Managing Technical Debt in Software Modernisation

I was a CTO at a company with a LOT of technical debt. Here's how I handled it. 1. I found someone in the org (non-exec) who cared about the issue and was organized. 2. We created a framework to rank our tech debt & built a common mini "language" to talk about it easily. 3. Next we documented the entire tech ecosystem & applied the framework to categorize it all. 4. We met with business stakeholders like Product & Sales to add their perspective into the ranking. 5. We grouped the tech debt into a) never touch, b) fix ASAP and c) fix incrementally. 6. We calculated the potential ROI on each item to help acquire funding to fix it. (This was difficult). 7. We built a plan for remediation and integrated the plan into the roadmap. 8. We created a tracking / monitoring best practice specifically for the tech debt remediation work. 9. We were pretty hardcore about reporting the ROI up to the CEO on all the tech debt fix work. 10. After a while of doing this tech debt remediation got baked into our organization. What's the big lesson? Anything can be done in an org if its important enough, you focus on it and you work hard to achieve it. Interesting in more content like this? Sign up for my free newsletter at https://buff.ly/4ccyrM0. #TechLeadership #softwaredevelopment #CTO

𝗧𝗵𝗲 𝗦𝗲𝗰𝗿𝗲𝘁 𝗞𝗶𝗹𝗹𝗲𝗿 𝗜𝗻𝘀𝗶𝗱𝗲 𝗬𝗼𝘂𝗿 𝗖𝗼𝗱𝗲𝗯𝗮𝘀𝗲: 𝗛𝗶𝗱𝗱𝗲𝗻 𝗧𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗗𝗲𝗯𝘁 Most teams feel technical debt. Very few teams can see it early enough to act. Mike Godfrey shares how loveholidays uses static analysis (CodeScene) as an early-warning system for technical debt, not as vanity metrics. What I like about this: it’s basically cybernetics for software delivery: sensors → signals → feedback → control actions. 𝗪𝗵𝗮𝘁 𝘁𝗵𝗲 “𝘀𝗲𝗻𝘀𝗼𝗿𝘀” 𝗿𝗲𝘃𝗲𝗮𝗹: - Hotspots: where change and effort concentrate (your real pressure points) - Change coupling: files that keep changing together → hidden dependencies - Knowledge distribution (bus factor): where knowledge is lost or stuck in "islands" - Team–code alignment (Conway’s Law): overlap often signals unclear ownership 𝗪𝗵𝗲𝗿𝗲 𝗶𝘁 𝗴𝗲𝘁𝘀 𝗿𝗲𝗮𝗹: They integrate it into the workflow with branch analysis, so PRs can be flagged/blocked when code health declines. That’s a closed feedback loop, not a dashboard. If you want sustainable speed, this is the game: Make technical debt observable, actionable, and governed by clear guardrails. Especially now in the age of AI. #TechnicalDebt #StaticAnalysis #CodeHealth #PlatformEngineering #DevOps

Your PM just spent 45 minutes in 2026 planning making the case for critical tech debt. They had everything: Last quarter's three production outages. Customer complaints about reports timing out. That security vulnerability that made the CISO lose sleep. Even showed how fixing this would save 200 engineering hours next year. The CEO listens politely. Then: "This sounds important, but can it wait? We really need that enterprise feature to close the xyz deal." Tech debt loses. Again. When you try to trade infrastructure work against revenue features one by one, infrastructure loses every single time. Revenue is tangible now. Technical risk is abstract future. In our recent Supra 2026 planning session, Rich Mironov shared an effective approach to scope tech debt. He doesn't fight feature by feature. He negotiates the entire portfolio upfront. His breakdown: ↳ ~50% on customer-facing features (stuff they ask for by name) ↳ ~35% on "keeping executives out of jail" tech debt (compliance, security, scalability)   ↳ ~10% on executive escalations (the random fires from sales) ↳ ~5-10% on innovation/discovery That second bucket; Rich literally calls it "keeping you from being arrested" work. When executives push back, he gets specific: - "Remember last month when the site went down during the customer conference and you had to apologize on stage?" - "Remember when the board grilled you for 20 minutes about why our main competitor's app loads 10x faster?" - "Want to explain to investors why we had to pause new customer onboarding because our database is melting?" Now they're listening. What makes this work is that you negotiate this percentage once at the start of the year. Not every sprint. Not every quarter. After that, that 40% is sacred. Someone wants to raid it for their pet feature? "We agreed that not getting sued or having the site explode was worth 40% of our capacity. Let's discuss in our next board meeting to ensure everyone is ok with the change." No more justifying individual infrastructure projects. No more death by a thousand "but can't this wait?" conversations. The portfolio is approved. The percentage is locked. I've watched too many product leaders burn out trying to defend every single piece of infrastructure work. Meanwhile, the technical debt compounds until something catastrophic happens, and suddenly it's "why didn't anyone warn us?" + the product leader is on the hook for the consequences. Rich's model flips the whole thing. Instead of begging for permission to keep the lights on, you're protecting executives from explaining to the board why everything caught fire.

"We'll clean Salesforce up later." Those five words cost companies millions. McKinsey found something brutal: 10-20% of every IT budget vanishes into technical debt. Gone! Burned on decisions made two years ago when someone said "just ship it." Here's the math on your Salesforce investment. $500K annual spend? You're throwing away $100K fixing yesterday's shortcuts. Team of 5 developers? One person exists solely to put out fires. That quick hack from Q1? It's consuming 40% of your Q4 budget right now. Stripe studied this. Developers spend 42% of their time wrestling with technical debt instead of building features. Nearly half their capacity locked in maintenance mode. The compound interest destroys budgets: Year 1: Hard-code a value, save 10 minutes Year 2: System breaks, 20 hours to diagnose, $3K in emergency consultant fees Year 3: Complete rebuild required, $25K project cost CAST Software proved technical debt grows at 15-20% annually when ignored. That's worse than credit card interest. The biggest debt creators in Salesforce: -Hard-coded values fail 35% of the time when systems change. -Undocumented automations take 3x longer to fix. -Duplicate processes create conflicting logic 60% of the time. -Bypassed validation rules cost an average $50K in data cleanup. Gartner predicts by this year that organizations will spend 40% more fixing than building. The solution exists. -Track your debt. -Budget 20% of dev time for cleanup. -Document everything obsessively. -Build right once instead of rebuilding twice. Smart organizations manage technical debt like financial debt. They track it, reduce it systematically, and refuse to accumulate more. Everyone else pays 20% interest on three-year-old decisions. Which approach does your team take?

The biggest threat to innovation? It’s not lack of talent. It’s not lack of funding. It’s technical debt. The reality: Every time an employee waits for a slow system to load, that’s lost productivity. Every time a business relies on outdated tools, that’s missed revenue. Every time IT has to patch instead of innovate, that’s stalled transformation. And the worst part? The longer you ignore it, the more expensive it becomes. How it happens: Enterprise leaders unknowingly accumulate technical debt when they: Delay critical system upgrades to “save costs” Patch legacy systems instead of modernizing them Ignore architectural debt while chasing short-term wins The result? A fragile, inefficient IT landscape that increases risk and makes transformation exponentially harder. The fix: ✅ Treat technical debt like financial debt → Proactively measure, manage, and reduce it. ✅ Invest in enterprise architecture → A strategic roadmap reduces redundant systems and optimizes total cost of ownership (TCO). ✅ Align IT and business strategy → Every IT dollar should drive measurable business outcomes. Real-world impact: At one of the global manufacturing companies I worked with, we faced overwhelming technical debt—multiple ERP systems, siloed applications, and legacy infrastructure slowing down operations. By implementing an enterprise-wide modernization strategy, we: ✔ Cut IT costs by 34% ✔ Eliminated redundant applications ✔ Freed up resources for true innovation Because technical debt isn’t just an IT challenge—it’s a business priority. The question isn’t whether you have technical debt—it’s whether you’re actively managing it. The sooner you address it, the less it will cost you. P.S. What’s the biggest challenge in addressing technical debt—cost, leadership buy-in, or execution? Drop your thoughts in the comments. And if you need help tackling it, let’s connect.

Tech debt isn't a technology problem. Most companies treat tech debt as an IT issue. That's why 56% say it's blocking new investment. Recent KPMG research surveyed 648 US tech leaders. ·      56% say tech debt prevents new investment ·      50% cite talent gaps as the primary barrier ·      40% experience weekly IT disruptions from legacy systems These look like three separate problems, but it is one failure in capital allocation showing up in three places. Breaking the cycle requires a shift in framing: 1. Connect debt to what it's actually blocking ERP not providing real-time financial visibility is working capital trapped in manual cycles. CRM/CPQ not providing pipeline clarity and win/loss insight impacts forecast accuracy and deal velocity. Data architecture not standardized across systems means analytics teams spend more time reconciling than analyzing. Instead of cataloging technical debt, quantify the strategic drag. 2. Prioritize by what delay actually costs Opportunity cost: What revenue isn't being captured because systems can't scale? Risk cost: What's the exposure when compliance gaps become audit findings? Competitive cost: How much faster are competitors moving without legacy constraints? Instead of the loudest noise, focus on fixing what unlocks enterprise value. 3. Anchor before you propel Before layering AI/ML on top, stabilize the foundation. Core systems. Data architecture. Security baselines. Not because it's leading practice. Because unstable foundations make innovation exponentially more expensive. The real question is capital allocation: Do we invest now to remove what's blocking growth? Or do we fund innovation that our infrastructure can't support? The companies breaking out of the 56% are connecting tech decisions to growth, margin, and competitive position. Tech debt stays debt when it is managed like a technology problem. It becomes a strategy when it is treated like a capital allocation decision. #Leadership #EnterpriseValue #AnchorMoatPropel #TechStrategy

You’re an engineering leader, a staff+ engineer, or a product owner who sees the cost of technical debt every day. But when you try to advocate for time to fix it, execs either nod vaguely or change the subject. You’re not wrong—you’re just not being heard. Here’s why that happens: When you say "tech debt," they hear "not urgent." When you say "refactor," they hear "money pit." When you say "architecture," they hear "someone else’s problem." But the reality is: Tech debt slows down your ability to ship new features. It increases the risk of outages or missed SLAs. It silently drives away your best engineers. So how do you make them care? I coach engineering and product leaders on how to frame technical priorities in business language—so they get the time, resources, and executive backing they need. Here’s the approach: Tie tech debt to business risk or cost: "This feature now takes 3x longer to ship because of X." Use executive language: Talk time-to-market, reliability, developer retention—not code quality. Frame it as an investment: "Fixing this sets us up for velocity in Q3." Make tradeoffs visible: "If we don’t fix this now, we’ll miss Y opportunity." Track real pain: Show data on cycle time, error rates, or turnover. Don’t wait for permission. If your leadership still sees tech debt as an engineering problem, it’s time to change the story you’re telling. This is where I come in. I help technical leaders communicate with power—bridging the gap between strategy and systems. Whether through coaching or fractional partnership, let’s get your org moving faster and smarter. #technicalleadership #engineeringmanagement #productstrategy #executivecommunication #startupgrowth

🧹 The Great Org Cleanup – Battling Salesforce Technical Debt Over time, Salesforce orgs tend to accumulate tech debt — unused fields, outdated automations, redundant code, and legacy workflows. It’s not just a developer problem anymore—admins, architects, and consultants all feel the drag as agility and performance suffer. In extreme cases, orgs become so unwieldy that companies consider starting over from scratch, though many experts caution that remediation is usually more prudent . ✅ Here's a practical cleanup roadmap I’ve been exploring: Audit your org – catalog custom fields, automations, code APIs, page layouts. Create a data dictionary for tracking usage and purpose, then flag components (<15% usage) that could be deprecated. Allocate cleanup time – dedicate ~10‑25% of each sprint or release cycle to technical debt reduction. Use cleanup tools like Elements.cloud or Metazoa Snapshot to detect stale assets, show dependencies, and even automate safe deletions. Build governance practices – ensure cleanup is ongoing; establish metadata reviews, documentation, and architecture oversight . 🔄 Your turn: How much technical debt is lurking in your org? Do you regularly incorporate cleanup cycles into your development process? Have you reached a point where rebuilding seemed the best option—or did you cleanup instead? Let’s compare experiences and best practices—share your tech debt nightmares and cleanup wins below!

Today, the world of tech startups is fast-paced, ‘technical debt’ is an inevitable companion, yet one that’s often misunderstood. 🛠️ Technical debt refers to the extra development work that arises when code that is easy to implement in the short run is used instead of applying the best overall solution. In the blockchain-driven telecom sector, this can mean shortcuts taken today might hinder scalability and innovation tomorrow. Here’s my blueprint for transforming technical debt from a looming threat into a manageable aspect of your growth strategy: ⚒ Understanding the trade-offs: Recognise that some technical debt is the result of strategic decisions to accelerate development. Identifying and understanding these trade-offs is the first step in managing them effectively. ⚒ Embrace refactoring: Make refactoring—a process of restructuring existing code without changing its external behaviour—a regular practice. This not only addresses technical debt but also improves your system’s adaptability and performance. ⚒ Promote code reviews: Implement a culture where code reviews are standard practice. This collective scrutiny helps catch potential debts early, ensuring higher code quality and shared ownership of the codebase. ⚒ Leverage automated testing: Automated tests can serve as a safety net, helping you catch issues before they become entrenched. This is particularly crucial in blockchain applications where security and reliability are paramount. ⚒ Maintain a debt inventory: Keep a running inventory of known debts and their potential impacts. This ‘debt ledger’ becomes a vital tool in prioritising which debts to address based on their impact on your project. ⚒ Continuous education: Foster an environment of learning where your team understands the implications of technical debt and is equipped with the latest practices to minimise it. Surfing the technical debt is to strike a balance between innovation speed and system integrity. For blockchain ventures in the telecom arena, managing this debt is critical to sustaining growth and ensuring that today’s shortcuts don’t become tomorrow’s roadblocks. #technicaldebt #blockchain #innovations

The older a platform gets, the harder it becomes to evolve. Not because it’s inherently better or worse but because of the layers of decisions, trade-offs, and expansions built up over time. Enterprise platforms in banking, fintech, and insurance aren't designed all at once. They’ve been expanded and modified for years, even decades. Add mergers & acquisitions into the mix, and suddenly, you're stitching together multiple systems, each with its own history and logic. The result? Technical debt. Most people think of technical debt as purely a bad thing. But in reality, technical debt isn’t a curse, it’s a tool. I’ve seen this firsthand working with hundreds of financial firms over 20 years. Technical debt (when used strategically) allows companies to move fast, delivering value before every piece of the system is perfect. But when ignored, it compounds, making innovation harder, slower, and riskier. So how do companies balance moving fast while managing technical debt? 1️⃣ Recognize that technical debt isn’t just a problem, it’s a strategic decision. 2️⃣ Build with awareness: technical debt is a tool, but only if it is managed responsibly (just like financial debt). 3️⃣ Align engineering and business teams so one isn’t slamming the brakes while the other floors the gas. 4️⃣ Modernize responsibly: replace what’s necessary, refactor what’s valuable, and don’t treat legacy systems as obstacles, but as histories of past decisions. If your Fintech is in need of an upgrade, the team at Praxent is here to help.