Why Software Development Teams Fail
The hidden cost of junior-heavy teams, overengineering, and founders playing CTO.
The words I write here are not theory. They're words of failure. Words that echo the pain of bad software I wrote, purchased, or inherited. The fifteen start-ups I watched go up in flames. And the countless founders I watched burn VC cash on the front lawn.
Most people question the process. Is it bad sprints? Do engineers use the wrong coding language? Could it be a bad product roadmap? There are many culprits, but the root cause is the same: weak leadership. Founders playing CTO. Googling their way through architecture. ChatGPT-ing their way to product specs. We let them because they write the checks.
I've spent thirty years watching the industry erode. Here's why teams really fail.
No clear product owner.
Teams fail when we cheapen the process. When gifted amateurs play make-believe. Emboldened by AI. You want failure? Put three people in charge. Let everyone weigh in. Let gifted amateurs steer the UI. You’ll be broke in no time.
One client told me he didn’t need “some T-shirt-wearing geek” telling him how to build. He trusted his gut and burned $1 million guiding a team of junior remote developers. They got halfway. That’s it.
Software isn’t typing. It’s thinking. College CS majors spend 90% of their time learning patterns, not code. Good products need experience, structure, and constraints, not optimism and vibes.
A product role is a bona fide position that commands respect. Many engineers get CS degrees. Note the word "science." These two roles complement each other like a quarterback and a wide receiver.
Teams fail when we confuse curiosity for competence and let AI confidence. When there is no product owner, you are planning to fail.
Overengineering too early.
The best teams start with goals. They iterate, stay small, and build like LEGOs.
Bad teams aim for Google-level scale on Day 1. They choose tools to impress friends, not to help customers.
I took over a project that used four databases, two caching layers, and three languages. It spanned three availability zones. The customer base? Fewer than 200 users.
That’s not architecture. That’s theater.
Great architecture is simple. Easy to understand. The code reads like an essay. Architects recognize that overengineering incurs costs, introduces technical debt, and hinders future opportunities.
Too many tools, not enough outcomes.
A mentor told me that great engineers can take any computer and a text editor to create an elegant program. Consider today's operating systems, which rely on programs from the 1970s. When's the last time TCP changed? How about GREP? SED? AWK? IP?
Cloud providers have menus of choices. AWS has over 1,500 tools to choose from. None of them guarantees an outcome.
Here's why engineers use those tools: their résumés. You pay for tools and training, which feed into their next job opportunity.
To ensure you don't overspend, define tangible outcomes. Focus less on tasks and user stories.
Too many teams work off bloated backlogs and templated user stories.
“As a user, I want to reset my password.”
“As an admin, I want to export a CSV.”
“Build endpoint X so frontend can call Y.”
Tasks. Tickets. Sprint burn-downs. None of them guarantees impact.
Here’s a better way:
“Reduce support tickets by 30%.”
“Shorten onboarding time to under three minutes.”
“Get customers from click to ‘aha’ in one session.”
Those are outcomes. They force alignment. They cut scope. They reveal waste — and kill nice-to-have features before they eat your budget.
When you drive toward outcomes, your engineers think like product owners. They solve. They prioritize. They ship what matters.
Founders trying to be CTOs.
One founder told me, “We should use S3. I talked to an engineer I worked with who uses S3 and MySQL."
The disrespect.
I paused. "What else did he tell you?"
The CEO shared a diagram from images.google.com. "We should do something like this."
He had no way of validating his friend's decisions. He had no clue if he was a subject matter expert. He had worked with a guy before. That was his vetting process.
There is a trend in the industry to dumb down architecture. Boxes, arrows, and triangles in Lucidchart. Anyone can do it, right?
But real builders know the difference.
If you're the founder using Google Images and Slack DMs for architecture, that's not leadership. That’s sabotage.
Industry experts will tell you that building the app is the easy part. Debugging is the skill. The person who safeguards your investment is the one awake at 3 a.m., going through logs. It's not the clown who recommended S3 without any context.
Find a CTO who wields a keyboard like a weapon and can drop the mic on a board call. Then get out of the way.
Junior-heavy team with no compass.
We’ve turned hiring into theater. Speed-typing LeetCode problems like it’s a game show. Junior devs memorize algorithms but struggle to break down real problems. No one’s teaching them how to think in systems. They ship features instead of outcomes. It’s not their fault. It’s the system. But if you stack a team with no compass, don’t be shocked when they paint themselves into a corner at your expense.
Somewhere along the way, we started worshipping cheap. Founders want billion-dollar outcomes on clearance-rack budgets.
One founder I know searched for “affordable” engineers for six months. It never crossed his mind that one high-paid expert could have finished in a third of the time.
It’s like driving 20 miles past every gas station to save a dollar and calling it a strategy.
He still hasn't shipped.
This is why software teams fail.
Not because of bad code. Because of bad judgment. Not because of weak talent. Because of weak leadership, misaligned incentives, and flashy processes that distract from the real work.
Fixing it means hiring people who can think, not just match résumé keywords. It means mentoring to build real skills, not to check a diversity box. It means ending interview games and focusing on what actually drives results.
The future isn’t a fight between humans and AI. The winners will be those who know how to build systems where both work together to solve real-world problems.
Great teams are not an accident. They are built by people who know what failure looks like—and refuse to repeat it.
As a founder, I find this article to be insightful. Understanding that you must trust the years of expertise a CTO has. Just because I write the check, doesn't mean I write the rules. Most of the time the ego is always in the way.