Why so many smart leaders make bad technology decisions (and how to stop)
People don’t set out to make bad technology decisions. In fact, most of the leaders we work with at Deliver Digital are smart, driven, and deeply committed to building effective, resilient organizations. And yet, almost all of them have found themselves stuck with tech tools that don't work, vendor contracts that underdeliver, and digital investments that somehow fall flat.
Why? Because the way most businesses make technology decisions is broken.
It’s not your fault. But it is your responsibility.
If you’ve ever:
Bought a tool that never got used
Had your team abandon a system three months after implementation
Gotten stuck in contract hell with a vendor you don’t even like anymore
Felt out of your depth in a technical meeting about your own company’s roadmap
…you’re not alone.
This blog will help you understand why this happens and how to change it. Not by learning to code or memorizing acronyms, but by reframing how you think about technology in your business.
The hidden psychology of tech decisions
If you’ve ever made a bad tech choice, it probably didn’t feel like one at the time.
Tech decisions are often made under pressure. You’re growing, you’re losing time, you’re trying to make people’s jobs easier. That urgency can mask the deeper issues behind the decision. Here are some of the psychological traps we see most often:
The illusion of progress: Buying new software feels like doing something. But it’s not progress unless it solves a real problem.
Fear of missing out: You heard your competitor is using a new tool, or your advisor mentioned AI in passing. You don’t want to fall behind.
Sunk cost fallacy: You’ve already spent $120K and six months implementing a system. It would feel wasteful to admit it’s not working, so you keep investing.
Charisma bias: The demo was slick. The salesperson made it sound effortless. But that’s not what your day-to-day use of the tool actually looks like.
These decisions aren’t made out of ignorance. They’re made out of hope. That’s why we take an empathetic, grounded approach to helping our clients make better ones.
What bad tech decisions really cost
When a tech decision goes wrong, the costs run deeper than the invoice. Yes, there are the obvious things: wasted spend on unused licenses. Time lost chasing fixes. Additional consultants brought in to troubleshoot.
But then there’s the less visible damage:
Loss of trust in leadership ("why are we doing this again?")
Morale hits when tools slow people down
Workarounds that become shadow processes
At the Calgary Chamber of Commerce, leadership knew something wasn’t clicking. Their IT systems were technically operational, but didn’t align with their evolving vision. What they needed wasn’t just better tools—it was clarity and momentum. By uncovering overlapping vendor contracts, addressing a CRM backlog, and identifying underused systems, the Chamber’s team was able to restore confidence in their tech strategy and shift IT from a cost center to a catalyst for progress.
The most common tech traps
If any of these sound familiar, take a breath. You’re in good company.
Buying before benchmarking. Found a tool you love? Great. But is it right for your needs, at your scale?
Treating IT as a support function. IT shouldn’t just "support operations." It should drive business strategy.
Making decisions in silos. If your ops team chooses a tool without consulting your finance team (or your end users), you're going to have a problem.
Prioritizing features over fit. Just because a platform can do something doesn’t mean it’ll do it well for your context.
Choosing tools that your team doesn't want. Adoption is everything. If your people won’t use it, it doesn’t matter how powerful it is.
What better looks like
Instead of starting with tools, organizations that succeed at scale begin with alignment—clarifying the real goals, mapping the vendor landscape, and identifying where systems are helping or holding them back.
Take Navacord, one of Canada’s largest insurance brokerages. Their rapid growth through acquisitions left them with a decentralized tech stack and disconnected teams. What they needed wasn’t just a CRM—it was a shared understanding of what “standardization” actually looked like across the business.
Through executive alignment sessions and a comprehensive technology discovery, Navacord clarified its future state and created a path to get there. Their leadership teams collaborated to eliminate redundancies, save costs, and build a governance structure that could scale. With the right partners in place, they moved from reactive IT to a proactive, business-aligned strategy.
In both cases, Navacord and the Calgary Chamber, it wasn’t the technology that changed everything. It was the people, their leadership, and their willingness to chart a new path. Our role was simply to meet them where they were, help them see clearly, and support their journey with tools and strategy that actually worked for their context.
Five ways to make better tech decisions right now
Here’s how to stop the cycle and lead more confidently:
Start with outcomes, not features. What are you trying to achieve? Build from that, not from what’s trending.
Talk to your people. Ask your team what slows them down. They know where the friction is.
Get visibility on your vendor ecosystem. You can’t optimize what you don’t understand.
Challenge your biases. Are you buying because it’s the best fit? Or because it feels safest, coolest, or most familiar?
Partner with people who meet you where you are. You don’t need a Big Four binder full of theory and a junior person to execute blindly. You need clarity, confidence, and action from trusted partners.
You’re not alone (and you’re not behind)
The pace of change in technology is overwhelming. But you don’t have to chase every trend or fear every gap. You just need a better way to make decisions.
If you’re ready to cut through the noise, choose better tech, and build systems that truly support your team and goals—there are partners who can help you get there. Reach out to us today.
Bonus: FAQ
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Because they often work with incomplete information, cognitive biases (like sunk cost fallacy or FOMO), and sometimes without a clear technology-business alignment strategy. This isn’t about intelligence; it’s about the process for selection.
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Beyond wasted money, poor tech decisions erode trust, lower morale, and often create hidden inefficiencies that scale with your business.
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Start by asking: Do they understand our business goals? If the answer is no — or if they only talk features, not outcomes — it’s a red flag.
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Not necessarily. Popular tools aren’t always the best fit. The right choice depends on your internal processes, team, and long-term vision.
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Gain visibility. Map your current vendors, tools, and systems. Identify overlaps, underused platforms, and areas of friction. That’s exactly where we start at Deliver Digital.
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No. You just need a better framework — and the right partner to guide you. That’s where we come in.