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How to stop issues from accruing by avoiding conflict.
Leadership debt refers to the ongoing cost of old mindsets, behaviors, and delayed decisions that lead to lasting problems in organizations, much like technical debt in software.
While the symptoms of leadership debt are universal, they might show up as:
- Delayed feedback
- Unresolved tension
- Accepting mediocrity
- Avoiding directness to seem “nice.”
Like technical debt, leadership debt compounds and, over time, erodes trust, weakens team culture, and undermines execution. So how can leaders work to avoid this scenario?
Why do leaders accumulate leadership debt?
Leadership debt isn’t brought on maliciously; most leaders have good intentions with their actions. Difficult conversations aren’t an easy skill to master, and leaders will avoid them for a myriad of reasons, including;
- Discomfort aversion: It is usually uncomfortable to say the truth. I once delayed a project because it felt awkward to confront fellow developers who were nearly my peers. I ended up doing most of the work, which almost led to burnout.
- Lack of conflict literacy: Many leaders hesitate to give feedback because they are ill-equipped to resolve conflicts that arise.
- Internalized beliefs: Many leaders hold onto comforting but harmful thoughts, like “people deserve space to grow.” These ideas begin as empathy but turn into excuses to avoid action.
- Cultural incentives to avoid friction: In some organizations, harmony is valued more than honesty. This makes leaders worry that sharing tough truths will make them appear “negative” or “difficult to work with.” A senior executive may commend a manager for smooth meetings and good morale, but might not realise that the calm is due to hidden dissent and emotional fatigue.
- Leadership immaturity: Some leaders fear being disliked. They choose popularity and approval over true alignment. Others prioritize shallow peace over clarity.
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The true cost of leadership debt
Emotional cost
Unresolved tension builds up as leadership anxiety, and can lead to emotional outbursts. For example, you might notice irritability in meetings, passive-aggressive emails, or a sharp tone that disrupts the team. As a result, retention and productivity may suffer.
I’ve learned that the fastest way to release emotional tension is an honest conversation. My approach to communication is a four-step framework.
- Be honest: I like to start with the question “Should I be honest?” It mentally prepares the other party for the conversation.
- Voice your opinion empathetically: There is no need to be harsh or use abusive words. Say the truth kindly. Then invite them with “What can you say about this?”
- Listen effectively to the other party’s concerns: Don’t be dismissive of their pain points. Make them feel seen.
- Extend grace: Give actionable points, but also give them time to process the difficulty.
Cultural cost
When leadership debt accumulates, employees begin to avoid telling the truth. High performers disengage, and low performers stay protected, which diminishes company productivity. A well-documented example is that of Away’s co-founder, Steph Korey. Former employees publicly complained of verbal abuse, intense pressure, and unrealistic demands under her leadership. Although she later apologized, the leadership approach left a lasting imprint on the company’s internal culture. Many employees also copied her bad behavior.
Cultural debt is harder to see, but its repayment starts with feedback.
How I love to give feedback:
- Start positively: “I appreciate your thoughtful approach. It means you think outside the box.”
- Include the negative feedback: “I think the animations are unnecessary here. This is an emergency platform, so users value speed and clarity.”
- Tell them what could be better: “However, this approach would be better for speed or performance.”
- Don’t forget to drop a timeline: “Can you fix this by Friday?”
- Sprinkle more positivity: “You did well, overall. Good job.”
Feedback is the lifeblood of a high-functioning team, and it should go both ways. Unfortunately, many leaders only give, but never seek feedback.
You can make it a monthly or quarterly ritual to ask your employees or juniors for feedback. A closed paper form or a face-to-face meeting will do that effectively.
A simple question like, “Tell me what you don’t like about my leadership style, or what do you think will make our team better?” can point you towards what needs to be addressed.
While there are many advantages to this approach, it is best suited to catching potential conflicts early. For example, if feedback unearths a disagreement between two team members, hold a meeting. Let each person share their views without interruption. Then, help them find a solution that works for both.
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Operational cost
Leadership debt increases the day-to-day cost of running a business by allowing avoidable problems to compound. When leaders skip code reviews or delay fixing known bugs, it creates problems. Teams have to work around these issues instead of solving them. Over time, this slows delivery, increases rework, and creates frustration across engineering and product teams. These patterns often appear as technical debt. However, the core issues are operational: unclear priorities, postponed accountability, and quick decisions made by leadership.
One way to offset these costs is to schedule periodic technical audits. These audits work by forcing leadership to revisit earlier decisions and understand compromises that could affect daily operations. For example, shortcuts made when releasing a minimum viable product (MVP) may be necessary at the time. Still, if they are never addressed, they can create extra work and slow down the company’s day-to-day operations.
Strategic cost
This refers to the long-term impact of leadership debt on an organization’s direction, growth, or market position. A notable example comes from Eric Schmidt, then CEO of Google. He admitted that he saw the threat from Facebook and LinkedIn. He even wrote memos about it, but didn’t give it enough attention. Schmidt kept his attention on Google’s daily operations. As a result, he overlooked crucial strategic conversations about the growing threat, and the company missed market opportunities.
Strategic debt represents the most expensive layer, and you can only pay it down through foresight. Foresight means leaders anticipate future challenges, identify emerging opportunities, and make decisions that prevent small problems from escalating into larger setbacks. Leaders must first tackle emotional, cultural, and operational issues. If these problems remain unresolved, they can cloud priorities and decision-making. For instance, if a team is discouraged by unresolved conflicts or unclear roles, a leader might miss an opportunity to act on a market threat, even if they see it.
Leaders should start by stabilizing daily operations and team dynamics. This builds clarity and capacity. With these in place, they can make proactive decisions that help protect the company’s strategic position.
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Final thoughts
Paying back leadership debt doesn’t mean ramping up hostile arguments and losing kindness at work. It means we need to express hard truths with care. This involves speaking with empathy, giving and seeking feedback, addressing operational inefficiencies early, and making proactive strategic decisions.
