Introducing ROB-ot, an LLM literally no one asked for.
A few months ago a dear friend told me about a professional network that she had joined and thought would be useful for me as I dove into my own career pivot and transition.
A group setting where you can show up safely, and vulnerably share can be pretty special. Sidebar is no different. I am part of a small circle of like-minded people that come together every week or so to chat through what they are working on, what’s on their minds or ask for advice on something they may be stuck on. People share book recommendations, practice elevator pitches or just listen. There are a mix of people with different skillsets, careers and personalities. Selfishly, it’s also helpful for my brain to have a recurring item on my schedule during my week, and it’s even more fun to connect with such smart and kind people. I definitely have the lowest IQ in the room and they even tolerate my dire confusion, terrible jokes and occasional already-proven, beyond-obvious point that is actually a breakthrough for me. It’s awesome; highly recommend.
During one particular discussion about careers beyond 2026, vibe-coding and work-life balance, I mustered the courage to share a silly idea that I’d be trying to bring to life.
Before I get there… Have you applied for a role in 2026? If you haven’t yet, it’s kind of a shit show and my advice: don’t. So far it has been a soulless, sketchy and unforgiving experience! Check out this line I saw in a description recently:
Make it stand out
Whatever it is, the way you tell your story online can make all the difference.
Let’s just say you are on the lower end of that required experience spectrum, six years of “relevant, hands-on experience in Generative AI…”
I mean, damn.. I am seriously impressed. That means you were cooking with Claude or a similar tool, about 2-3 years before OpenAI even released ChatGPT to the public in Nov. ‘22! Like.. heart of the pandemic while all of us were trying to figure out how to make Sourdough Bread, you were vibe-coding way before it was even a vibe!
Obviously some people had access to generative AI before 2022, and I’m not saying it’s impossible. Nor am I completely attacking the very respected company that posted this role recently… but, uh, something feels a bit off in job posting these days!
“siri, is it raining outside?” was the extent of my gen. AI experience 6-10 years ago
Anyways.. I mentioned this silly idea in my professional group as an option to connect with recruiters, to continue building my AI fluency and to try to inject a bit of personality into a world of internet content that lives at the intersection of AI-slop and complete, and self-promoting, and fabricated gibberish. (oh my!)
A Sidebar friend sent me a link to a site that she had interacted with a while back called Ask Sila. I won’t pretend to understand every function of their tool, but it was really easy to set up and train. I believe the initial goal of their tool was to help companies better connect their workforce who may be spread throughout the world in vastly different time zones. It can be really tough when you have a “hot request” and your teammate won’t be in-office for like six more hours. I experienced this a bit when I would wake up for early morning meetings in London time when I was still in Houston preparing to move. If I were able to train my “twin” to share context that only I held or help it provide additional context on budget questions, where a brand guidelines doc is located, etc., that may have saved me a few hours of beauty rest and kept my friends in the UK office in the know.
There is also a b2c-type use case where you can go onto the site and ask experts their high-level opinions on whatever subject. It can be a great discussion entry point that could lead to a more robust connection in-person. Now that I’m thinking about it, I may find one of those recruiters on it and ask them how it is feasible to have 6-10 years of generative experience in 2026…..
Anyways, I spent a few hours learning the system. I got ROB-ot cooking with a few instructions, a basic md file and some silly personality. When I thought it was about ready for the world, I noticed a small issue where the widget wasn’t loading fully on certain browsers or operating systems. I took a few notes of AI-technical-gibberish and sent an email into the service desk, not expecting anything in return. A few days later, an amazing engineer reached out to see if I could talk through some of my findings on a Friday afternoon. I shared a few things I noticed for my not-so-common use case and he generously shared some advice on getting the ROB-ot back up and running. What a cool company culture to even spend just a few minutes chatting with a non-technical, marketing, creative, confused person! Thank you, sincerely, to the Ask Sila team.
So, what is the point of ROB-ot? I have a few use-cases I’m working through with my silly experiment:
Can I use this as a conversation piece for recruiters? I’ve spent a ton of time working on custom artifacts for recruiters and hiring managers.. could ROB-ot help serve up some timely, surprise artifacts I’ve easter-egged into the background. Maybe.. maybe there are some already in there….. 👀
Can human personality shine through an AI bot? I think it is possible to have an authentic voice and tone on your behalf, at least what I’ve seen so far. Do I think this will ever fully replace the beautiful human perspective, humor or tone? No. Will this ROB-ot take on a mind of its own, participate in sketchy office politics on me behalf? I hope not. But, can this tool help share some of the basic facts about me, general knowledge, what I am seeking, in my voice in the prospecting phase of my career search. I think so.
Can I continue learning? This is my entire motivation for anything I do. Not in a cheesy way; it is the truth. The world is constantly changing, and I truly believe we are living in a real-life AI-fueled Renaissance at this very moment. This is a fun little place to take my thinking, curiosity and experimentation into an engaging home on my showcase website.
Interviewing Use Case: One of my biggest frustrations with career search in 2026 is that the first 15-20 min of any interview with a recruiter or team is spent talking about almost anything except strategy for the role. Could a hiring manager jump in and ask me about my working style, or have a “safe space” to ask a hard question that would be awkward in person? Sure. Could they ask the ROB-ot what my thoughts on how brand strategy for a commodity differs from my time branding a world-wide sports brand? Yes. Could my father-in-law come to the page and express his disappointment in my rating of Nicholas Pizza, his hometown Scranton pizza joint, 10 years ago while my wife and I were just dating? Why, yes, he can. AND ROB-ot will tell him that I stand by the 6.5 I gave it, which on my personal pizza scale is actually a very good rating! I will die on this hill, Mr. V.
This whole thing is a bit of fun, a bit of strategy, and most importantly, a chance to authentically connect in a world that is starting to feel a lot less authentic. It’s a glimpse into my own unique voice, my work experience, my intentions in career pivot, and with a bit of personality. If you have a few minutes to try to break ROB-ot, please do. It’s on the bottom right of my website, so fire away. Nothing is off limits! (except for the info I told it IS off limits and to deliver that news with the same dignity, grace and understanding I would.)
Thank you, again to the Ask Sila team for your patience as I fumbled my way through some not-so-technical terms and helped with a solution. You didn’t have to take your time. And no, I am not a LinkedInfluencer, nor getting paid for this.
Please reach out if you have questions, want to connect, or are looking for a wildcard brand marketer, tinkerer, thinker-er. I can’t promise I have all the answers, but I can commit to staying curious, and sprinkling a bit of levity into a world that desperately needs it!
-rob (ot?)
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