distract from it.

Find Katie here: pointvalue.co | linkedin.com/in/katharineburkhart