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Career mapping with AI + the 2 questions to ask of any resume
And, in other news, we're getting to the bottom of how to make email suck less.
Welcome to this week’s edition of The DesAI Digest. We’ll cover:
🛠️ Career Strategy = The Secret to a Great Resume
🤖 AI Tactic = Map out your career path
⚡️ Execution Insight = Transform your email into a to-do list
💼 Job Board = 3 lucrative, remote jobs
🛠️ Career Strategy
The secret to a great resume
What does a great resume actually do? It makes someone say, “I want to talk to this person.” That’s it.
So how do you get someone to say that?
You start with your resume bullets. A bullet is the basic unit of a resume; without great bullets, the resume will never be great.
For each bullet on your resume, ask yourself two questions.
First: What exactly did I do, in a way that a smart 13-year old could explain?
This is important because many recruitment professionals are in their 20s. While they are probably smart and good at their jobs, they likely lack specific experience with your job function. Being very clear about what you do will help them see how you’ll fit the job requirements.
Second:
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🤖 AI Tactic
Map out your career path 🗺️
At the Chief of Staff Network, I re-released our Leveling Framework based on manual analysis hundreds of LinkedIn profiles in 2024. I wanted to create a resource that would help Chiefs of Staff navigate their careers more easily, given how varied the seniority and responsibilities of the title can be. It was exceptionally tedious but I’m really proud of the result.
More recently, I’ve been wondering whether AI could replicate a Leveling Framework like this for other professions. And after tons of trial and error, it turns out Deep Research does a pretty good job.
Here’s the prompt to run with ChatGPT o3 Deep Research, just fill in the bracketed sections:
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⚡️ Execution Insight
Transform your email into a to-do list
Last week, I gave a talk about ops and automation at a local VC fund called Cintrifuse. I wondered what to talk about, what all companies have in common. After a while, it hit me: email is still the most used business app. And most people still suck at managing their inboxes.
So I came up with a few tactics to help:
Turn on undo send, shortcuts, auto-advance, and templates in Gmail Settings
Try an app like Simplehuman to learn shortcuts and get some quality of life features
Try Andreas Klinger’s approach to “Getting Things Done”
Let’s dig into the third one. The general premise is:
An email comes in
Handle those you can instantly
The others mark as todo (Box 1)
If you want to keep track of them when you replied, you mark them as “Awaiting Reply” or “Delegated” (that way you can always quickly find them and follow up)
Make sure to archive all emails
And the way to achieve it is:
Setup Multiple Inboxes in Gmail
Decide on Your Special Stars / Icons
Link Special Stars to Your New Inboxes
Enable the Inbox Layout

Here’s an example of this layout
For full guidance, check out Andreas Klinger’s blog here.
💼 Job Board
Payola (I wish) from Products I Use
Here are the 3 most interesting remote job openings I’ve seen this week:
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That’s it for this week.
-Rahul from The DesAI Digest
P.S. Reply back to this email with a business or career challenge you’re facing! I’d love to help.
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