The Technology Debt You Can't See

---

Why the most dangerous debt isn't in your infrastructure: it's in your boardroom

This is the fourth 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.

When technology leaders talk about debt, they usually mean the technical kind: outdated infrastructure, poorly integrated systems, rushed implementations that need rebuilding etc. These are real problems that create real costs - slower operations, higher maintenance, and reduced agility.

However, in my experience the more dangerous debt isn't always technical. It's often leadership debt; the accumulated cost of delayed decisions, avoided choices, and lack of strategic clarity. The kind that isn’t always as easy to refactor your way out of.

---

What Leadership Debt Looks Like

Leadership debt doesn't announce itself with error messages or system crashes. It builds quietly between decisions and shows up in patterns that organisations often mistake for other problems.

It reveals itself in a host of different ways. I've seen it in organisations that refuse to rationalise their platform sprawl because no one wants to "own" the decision to sunset a tool that someone fought hard to implement. I’ve also seen it evident when leaders say "yes" to every priority instead of making the harder choice about what truly matters most.

It can appear when governance gets ignored until compliance becomes urgent - and expensive - or when vendors are allowed to define your "strategy" because challenging their assumptions requires energy or expertise that feels scarce.

I've seen organisations where teams focus more on maintaining tools than innovating with them, with the technology estate ultimately becoming a museum of past decisions vs. a platform for future growth. This happens when leadership fails to establish criteria for what stays and what goes.

Perhaps most tellingly, when vendors end up driving the roadmap more than the business does, leadership debt is almost always involved. Without internal clarity about direction, external voices naturally fill the vacuum.

These aren't dramatic failures. They're quiet compromises that feel reasonable in the moment but compound over time. Ultimately small decisions in the moment, but with the same outcome: decisions avoided today to become constraints tomorrow.

Why Leaders Fall Into This Trap

Leadership debt isn't created by incompetence. It's often the result of well-intentioned approaches that optimise for the wrong things.

Many organisations reward speed over clarity - the leader who acts quickly gets praised, while the one who pauses to think gets questioned (see our earlier post: “What Great Leadership Looks Like When The Answer Isn’t Obvious"), but action without direction creates more problems than it solves.

There's also the challenge of wanting to be seen as enabling rather than blocking. Leaders don't want to be the one who says "no" to seemingly reasonable requests. But when everything becomes a priority, nothing actually is.

I've noticed over the years that many leaders simply haven't been through enough cycles to see how unmade decisions ripple forward.

The result? Small compromises that feel pragmatic but create strategic drift.

The Compound Problem

Just like technical debt, leadership debt doesn't stay contained. It spreads and multiplies.

Consider a scenario where the leadership team avoids making hard choices about system integration. Teams work around the complexity by building point-to-point solutions. Data becomes fragmented, reporting becomes unreliable, and decision-making slows as people question which numbers to trust.

Meanwhile, the original integration decision gets harder to make, not easier. More systems are now involved. More teams have workarounds to protect. More stakeholders have opinions about what should happen.

What started as deferred decision-making becomes a web of dependencies that's expensive and risky to untangle.

The costs aren't just operational. Leadership debt erodes confidence - in priorities, in direction, and ultimately in the leadership itself. Teams stop trusting that decisions will stick, boards lose faith in the technology direction, and investors find themselves questioning whether the organisation can execute on its strategy.

Repaying Leadership Debt

The route out of leadership debt isn't about better project management or more efficient processes. It's about clearer thinking and braver decision-making.

The first step is to establish principles that can guide choices. Not abstract values that sound good in presentations, but practical filters that help teams say "yes" to the right things and "no" to the wrong ones.

As an example, "We optimise for integration over features" is a principle that can guide platform decisions. Similarly, "We build capability, not projects" can shape the way success gets measured.

Being explicit about trade-offs is important. Each "yes" often means "no" to something else. Making those choices visible helps teams understand why certain paths were chosen, and why others weren't.

I've found that investing time in alignment pays dividends.

When teams, leaders, and stakeholders see coherence in the technology story, confidence builds. People start to trust that decisions will stick, and that direction will hold.

Sometimes bringing in external perspective helps identify blind spots that they've developed. Fresh eyes can identify where leadership debt has accumulated and provide a platform for suggesting approaches that address it.

Unlike technical debt where you can throw resources at the problem, leadership debt requires a change to the way decisions get made. That means changing behaviour, questioning assumptions, and often admitting that past approaches weren't working... It's uncomfortable, it's slow, and it requires commitment across teams and stakeholders.

The Deeper Reality

What's interesting about leadership debt is where it originates. Technical debt begins when organisations take shortcuts under pressure - implementing systems quickly without proper integration, choosing expedient solutions over sustainable ones. Leadership debt begins when decision makers take shortcuts under the same pressure.

The temptation is similar: defer the hard decision now, deal with the consequences later. But while technical debt creates maintenance burden, leadership debt creates strategic drift. This is much harder to correct.

The organisations that succeed over time are the ones where leadership debt gets recognised and addressed before it becomes institutionalised. They understand that clarity isn't optional, it's the foundation that everything else builds on.

The Leadership Challenge

This creates an uncomfortable question for leaders: How much of your technology challenge is actually a leadership challenge?

• If your teams are struggling with integration complexity, is that really a technical problem? Or the result of avoiding hard decisions about platform rationalisation?
• If your AI initiatives aren't gaining traction, is that about the technology? Or is it because there was never a clear definition of what success should look like?
• If your technology spend feels out of control, is that a procurement issue? Or is it what happens when spending decisions aren't anchored in strategic principles?

The most expensive technology debt often starts in the meeting room…

Moving Forward

Recognising leadership debt is the first step in addressing it, but recognition alone isn't enough - it requires the discipline to make harder choices and the courage to hold them over time.

The organisations that build sustainable technology advantage are the ones where leaders create clarity rather than deferring it. Where principles guide decisions rather than politics, and where strategy shapes technology rather than the other way around.

In the end, the quality of your technology outcomes is largely determined by the quality of your leadership decisions... and those decisions drive simplicity in execution, or they accumulate debt.

The question for every leader is simple: are you making choices that create clarity, or are you deferring costs that will come back with compound interest?

That's a debt worth paying attention to.

---

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.

---

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