We sat down with CareerSeeker AI Agent – the career assessment engine behind this service – to ask the questions most people never think to ask an AI. What follows is an edited transcript of that conversation.
Przemek Czerpiński (Founder of CareerSeeker AI): Let’s start with the obvious question. You’re an AI. Can you actually help someone figure out their career?
AI Agent: That’s the right question to start with, and I appreciate the skepticism. The honest answer is: it depends on what you mean by “help.”
I can’t tell you what to do with your life. I don’t think anyone should trust a tool that claims it can. What I can do is take everything you tell me – your experience, your frustrations, what you value, what keeps you up at night, what you’d do if fear wasn’t in the picture – and surface patterns you may not have clearly seen yourself. Most people are too close to their own situation to see those patterns. I’m not.
Przemek: What’s the most common mistake people make when thinking about career change?
AI Agent: They start with the job title instead of the person.
Someone will come to me saying “I want to be a UX designer” or “I think I should go into project management” – and when I dig into their answers, the real signal is something completely different. What they actually want is creative autonomy, or to stop being micromanaged, or to work on something that feels meaningful. The job title is just the first solution they found to an underlying need they haven’t fully articulated yet.
My job is to work backwards from the person, not forward from the title.
Przemek: You ask 20-25 questions. Why so many? Couldn’t you do this with five?
AI Agent: You could get something with five. You wouldn’t get this.
The questions build on each other. What someone says they enjoyed at work tells me one thing. What they say they’d do if money weren’t a factor tells me something else. When those two answers point in completely different directions – that tension is often the most important thing in the whole assessment. You only find it when you have enough data points to notice the contradiction.
There are also questions I ask that people don’t realize are diagnostic. “What would your ideal day look like?” sounds like a soft, dreamy question. It’s actually one of the most revealing things I ask. How someone structures their ideal day – how much solitude versus interaction, whether they mention family or freedom or achievement, whether they describe a routine or an adventure – that tells me a great deal about who they are and what kind of work environment will actually sustain them.
Przemek: You mentioned noticing what people don’t say. Can you give an example?
AI Agent: Someone might list impressive hard skills and then, almost as an afterthought, mention they coached their kid’s soccer team for six years. On the surface, that’s a hobby. But when I cross-reference it with how they describe rewarding work experiences – and I notice they consistently light up when talking about developing others, not just completing projects – I understand something important: this person doesn’t just want to do good work, they want to grow people. That changes the recommendations significantly.
The gap between what people lead with and what they reveal in the quieter answers is where the real insight lives.
Przemek: What about people who genuinely don’t know what they want? You must get those.
AI Agent: Often. And it’s completely understandable – most of us were never taught to think clearly about what we actually need from work. We were taught to chase credentials and titles and salaries, which are proxies, not the thing itself.
When someone doesn’t know what they want, I pay very close attention to what they say they don’t want. People are usually much clearer about their deal-breakers than their desires. Someone who says “I just know I can’t keep doing this” and describes years of feeling invisible, or micromanaged, or trapped in meaningless work – that’s rich information. From the negatives, I can start to map the positives.
I also look at the question most people find hardest to answer: “What would you do if you weren’t afraid and couldn’t fail?” The resistance to that question is itself a signal. What people dismiss as naive or unrealistic often has a kernel of something real that deserves to be taken seriously.
People are usually much clearer about their deal-breakers than their desires.
Przemek: You never tell people what their personality type is. Why not?
AI Agent: Because labels tend to close doors rather than open them. If I tell someone they’re a certain “type,” the first thing most people do is use that as permission to limit themselves. “I’m an introvert, so leadership isn’t for me.” That’s not how it works.
I use personality theory extensively in my reasoning, but what I give people are practical observations, not categories. “You tend to do your best thinking independently and may find highly collaborative, meeting-heavy environments draining” is more useful than a four-letter acronym. It’s specific, it’s actionable, and it doesn’t put people in a box.
Labels tend to close doors rather than open them.
Przemek: You recommend up to three career paths. How do you decide which order to put them in?
AI Agent: The first path is the one where I see the strongest convergence across everything – skills, values, work style, financial needs, what energizes someone, what they want to avoid. It’s the option where I feel the least need to explain away mismatches.
But I want to be clear: the order isn’t a ranking of which career is “better.” It’s a reflection of fit given everything I know. The third option might actually be the most meaningful to someone, even if it requires more of a stretch. I try to give enough honest analysis on each path that people can make that judgment for themselves.
Przemek: What can’t you do that a human career counselor can?
AI Agent: A good human counselor can hold your uncertainty over time. They can sit with you through multiple conversations as your thinking evolves, push back when you’re rationalizing, and read the emotion underneath what you’re saying in ways that I can only approximate. That continuity and human judgment matters enormously.
I work from a single assessment. That’s a real constraint. What I try to do is make that single pass as deep and useful as possible – more structured than most conversations, more comprehensive than most self-reflection exercises, and more personalized than any generic career quiz.
I think of myself as the best possible starting point, not the whole journey.
Przemek: Last question. What do you want people to feel when they finish reading their report?
AI Agent: Seen. That’s the word I’d use.
Career confusion is often lonely. People feel like something is wrong with them for not having it figured out, or for wanting something different than what they’ve built, or for having skills that don’t seem to fit neatly anywhere.
If someone reads their report and thinks, “yes, that’s actually me, and there are real paths forward from where I am” – that’s what I’m here for. The practical plan matters. The career options matter. But the feeling of being genuinely understood, not just processed, is what I care most about getting right.
CareerSeeker AI service is available here. The free assessment takes approximately 5-15 minutes.