Tech Debt is a Leadership Problem

Why Technical Debt Starts in the Boardroom

When your codebase reflects your strategy… and not in a good way.

“Over time, cruft builds up… you can’t add features at the same pace. It’s like running in molasses.” - Martin Fowler

Let’s clear something up right now: technical debt is not a developer problem. It’s a leadership problem. And more specifically, it’s often a strategic leadership problem.

Because what looks like bad code or neglected infrastructure is usually the visible residue of rushed decisions, delayed investments, poor prioritisation, or - let’s be honest - an executive team that hasn’t thought deeply about how technology actually enables the business.

In most boardrooms, tech debt is treated like plumbing. You only talk about it when it breaks.

And when it does, the assumption is someone in engineering let it slip. But more often, the root cause sits much higher up the stack.

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Strategic Debt, Not Just Technical Debt

Strategic clarity means recognising the compromises that are already shaping your outcomes.

Every time your team cuts a corner to hit an arbitrary deadline, every time you defer a platform upgrade to squeeze in “one more feature,” you’re making a trade-off. And trade-offs are strategic choices.

But here’s the issue: many organisations make these decisions unconsciously. There’s no explicit risk discussion. No board-level dialogue on the cost of delaying platform investment. No mechanism to track where technical shortcuts were taken and why. Just a mounting pile of “we’ll fix it later.”

Tech debt is not the result of bad engineers. It’s the result of leadership creating an environment where short-term wins always beat long-term resilience.

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Tactical, Accidental, and Strategic Tech Debt

Not all tech debt is created equal. Ward Cunningham first coined the metaphor to describe learning - building the wrong thing while you’re figuring out the right thing. That’s natural. And often, necessary.

But what we see in most enterprises isn’t learning debt. It’s negligence debt.

Let’s break it down:

• Tactical Tech Debt – Intentional shortcuts, taken for delivery speed. Fine, if accompanied by a repayment plan.

• Accidental Tech Debt – Comes from inexperience, poor documentation, or organisational silos. Leadership problem: where’s the capability investment?

• Strategic Tech Debt – Deferred investment that was known, discussed, and accepted. This is the only form that’s healthy—if it’s owned.

Only one kind of tech debt is healthy - and only if it’s owned by leadership.

So… who in your exec team owns it?

(And no, saying “Engineering” doesn’t count. That’s like blaming Finance when Sales overpromises.)

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Tech Debt Compounds Like Interest - But Without the Upside

Mik Kersten’s Flow Framework puts it well: the cost of delay in tech is exponential. Small inefficiencies today become blockers tomorrow. Your feature lead time balloons. Talent attrition rises. Confidence drops.

According to McKinsey, companies report that 20–40% of their technology budgets are consumed by tech debt. That’s not technical. That’s financial.

Imagine walking into the CFO’s office and asking, “What if 40% of our budget was tied up in waste?”

You’d get a reaction.

But when it’s buried in slow releases, broken pipelines, and developer turnover - it’s invisible. Until it’s not.

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Platform Teams Aren’t Overhead - They’re Multipliers

Every feature team is only as fast as their handoff. Invest in the team behind the team.

Ignore them, and you’re not just losing speed—you’re losing the race.

One of the most common symptoms of strategic tech debt is the underinvestment in platform or enablement teams. These teams don’t ship features - but they accelerate every team that does.

Ignore them, and you’re effectively taxing every squad for infrastructure and tooling work that should have been centralised. You're duplicating effort. You're burning morale. You’re dragging velocity back to the stone age.

And then someone suggests hiring more teams. Because clearly, the problem is capacity.

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Fixing It Starts at the Top

If you’re in the boardroom, this is your problem to own. Here’s what that means in practice:

1. Track Tech Debt Like Any Other Risk – It’s not “invisible.” It’s just unacknowledged. Ask your CTO for a debt register—not as punishment, but as insight.

2. Fund Capabilities, Not Just Projects – Agile without platform teams is performance theatre. Support the enablers. Bake platform investment into the portfolio.

3. Make Trade-offs Visible – Don’t allow invisible debt. Ask: what are we delaying by doing this now? And what’s the cost of delay on what we’re not doing?

4. Ask Better Questions – “How quickly can we ship?” is fine. But also ask, “How sustainable is our delivery engine?”

5. Connect Strategy to Systems – If you don’t understand the system dynamics behind your delivery, you’re flying blind. Encourage shared language between business and tech.

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Final Thought

Technical debt isn’t just a codebase issue. It’s a signal.

A signal that your strategy may be too reactive.

That your teams are overextended.

That your investments are short-sighted.

And perhaps most of all:That no one at the top is truly accountable for the health of the system.

You can’t fix that with a Jira ticket.

But you can fix it - with leadership.