The Coffee Chat Advice Students Wish They Heard Earlier

(Most students are doing this wrong)

Students often tell me:

“I’ve done 15 coffee chats, and nothing happened.”

That’s usually the first sign they’re approaching coffee chats the wrong way.

One of the biggest misconceptions students have is that coffee chats are a box to check.

They think:

“If I do enough coffee chats, eventually I’ll get a job.”

That’s not how it works.

The students who get the most out of coffee chats approach them very differently.

They treat them as purposeful conversations designed to gather information and deepen their understanding of the job.

Every question they ask has a reason behind it.

They’re not just asking questions.

They’re building knowledge.


The Real Goal of a Coffee Chat

There are two main goals.

1. Gather Information

You’re trying to understand:

  • What the job is actually like
  • What the day-to-day really involves
  • Whether this is something you truly want to do

This matters more than most students realize.

Every year, people enter jobs and quickly discover:

“This isn’t what I thought it would be.”

That creates problems for everyone.

Employers want people who understand the role before they join.

Coffee chats help you reduce that risk.

2. Understand What Great Looks Like

  • What makes someone excellent at this job?
  • What separates the all-stars from everyone else?

The more you understand what excellence looks like, the better prepared you’ll be to develop those skills.

And, especially if you have those skills, you’ll know the importance of highlighting them on your resume and in the actual interview process if you get selected.

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3. Generating advocates

Finally, you are trying to make a good enough impression that this person would be willing to pass your resume along when it comes time to select people to interview

The reality is that it won’t happen every time, but the more you do the “right” things – the types of things we highlight in this newsletter, the better your chances of this happening.

The Students Who Stand Out

The students who do coffee chats well usually show a few things:

  • They’ve already built some understanding of the industry
  • They ask thoughtful follow-up questions
  • They show genuine curiosity

They’re not asking the most basic questions.

Instead of:

“What does your day-to-day look like?”

They ask more nuanced questions about the subtleties of the job.

That signals they’ve been thinking seriously about the career.

Ask “Second-Level Questions”

One of the easiest ways to stand out is to ask what I call second-level questions.

These go beyond basic information.

For example:

Instead of asking someone to walk through their resume, you might say:

“I noticed on LinkedIn you moved from Company A to Company B. What was driving that decision, and did the reality match your expectations?”

That shows two things immediately:

  1. You prepared for the conversation
  2. You’re trying to learn something meaningful

Those are exactly the kinds of conversations professionals enjoy having.

3 Coffee Chat Questions That Work Extremely Well

If you’re unsure what to ask, these are excellent starting points.

1️⃣ Understanding the role

“What parts of this job are hardest for people to understand from the outside?”

2️⃣ Understanding success

“What separates the people who become really good at this job from everyone else?”

3️⃣ The ‘amazing hire’ question

“If someone joined your team and after 12–24 months people said ‘Wow, that was an amazing hire,’ what would that person have done?”

The answers are often incredibly insightful.

What Makes Someone Want to Help You

Sometimes a coffee chat goes so well that the person thinks:

“I should introduce this student to someone else.”

That usually happens when a student shows:

  • Good judgment
  • Thoughtful engagement
  • Genuine interest in learning

There’s also something students often miss.

When someone introduces you to another person, their reputation is on the line.

They’re thinking:

“If I send this student to someone else, will they represent themselves well?”

The more confident they feel about that, the more likely they are to help.

What to Avoid

Some mistakes make a coffee chat feel like a waste of time.

Don’t ask questions you could easily answer yourself.

If something can be found in two minutes on Google or LinkedIn, it’s better to build on that information instead of asking for it directly.

Also, avoid asking questions that don’t seem to have a clear purpose.

If someone finishes the conversation wondering:

“What did this student actually get out of that?”

…it usually means the student didn’t approach the conversation thoughtfully.

You’d be surprised how often this happens, and it’s typically someone who is approaching coffee chats like a “check the box” exercise.

What Makes Someone Memorable

Interestingly, people rarely remember students because of one amazing conversation.

What they remember are students who take advice and run with it.

For example:

  • Listening to a recommended podcast and following up about it
  • Acting on suggestions
  • Implementing feedback

One thing I often encourage students to do is write on LinkedIn.

It shows:

  • thoughtfulness
  • commitment
  • interest in the field

When someone actually does it and follows up later, that stands out.

Because surprisingly few people implement the advice they receive.

The One Rule for Every Coffee Chat

If there’s one rule students should remember, it’s this:

Have a conversation.

Bring a list of questions.

But don’t treat them like a script.

Listen carefully.

Ask follow-up questions.

Follow your curiosity.

The best coffee chats feel natural because the student is genuinely engaged in the discussion.

And when someone feels like you’re really listening to them and thinking about what they’re saying…

That leaves a very positive impression.

Coffee Chat Checklist (Save This)

Before the chat:

✔ Research the person 🧐
✔ Prepare thoughtful questions 🙋🏻‍♀️
✔ Understand the basics of the job

During the chat:

✔ Listen carefully
✔ Ask follow-up questions
✔ Treat it like a conversation

After the chat:

✔ Send a thank-you note 📝
✔ Act on their advice
✔ Follow up later with what you learned

The students who do this well aren’t just networking.

They’re learning faster than everyone else.

And that’s what eventually sets them apart.

 
 

 

 

 

If you develop this keystone trait – you can work out everything else!

video preview

Ashley Misquitta is a guest for a fireside chat at Appleby College’s Leadership Conference on Nov 22nd 2025. In this clip, Ashley discusses high agency.