In the early days, your best engineer moved mountains. They stood up payments, fixed the scary bugs, and shipped under impossible deadlines. Documentation was a “tomorrow” problem. Knowledge sharing felt like a luxury. Now that code is load‑bearing, and the person who wrote it just updated their LinkedIn.
Why this matters right now
Many developers are open to a move. Roughly three‑quarters say they’re actively looking or open to new roles.
One‑person dependencies are common. About 65% of projects studied had a single maintainer whose departure could stall progress.
The talent market is hot. Counteroffers only go so far.
If you wait, it gets expensive
Technical debt quietly taxes your roadmap. Developers spend about 42% of their time on maintenance and rework—the hours you thought were going to new features.
Big rewrites pause growth. A full rebuild can take 6–18 months. At a $200K monthly burn, that’s $1.2M–$3.6M in opportunity cost before you ship something new.
Here’s the way out Turn personal know‑how into institutional knowledge. When the how and why live in simple, shared notes—not just one person’s head—work stops depending on who’s online at 3 a.m. Keep it lightweight, not perfect: a runnable README, a short operations checklist, and a plain‑English note about why key decisions were made. Make sure at least two people can ship, fix, and extend every revenue‑critical path. Keep it small and continuous so it fits into normal work, not a once‑a‑year documentation push. With that mindset, you’re not fighting fires—you’re lowering risk every week. Small, steady habits beat sporadic heroics—and over time, they make the greatest impact.
A simple plan for the next two weeks
Map your risk. List the 5–10 systems that would stall if one engineer left tomorrow. Circle anything both revenue‑critical and owned by one person.
Turn know‑how into shared knowledge. Run two short, recorded walkthroughs of your top‑risk system. Transcribe them. Add simple decision notes (ADRs) in plain English that explain why key choices were made.
Make it part of the sprint. Add knowledge‑sharing tasks with owners and acceptance criteria: a runnable README, an operations runbook, and at least one change from a second contributor.
Modernize in motion. Use a “modernize in place” approach (also known as strangler fig): replace one risky piece at a time while the system keeps running. Start where revenue meets single‑owner risk.
Spread ownership. Require code review on critical paths and make sure at least two engineers can ship and fix each money‑moving subsystem.
Build habits for next quarter
Block time every sprint for knowledge sharing; treat docs and runbooks as part of “done.”
Rotate stewardship of critical systems so expertise never lives in one head.
Measure risk burn‑down weekly: how many revenue‑critical systems still have a single primary owner?
Bottom line You don’t need heroics—just steady habits and a partner who knows how to make them stick. Midwestern embeds with your team, turns individual know‑how into shared capability, and modernizes in place so you can scale responsibly. If you want help de‑risking a single‑owner system this month, book a call. We’ll meet you where you are and get to work.