Getting people to agree to informational interviews with you
- What you’ll get out of this chapter
- The 7 key elements
- Similarities
- Right person
- Right company
- Right conversation
- Offer to help (optional)
- Specific times
- Specific venue
- Before you send your excellent email
- Other scenarios: live interaction, warm requests, forwardable intros
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:
- Similarities
- Right person
- Right company
- Right conversation
- Specific times
- Specific venue
- Offer to help (optional)
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:
- Do you have any friends in common? This is often best, and makes it much easier to get a second informational interview at a company once you can bring up someone else’s name.
- Do you have any shared schools, majors, or interests?
- Have you both spent time in the same country or city (ideally not the current one)?
- Have you both made a similar career transition in the past, like moving from developer to PM, or from a very large company to a startup?
- If you can’t think of anything else, are there concepts you might both believe in? For example, ex-consultants usually value structured and honest feedback, which you can bring up if you care about it even if you weren’t a consultant.
Some good examples of quick similarities include:
- “My name is Sender, and I am a fellow Badger living in San Francisco” (same college)
- “We've never met, but I’m very interested to hear about your PM experience @ ExampleCo, particularly because it looks like you have a Finance background as well.”
Some examples that are too generic would be:
- “My name is Sender, and we’re both interested in product management”
- “We’ve both had really interesting career paths”
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:
- “Because ExampleCo has a very developer-focused culture and we both have non-technical backgrounds, I want to speak with you to see if your background has made it hard to influence strategy”
- “You successfully made the transition from a very large company to a small startup, and because I’m not sure what size companies to apply to, I’d love to hear how you’d compare your experience at those two jobs”
Some examples that are too generic would be:
- “I would like to talk to someone who works at ExampleCo”
- “You’ve had a lot of different experiences”
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.
- “Your app let me get rid of my car and see my friends more often, and I use it every day” (ridesharing)
- “I’ve spoken with Person X and Person Y about ExampleCo, and they both raved about how willing the company is to invest in employee’s growth”
Some examples that are too generic would be:
- “ExampleCo has a great culture”
- “I think mobile games are really exciting”
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.
- “I’d like to speak with you about management’s style and priorities, and what you feel the biggest risks to the company’s long-term success are”
- “I’d appreciate the chance to learn about your transition from academia to corporate work, and what was most difficult about that change at first”
Some examples that are too generic would be:
- “I’d like to learn more about the company culture”
- “What’s your favorite thing about working at ExampleCo?”
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:
- “I have a lot of friends in sales and it looks like your team is recruiting. I’m happy to tell them about your open roles, if you’d like!”
- “It looks like your design team does a lot of user testing. I’d be happy to volunteer if that’s easier than finding someone online.”
- “If you want any tips on fun family activities since you’ve just moved to Chicago, I’ve lived here for eight years and would be happy to recommend a few things to do.”
Some examples that are too generic would be:
- “I’d be happy to help in whatever way I can”
- “Let me know how I can be helpful”
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.
- Make sure that times are in the time zone of the person you're emailing, and label that clearly.
- Offer some time during the workday, and some time in the evening or weekend, since you're not sure what time would be most natural for them.
- Offer times well in the future. You’ll probably want to have the conversation right away, but most people know exactly why they’re busy tomorrow, but not why they might be busy in a week. Make it easy for them to accept by offering at least one time slot that’s four days or more from now.
- Create the perception that you’re somewhat busy. If you give times like “I'm free anytime on Monday, Tuesday, Wednesday, or Thursday,” that clearly demonstrates you're not doing other interviews and are not in demand. Make a habit of offering different time ranges that create the illusion of busyness, even if you're not very busy right now.
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:
- Short phone call (15-20 minutes requested)
- Long phone call (30-60 minutes requested)
- Video call
- Getting coffee together
- Getting a drink together
- Getting a meal together
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.
- First, make sure the spelling, grammar, and formatting are correct. If you can find someone else to proofread your first few emails that’s probably best. Otherwise, reading the whole message out loud will help you catch any errors. If you’re copying the email from a template, pay special attention to the font and font size, since it’s easy to have one style from the copied template and one style from where you’re making changes in your email program. Doesn’t that look bad?
- Second, make sure to send your email at a good time of the week. There's no universal answer on when to send, but here are a few guidelines. Based on several email marketing studies, the ideal time to send email is probably late morning or early afternoon on Tuesday, Wednesday, or Thursday in the home time zone of the person receiving the email. This strategy is mainly built around avoiding being in the “weekend pile of email”, in which many people come in Monday morning to face all the messages they got from Friday afternoon to Monday morning. In that giant stack of email, your informational interview request is easier to dismiss than if they only have one or two emails in their inbox during the middle of the week.
- Finally, it's very possible that someone is totally willing to speak with you, but happens to get your reachout at a busy time. So, make a note to follow up at least once a few days later! You can use a simple reminder program like followupthen, or put a task on the spreadsheet you’re using to organize your search. For sales or business development roles, where persistence and reaching out is a part of the job description, feel free to follow much more often since this is usually considered a demonstration that you’d be good at the job.
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:
- Worst: Give them your email or phone number because they say they’ll follow up with you. If they don’t get in touch, you don’t get the interview.
- Better: Get their information, since that way you have the ability to follow up. But this will still fail often, since it’s polite and easy for someone to agree to talk in the future when you’re bonding in person, but then ignore your email later on when they get busy.
- Best: Live schedule the informational interview. If they say yes to talking with you, immediately open up your calendar and schedule a time right there. By making a specific commitment to a time and venue, you have a much higher chance of the conversation happening like you planned. I like to pre-plan three or four time slots before going to an event, so that I can quickly offer them if I need them.
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.