Why does it feel so weird to make an "ask" at the end of a informational interview?

I've been having a few conversations per week. I've been having solid success with contacting alumni. For the life of me, I cannot make "the ask". After 5-10 minutes and when I run out of questions, I usually just say "Thank you for taking the time to speak with me today, I was able to learn a lot etc" and end the conversation. I just don't know how to fit in a simple "Is there anyone who you think would share their experiences with me/would talk to me about their experiences?". The one time I asked an alumni, he said he would refer me and just never replied even when I sent a thank you email. I know it's that simple but where do I say it in the conversation?

 

Maybe you are but, focus your networking. I found one company I was really set on and found an alumni, called him, called other alumni, flew out to meet with them, got introduced to others in the office, met the recruiters, got put in the pipeline for SA interviews, etc.

Everyone knows why you are calling, no one just wants to call strangers half way around the country and talk to them about their job. They respect that you are working your butt off, that you have self selected for making the effort to contact them, most just are not decision makers. If they like you, they can get you in touch with decision makers, but that is a big ask if they have never met you. It is also a big ask for them to connect you to their network. The best way to ease peoples concerns is to sell them on why you are smart and why you are talking to them, in their position, in their industry, at their company. If they know the why to all those questions and then they tell you about an opportunity for an SA position or a full time position, you need to express huge interest in it, tell them you will try to fly out (if you can) on your own dime,

 
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My first contact to alumni was always by email and I attached my resume to all of those emails, your resume will help, but the phone conversation is where they can really get an idea of how you think. When I take phone conversations I let whoever is calling me take the lead, I want to see how they direct the conversation, how much thought they have put into their preparation, where their head is at, how well they know the industry, what questions are they asking me? Are they basic that they should already know? Are they things they could google? Did they even prepare questions? Did they study my firm? What do they like about my firm specifically? Is there a good reason they are using my time and their time? I can tell within the first 30 seconds or so where someone is at, it usually comes out quickly in the "tell me about yourself" question. When students from my school call, I have been disappointed sometimes. I helped one kid a lot more than I should have, I shared models with him, sat on the phone and walked through a model with him, explained how cap rates worked, IRR, stuff he should have had a good grasp of long before he started talking to me, anyway, he just was not too bright, he was studying economics because he did not get into the finance program from my school, so he just didnt have the right coursework, mindset for how to think about stuff and didnt put in the work to learn it/he didnt know what he didnt know. Anyway, I am sure your story is different, you have good internships and experience. Speaking plainly, if you have had an IB and 2 RE internships, you should have a pretty good idea of the industry, and you should be pretty confident in your knowledge. You should sound good on the phone. It is likely you connect pretty well with the people you are calling. If you think the call is going good, just straight up ask them, "I really like what I have read about your firm and your group for reason XYZ, do you all have an internship program?" "I am pretty flexible in terms of location, do you know of any groups at your firm that are looking for an analyst?". I guess my question to you is, from the calls you have had, can you tell if they have gone well or not? As you have read through what I expect on a call, are there points you felt less confident on?

Edit: I would actually be surprised/disappointed not to get this question if I had a good call with a student from my school (did they not have confidence?). I know they want a job, and I want to help them. If someone was not prepared they will be embarrassed and want to get off the phone ASAP. But If someone knows their shit and and is checking all the boxes, I for sure open up my network. I get offers to interview for some pretty solid positions from recruiters/head hunters on linked-in, I send those to students who have impressed me all the time. That is another good question to ask, "ok, your firm is not hiring, have any headhunters reached out to you with available positions?" The Rice University Endowment fund is taking the RE investment in house and building a new team, a headhunter asked me if I was interested, I said no because I am in a good place, but I forwarded his contact info to everyone I knew that might want it. If a solid student called I would have been happy to send them that.

 

Excellent comments! Completely agree.

The reason OP is uncomfortable asking (for anything) is this is actually a sales call (selling yourself) and needs to be thought out. It's part of the overall sales process and, like everything else in sales, you need to be closing for something (the next call, a referral, a resume review, an interview, etc.) OP likely has never had to do this before so it's foreign. There are steps and you just need to take them. There will be fear involved, but each time is an opportunity to overcome that fear and gain experience.

Look at it this way. If we agree to take your call, we want to help you. Why else would we take your call? It's actually disappointing to us when you're not prepared and you don't ask for the next step.

 

I luckily had some really bad calls with investment bankers when I was a sophomore. They chewed me out on the phone for not having my shit together and wasting their time. Every call after that was very well thought out and prepared. You need to lead the call. With the amount of internships you have had, these are not informational calls anymore, you should have a pretty specific field you are targeting and you should be prospecting for a job/internship that will lead to a job. Dont think of it as "yes! this person is open to take a call with me!" think about your time, you need to operate efficiently with your time, there needs to be a reason you are on the call and the person you are calling needs to feel that. Dont worry about sounding robotic, right now your biggest concern should be what you said above: "going with the flow", it sounds like your problem is that you are too passive, you should sound like a wolf on these calls. When you say you go with the flow, I get the impression the call would be a fail for me. If you were a sophomore or a freshman, letting the alumni take the lead and direct the call at points is understandable because they want to understand you to help point you in the right direction. But when you are a junior or a senior, you should have a direction (even if you dont, you cant sound like that on the phones, not having a direction/focus, and a good reason behind it is a big red flag)... so once you are a junior or a senior, they are not expecting to lead any portion of the call, and if they have to at any point, they will not think the call went well. Keep in mind, the people you are talking to were successful in the recruiting process, they get this stuff, they will be looking for/expecting it.

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