Generic questions get generic answers. "What do you like about your job?" is hard to answer honestly and the answer is hard to interpret. And it's unrealistic to expect someone to give you thoughtful, personalized advice with only the context of a half hour conversation.

Instead, treat career conversations as structured fact-finding. You should listen for wisdom (because advice is a two-way street), but make sure you're building a mental model of the industry, role, and firm.

I suggest three concrete questions that give you a real sense of what a career in a specific field, industry, and firm actually looks like.

Question 1: Tell me what your day looks like

The first question is simple: tell me about your day. Literally, hour by hour.

What did you do in the morning? What did you do in the afternoon? Were your hands on the keyboard? Was there a phone to your ear? Are you on Zoom calls? Are the meetings in person? Did you stand at a whiteboard? Was your boss in the room?

Go nuts! Are you writing code? How many meetings do you have in a typical day? How many are external facing? Do you make presentations? Or maybe you create demos?

This gives you a better sense of what the work actually is.

Then zoom out: on a weekly basis, what are the biggest deliverables? What would a successful week look like? A successful month? A successful quarter?

Without this granular detail, it's hard to tell what a job actually feels like. Job titles and company names don't capture the rhythm of the work, the cadence of meetings, the balance between deep work and coordination, the tools you use, and the pace of deliverables.

Question 2: What does success look like in your industry early in career?

The second question is about understanding the different paths to success.

Every industry has multiple archetypes of people who succeed — the strategist, the craftsman, the grinder, the networker, the dealmaker, the politician. Different firms reward different types. What works early in career may not work late in career.

What does a successful person look like in your industry? What are the different types of successful people? Does your firm prioritize one archetype over another? Is success one high visibility win or daily execution? Who gets promoted quickly and what do they do to achieve that? Which type do you aspire to be?

In venture, as I've written about, there are different types of successful investors. One firm may prioritize a product person, another a networker, a third a deal maker. In product, the same applies - the planner, the craftsman, the strategist. Get to know the different archetypes that can succeed in the industry and each firm.

Question 3: How does the work and payoff evolve over time?

The third question has to do with trajectory and payoff. Every career has a "payoff shape": the relationship between experience, time, and what you get in return.

Some careers tie pay to hours. Consultants and lawyers earn a lot, but even after a successful career they work long hours and bill by time spent. This was always unappealing to me.

Other careers have horrendous early hours and later autonomy. Banking often has brutal early years, then higher pay and more golf. This made more sense, even if it wasn't the path I wanted.

Others front-load compensation. Engineers get great starting salaries and more flexibility, but can hit a ceiling unless they move into management or entrepreneurship. Sometimes they control the craft, but not the product direction.

Some careers have different leverage. Academics have lower pay, but higher autonomy, in-group recognition, and a different type of impact. Investors can untether their income from their hours after they build credibility, capital, and trust.

The questions: What do you value in your job? If you were promoted, would you value the additional money or the autonomy more? At what point in your career in this industry, do you feel like you'll be the person in charge? Why do executives leave? Can you get rich as an IC? What's the best job at the company?

Whether you value money, impact, prestige, autonomy, balance, or some other thing, you should think through how the payoffs change as you grow in your career. You're trying to understand the slope of the next 30 years.

Why these questions work

These three questions work because they're concrete. Not everyone's going to have time for 20 questions, but I have learned a ton from the people who took the time to answer them even when they hardly knew me.

Ideally, you'll identify a career that fits you and your goals. At the very least, you'll learn what makes a good consultant, engineer, product manager, investor, lawyer, etc. Practically, I think you'll get more out of each conversation.

Two notes

First, please don't just ask these questions after someone graced you with their time. There's a secret contract between mentors and mentees where mentees ask open-ended questions and mentors impart sage wisdom. The sage wisdom is often genuinely useful, but can be incomplete and hard to apply. These questions are for you to keep in your mind and work into a broader conversation. Always remember to send a thank you.

Second, there were a few special mentors for whom I did not need this framework. These people were able to put themselves in my shoes, understand my concerns, my strengths, my weaknesses, and my goals and advise me directly. In my opinion, this is a special talent, not just the sign of a caring friend. If you have a mentor like this, value them, thank them, and help them how you can.