Articles

How Great Software Fails at the Finish Line—And What to Do About It

Christie Pronto
May 2, 2025

How Great Software Fails at the Finish Line—And What to Do About It

You can build the most elegant system in the world. If it falls apart between development and deployment, it fails. Not quietly. Not later. Publicly and painfully.

It’s not a code problem. It’s a trust problem. The cracks aren’t always visible in staging—but once the software is in the hands of users or support teams, those gaps turn into outages, missed revenue, and frustrated staff.

This is where good teams get blindsided. Because finishing the build isn’t the same as finishing the job.

Handoff isn’t a step. It’s a culture. And if that culture isn’t rooted in clarity, shared understanding, and long-term accountability, then the only thing you’re delivering is a delayed crisis.

Here’s where software handoffs fall apart—and what high-trust teams build differently to prevent it.

Why "Done" Doesn’t Mean Deployed

Too many teams treat the last commit as the finish line. It’s not. It’s the start of real-world scrutiny. The moment users interact with the product, the veneer of "it works in staging" fades fast.

A clean build is meaningless if it requires tribal knowledge to run.

This isn’t just a startup problem. 

In 2018, TSB Bank in the UK migrated 1.3 billion records to a new core banking system. On paper, the software was complete. 

But the handoff to deployment had gaping holes: missing access credentials, poor test coverage, and no clear fallbacks. 

Nearly 2 million customers were locked out of accounts for days. Some for weeks. The CEO eventually resigned.

That’s the scale of damage a broken handoff can cause.

But even at smaller scales, the effects are real: delayed onboarding, mounting support tickets, broken team morale, and hidden costs that spiral fast.

Until your system is fully operational in the hands of people who didn’t build it, you’re not done. 

Period.

CrowdStrike cybersecurity software displayed on screen next to the computer blue screen of death with Windows error.

CI/CD That No One Understands Is a Liability, Not a Feature

CI/CD is often framed as the solution to speed and efficiency. But when it’s rolled out without shared understanding, it can become the most opaque and brittle part of your stack.

In 2020, GitHub suffered a major outage triggered by a deployment script with no rollback plan and undocumented behavior. It wasn’t the system that failed—it was the team’s inability to respond. That’s the danger of automation without alignment.

When CI/CD becomes the dev team’s private domain—tuned to their workflow, undocumented, reliant on specific people—it’s not resilient. It’s risky.

Here’s what high-functioning teams build instead:

  • Pipelines that publish to people, not just logs
  • Build stages that align with actual business logic, not engineering shortcuts
  • Alerting that says “here’s what broke and why,” not just “fail”

And most importantly, documentation that makes the system navigable by other roles—QA, ops, client IT staff. 

If the pipeline can’t be understood, it can’t be trusted.

Documentation Isn’t a Bonus. It’s the Product.

Every software project creates two products: the code and the understanding of how to run it.

Most teams obsess over the first and treat the second like an afterthought. And that’s why most handoffs feel like cliff dives.

When a handoff goes well, it’s because someone thought about:

  • What happens when an endpoint fails silently?
  • How is this app monitored after go-live?
  • Where does the documentation actually live (and who owns it)?

This is where Stripe’s research comes into play: $85 billion lost annually due to bad code and worse documentation. 

That’s not a niche issue—it’s a systemic problem across every industry that builds software.

Documentation isn’t about edge cases. It’s about making the system resilient by design. 

A strong handoff means documentation that doesn’t just say what to click, but why it works—and what to do when it doesn’t.

Silence from Stakeholders Isn’t Confidence

The handoff isn’t just technical. It’s interpersonal.

One of the most insidious failure patterns we see is silence. Not angry feedback. Not bug reports. Just... nothing. The people who are supposed to own the system don’t respond. Or worse, they smile and nod and go back to their old tools.

This is what happened with Hertz. 

Accenture delivered the code. But the features didn’t reflect real-world workflows. There was no stakeholder validation during development. 

And when the platform rolled out? 

Total mismatch. And a $32 million lawsuit.

Real stakeholder buy-in isn’t a demo. It’s a co-designed process.

Teams who avoid handoff disasters are the ones who:

  • Identify every role impacted by the product
  • Validate functionality in the hands of non-technical users
  • Iterate before launch, not just after

It’s not about getting buy-in at the end. It’s about never losing it in the first place.

Testing Isn’t QA

In a true handoff, testing isn’t a gatekeeper. It’s a translator.

At Netflix and Etsy, test suites aren’t just regression tools. 

They’re living documentation. They describe how the system should behave—so that future developers, product owners, and even support teams can understand what “good” looks like.

The problem most teams face isn’t bugs—it’s ambiguity. Tests that pass in staging but fail in production environments. Tests that check for output but not for user experience. Tests that are invisible to the people who need to trust them.

Want a better handoff? 

Write tests that:

  • Reflect real user behavior, not just technical input
  • Are named clearly and describe expected context
  • Fail with clarity, not mystery

Testing is how you show—not just tell—that your work is production-ready.

A Real Handoff Doesn’t Disappear

Deployment isn’t the end of the engagement. It’s the start of credibility.

Teams that get this wrong vanish after launch. Issues surface, and all that’s left is a general support inbox or a buried comment in the repo.

But teams that get it right? They stay close. 

They ensure:

  • Someone is watching error logs, not just waiting for support tickets
  • Someone is still answering questions with clarity, not just pointing to confluence
  • Someone is still listening when the end user says, “this doesn’t feel right”

A real handoff includes human presence, not just technical precision. It creates space for feedback. It invites context. 

And it finishes when the software is no longer fragile—not when the invoice is paid.

At Big Pixel, we believe that business is built on transparency and trust. We believe that good software is built the same way.

And the handoff? That’s where those values get tested.

Get it right—and you don’t just ship a product. 

You deliver trust.

This blog post is proudly brought to you by Big Pixel, a 100% U.S. based custom design and software development firm located near the city of Raleigh, NC.

Biz
Dev
Strategy
Christie Pronto
May 2, 2025
Podcasts

How Great Software Fails at the Finish Line—And What to Do About It

Christie Pronto
May 2, 2025

How Great Software Fails at the Finish Line—And What to Do About It

You can build the most elegant system in the world. If it falls apart between development and deployment, it fails. Not quietly. Not later. Publicly and painfully.

It’s not a code problem. It’s a trust problem. The cracks aren’t always visible in staging—but once the software is in the hands of users or support teams, those gaps turn into outages, missed revenue, and frustrated staff.

This is where good teams get blindsided. Because finishing the build isn’t the same as finishing the job.

Handoff isn’t a step. It’s a culture. And if that culture isn’t rooted in clarity, shared understanding, and long-term accountability, then the only thing you’re delivering is a delayed crisis.

Here’s where software handoffs fall apart—and what high-trust teams build differently to prevent it.

Why "Done" Doesn’t Mean Deployed

Too many teams treat the last commit as the finish line. It’s not. It’s the start of real-world scrutiny. The moment users interact with the product, the veneer of "it works in staging" fades fast.

A clean build is meaningless if it requires tribal knowledge to run.

This isn’t just a startup problem. 

In 2018, TSB Bank in the UK migrated 1.3 billion records to a new core banking system. On paper, the software was complete. 

But the handoff to deployment had gaping holes: missing access credentials, poor test coverage, and no clear fallbacks. 

Nearly 2 million customers were locked out of accounts for days. Some for weeks. The CEO eventually resigned.

That’s the scale of damage a broken handoff can cause.

But even at smaller scales, the effects are real: delayed onboarding, mounting support tickets, broken team morale, and hidden costs that spiral fast.

Until your system is fully operational in the hands of people who didn’t build it, you’re not done. 

Period.

CrowdStrike cybersecurity software displayed on screen next to the computer blue screen of death with Windows error.

CI/CD That No One Understands Is a Liability, Not a Feature

CI/CD is often framed as the solution to speed and efficiency. But when it’s rolled out without shared understanding, it can become the most opaque and brittle part of your stack.

In 2020, GitHub suffered a major outage triggered by a deployment script with no rollback plan and undocumented behavior. It wasn’t the system that failed—it was the team’s inability to respond. That’s the danger of automation without alignment.

When CI/CD becomes the dev team’s private domain—tuned to their workflow, undocumented, reliant on specific people—it’s not resilient. It’s risky.

Here’s what high-functioning teams build instead:

  • Pipelines that publish to people, not just logs
  • Build stages that align with actual business logic, not engineering shortcuts
  • Alerting that says “here’s what broke and why,” not just “fail”

And most importantly, documentation that makes the system navigable by other roles—QA, ops, client IT staff. 

If the pipeline can’t be understood, it can’t be trusted.

Documentation Isn’t a Bonus. It’s the Product.

Every software project creates two products: the code and the understanding of how to run it.

Most teams obsess over the first and treat the second like an afterthought. And that’s why most handoffs feel like cliff dives.

When a handoff goes well, it’s because someone thought about:

  • What happens when an endpoint fails silently?
  • How is this app monitored after go-live?
  • Where does the documentation actually live (and who owns it)?

This is where Stripe’s research comes into play: $85 billion lost annually due to bad code and worse documentation. 

That’s not a niche issue—it’s a systemic problem across every industry that builds software.

Documentation isn’t about edge cases. It’s about making the system resilient by design. 

A strong handoff means documentation that doesn’t just say what to click, but why it works—and what to do when it doesn’t.

Silence from Stakeholders Isn’t Confidence

The handoff isn’t just technical. It’s interpersonal.

One of the most insidious failure patterns we see is silence. Not angry feedback. Not bug reports. Just... nothing. The people who are supposed to own the system don’t respond. Or worse, they smile and nod and go back to their old tools.

This is what happened with Hertz. 

Accenture delivered the code. But the features didn’t reflect real-world workflows. There was no stakeholder validation during development. 

And when the platform rolled out? 

Total mismatch. And a $32 million lawsuit.

Real stakeholder buy-in isn’t a demo. It’s a co-designed process.

Teams who avoid handoff disasters are the ones who:

  • Identify every role impacted by the product
  • Validate functionality in the hands of non-technical users
  • Iterate before launch, not just after

It’s not about getting buy-in at the end. It’s about never losing it in the first place.

Testing Isn’t QA

In a true handoff, testing isn’t a gatekeeper. It’s a translator.

At Netflix and Etsy, test suites aren’t just regression tools. 

They’re living documentation. They describe how the system should behave—so that future developers, product owners, and even support teams can understand what “good” looks like.

The problem most teams face isn’t bugs—it’s ambiguity. Tests that pass in staging but fail in production environments. Tests that check for output but not for user experience. Tests that are invisible to the people who need to trust them.

Want a better handoff? 

Write tests that:

  • Reflect real user behavior, not just technical input
  • Are named clearly and describe expected context
  • Fail with clarity, not mystery

Testing is how you show—not just tell—that your work is production-ready.

A Real Handoff Doesn’t Disappear

Deployment isn’t the end of the engagement. It’s the start of credibility.

Teams that get this wrong vanish after launch. Issues surface, and all that’s left is a general support inbox or a buried comment in the repo.

But teams that get it right? They stay close. 

They ensure:

  • Someone is watching error logs, not just waiting for support tickets
  • Someone is still answering questions with clarity, not just pointing to confluence
  • Someone is still listening when the end user says, “this doesn’t feel right”

A real handoff includes human presence, not just technical precision. It creates space for feedback. It invites context. 

And it finishes when the software is no longer fragile—not when the invoice is paid.

At Big Pixel, we believe that business is built on transparency and trust. We believe that good software is built the same way.

And the handoff? That’s where those values get tested.

Get it right—and you don’t just ship a product. 

You deliver trust.

This blog post is proudly brought to you by Big Pixel, a 100% U.S. based custom design and software development firm located near the city of Raleigh, NC.

Our superpower is custom software development that gets it done.