Your CTO asks in Slack: "What did engineering ship this week?" You panic. Was it the API thing? The performance fix? That refactor everyone kept talking about?
You could read through 23 pull requests with titles like "fix: handle edge case in user validation" and "refactor UserService for testability." Or you could spend an hour writing a summary from scratch.
Neither option is great.
The information your leadership needs is already in those PRs. It's just written in code and commit messages, not in language that answers "why does this matter to the business?"
This post shows you how to turn PR documentation into updates your CTO actually wants to read.
The Real Problem: Translation, Not Information
I once watched a VP of Engineering try to explain to the board what her team accomplished in Q2. She had data: velocity charts, sprint completion rates, story points burned down. What she didn't have: a clear answer to "what did we build and why does it matter?"
The board meeting didn't go well. Not because the team wasn't productive. They shipped a ton of code. But none of the executives understood what any of it meant for customers or revenue.
Here's what engineering leaders actually need:
Progress in plain language. Not "merged 47 PRs." Something like "we launched SSO, which unblocks $2M in enterprise deals."
Strategic alignment. Are we building the things that actually matter? Or are we gold-plating features nobody asked for?
Early warning signs. If a PR reveals gnarly technical debt or a dependency on a flaky third-party API, leadership needs to know before it blows up.
What they usually get instead
Commit messages that say "refactor UserService." JIRA ticket IDs with no context. Sprint burndown charts that show velocity but not value. Status reports written three days after the work shipped, already out of date.
Or they get nothing at all, which might actually be worse.
When leaders don't have visibility, they either micromanage (asking for constant updates) or operate blind (making decisions without understanding engineering constraints). Both are bad.
So why not just read the PRs?
Because a CTO reading 50 pull requests per week isn't scalable. It's also not a good use of their time. They don't need to understand every code change. They need to understand business impact.
Every merged PR already contains the information leadership needs. The problem is it's written for developers. Code diffs, technical implementation details, function names.
What if those same PRs could generate documentation that explains both the technical details AND why any of it matters?
What good PR documentation looks like
When Code2Docs analyzes a merged PR, it generates:
A plain-language summary that explains what changed without requiring you to read code. "Implemented connection pooling" becomes "made the database handle 10x more traffic without slowing down."
Business impact context. Not just what shipped, but why it matters. Does it unblock a deal? Reduce costs? Fix a customer pain point?
Strategic framing. How does this work connect to quarterly goals? Does it move the needle on the OKR everyone's been stressed about?
Technical depth when needed. CTOs and VPs who came up through engineering still want to know about architectural decisions. Just not in every update.
The key insight: one PR can serve multiple audiences. Engineers get technical details. Leadership gets business context. Nobody has to write two separate documents.
Here's what I mean
Infrastructure work that actually matters
Original PR description:
feat: Implement database connection pooling
- Add PgBouncer connection pooling
- Max pool size 50, connection timeout 30s
- Infrastructure now handles 10x current load
Cool. But what does that actually mean for someone who isn't elbow-deep in database optimization?
Code2Docs generated documentation:
Management update:
Implemented database connection pooling to support significant user
growth. This infrastructure improvement supports the Q2 goal of scaling
for enterprise expansion without increasing hosting costs.
Product update:
Database infrastructure upgraded with connection pooling, enabling the
system to handle 100K active users (up from current 10K capacity). This
prevents performance degradation during traffic spikes and prepares the
platform for large enterprise customer onboarding.
Engineering context:
Implemented PgBouncer connection pooling with a maximum pool size of 50
connections and 30-second timeout. Standard best practice for database
performance at scale.
See the difference? Same work, but now it's accessible to different teams.
The feature that unblocks revenue
Original PR description:
feat: Add Enterprise SSO support
- Implement SAML 2.0 IdP integration
- Add JIT provisioning and role mapping
- Supports Okta, Azure AD, and OneLogin
If you don't know what SAML is, this tells you nothing. If you do know what SAML is, you're probably an engineer who didn't need the update anyway.
Code2Docs generated documentation:
Management update:
Launched Enterprise Single Sign-On capability, removing a critical
blocker for enterprise deals. This feature supports the goal of
expanding into Fortune 500 accounts and achieving feature parity with
competitors.
Sales update:
The Enterprise SSO feature unblocks approximately $2M in pipeline where
SSO was a hard requirement. This capability can be leveraged in
conversations with enterprise prospects to demonstrate security
compliance and IT integration capabilities.
Product update:
Implemented Enterprise Single Sign-On supporting Okta, Azure AD, and
OneLogin. Employees can now log in using their company credentials with
automatic user provisioning and role-based access control.
CS update:
The Enterprise SSO launch may require updates to onboarding
documentation for IT administrators. Consider creating setup guides for
the three supported identity providers.
Those updates work for different audiences. Management sees the strategic impact. Sales knows how to pitch it. CS knows what support materials they need.
The feature customers kept asking for
Original PR description:
feat: Add CSV export functionality
- Build CSV export endpoint with streaming support
- Add filtering and custom column selection
- Handles large datasets efficiently
Code2Docs generated documentation:
Management update:
Delivered the CSV export feature, addressing the #1 customer request for
Q1. This improvement supports retention efforts in the financial
services vertical and closes a feature gap with competitors.
Sales update:
The CSV export feature addresses a common objection from financial
services prospects who require Excel integration. This capability can be
highlighted in conversations with customers who need data portability.
Product update:
Users can now export their data to CSV format with custom filtering and
column selection. The export function uses streaming to handle large
datasets, supporting enterprise customers with millions of records.
CS update:
The CSV export feature resolves 67 open support tickets. Consider
creating a help article explaining export options and any row limits for
different subscription tiers.
Turning PRs into weekly updates
Most CTOs don't want to read 50 individual PR summaries each week. They want a digest: the highlights, the context, the "here's what you need to know."
Using weekly digest emails
The good news: you don't have to manually compile weekly updates. Code2Docs can send weekly digest emails to each team member based on their function.
Here's how it works:
1. Invite leadership to your Code2Docs team. Assign them the "Management" function so they see management-focused updates.
2. They choose their email preference. Weekly digest gives them a summary every Monday morning of all PRs merged that week, with just the management updates.
3. The digest automatically groups by theme. Features, performance, infrastructure, bug fixes - all organized and ready to read.
4. Leaders can click through for details. Each PR links back to the full documentation if they want more context.
For CTOs who want even tighter summaries, you can have an engineering manager review the digest and add a 1-paragraph executive summary at the top before forwarding. But many leaders are fine with the auto-generated digest as-is.
What it actually looks like
Engineering Update: Week of Jan 15-19
This week we focused on enterprise readiness. Shipped SSO (unblocks $2M in deals), made reports 5x faster for large customers, and launched the CSV export everyone's been asking for. Everything ties back to our Q1 goal of landing those first five enterprise customers.
Big wins:
- Enterprise SSO live → 5 deals can move forward (PR #847)
- Report speed improved 5x → better experience for power users (PR #849)
- CSV export shipped → closes #1 feature request, 67 tickets (PR #851)
- Database scaled 10x → ready for growth spike (PR #850)
By the numbers: 12 PRs merged, 95% of planned work done, zero critical bugs.
Next week: Mobile performance, API docs, security audit prep.
Full PR docs available if you want technical details.
With weekly digest emails, this summary gets auto-generated and delivered every Monday morning. Leadership gets caught up in 2 minutes of reading.
Things that actually matter
Always connect to business goals
"We improved performance" is useless. "We improved performance, which supports our Q2 enterprise expansion by making the product viable for Fortune 500 customers" tells the real story.
If you can't connect a piece of work to a business goal, either dig deeper to find the connection or don't include it in the update.
Use numbers
Numbers make impact concrete and memorable:
- "5x faster" hits harder than "improved speed"
- "$2M in pipeline unblocked" beats "launched SSO"
- "67 support tickets closed" shows real customer pain
Don't hide problems
Here's what nobody tells you: if every update is sunshine and rainbows, leadership stops trusting them.
When a PR reveals technical debt that's slowing the team down, include it. When there's a risky dependency on a third-party API that might break, flag it. Leaders need to know about problems before they become crises.
One VP told me she only started trusting her engineering updates when they started including the bad news. "If everything's always perfect, something's wrong."
Make it scannable
Your CTO has 47 unread Slack messages and a board meeting in 20 minutes. If your update takes more than 60 seconds to scan, it won't get read.
Bullet points. Bold text for key info. One paragraph summaries.
Be consistent
Pick a day. Pick a format. Stick to it. Leaders learn to rely on updates that show up predictably.
Weekly works for most teams. Monthly if you're slower-paced. Daily is probably overkill unless you're in a crisis.
How to actually set this up
Start simple:
Week 1: Install Code2Docs on your repos so PRs get documented automatically.
Week 2: Invite your CTO/VP to the team. Assign them the "Management" function. Have them turn on weekly digest emails.
Week 3: Check in: is the digest useful? Too much detail? Missing context? Adjust which repos or types of PRs get included.
Week 4: Add other functions - invite product managers, sales leads, etc. with their appropriate function assignments.
Within a month, everyone's getting the updates they need via email. Leadership has visibility without interrupting engineering. No manual status reports needed.
What usually goes wrong
Including everything
Not every bug fix needs to be in the executive update. Focus on work with actual business impact. Internal refactoring? Mention it briefly or skip it entirely.
Missing the "so what?"
If you can't explain why something matters to the business, don't include it. "We refactored the auth service" means nothing. "We refactored the auth service, which sets us up to add SSO next quarter" has a point.
Being sporadic
Sending updates only when things are going well trains leadership not to trust them. Send them every week, good or bad.
Only sharing good news
The fastest way to lose credibility is pretending everything's perfect. Include the challenges. The blockers. The technical debt eating into velocity. Leaders can't help if they don't know.
Why this matters
Good documentation isn't about writing more. It's about writing the right things for the right audience.
Your PRs already contain the information leadership needs. You just need to translate it from "technical implementation" to "business impact."
When you get this right, something interesting happens. Leadership makes better decisions because they understand engineering constraints. Engineering gets more autonomy because leadership trusts the process. Meetings get shorter because everyone's already caught up.
And your CTO stops asking "what did we ship this week?" in Slack. Because they already know.