Learning and impressing with informational interviews

What you’ll get out of this chapter

Most of the Unusually Difficult system focuses on how to get informational interviews and use them well. These interviews are going to be your main advantage over the hundreds or thousands of other applicants, so we’ll cover informational interviewing in a high amount of detail.

First, we’ll look into the two main goals of informational interviews, learning and impressing. Then, we’ll look at the structure of an informational interview and see some sample question types appropriate for each phase. Next, we’ll introduce a rubric for examining your own interviews, so you can see what to shoot for. This is followed by some tips you can use to improve your interviews.

Goals: learning vs. impressing

Recall from the introduction of the Unusually Difficult system that it’s an informational interview if learning, rather than assessing, is the main publicly stated goal. This does not mean learning is always the actual goal.

You’re going to have two main goals when you conduct informational interviews: learning and impressing. These aren't clean, separate objectives; they will be mixed, but usually when you do a lot of one of them it makes the other goal less effective.

One goal is learning: to learn as much as possible about the company and the role, which will involve you seeming less knowledgeable in order to ask the questions that you truly have. If you’re heavily prioritizing this style, don't worry about looking stupid or asking basic questions, just focus on what you need to know. For interviews where you’re mainly focused on learning, your two main goals are going to be 1) to decide if the company is a good fit for you and 2) to learn enough about the company to develop reasons you truly believe that the company should hire you over other candidates.

Another goal is impressing: to make a positive impression on the interviewer and get a referral. This could be a referral to the company they’re working at, or an introduction to someone else who they know. Ideally, you have a lot of knowledge coming into this conversation, and you make a positive impression about how much you know about the company and the role. This helps the interviewee feel comfortable recommending you. For interviews that focus on getting a referral, your initial goal is for people to introduce you / pass on your resume, but as you get more comfortable your goal should be to make this person into an advocate for your candidacy, not someone merely passing your information along.

Knowing a lot about the company is not a prerequisite to getting a referral, and it's certainly possible to learn and get a referral in the same interview, but tension exists between these goals. In practice it's often helpful not to ask basic learning questions when your goal is getting a referral to a job role (impressing).

For example, if you’re trying to impress, you might prefer to ask a question that seems insightful instead of a question you really need to know. Asking a question like “It seems like this industry relies a lot on repeat customers, how do you keep people coming back?” shows you know the company and industry, and helps you be impressive. Asking a question such as “What is the culture at this company like?” is more important to know if you want to work there, but doesn’t usually help impress.

Because of this tension, for job openings you really care about, I recommend you do at least one pure learning interview before you focus on impressing someone else at the same company and getting a referral. You’ll often be able to get a much stronger referral from your second conversation focused on “impressing”, where you’re starting off with a lot of company-specific knowledge from your first “learning” interview.

Informational interview structure

Before we get into tips and how to improve, it’s important to have a shared idea of what actually happens during the interview. I encourage you to think of the interview in four phases: the opening, the content, the intimate questions, and finally the closing and next steps.


The goal for the opening of the interview is to get the other person settled in and comfortable talking. This could be as short as one question or a short conversation about the weather. Alternately, it might take a few questions, if you don’t hit it off immediately. You’ll want to keep the questions positive to start.

Example questions include:


As you shift out of the opening phase, you get into the main content phase of the interview, where you ask the questions you’re most curious about (goal: learning) or that make you seem insightful / a good fit (goal: impressing).

These questions shouldn’t be too controversial or negative, especially as this phase begins. Most interviews will spend most of their time in this phase.

Example questions include:

Intimate questions

If the content phase goes well, you might want to shift to answering intimate questions, which I’d define as questions most people wouldn’t honestly answer to a stranger. They also usually involve potential negativity. For example, if a stranger asks you “Are you happy with your job?”, most people reflexively answer yes, especially if a detailed “no” answer might get back to their boss or team.

These questions are often the most important thing about the interview: they build relationships between you and the interviewee, tell you deep truths about the company, and give you enough information to do a great job in first-round interviews. However, if you force difficult questions and don’t have rapport with the interviewee, it creates distance and you’ll often get useless, politically correct responses instead of the truth.

After over 500 informational interviews, I still don’t use questions like this every time, since sometimes I don’t click with people well enough. It’s OK that not every interview results in a great connection. However, if you feel that you’re getting along well, try inserting one of these questions and see if it opens up a better discussion than you were having earlier.

Example questions include:

Closing & next steps

Finally, as you near the end of your allotted time or decide it’s time to finish, you’ll want to use the last few minutes to close the interview.

If your main goal was to get a referral to the company, now’s the time to ask. If things didn’t go well and there are other people you can talk to, it’s OK not to ask.

If your main goal wasn’t getting a referral to a company in this interview, you’ll probably want to ask for intros to other people, whether it’s at their current company (to try and impress, and get a referral as you apply), or people in similar roles at other companies (ideally, look at LinkedIn in advance, and have names of their connections in mind). If we’re getting along well, I’ll often ask who they learned the most about their role from, and ask for an intro.

Finally, this is a good time to offer to help them. If anything specific has come up in your preparation or conversation that you could help the interviewee with, whether that’s an introduction to others in their field, a personal favor, or something else, it’s nice to offer, since this person just voluntarily spent time helping you.

As with many other places in this book, it’s important to quickly follow up on these introductions, referrals, and offers to help within a day or two while the interview is still fresh in their minds. Use your existing organizational system to make sure you get a response to your followups, by updating your master tracker and your folder about the target company.

Example questions include:

A note on referrals

The entire book has been building up to asking for referrals to open job postings: all of your introspection, research, email, and informational interviews has led to this point. Congratulations!

You should find, as my one-on-one clients have, that getting a recommendation from the right person to the hiring manager is a lot of hard work, but will produce a first-round interview over 75% of the time if you are being referred to a specific open job posting.

If you’ve been sending in a lot of applications without success, hopefully this is a breath of fresh air. Additionally, you’ve learned a lot about what you want and what companies want along the way. This will help you do very well in first-round interviews and later rounds.

Measuring whether interviews are going well

Sending out a cold email has a clear, measurable outcome: did they say yes to an informational interview or not? Informational interviews are less clear, since usually you’ll have a pleasant conversation and learn some things, but it can be hard to self-diagnose what’s working and what isn’t.

If your goal is to create strong connections with people in informational interviews, so that they’re not merely passing your resume to the recruiter but instead actually recommending you, the bad news is that there isn’t one simple answer for how to make genuine connections with people. Thousands of sales, relationship, networking, and psychology books have been written on the subject of connection. A simple book that’s stood the test of time is Dale Carnegie's How to Win Friends and Influence People, which you’ve probably heard of before (for good reason).

Though I don’t know how to show you how to bond with people in a few short pages, I can provide some guidelines for designing informational interviews that have a higher chance of creating meaningful connection. Since the most effective practice of two-way conversation is having real conversations, this is a framework to prepare for an interview, and assess how it went afterwards as a way of improving over time.

That’s why I’d encourage you to print out a few copies of the next page (to be added - email me if you see an early version of this webpage) and use them for self-feedback after your interviews, to see what you need to focus on. If you do this right after your interviews when it’s fresh in your brain, you should improve quickly.

Tips for improvement

Many of the most important tips for preparation and how to flow through the interview are covered by the previous sections, but now that you’ve seen the structure of the interview and how I recommend you prepare and assess, there are a few areas that could use some more detail.


If you’re going to invest limited time in preparing, here’s the priority order I’d suggest for how to spend your time. Please always try to do at least the first three steps, even if you have only ten minutes to prep.

  1. Are you mainly learning or impressing this interview?
  2. If you’re learning, write out what you want to learn in this interview. If you’re impressing, write out why you think you’re a fit for this job.
  3. Spend some time researching the interviewee’s background, so you can link the questions to their employment history. It’s a slap in the face to interview someone and not know the basics of their past.
  4. Figure out the intimate questions you plan to ask if things go well.
  5. Figure out what you’re going to ask for during closing if things go well.

It’s very important to know what you’re looking for in advance. If you skipped the “Finding your own priorities” exercise, this would be a good time to revisit it.

The interview

Just like the first two lines of a cold email, I try to make clear in the first minute or two that I’m familiar with the interviewee’s background, because that’s a respectful and flattering way to start things off.

I frame the interview very early, by outlining a few areas I’ll be asking about in advance and why, and asking if that agenda sounds good. This helps steer the conversation back on course if the interviewee tries to talk about one topic the whole time, since I can refer back to the stated agenda as I interrupt.

People really like talking about themselves! They should be talking a lot more than you’re talking. If you’re talking even 40% of the time in an informational interview I’d recommend thinking about how to make it more about them, since this will help them like you more.

Most people, myself included, need to take notes during conversations to remember the details. I prefer pen and paper, since I find it easier to be present in a conversation when writing vs. typing, and usually take a picture later and store that image with my job search materials. I type when it’s a phone/video call since it’s less alienating to do that when the interviewee isn’t in the same place. For super high value interviews, you can use an audio recorder (with interviewee permission) and take notes later, which lets you fully focus on the conversation.

Finally, you’ll often run into a situation where you booked 20 minutes, and at minute 15 the conversation is flowing really well and you wish you had more time. Rather than keep going and hope for a few extra minutes, I find it respectful and effective to explicitly call out that you’re reaching the allotted time, say you’d love to continue, and ask their permission to do so. You’ll often get a yes, and it’s much easier to have a relaxed conversation with that out of the way than when you’re constantly worrying that they want to wrap up now and they’re getting annoyed you’re going over.


Remember how in the “Target qualities” section of the book you created a document about what employers are looking for? Your first guess about what hiring managers are looking for, or how to tell a good from a bad opportunity, is not going to be correct most of the time. Informational interviews are the best way to get better information, and so I'd encourage you to revisit that document and update it over time.

This does a few things for you. First, when you do a few informational interviews and your document doesn't change, it's a good sign you fully understand the role and can spend less time in “learning” interviews and more time in “impressing” interviews. Second, sharing that documented understanding of what makes a great product manager, designer, or whatever role you're looking for is a great topic of conversation. When you show the interviewee what you think right now, they will either correct some of your assumptions, or be impressed by how accurate the report is. You win both ways, since you either get better information or come off well. Finally, when you're talking to a lot of different people who have different job roles at different companies, you’re going to forget the details unless you have a truly exceptional memory. This style of cumulative note taking allows you to preserve what's important across time.

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