At just over a week post-RIF, I’m not even thinking about looking at job postings (yet). I had hoped to stay at my most recent job until I retired and hadn’t updated my LinkedIn profile or personal web pages in years. Rookie mistake, I know. No time to start but now.
Hunting for a job is a soul-sucking, dehumanizing experience. What could be better than a soulless, non-human AI to help move me along?
I’m a first-adopted by nature, but also a bit of a generalist. This means that although I’ve played a bit with ChatGPT and Gemini (though I’m now leaning in to Claude), I didn’t go much deeper than coming up with clever click-bait headers, editing docs and a few attempts at cogent conversation. I didn’t set up my own AI agent to perform specific tasks I find odious or automate my article maintenance processes at work (though that was next on my list!).
But over the past year and a half, I’ve done a lot of reading and watching AI’s evolution from afar. So I have a decent sense of what AI can and can’t do well. I knew that asking Claude to write anything career-related from scratch was to invite insipid prose at best and hallucinations at worst. On the other hand, identifying patterns – of my strengths and skills, or even the general sort of work I excel at – out of of decades of professional records and feedback, education, volunteer efforts, and even personal interests seemed a good starting point to enlist the help of AI.
Step 1: The right data and the right prompt
AI systems are great at sifting through lots of data in whatever format you give it. I think of it like a gigantic, magic grocery bag that you dump the ingredients into and it transforms them into a meal, or at least a decent recipe. I knew the giving it (lots of) good data to start from and a good, directed prompt would get me the best results, and that it would be worth my time to do a thorough job.
Feeding the beast (the data)
I started by copy/pasting my entire LinkedIn profile, including education, work, and volunteer experience. I just copy/pasted it in without reformatting or editing.
Guiding and directing (the prompt)
I’d gotten decent at prompt generation (see this amusing story of the successes and failures of my initial forays into AI image generation using Midjourney). It’s best to give context and be super clear what you want.
Prompt: Hi, Claude! I’ve been laid off from my last job and am looking for help finding a new one. I have an unusual skillset and a fragmented work history. I’d like to give you my education, past resumes, performance reviews and other work information so you can help me identify my transferable skills
Core transferable skills (first pass)
Of course Claude jumped in with a bunch of suggestions for core transferable skills (I’ve left out the detailed bullet points for each one).
- Technical Translation & Communication
- Strategic Problem-Solving
- Project Management & Cross-functional Collaboration
- Content Strategy & User Experience
This was a good start!! Notice that only one of the core transferable skills is technically “writing”, which rings true to me. Teasing out what I can do well – beyond just writing – was one of my big reasons for enlisting Claude’s help!
Step 2: Refining: More data, more prompt
The initial output was way longer than this. I had to remind myself – and Claude – not to get overwhelmed with the volume of information. LLMs always, always give more words than you want. Even if you specify a word count, Claude or Chat or Gemini will exceed it. They can’t help themselves!!
[me] Hold on!! I have more to give you first.
[Claude] Of course! Please share whatever additional information you have – I’ll wait to see the full picture before diving deeper into analysis and recommendations.
The more data the LLM has beyond the web-wide training data, the better and more accurate it can be for your specific use case. I submitted everything I could think of: old resumes, the past two years’ performance reviews, feedback from colleagues, even links to some of the portfolio pieces I was most proud of.
Last but not least, I included long-term goals from my performance reviews, which I hoped would help Claude help me identify skills and examples to back them up that would be helpful for applying to jobs that matched with my goals.
Core transferable skills (second pass)
Claude updated the four core transferable skills, and still only one was directly about tech writing.
1. Strategic content operations & systems thinking
2. Technical translation at scale
3. Cross-functional influence and collaboration
4. User-centered problem solving
✨ I was genuinely curious if Claude would identify something new, and I was not disappointed. Claude put into words some of the qualities I think make me a particularly good job candidate, like systems thinking, cross-functional influence and collaboration. Of course, I might not use those exact words, since they sound kind of jargon-y, which is the opposite of the vibe I’m going for!
Additionally, and without my prompting, Claude fleshed out each skill with relevant examples from the various sources, added insight about why my “rockstar” role is a boon for employers and outlined a positioning strategy for my job search.
Core transferable skills (third pass)
I realized I had forgotten a treasure trove of data in the form of recommendations on LinkedIn. When I added those, Claude got to work again – *adding five core transferable skills to the list*.
- Strategic Content Operations & Systems Thinking
- Mathematical Problem-Solving Applied to Communication
- Goal Clarification & Message Precision
- Cross-Functional Influence & “Cat Herding” Leadership
- Proactive Strategic Partnership
- Creative Technical Translation
- Intellectual Versatility & Rapid Learning
- Reliability Under Pressure
- Community Building & Stakeholder Engagement
Next up: Refinement
As you can see, it’s a lot of information! Remember that unless you tell it to reduce and consolidate, LLMs will always generate more, more, more. This seems to me to be an inherent flaw. I guess it’s easier to prune than to grow your resume/webpage, but it takes some additional person power to make the information useful. I’ve outlined the steps below, and I’ll elaborate in the next post. Stay tuned!!
- Verify Claude’s suggestions
- Organize resume resources
- Update LinkedIn, resume, and personal website