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Getting people to agree to informational interviews with you

What you’ll get out of this chapter

Using the information from the last chapter, you've now got a person you want to talk to, and a way of getting in touch. The next step is to get them to agree to an informational interview with you, since informational interviews are the key to getting a personal introduction that will result in a first interview.

This chapter covers the seven things that should be present in your communication to maximize your chance of success as you ask for an informational interview. Most of the content in this chapter will focus on cold written reachout through email, LinkedIn, or similar platforms, but we’ll have sections at the end for special cases like meeting at a live networking event or writing forwardable introductions.

If you don’t feel like we’re overthinking cold email by the end of the chapter, I’ll be very surprised, but this level of detail should quickly help you get more responses. It will take time to write your first few emails in this style, but as you find a template you like, your speed will go way up.

The 7 key elements

Before we go further, let’s look at a real example of an effective reachout email that received a reply. We’ll then highlight the seven most important things about this email and go through each element in detail.

I’ve removed the names and the company, but the rest is real. It’s important context to note this message is to someone working on international expansion at a powered skateboard company, and that Sender and Receiver had never spoken and have no known mutual friends.

Hi Receiver, I’m Sender, an entrepreneur and skateboard/surfing/snowboard fan, looking to join a growing company like ExampleCo. I've done substantive work for companies on three continents and speak English, Spanish, and German, so might be helpful as you work on continuing ExampleCo’s international expansion. Is there a way we can talk for 15min, to learn if someone with a long history of working in entrepreneurship and robotics like me would be a good fit? I am planning to apply for a position, but would like to learn more about whether a PM or business role would be most appropriate. I can jump into a 15 minute phone conversation (all times PST) Thursday between 2PM and 7PM, Friday between 2PM and 8PM, or Monday between 10AM and 4PM. If you're willing to talk, when's best and what phone number should I use to reach you then? Thanks for considering, and hope to talk with you soon, Sender

This is not a perfect example, but I chose it because it was written by a client who heavily changed his style to write like this and saw much better results as a consequence.

There are 7 elements I recommend you try to have in your messages:

Before we explore each of these elements in detail, let’s keep in mind our overall goal in writing these emails, which is to make it easy to say yes to your request for an interview, and hard to say no.

We’ll make it easy to say yes by showing why the interview would be important (right person, company, and conversation) and reducing the mental work they have to do to accept (specific time and venue specified).

We’ll make it hard to say no because the request will seem reasonable and credible. Additionally, writing a great email may make the receiver feel like there's a high chance you’ll get an interview or job. This would make it awkward for the receiver if you meet and you both know that the receiver never responded to your outreach. If they fear that outcome, they’ll probably take the time to talk.

Finally, you’ll be able to re-use a lot of what you write as a template for the next email. I often reuse the right company, right conversation, specific times, specific venue, and offer to help when sending a batch of emails.

Similarities

Usage in example email: “an entrepreneur and skateboard/surfing/snowboard fan”.

Receiver is both a former entrepreneur and a current employee of a skateboard company.

It’s important to show you have something in common early in the message whenever possible, since that creates a bond between you and the interviewer instead of just having you be a stranger asking for a favor.

As you try to think of similarities, think about:

Some good examples of quick similarities include:

Some examples that are too generic would be:

Right person

Usage in example: “I've done substantive work for companies on three continents and speak English, Spanish, and German”.

The receiver is also multilingual, and focuses on international expansion, both of which are uncommon at ExampleCo.

The goal here is to make it clear that the exact person you’re emailing is someone that you need to talk with, by showing how their unique background is suitable for you. A good way to test this is thinking about “How many other people could I send the same message to?”. If you could send this to many other people at the same company, get more specific.

In many cases, similarities (above) are enough to show you have the right person, since you’ve already brought up their unique perspective.

Some good examples of right person include:

Some examples that are too generic would be:

Right company

Usage in example: “I’m Sender, an entrepreneur and skateboard/surfing/snowboard fan, looking to join a growing company like ExampleCo”...”Is there a way we can talk for 15min, to learn if someone with a long history of working in entrepreneurship and robotics like me would be a good fit?”

Sender is a skateboarding fan with robotics experience looking to join a growing company, which fits ExampleCo perfectly.

This is very similar logic to right person (above), in that the best test is “Would this apply to a lot of other companies?”, so do enough research that it’s personalized well. If your message feels like you could send it to every company, it won’t feel special to the receiver.

Some examples that are too generic would be:

Right conversation

Usage in example: “I am planning to apply for a position, but would like to learn more about whether a PM or business role would be most appropriate.”

Even if the receiver of the message is pretty sure that you’re a good fit for the company, it can help them decide to commit to talking if you’re clear that the conversation itself will be valuable. Most people have probably experienced a boring, generic conversation about their workplace, so use a sentence or two to show detailed topics you want to discuss.

It’s OK to reuse these topics in different messages, but make them detailed enough to be interesting. Ideally, you’ll want 2 or 3 conversation topics, as long as that doesn’t take a long time to explain.

Some examples that are too generic would be:

Offer to help (optional)

Usage in example: none

Offering to help the interviewer with something is a great tactic if you can do it in a genuine way. If you have something specific to offer that might fit their needs, go for it! But if you don’t have a specific offer, it can feel manipulative and detract from the effectiveness of your message.

Some good examples of offering to help include:

Some examples that are too generic would be:

Specific times

Usage in example: “I can jump into a 15 minute phone conversation (all times PST) Thursday between 2PM and 7PM, Friday between 2PM and 8PM, or Monday between 10AM and 4PM.”

This, along with “Specific venue” (the next element), is important because it lets the receiver confirm the meeting without sending multiple emails back and forth. I have noticed a lower conversion rate among myself and my clients when asking people to "have an informational interview sometime" vs. "have a 20 minute phone call Wednesday 3PM PT". Not only does the second email get more responses, but also I've seen several examples of receivers agreeing to the informational interview “sometime”, but then not responding to email once you send specific times in a followup.

Timing is simple once you get it right, but there are four things to watch out with for the times you offer.

Specific venue

Usage in example: “I can jump into a 15 minute phone conversation”

When you send a request for an interview, be specific about the amount of time and the format for the meeting, to make it clear and easy to say yes.

Here are six possible ways of having a conversation, from the lowest amount of commitment to the highest amount of commitment:

The advantage to picking low-commitment activities is that you have a higher chance of the receiver saying yes to the meeting. For example, if you're messaging someone you've never spoken with before and you don't have an especially strong connection, they're unlikely to agree to get dinner with you, but they might take a 15 minute phone call. Another advantage is that low-commitment activities take less of your time, so if you’re not sure someone will be helpful, this is a good pick.

The advantage of higher commitment activities is that you'll be able to create a greater personal bond, which will increase the chance that the informational interviewee gives you valuable information or enthusiastically recommends you for a job. So if you're talking to someone who you have a lot of shared connections with, went to the same school as you, or has a very similar hobby, you may want to ask for in-person interaction.

Before you send your excellent email

Now that you have an email drafted, there are three quick things to do before you send it.

Now, finally, send that lovingly crafted email and start the next one!

Other scenarios: live interaction, warm requests, forwardable intros

So far we’ve been talking about cold email outreach to people you don’t have a social connection to. But there are a few situations worth discussing where you’ll do things a little differently.

Live interaction

If you meet someone at an event and want to do an informational interview together, it’s still useful to explain factors like right person, right company, and right conversation to convince them to have a later one on one conversation together. Here are three ways you can exchange contact information, from worst to best:

Warm requests

It’s great when you want to interview someone you know already, since they have a much higher chance of saying yes to an interview, and are also much more likely to tell you useful information and recommend you for a job. The better you know someone, the more you can ignore the guidelines in this chapter, and you can push for meals or drinks instead of a phone call.

Even with people I know well, I like to follow the “right conversation” guide and be specific in advance about what we’ll be talking about, to give them some time to think about it before the meeting. I also like to carefully plan what I’m asking for, since most people are happy to do one or two introductions, recommendations, or interviews with you but might start getting annoyed if you ask for five+ things.

Forwardable introductions

A special case of interacting with someone you know well (we’ll call this person “Friend”) is asking for an introduction to someone else who you don’t know (we’ll call this person “Stranger”).

Simply asking Friend “Can you intro me to Stranger?” makes Friend have to write a full email explaining the situation. That’s a lot of work! Most people are willing to do this once or twice, but that gets annoying very fast.

Instead, I recommend first sending an email to Friend, asking if they’d be willing to introduce you to Stranger. In that email, it’s good to cover right person, right company, and right conversation, so that Friend knows this intro won’t be annoying to Stranger. After explaining why the intro makes sense, I usually say:

“To make this as easy as possible for you, I can send you a forwardable introductory email addressed to Stranger. If you feel it’s good enough to send along, great; otherwise, let me know and I’ll make some edits.”

Then, when Friend says yes, I send two emails. One is a quick thank you to Friend, saying I’m sending the forwardable introduction now. The other is sent to Friend as well, but is addressed to Stranger in terms of name, subject line, and email body, and is using the 7 key elements from this chapter. The similarity I highlight in the first sentence is that I know Friend. Friend can either quickly hit the Forward button and pass it along to Stranger, or add some context if they want to.

Because you’re doing most of the writing, this lets you get a few introductions from each friend you have without being annoying. For more detail and examples, here’s an online guide I have on this subject.

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