COFFEE CHAT GUIDE
Everything you need to request, prepare for, and follow up on a coffee chat with a Oscar Health employee. From the initial email to the thank-you note, this guide covers every step.
The key to getting a "yes" is making your request specific, concise, and easy to accept. Ask for exactly 15 minutes (not "some time" or "whenever works"). Mention a specific reason you want to talk to this person, not just their company. And always provide your availability to reduce friction.
Sample Coffee Chat Request Email
Subject: [University] student, 15 min on your Oscar Health experience
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Hi [First Name],
I'm a [year] at [University] studying [major]. I came across your profile and was interested to see that you work in Oscar Health's Insurance group. [One personalized sentence about their background or career path.]
I'm exploring healthcare careers and would love to hear about your experience at Oscar Health. Would you have 15 minutes for a quick call? I'm flexible and happy to work around your schedule.
Best,
[Your Name]
[University] '[Grad Year] | [Major]
Preparation is what separates a forgettable conversation from one that leads to a referral. Here is your pre-chat checklist:
Research their background
Review their LinkedIn profile thoroughly. Know their current role, division (Insurance, Technology, Clinical), and tenure at Oscar Health. Note any shared experiences.
Study Oscar Health's recent news
Read about recent deals, product launches, or company developments. Being able to reference something current shows genuine interest and helps you stand out.
Prepare 7 to 10 questions
Have more questions than you need so the conversation flows naturally. Prioritize questions that cannot be answered by a Google search.
Practice your "story"
Be ready to explain who you are, what you are interested in, and why you are exploring this career path in under 60 seconds. Keep it natural and conversational.
Set up your environment
If the call is virtual, test your camera and microphone. Find a quiet, well-lit space. Have your questions and notes ready but avoid reading from a script.
Plan your follow-up in advance
Before the call, draft a skeleton thank-you email so you can fill in specifics immediately after the conversation and send it within 24 hours.
What does a typical week look like in your role at Oscar Health?
What types of projects have you been working on recently?
How much do you interact with other teams at Oscar Health?
What skills have been most important in your role?
What has been the most rewarding project you've worked on at Oscar Health?
How would you describe the culture at Oscar Health in your own words?
What is the mentorship structure like for junior employees?
How does Oscar Health support professional development and growth?
What do you enjoy most about working at Oscar Health?
Is there anything about the culture that surprised you when you joined?
How important was networking in your path to Oscar Health?
What did the interview process at Oscar Health look like?
What should I prioritize to prepare for Oscar Health's interviews?
What does Oscar Health look for in candidates beyond technical ability?
What advice would you give to someone applying to Oscar Health this cycle?
Asking for a referral in the first conversation
Build a genuine relationship first. If the conversation goes well, referrals often happen naturally or in a follow-up conversation.
Asking questions you could Google
"What does Oscar Health do?" or "How many employees does Oscar Health have?" signals that you have not done basic research.
Talking about yourself for more than 30 percent of the time
The conversation should be about them and their experience. Ask questions and listen actively. People remember good listeners.
Going over time without asking
When you hit 15 minutes, say "I know I asked for 15 minutes and I want to be respectful of your time. Is it okay to keep going?" Let them decide.
Asking about compensation or work-life balance directly
These are important topics, but asking about them in a first conversation comes across as transactional. You can learn about these from online resources and Glassdoor.
The follow-up is where most students drop the ball. A thoughtful thank-you email within 24 hours keeps you top of mind and turns a single conversation into an ongoing relationship. Reference something specific from your chat to show you were genuinely engaged.
Follow-Up Email Template
Subject: Thank you for your time, [First Name]
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Hi [First Name],
Thank you so much for taking the time to speak with me today. Your insights about [specific topic from the conversation] were incredibly helpful. I especially appreciated your point about [specific takeaway].
I'm going to [specific action you plan to take based on their advice]. I'll keep you posted on how my recruiting process goes this [season].
Thanks again for your generosity with your time.
Best,
[Your Name]
Plan for 15 to 20 minutes. This is long enough to build a genuine connection and ask meaningful questions, but short enough to respect their time. Always ask for 15 minutes when scheduling, as this makes it easy for them to say yes. If the conversation is going well, they will often extend it naturally.
Avoid asking about compensation, hours, or work-life balance directly. Do not ask questions you could answer with a simple Google search (like "What does Oscar Health do?"). Never ask for a referral during the first conversation. And do not dominate the conversation by talking about yourself for more than 30 percent of the time.
Send a thank-you email within 24 hours. Reference a specific topic from your conversation and mention a concrete action you plan to take based on their advice. Keep the follow-up under 100 words. Then check in periodically (every 4 to 6 weeks) with brief updates on your recruiting progress.
Aim for 3 to 5 coffee chats at Oscar Health over the course of a recruiting cycle. This gives you a well-rounded perspective on the firm and builds enough internal connections that someone is likely to advocate for you during the hiring process. Spread your conversations across different divisions or teams.
Technically no, but in healthcare recruiting, coffee chats are often informal evaluations. The person you speak with may share their impression of you with the recruiting team. Treat every conversation as an opportunity to make a positive impression: be prepared, ask thoughtful questions, and be genuinely engaged.
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