Leveling Up Hacks - Share Your Progress

A new series to help you level up in your engineering career faster

Welcome back to Path to Staff! I hope you all are having a great 2025 so far.

Jordan and I are working on WriteEdge - a tool that helps engineers write design docs (TDDs) faster and better. Sign up here for the waitlist – we're slowly releasing early access.

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Happy New Year! I'm starting a series called Leveling Up Hacks. These hacks are designed to help software engineers like yourself accelerate their careers.

Reflecting on my 15-year career, I see patterns among engineers who've risen quickly to Staff and beyond. These patterns are not taught in engineering bootcamps or college. Instead, they're subtle skills you pick up on as you dive into the workforce.

The first hack to level up quickly is to share your progress.

Several engineers I mentor ask for feedback on how to improve. My advice is simple: share your progress! Share what you're working on. The best way to start is to document your project's progress.

Start writing down what you're thinking about. Your teammates want to know how you got to where you are, how you're thinking about your project, and how you're building it out.

What I've seen sharing turn into:

• Promotion artifacts: "This person was able to communicate clearly and thoughtfully. This is proof of their collaboration skills and project complexity. We can also see how many engineers it took to accomplish this effort and how gargantuan it was."

• Better reputation across your company: "This person has a clear head for thinking and must have tackled this problem for a long time. I'll go to them for questions since they probably will have the answer I'm looking for."

• Reflections on your projects: As a TL or even a project lead, you can unlock new insights and make more progress. "Oh, by writing this out, I missed another way I could have implemented this."

• Influence: Other teammates are convinced about your mission and want to join you. They respect your leadership and sense of ownership.

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How to share

• Start with a draft. Write as much as your brain will allow you to. Use a template like the one below.

• Revise and iterate. Make it highly concise. This is where AI tools are your friend. I like using Grammarly to help edit my documents.

• Socialize it with teammates: Share it with teammates individually to get early feedback. (see the Japanese practice of Nemawashi)

• Pick the right channel. Look for formats and mediums that work well. You can do this by copying others and observing feedback from different styles. No one template will work across teams and companies. You have to find what works best for you & your team.

• Embrace imperfection. We all get it wrong at the start. It's okay. Make progress over perfection. I was terrible at communicating when I first started, but I slowly improved after practicing this daily.

Templates

Here's a simple template to get started. I like to use this for bi-weekly updates. If you are interested, this is what some formats are at Meta or Asana.

Also, we'll be building this into WriteEdge as well to help you draft these faster.

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Project Update (1/19 Update)
TL;DR: Key takeaways from your project's progress so far.

Highlights

• Progress on your project thus far

• Surprises, mini-projects that turned out well

• Celebrations

Lowlights

• Experiments that didn't ship

• Lessons learned

• What you didn't expect

Next Steps

• What your team is working on next

• What you're personally thinking about

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Let me show you how I use this template for a fake project, Project Cosmos. Project Cosmos will be a migration project, something that most of us tend to work on at larger companies.

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Project Cosmos – Progress Update (1/19)
TL;DR: Migration from AWS to Google Cloud is 60% complete, tracking towards a 20% cost reduction. No major blockers, but some surprises along the way.

Highlights

• Core Migration: Completed for 3 out of 5 services, now running smoothly on Google Cloud. Thanks Josh for helping drive this.

• Cost Savings: Early projections confirm we’re on track for the 20% savings goal. We've run some experiments on the public and hope to share more results soon.

Lowlights

• Data Transfer Delays: Higher-than-expected data egress costs during the migration phase; exploring optimizations.

• Unexpected Work: Retrofitting an outdated service to ensure compatibility with Google Cloud tools.

• Lessons Learned: Need for tighter collaboration with finance teams on early cost forecasting. We have marked these in our template to reference for future migrations.

Next Steps

• Near Term: Focus on migrating the final two services, targeting completion by early February.

• Exploration: Investigating long-term strategies to optimize cloud-native services for even greater cost efficiency.

• Personal Priority: Refining our knowledge-sharing process to improve future migrations.

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That's it! Hopefully, it wasn't too hard. By jotting this update down, you will have something to reflect on as you progress throughout your project.

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Pro Tips

Lastly, here are some tips of mine for sharing project updates. Remember, keep it short and simple.

1. Know your audience: Understand who you're writing for. Assume they are smarter than you but are forgetful. Provide as much context as you can. And don't pick an audience that's too small – it might not be worth writing for.

2. Find your cadence: Bombarding people with updates can backfire. If it's a long project, don't send updates daily. Start small, e.g., once a month, before ramping up. Again, see what works at your company and try to replicate it.

3. Double-check permissions: If you're using Google Docs or a similar tool, open it for access so the recipient can see your writing. I've received an “access denied” message so many times. Having others request permission will impact your funnel open rates.

4. Save great examples: I once asked an ex-colleague at Lyft how she wrote her emails so well. Her secret? She bookmarks her favorite emails. Do the same! Save any updates, proposals, or documents you admire. What resonates with you will likely resonate with your readers.

5. Read more: Good writing comes from good reading. If you haven't read, start a habit in the new year. I aim to complete 1–2 books a month.

I hope you enjoyed this hack. I'll be sharing more hacks on leveling up in the weeks to come. If this piece resonated with you, like, comment, and share with your friends.