How to make use of LinkedIn Connections for Job I applied to

Question

I just applied to a job at a unicorn. LinkedIn helpfully told me that I have a mutual connection. That mutual connection turned out to be someone I was in university with 8 years ago who was and is super smart and is now a Principal at the unicorn. LinkedIn encouraged me to make use of the connection, and helpfully prepopulated a message to send:
"Hi John, I hope you're doing well! I recently applied to this job ({linkedin link}) at {unicorn}. Would you be willing to tell me more about your experience at the company? "

I added (because you can't just use the prompt):
"Really cool that you're a Principal at {unicorn} and got to build it from the ground up!"

I got back an instant reply:
"Hey Bill. Hope you're doing well. Yeah sure, what do you want to know about it?"

At this point, I realized I am in a pickle, and am making all the classic networking errors. I'm trying to use my alum acquaintance to help me get into the company and give me some sort of edge. But this is always very transparent and unattractive.

I'm not sure what I should ask him to turn this interaction positive. I don't want to ask him pointless questions or questions that are easily searchable. I've already submitted an app, so not sure he can refer me. And I'm not dying to get into this particular company, it's just one of a bunch of apps I sent out. I suppose I could ask him some of the questions to ask to a potential new team. That's probably best.

I still have to watch the masterclass on building deep relationships quickly in tech and that will probably give me some insight into how to approach this going forward.

All suggestions are welcome!

Rahul Pandey · Accepted Answer

I don't think you're in too much of a pickle. Here's how I'd frame this interaction:

I applied to this company already and would love to genuinely learn more about your experience - this will help me understand what rapid career growth looks like, and I'd love to hear about the specifics of this company.

This doesn't feel transactional to me at all, since:

You are ideally open to a longer-term relationship, and you're sharing your own story.
Even if you get the offer, there are many reasons why it may not be a good fit, so hopping on a 30 min call won't be viewed from a negative lens.

I agree with you that you shouldn't ask questions that are easily searchable, or anything which has a binary yes/no answer. Some of my go-to questions were:

How formal is the interaction between engineering and design?
How are new frameworks/libraries introduced into the codebase? (e.g. Dagger, Retrofit, or Kotlin)
What is the company's view on in-person collaboration, conferences, and travel?

How to make use of LinkedIn Connections for Job I applied to

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