In the past, I have written about technical debt not being real and now keep hearing people talk about “leadership debt.” Deferred conversations. Postponed decisions. Organizational shortcuts that accumulate like compounding interest until your team collapses under the weight of it all.
It’s a tidy metaphor. I get why it’s appealing. But I think it’s wrong, and worse—I think it lets us off the hook when it comes to the actual problem.
The Problem With Debt Metaphors
When we call something “debt,” we’re invoking a financial framework that doesn’t actually apply. Real debt has specific characteristics:
- You borrow something tangible today
- You owe a specific amount in the future
- There’s an interest rate you can calculate
- You can pay it off and be done with it
However, you haven’t borrowed anything in reality. You just made a choice—and that choice created consequences.
The debt metaphor suggests that at some future point, you can “pay it off” and return to a clean slate. But that’s not how organizations work. The engineer who watched you avoid hard conversations for two years? They’ve learned something about you. The ambiguous role boundaries? They’ve shaped how people work together, formed habits, created informal power structures. You can’t just write a check and reset to zero.
It’s Actually Decisions
Here’s what actually happens: Every day, you make choices about where to invest your limited time and attention.
You choose to ship the feature instead of addressing the team conflict. That’s not debt—that’s prioritization. Maybe it’s the right call. Maybe the feature matters more than the conflict this week.
You choose to let that hiring bar slip because you need someone now. That’s not debt—that’s a trade-off. You’re betting that having an adequate person now is better than waiting three months for a great one.
You choose not to clarify role boundaries because everyone seems to be figuring it out. That’s not debt—that’s delegation and trust. You’re betting that people will work it out better than you could design it.
These choices aren’t inherently wrong. What’s wrong is pretending they’re temporary loans you can pay back later rather than permanent decisions that change your organization.
The Real Question
When you frame something as “debt,” the question becomes: “How do I pay this off?” But that’s the wrong question because it assumes the problem is quantifiable and reversible.
The better questions are:
What did I choose?
Not what debt did I incur—what actual decision did I make? Did I choose to keep someone on the team who isn’t performing? Did I choose not to provide clear feedback? Did I choose to stay in a meeting instead of having a hard conversation?
What am I choosing now?
Right now, you’re making another choice. You’re choosing whether to address that underperformer today or wait another week. You’re choosing whether to clarify roles or let it remain ambiguous. Every moment is a new choice, not a payment on old debt.
What are the consequences of my choices?
Not “how much interest is accruing”—what is actually happening as a result of my decisions? Is the team less effective? Are people confused? Is trust eroding? These are observable outcomes, not abstract debts.
What choice do I want to make going forward?
This is where you have agency. Not in “paying off” the past, but in choosing differently right now. Want to be someone who has hard conversations quickly? Start having them. Want clearer role boundaries? Define them today.
Why This Matters
The debt metaphor does something insidious: it makes passivity sound financial and prudent. “We’ll address that leadership debt next quarter” sounds so much more reasonable than “I’m choosing not to deal with this problem.”
But that’s what you’re doing. You’re choosing not to deal with it. Own that choice.
Maybe it’s the right choice! Maybe there really are higher priorities. Maybe the team genuinely needs to focus on shipping right now. Fine. But that’s different from telling yourself you’re “accruing debt” that you’ll “pay off later.”
You’re making a bet that the consequences of not addressing this now will be acceptable. Sometimes that bet pays off. Sometimes it doesn’t. But either way, it’s not debt—it’s leadership.
What To Do Instead
Stop asking “What leadership debt do I have?” and start asking “What choices am I making?”
Name the choice explicitly.
“I’m choosing to let this role ambiguity continue because I believe the team is self-organizing effectively” is very different from “I’m accruing organizational debt.” The first forces you to articulate your reasoning and test your assumptions.
Track the consequences, not the debt.
Don’t maintain a mental ledger of “things I should deal with someday.” Instead, notice what’s actually happening. Is the ambiguity causing problems? Are people complaining? Are deadlines slipping? Reality is better feedback than guilt.
Decide again.
You made a choice last month. You can make a different choice today. You’re not paying off debt—you’re steering. Sometimes that means holding steady. Sometimes it means course-correcting hard.
Accept that some consequences are permanent.
That great engineer who left because you didn’t address the toxic teammate? They’re gone. You can’t “pay off” that outcome. You can only choose better going forward and rebuild trust with the people who remain.
How AI Changes Everything (And Nothing)
AI tools and usage are making this tension more acute in two ways:
First, AI accelerates the consequences of your choices.
When your team can ship features 3x faster with AI assistance, that role ambiguity you’re tolerating? It causes 3x more collisions. That underperformer you haven’t addressed? They’re now blocking 3x more work. AI gives you more velocity, which means your organizational choices—good and bad—compound faster.
You can’t outrun dysfunction with better tools. You can only make it more obvious.
Second, AI is forcing new choices you’ve never had to make before.
Should you let junior engineers use AI as a coding copilot, or are you worried they won’t learn fundamentals? Should you require code review for AI-generated code differently than human-written code? What does seniority even mean when a junior engineer with good AI prompting skills can outproduce a senior without them?
These aren’t hypothetical. You’re making these choices right now, whether you realize it or not. When you don’t provide guidance, you’re choosing to let everyone figure it out themselves. When you ban AI tools, you’re choosing to handicap your team versus competitors. When you ignore the question entirely, you’re choosing to let informal norms develop without your input.
The temptation is to frame these as “AI debt we’ll address when things settle down.” But things won’t settle down. AI capabilities are changing monthly. Every week you wait to make clear choices about AI usage, you’re not accruing debt—you’re making a choice to let chaos be your strategy.
Here’s what I’m seeing go wrong:
Leaders who won’t clarify AI usage policies because “it’s all moving so fast.” Meanwhile their teams have wildly different practices—some are using AI for everything, some refuse to touch it, and nobody knows what “good” looks like anymore.
Leaders who haven’t addressed what “junior engineer” means in an AI-assisted world. They’re still hiring and promoting based on pre-AI definitions of productivity while their teams are quietly redefining what value looks like.
Leaders who are choosing not to invest in helping their teams learn AI tools effectively because “people should figure it out themselves.” Then they’re frustrated that some team members are 10x more productive than others, not realizing they created that disparity through inaction.
These aren’t debts you’ll pay off later. These are choices that are reshaping your organization right now. Your best people are learning whether you’re the kind of leader who helps them adapt to new tools or leaves them to sink or swim. Your team culture is forming new norms around AI assistance. Your competitive position is shifting.
The Hard Part
Here’s what makes this uncomfortable: if it’s not debt, you can’t pay it off and be done with it. Every single day, you’re making new choices. You don’t get to a clean slate. You’re always in motion, always creating new consequences, always steering.
The debt metaphor promises eventual resolution. The truth is messier: you’re constantly making imperfect decisions with incomplete information, and some of those decisions will turn out to be wrong, and you’ll have to live with the consequences while also making new decisions. And now AI has accelerated the rate at which your choices compound. You have less time between “that seems manageable” and “this is a crisis.” That’s not debt. That’s just the need for faster leadership.