Beyond the Resume: The Questions I Ask Before Giving Career Advice

I often get messages from people asking for a job or looking for guidance because they’re thinking about making a career change. It’s a vulnerable moment — sometimes filled with doubt, sometimes with excitement — but almost always with a big question behind it: What should I do next?

And before I give any advice or consider someone for a role, I always start with one thing: asking questions.

Not to evaluate their résumé, but to understand the person behind it.

These questions help me (and often help them) uncover where they are today, what energizes them, what they’ve already mastered, and where they want to go.

Here are some of the questions I usually ask:

🧠 Understanding Your Current Strengths

• What are the tasks or activities you do most often in your day-to-day work?
• What are the tasks you feel most confident in — the ones where you know you’re good?
• What tools, platforms, or methods do you know inside out?
• If you had to compete in a challenge today, what kind of problem could you confidently solve better than most people?

This last question is the most important one for me.

💡 Imagine there’s a global competition to solve a very specific problem. What would be the challenge where you’d likely be a finalist or even win?

This helps surface real, earned experience. It shows me whether the person understands the specific kinds of problems they can already solve well — no matter how niche or small they might seem. And that clarity can be a superpower.

🚀 Mapping Growth and Curiosity

• What types of work or skills are you curious about, even if you haven’t done them yet?
• Are there any roles or projects you’d love to try someday?
• What kinds of teams, tools, or problems are you excited to explore in your next chapter?

✨ Learning from Your Past Experience

• What did you like about your last job that you’d love to keep in your next one?
• What didn’t you like, and hope to avoid or improve?
• What type of team culture helps you do your best work — structure, autonomy, flexibility?

⚡ Energy Drivers & Drainers

This is often overlooked but deeply valuable:

• What kinds of tasks or situations give you energy and make you feel more engaged?
• What kinds of tasks or situations drain your energy, even if you’re good at them?
  

Knowing this can help you (and your future team) design a role that’s not just productive, but sustainable.

🌍 Your Setup and Work Style

• Where are you currently based?
• What hours of the day do you typically work best?
• What computer and internet speed do you use today?
• How do you feel about your English — writing, listening, and speaking? (Be honest.)
• Do you prefer to disconnect fully outside work hours, or are you okay with the occasional off-hours message?
• And finally: How would you describe your personality and a typical day in your life?

🎧 Curiosity & Outside Interests

To me, curiosity is one of the clearest signs of long-term potential.

So I like to ask things like:

• What podcasts, YouTube channels, or creators do you follow regularly?
• Have there been any books — fiction, non-fiction, work-related or not — that shaped the way you think?
• What do you usually explore when you’re in a YouTube or Wikipedia rabbit hole?
• What hobbies or creative outlets do you enjoy outside of work?
  

These questions aren’t just small talk. They tell me how a person thinks, what excites them, and how they keep learning when no one is watching.

Why All These Questions Matter

I’m not trying to do a personality test. I’m trying to help people uncover patterns — and name their edge.

Sometimes, we’re so close to our own strengths that we can’t even see them. These questions are a mirror. They help people realize what they already know how to do, what excites them, and what they should double down on.

If you’re thinking about a job change or feel a little lost, I recommend answering these for yourself. It’s not just a career exercise — it’s a self-awareness one.

And often, it’s where real clarity begins.