Career Search Keys: Landing Meaningful Informational Interviews

Informational interviewing has plenty of value to offer job searchers, career changers, or simply those looking to develop professionally while expanding their networks. Whether you’re struggling to get your cover letter and resume noticed by your dream employer, or just aren’t quite sure what to do next in your career, informational interviewing is a strategy worthy of adding to your repertoire. Formal job interviews rarely generate authentic connection; informational interviews can more closely resemble a mentor-mentee dynamic.

After hundreds of calls and appointments, I can confirm: people generally respond favorably to someone taking an interest in them or what they do. Whenever I’ve considered changing jobs or moving into a new field, I connect with as many people as possible whose work is even tangentially related. I’ve also found informational interviewing a fruitful place to reach for connections above my pay-grade. Look for second-degree connections, alumni of programs or institutions you’ve attended, or people whose interests uniquely align with your own. Most people remember the doldrums and drudgery from stages of their own career or past job searches. You might find yourself pleasantly surprised by who’s willing to share some insights and make your process a little more positive.

Here are five keys to successfully landing informational interviews, learning others’ stories, and building professional relationships that endure for the long-haul.

1. Introduce Yourself

Give your recipient a reason to read the rest of your email — and show that you’ve thoughtfully considered why it makes sense for the two of you to connect. A strong introduction should (1) explain who you are, (2) quickly cite your connection to the recipient (if any), and (3) give at least a preview of why you’re reaching out. For example:

Hello NAME,

Luke Chitwood here, reaching out because Cindy from Client X suggested we connect about our mutual interest in leadership development writing.

2. Set Clear Expectations

A few examples of good (and less good) ways to set expectations:

Good: I’m interested in learning more about your experience with [Industry, Job Title, or Company Name]. Do you have 15–20 minutes for a call or coffee in the next few weeks?

Bad: I really want to work for [Company Name]. When are you free to get lunch to talk about it?

Ugly: I have lots of expertise in [Industry/Field]. Let’s get together to talk about it!

3. Affirm Your Connection — showing how much you respect their time

If you have trouble imagining such a short conversation fulfilling your goals for the info interview, then pause for some additional reflection and editing of your own questions and expectations. Come with enough questions and conversation ideas for 45 minutes, but also know your must-ask items in case 10–15 minutes is all you get.

4. Streamline Logistics and Minimize Scheduling Back-and-Forth

Answer potential logistical questions with preemptive suggestions, and save time for both you and your interviewee. At minimum, your initial outreach should offer:

  • (A) an introduction and a reason for getting together (see #1 above)
  • (B) some options on dates and times
  • (C) an anticipated duration
  • (D) a potential meeting place (a general area, if not a specific location) and/or medium (i.e a form of remote communication).

This isn’t a cover letter or a job application — 1–2 sentences for item (A) should suffice. If you have a mutual connection or met at a specific event, briefly remind your contact of that here as well.

For scheduling, I recommend providing a range of 3–4 dates/times from at least two different weeks. This maximizes the possibility of connecting, without making it appear that you have nothing else scheduled. Tools like or Doodle are great for most forms of scheduling, but, for this type of outreach, it’s best to keep all necessary information contained in one message or app.

As far as the location or type of meeting, I personally prefer to suggest an in-person conversation (since it offers great potential for meaningful connection), but still provide a softer ‘ask’ with a phone call or video chat as a backup option. Meeting up in-person requires more effort and planning on the part of both parties, which I’ve found actually makes follow-through on an appointment more likely. It’s low-cost to cancel a phone call 15 minutes before it’s scheduled to occur; doing so with a face-to-face meeting amounts to a much larger inconvenience and breach of social ettiquette, which your interviewee is (hopefully) less likely to do.

5. Respect Yourself

From an efficiency standpoint, it may suit your availability and personal preferences to schedule a number of networking or informational meetings in close proximity to one-another and/or within a focused time-frame. This certainly helps to minimize costs, especially in terms of transportation, and it offers the least drain on other work-related activities — and on your productivity in general. At the same time, make sure to balance efficient scheduling with providing room for flexibility, and ensuring you have time between appointments to relocate, recharge, and regroup, as necessary.

Photo by rawpixel on Unsplash


For the original post and more of my writing, see my full site,

Writer, Storyteller, Problem-Solver. Beginner-level Husband and Father. Coffee drinker since age 1. #CollegeAccess, #Writing, & #HigherEd.

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