The Better Way to Take, and Give Career Advice

As the year draws to a close, I've been reflecting on key patterns among people who have successfully transformed their careers—moving from feeling stuck to finding clarity and purpose.

A common thread is their perseverance to figure things out, even when the path isn't clear. Unlike in school, where there are a finite number of majors to choose from, life presents infinite ambiguity. Rather than fighting this uncertainty, many have benefited from embracing it, freeing themselves from the search for the "most optimal" choice. I've witnessed the benefits of testing and making micro shifts in mindset day by day when the final destination is still elusive. One day, the dots will connect — as long as you keep collecting them.

Seeking career advice from people you respect is a common way to find the dots. Yet, I find that some people might focus too much on "what to do" suggestions without adequately examining the "why" and "how." 

As someone else's decisions might align with their goals and circumstances but may not suit yours, you can find insights more effectively by asking the right questions.

The better way to ask for career advice: stop collecting stories, start finding frameworks

The key is understanding how someone reasons through their solution, rather than just knowing what solution they chose. Then, evaluate how your own goals and resources (skills, finances, etc.) align with their reasoning to find your path.

Here are some examples of moving from "what" to "how" and "why":

❌ Less effective: "What do you like about product management?" (These surface-level insights are readily available online)

✅ Better: "How does product management align with or challenge your career goals?" (This reveals the strategic fit between role and aspirations)

❌ Less effective: "What drove your success?"

✅ Better: "Why did you choose this approach? Where did it prove most effective, and where did you encounter limitations?" (Uncover the nuanced thought process and learnings behind career success)

❌ Less effective: "What should I do?"

✅ Better: "How would you think through this decision if you were me?" (Understanding their decision framework so that you can plug in your full circumstance yourself)

Generally, you want to probe for:

• What drives their career decisions?

• How have their choices served or hindered their goals?

• What specific resources and circumstances enabled their success?

• Which assumptions underpin their decision-making?

Crafting powerful follow-up questions

Going a step further and dig for specific details will help you clarify the assumptions and thought process. Advisors are just humans - they are not your consultants. Sometimes, they could be imprecise or incomplete in what they share. It's your job, not theirs, to think critically about their teachings, and draw the right conclusion for you.

1. Extract Concrete Details

"Would you mind sharing a specific instance where you applied this approach?"

"What was the key message or phrasing that resonated most in that important conversation?"

2. Identify Limitations

"In which circumstance would this approach have failed to deliver?"

"What would your revised strategy look like?"

3. Surface Hidden Assumptions

"What resources were essential to your success?"

"How might different circumstances have led you to choose another path?"

Obviously, while these questions aim to uncover deeper insights, you should also reflect on the broader purpose and context of their conversations. The specific questions and whether you are at a point to ask these more in-depth questions are up to your discretion and goals. The guidance here is to help you gather relevant information to find effective solutions. In some cases, you might just want to network to get your names out there, or don't feel the willingness of the contact - then these are not appropriate.

On the other hand, note that even if you just want to make a connection (rather than really finding information), many people (myself included), prefer smart, thoughtful questions that show true curiosity and critical mind. Generic questions and superficial follow-ups can be interpreted as either lazy or inauthentic. When you are truly curious and thoughtful about your career, people might be more willing and invested to help.

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Interestingly, emotional biases often lead us to be less rigorous in career decisions than in other areas. Whether it's rushing to closure or struggling to accept personal limitations, these biases can cloud judgment.

Think of career planning as strategic problem-solving. While advice provides valuable input, it's not a complete solution. Remember: casual advisors aren't accountable for conducting thorough analyses. You must become your own strategist, critically evaluating each piece of information.

Before ending this post, I would like to leave you with this quote from the wise Matsuo Basho: “Do not seek to follow in the footsteps of the wise; seek what they sought.”

Happy New Year 🎆!