“Hey, I want to pick your brain about a new opportunity I’m considering. Can you grab a coffee next week?” My recoil when receiving these emails isn’t because I don’t want to help – I love aiding talented folks find the roles and cultures in which they can thrive! Rather it’s attributable to my concern they’re asking the wrong people for advice. And this may cause them to make a poor decision.
Here’s what I believe: when considering a specific career path decision or evaluating an offer with a particular company, I’ve found people tend to concentrate mostly on the opinions and inputs of two groups: their friends in similar jobs and the most “successful” people they know within the industry. Seems like a reasonable strategy, right? Depends.
Industry friends and luminaries tend to tell you what *they* would do given your situation, but often aren’t able to see the choice and the trade-offs through your eyes. “If I were you….” is the common opening of a response, which says “I’m not thinking about you, I’m reacting based on my own values and interests.” It’s not that these groups are useless conversations but with them I’d focus on two pieces of information: across both groups is there consistency in the recommendations they make and, especially for the latter group, what questions did they tend to ask themselves when making similar decisions?
Ok, so who do advice seekers usually *undervalue*? (A) People who know you very deeply regardless of expertise in your specific professional work and (B) individuals who have direct experience with the company, role and people you’re considering.
The people who know you well are more readily able to actually see the opportunity through your own eyes and challenge (or confirm) your sense of self. I don’t believe they actually need to understand the specifics of the career, they just need to hear you describe it – what’s interesting about it, what concerns you, and so on. “Knowing what you know about me, am I thinking about these opportunities in a manner which makes sense to you? Am I correct about when I’m happiest and doing my best work? Are there things I’m afraid of which cause me to overestimate or underestimate the risks?” Pick the right people and it’s like holding a truth mirror up to yourself.
As for the individuals with specific experience, but who might not even know you – what you’re seeking there is confirming or disconfirming information about how you’re understanding the role. Let’s say you’re considering a Google PM offer. What you want to do is find some Google PMs and ask “hey, what intrigues me about this opportunity is that I’m interested in learning how a large company runs itself and even though I know it might take longer to ship a product, I want to know that product will have a big impact. Does this correlate with how you experience the role day-to-day?” With this information you can get very specific around the pros and cons of the opportunity — ensure that you are seeing it with realistic eyes to confirm that it’s what you believe it to be.
And that’s it – if you have people who know you and can validate your thinking given who you are as an individual, and if you have people who understand the job deeply and can validate your understanding of the work, the culture, the company, well, you should be in a position to make a good decision.