You can't outsource your way out of documentation
A startup CEO recently asked: “Can I just hire someone to document everything and be done with it?”. The company had grown from a team of 1 to 12 in just a year. Initially, the product was built with a focus on shipping features quickly—a practical and necessary choice for an early-stage startup. However, as customers and revenue grew exponentially, so did the workload and feature requests. The team expanded to meet the demand, yet development slowed over the past few months instead of speeding up.
The quickly shipped features were perfect for the first wave of customers but weren’t built to handle the scale or complexity of growth. Knowledge about key systems was siloed within the CTO. Onboarding new developers required hours of handholding via Zoom calls. The CTO became a bottleneck, and documentation was nonexistent. When the CEO proposed his solution, I understood his point of view, however:
Documentation is an ongoing discipline. Hiring an external technical writer is rarely the right answer.
- Knowledge lives with your team.
The people who designed and built the system best understand its nuances. They know why decisions were made, how systems interconnect, and where the pain points are. These insights are invaluable and can’t be fully captured by someone external. - Documentation inspires improvement.
Writing documentation often reveals inefficiencies, technical debt, and opportunities for improvement. Your team will naturally uncover and resolve these as they document their work. An outsider won’t have the same depth of understanding or authority to address these gaps. - It's a continuous process.
Systems evolve, and so should documentation. It needs to be embedded into your team’s culture and workflows. A one-off technical writer won’t stick around to update the documentation as things change. If this responsibility isn't owned internally, you’ll be back to square one in six months.
How do you build a culture of documentation?
- Start small: Have your team document critical systems first.
Make it collaborative: Ensure engineers proofread each other's documentation. If someone is new to the team, ask them to correct and contribute to the documentation before using it to onboard. - Embed it in your development process: Add documentation to your team's definition of done.
- Review regularly: Treat documentation as a living artefact. Revisit it as your systems evolve.
No, you can’t simply hire your way out of documentation. Instead, embrace it as an integral part of your workflow. When done right, it becomes a powerful enabler for your team, saving countless hours and fostering efficiency.