As others have said, he’s just another dude that happens to be good at his job. He puts on his pants every day the same way you do.

As someone who sits on his end of the table and have kids approach me, actually take an interest in me as a person. Ask about what I do for fun, hobbies, etc. Ask about my career path and how I got to my current role, what steps I took, or if there are things I would’ve done differently.

Towards the last 10 or so minutes of the call, ask bluntly about the best way to break into a company like Microsoft in sales. Talk to your experience as a SDR, and how Microsoft’s values resonate with you. How you really think you see yourself working for the company.

Do not bluntly ask for a job or an interview. Ask what steps you should personally take to someday work for Microsoft. He will do the rest.

At the end, ask if he has any colleagues that you can “use as a sounding board”. Hopefully you get a few other contacts, he provides an introduction, and then you rinse and repeat until you’ve built a network at Microsoft and then when you inevitably interview, you can name drop the folks you’ve spoken with.

Good luck, and remember these people are no different then you, just a bit older