2 quick updates:

“There’s no stupid questions!”

We’ve all heard this before. True in some circumstances, but also misleading. Often, others absolutely form opinions about you based on the quality of your questions.

Best way to learn the ‘art’ of asking questions is through visual examples. See below for the 3 most common mistakes we see at work / during networking conversations.

Fix your approach to these, and you’ll impress more simply by the depth & thoughtfulness of your questions 🙂.

Mistake 1 — asking for advice with limited context

❌ “So…..should I major in Finance?”

Why this is a bad question: it’s WAY too vague! There’s no way to even BEGIN answering this without more information. For example –

✅ “I’m currently a Finance major and aiming for Investment Banking – I love the intellectual rigor and how fast the space moves. However, I’m also very interested in Software Engineering – loved & aced all my programming classes. Do you have a framework for making a decision on which to pursue? I care less about work-life balance than long-term career stability…..how would you go about a decision like this?

Mistake 2 — asking for a favor with limited context

❌ “Can we have a coffee chat please?”

Professionals are not just waiting around to have coffee chats! Between work, loved ones, hobbies, and friends, grabbing coffee with someone they barely know is likely the last thing on their list (if it even makes it on the list). There’s a lot of insights to unpack here, but for now, you’ll have greater success simply by making your ask as specific as possible. This shows thoughtfulness, preparation, and high EQ.

✅ “I saw that you transitioned from Consulting to Tech, and I’d love to better understand your decision here as I too see Consulting as a training ground before I tackle corporate leadership. I also saw that you were a former president of SMU Growth-X — I recently joined the executive board in the organisation, and would love to get your perspectives on how I can best take advantage of the resources/network available while giving back to make the organisation even more impactful for members (my philosophy is always to “leave a place better than I found it”).

I know you must be very busy; happy to meet anywhere around your office, or jump on a quick 10-15min call. Thank you so much in advance for your time!”

Mistake 3 — asking for solutions

❌ In general, any form of “so….what do I do / what should we do?”

You’ll encounter challenges ALL the time at work (and of course in your personal life). Proactively do your best to tackle the problem without expecting someone else to solve it for you. Even if you’re wrong, they’ll appreciate the proactiveness! As my ex-McKinsey manager used to say — “come to me with solutions, not problems” 😂.

✅ “Our monthly subscription dipped by XX% this past month. I dug into the data, and found the root cause to be lackluster marketing campaign conversions, specifically among our Gen Z segment. To tackle this, I believe we have 3 options — X, Y, and Z. I’d prioritise option 1 for [these reasons]. Let me know if I’m on the right track?”

📣 Across our career mentorship for 10,000+ youths this year, the question we’ve gotten the most is around how to squeeze value out of AI to improve career prospects. The only AI resource we use is Superhuman (for the past 10+ months), with thousands of tested-and-proven prompts to level up your career across different industries. Linked below if you want to level up on AI for your own career 👇

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Best,

Vincent (follow our Instagram for bite-sized career insights & updates 🙂)