I wasn't expecting a raise or promotion this year, so I let my brag doc slide.

Big mistake. 🤦‍♀️

Now it's December, and I need to write my self-assessment. I'm staring at a blank document, trying to remember what I did in February. Or March. Or honestly, even two months ago.

This was going to take forever, and I was dreading it.

A brag doc would have saved me. But since I didn't have one, I had to figure out how to build one fast--and that's where AI came in handy.

What took me a few hours would have taken me days (if not weeks 🙈) of manually digging through emails, Slack, and my calendar. More importantly, I now have a process I can reuse every month to keep my brag doc alive with minimal effort going forward.

Last year, when I gave my manager my brag doc, he thanked me. He said having all that data made his life so much easier going into talent planning--which increases the chances I'd get a raise or promotion.

Whether you're in tech, running a business, or working toward any kind of professional goal, a brag doc is one of those simple tools that pays dividends. Here's how to build one (with AI doing the heavy lifting).

Why brag docs matter

A brag doc (again, kudos to Julia Evans) is simple: it's a running list of your accomplishments, feedback, and impact over time.

When it comes to job hunting, performance reviews, and career growth:

• Your manager has concrete evidence to advocate for you during talent planning
• You won't undersell yourself because you forgot what you did six months ago
• Writing your resume or negotiating a raise becomes infinitely easier

When it comes to your personal growth, record-keeping, and resiliency:

• You can actually see your progress over time (which is huge when you feel stuck)
• It gives you a boost when things feel hard or your efforts don't seem to be working
• It captures the struggles you overcame, the wins you experienced, and the growth you've made

I use brag docs with my coaching clients for exactly this reason.

As the year goes on, they quickly forget where they were three months ago. They forget the challenges they faced, the things they accomplished, the ways they've grown. A brag doc helps them remember--and that perspective shift can be powerful when motivation is low.

How to use AI to build your brag doc

Step 1: List every source of evidence

Start by making a list of every system, tool, or document that holds evidence of your contributions, feedback, or results:

• Places you receive praise or feedback (Slack, email, performance management tools) 🗣️
• Your calendar (What meetings did you lead? What projects were you involved in?) 📆
• Documents you've written (proposals, reports, presentations) ✍️
• Award nominations or recognition programs 🏆
• Meeting notes 📝

The goal is to identify where your work lives so you can extract it.

Step 2: Extract the data (a.k.a. let AI do the work)

Now go through your list one source at a time. The goal is to move relevant data into a single document--your brag document.

For some sources (like meeting notes or feedback forms), you can simply copy and paste the text directly into your brag doc.

For other sources (systems that don't allow easy text extraction, or sources with overwhelming amounts of data), let AI do the heavy lifting:

1. Export or take screenshots of the source
2. Upload them to your AI tool of choice
3. Use a prompt like this:

The AI will scan through everything and pull out what's relevant. You'll still need to review it (and add context where things are unclear), but it beats manually combing through thousands of Slack messages.

Step 3: Fill in the gaps

Once you've extracted data from all your sources, you'll have a document populated with examples of your growth and impact.

But there will be gaps--things AI can't extract because they only exist in your memory. Go through and add:

• Context for why something mattered
• Results or outcomes that weren't documented
• Challenges you overcame that weren't visible to others

Do this monthly (or at least quarterly). The longer you wait, the more you'll forget. If you build this habit, maintaining your brag doc becomes a 10-minute task instead of a multi-hour scramble at the end of the year.

Bonus: Use AI to draft your self-assessment (if you need one like me 🤪)

If you work somewhere that requires self-assessments or performance review reflections, AI can help here too.

Step 1: Gather your framing documents

Make a list of things that provide guidance on what's relevant for your performance review:

• Company values
• Your job description
• Any rubrics or templates your company provides
• Competency frameworks or expectations for someone in your role

These help the AI understand what kind of reflection your company is looking for.

Step 2: Start the draft (but don't skip the thinking)

Don't just ask AI to write your self-assessment. That's lazy, and it'll show.

Instead, engage with the AI to help you think through what matters before writing. Try a prompt like this:

This turns the AI into a thinking partner. It'll ask you questions that help you clarify impact, prioritize what matters, and articulate things you might not have considered.

Once you've worked through those questions, then ask it to draft. And always proofread--this is just a starting point, not a finished product.

The Bottom Line

AI won't completely automate this for you (nor should it--your career deserves more than a copy-paste job). But it can take an overwhelming admin task and make it much, much easier.

And if you build the habit of maintaining your brag doc throughout the year? Future You will thank you when December rolls around and you need your brag doc for something.

Have a terrific week,

Tyler

PS: I'm offering 30% off coaching packages until December 31, 2025. Looking to make the coming year count? Hit reply and let's chat 😊