What Technology Leaders Get Wrong About Strategy

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Why roadmaps, tools, and transformation plans aren’t strategy; and what good really looks like.

This is the second edition of Enable Great Conversations - a series unpacking the leadership challenges behind technology decisions, exploring how clarity and confidence can be built through open conversation and experience.

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"We've got a strategy - here's our roadmap" is a phrase I’ve heard on lots of occasions from technology leaders. I've seen beautifully crafted documents filled with timelines, project names, and vendor logos. The slides are polished, the roadmaps colour-coded, the graphics reassuringly professional…

Except a roadmap isn't a strategy.

A roadmap tells you what you plan to build, not why it matters. It's a project plan dressed up in strategic language - and the confusion between the two is costing organisations hugely.

The Activity Trap

I've seen it regularly over the years: polished presentations showing comprehensive platform migrations, new analytics tools, and broad digital transformation programmes. The timelines stretch for 18 months or more, the budgets often hit six figures, and the business cases promise efficiency gains and "future-readiness."

It looks impressive. It feels comprehensive. But what it represents is what I've come to call the activity trap - the dangerous assumption that motion equals momentum. Teams stay busy, budgets get spent, and systems get upgraded. When the dust settles however, the fundamental question remains unanswered: how does any of this create sustainable competitive advantage?

Motion ≠ Momentum.

The problem isn't that these activities are wrong, it's that they're disconnected from strategic intent. They emerge from vendor conversations, competitor benchmarking, or internal pressure to "do something with technology" - not a clear understanding of how technology should serve the organisation's future or improve the user experience for employees and clients alike.

Why Leaders Fall Into the Trap

The confusion between activity and strategy isn't accidental. There are reasons that even capable leaders drift into this pattern.

First: visibility. Projects are tangible. A new platform launch, service release, or system upgrade provides clear evidence of progress. Strategy, by contrast, is about framing and trade-offs - harder to picture in a board presentation.

Second: external pressure. Boards want "the technology strategy" document. Investors ask about "digital transformation plans." Leaders respond by packaging their roadmaps up as strategy, when those documents should flow from strategic thinking, not replace it.

Third: the comfort of detail. It's easier to discuss features, timelines, and vendor comparisons than it is to confront harder questions about capability, risk, and competitive positioning. Detail feels concrete; strategy can feel abstract.

The result is that you can find yourself mistaking ‘busyness’ for direction. They spend heavily on technology, but struggle to articulate why it matters or whether it's working.

The Hidden Damage of Bad Strategy

When strategy gets reduced to roadmaps, the consequences compound over time.

Misalignment becomes endemic. Technology decisions get made in isolation from business context. Systems multiply, platforms proliferate, and integration becomes a nightmare… not because of poor execution, but because there was no coherent framework guiding those choices in the first place.

Credibility erodes; and leaders lose trust with boards who see technology as a cost centre rather than a capability builder. Teams lose confidence in direction when priorities shift with each quarterly review. Stakeholders start viewing technology investment as necessary overhead rather than competitive advantage.

Perhaps most damagingly, organisations develop strategic short-sightedness. Teams become locked into quarterly delivery cycles, unable to step back and see the bigger picture… By the time you realise there’s a problem, you’re playing catch-up with competitors who framed their technology choices more thoughtfully from the start.

So What Does Good Look Like?

Technology Strategy is the set of choices that determine how technology enables your organisation's future. It's not about what you're building - it's about why it matters and how it fits together.

Great technology leaders anchor every decision in business vision. Don't start with tools or vendors, start with the operating model, growth priorities, organisational culture, and customer need. Ask: “what do our technology capabilities need to be in order for our business strategy to succeed?”

Set principles, not just projects. Instead of managing an endless backlog of requests, define the foundational values. "We optimise for speed over customisation." "We avoid vendor lock-in wherever possible." "We invest in resilience as a differentiator, not to tick a compliance box." These principles guide the daily-to-day micro-decisions that never make it to the executive team.

Make compromises visible. Good leaders don't pretend you can have everything. They bring clarity by showing what you gain, and what you lose, with individual choices. They help the business to understand that choosing cloud-native architecture means accepting initial complexity for long-term flexibility, or that standardising on fewer vendors means giving up some features in exchange for better integration.

Most importantly, build capabilities not just deliverables. Roadmaps end. Features get removed. Vendors get acquired. Capabilities endure, and strategic leaders frame investments as capability-building exercises that compound over time - rather than project completions that need constant renewal.

The Leadership Gap Nobody Talks About

Not every organisation has someone in the CIO or CTO position who can do this work.

Sometimes there's an operationally-focused IT lead holding the strategic pen. Sometimes a vendor fills the gap, writing a "strategy" that conveniently aligns with their product suite. Sometimes a well-meaning leader delivers a plan that looks impressive in PowerPoint, but misses the fundamentals of strategic thinking - or misunderstands the technology completely.

This highlights a common misconception of technology leadership: strategy requires experience, perspective, and independence. It's not about writing the slickest presentation or knowing the latest buzzwords. It's about asking and answering the questions that shape your organisation's future:

• What will technology give us that we don't have today - in terms of capability, not features?
• What will it cost us, not just in budget, but in risk, flexibility, and opportunity?
• What role does technology play in the story we're telling our board, our investors, our customers, and our own people about where we're heading?

These aren't questions you can answer by looking at a roadmap. They demand leadership - and not every organisation has access to that leadership internally… So how do you bridge the gap?

The Strategic Conversation Your Organisation Needs

For many organisations (especially smaller ones, or those in transition), the answer isn't necessarily hiring a permanent strategic technology leader. It's ensuring that someone with the right experience and independence is asking the right questions.

This is where external perspective becomes invaluable - not to outsource decision-making, but to sharpen it. A good advisor doesn't arrive with pre-packaged solutions, they help frame the questions that matter, test assumptions that haven't been challenged, and highlight blind spots that internal teams might miss.

They provide access to strategic thinking without the overhead of a full-time hire. They ensure technology choices get evaluated independently of vendor marketing or internal politics. Most importantly, they create a bridge between business strategy and technology execution - ensuring the two actually align.

For organisations trying to scale, attract investment, or professionalise their operations, this isn't a luxury. It's often the difference between owning technology decisions and being able to genuinely lead and influence them.

Questions That Reveal the Truth

If you're wondering whether your organisation's technology strategy is really that, then ask these questions:

• Can we explain our technology strategy without naming a specific tool, vendor, or platform?
• Does our roadmap show how technology enables our business model, or just the projects that are scheduled next?
• When we make technology decisions, do we understand the trade-offs we're accepting?
• Who in our organisation is responsible for defining the principles and direction - not just managing delivery?

If the answers make you uncomfortable, that's not a failure. It's valuable information! It suggests that what you have is activity masquerading as strategy… and recognising that is the first step towards something better.

The Bottom Line

The best technology leaders I’ve worked with resist the temptation to equate motion with progress. They step back from the project noise and focus on the bigger picture. They build clarity to the areas where technology creates advantage, the trade-offs they're willing to make, and how their actions turn investment into lasting capability.

They understand that strategy isn't about having all the answers; it's about asking better questions, making conscious choices, and ensuring that those choices compound over time into sustainable, competitive advantage.

Strategy isn’t about having all the answers. It’s about asking better questions.

Most importantly, they recognise that in a world where every organisation is becoming a technology organisation, strategic technology leadership isn't optional anymore. It's the difference between technology as a cost centre, and technology as a competitive weapon.

The question isn't whether your organisation needs technology strategy.

The question is whether you're getting it, or whether you’re just getting busier.

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Enable Great Conversations

The best decisions don't happen in isolation. They happen in conversation - with trusted peers, experienced advisors, and teams who know what it’s really like.

That's what Enable Great Conversations is about: a series exploring the real moments – the ambiguous ones, the uncomfortable ones, the ones that don’t fit neatly in a playbook - where leadership is tested, and clarity is found. Each release aims to capture a single insight, decision, or challenge that helps move organisations from noise to clarity.

There are many more of these moments worth unpacking and we’ll continue to explore them in the weeks and months ahead. We hope you’ll follow along, or join the conversation in the comments below, or follow along via the Enable Great page.

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This article was originally posted on LinkedIn. You can read and comment on it here.