01→
What's your name?
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02→
What's your email?
We'll only use it to share results and follow up if you'd like.
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03→
What's your role?
A
CTO / VP EngineeringYou own the roadmap and the technical debt.
B
Engineering Manager / Tech LeadYou feel the pain most directly on your team.
C
Senior / Staff EngineerYou're probably the one who has to touch it.
D
Software EngineerYou've been warned not to touch certain files.
E
OtherProduct, founder, consultant, or curious bystander.
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04→
How old is your oldest production system still in active use?
A
Under 5 yearsGrowing pains, not legacy debt. Yet.
B
5–10 yearsStarting to accumulate the wrong kind of character.
C
10–15 yearsIn the danger zone, dependencies are going EOL.
D
15–20 yearsA veteran of multiple reorg cycles and CTO changes.
E
20+ yearsIt predates most of the team. Possibly the company.
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05→
What language is it written in?
A
Java / KotlinPre-Spring Boot, probably. EJBs lurking somewhere.
B
Python 2 / older PythonStill running on a server nobody wants to restart.
C
PHPThe kind that went straight from idea to prod with no framework.
D
Ruby / RailsUnmaintained gems, Rails 3, and vibes.
E
COBOL / Fortran / CYou are the protagonist of a cautionary talk at every conf.
F
Something elseJavaScript soup, .NET Framework, or a language that no longer exists.
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06→
How many engineers in your team can confidently modify it?
Think of your most critical legacy system.
A
0 - Nobody goes near itThe last person who understood it left years ago.
B
1–2 - One or two brave soulsThey're the single points of failure your team prays stay healthy.
C
3–5 - A small priesthoodKnowledge exists, but it lives in their heads, not the docs.
D
6–10 - A decent chunk of the teamManageable, but velocity still suffers.
E
10+ - Most people know itLegacy, but well understood. The real problem is something else.
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07→
Has a planned modernisation or migration of this system ever been cancelled or significantly delayed?
A
Yes, cancelled entirelyRisk, cost, or a reorg killed it before it started.
B
Yes, significantly delayedStill "on the roadmap." Always on the roadmap.
C
Yes, multiple timesIt has become a running joke at retros.
D
Not yet, but I wouldn't be surprisedThe stars haven't aligned yet.
E
No - we pushed throughScars, but we shipped it.
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08→
What's your biggest concern about touching it?
A
Breaking something in productionNo staging environment. No rollback plan. Just vibes.
B
Zero test coverageWe'd never know what we broke until a customer called.
C
Undocumented behaviourThe code does things nobody fully understands anymore.
D
Data corruption or migration riskThe schemas have evolved in ways that defy explanation.
E
Nobody to review it properlyA PR would sit open with zero confident approvers.
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09→
Have you ever had to bring back a retired engineer to maintain it?
A
Yes - they weren't exactly thrilledHad to talk them back in with nostalgia and cash.
B
Yes - at consultant ratesThey charge a premium for the privilege of caring again.
C
Not yet, but we've discussed itThe conversation has happened. Quietly.
D
We don't even know who built itNo git blame. No legend. Just the code.
E
No - managing fineFor now.
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10→
How much of your engineering capacity does legacy maintenance consume?
Very little Almost everything
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11→
Have you used AI coding tools on this codebase?
Copilot, Cursor, Claude, Devin, or similar.
A
Yes - it helped meaningfullyMade a real dent in the backlog.
B
Yes - mixed resultsUseful in places, useless in others, hard to predict.
C
Yes - it made things worseConfident hallucinations, wrong patterns, new bugs.
D
Tried, but the codebase defeated itToo complex, too undocumented, no context to work from.
E
Not yet, but we plan toOn the shortlist.
F
No - we don't trust AI on production systemsReasonable. That's exactly why Bosun exists.
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12→
Would you be open to a demo or a trial with free credits?
No commitment. We'll show you it working on a real codebase.
A
Yes - book me inLet's see what Bosun can do with ours.
B
Send me more info firstHappy to read before committing to a call.
C
Maybe laterTiming isn't right but I'm watching.
D
Not right nowAppreciated, but no.
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// thanks for sharing
You're not
alone.

78% of engineering teams say fewer than 3 people can safely touch their most critical legacy system. That's not a knowledge problem, it's a tooling problem. We built Bosun for exactly this.

78%
Teams with <3
safe modifiers
15×
Faster migration
with Bosun
0
Regressions in
automated PRs
Book a demo → Back to home
Bosun - State of Legacy Software