How to deal with the emotional rollercoaster of informational interviewing

So, you’ve decided you need to get from point A to point B in your vocational life. You’re convinced that informational interviewing is the best way to get you there. You’ve started the process of reaching out to people and lining up interviews. Congratulations, you’re on your way!

If only that were all there was to it.

When I’m talking to friends, younger siblings, and favorite baby cousins about informational interviewing, I often find myself wishing that we could all be a little more like robots when it comes to doing what’s good for us. Because unfortunately knowing the correct steps, and committing to them can’t prepare you for the emotional rollercoaster of informational interviewing.

Picture this: I’ve just fired off an e-mail to a family acquaintance asking if he’ll meet me for lunch to talk about his work in solar technology. I’m pleased with myself for reaching out, so I hop over to LinkedIn for some mindless scrolling (I know, cringe). I see an alert: someone has looked at my profile. It’s the solar technology guy! He must have seen my e-mail. I hop back over to my inbox and click refresh, but no response materializes. The minutes tick by, and still no e-mail. Did he look at my LinkedIn profile and decide I was a waste of his time? Am I not as impressive as I think am? Do I have an inflated sense of my worth? Was it presumptuous of me to reach out in the first place? What hubris to think an accomplished professional like Mr. Solar Technology Guy would want to spend his time on me! By the following morning, I’m not sure I should even have a professional life at all. Maybe I should retreat to the woods and live off the grid! At least then I wouldn’t be contributing to climate change!!

You get the picture. This is the kind of spiraling that can easily happen as you put yourself out there and start informational interview. Spoiler alert: the solar technology guy did email me back the next day and we had a lovely time chatting about the energy transition. But even when people respond, and you get the chance to talk with them, emotional pitfalls abound. Sometimes people are dismissive or unkind. Sometimes it’s just a terrible fit, and you don’t click. Sometimes you say something you regret (I once was a little too emphatic in my criticism of a previous employer. It wasn’t a good look).

There are many reasons an informational interview can be less than thrilling or affirming. This is a normal part of the process and something you need to be prepared for. If you let these less-than-fun interview experiences derail you, it’ll just take you that much longer to get where you are trying to go.

In this article we’ll take a look at common un-fun experiences so that you’re prepared when they inevitably arise. Here are a few:

1. You don’t get a response — This is probably the mildest of the typical bummer informational interviewing experiences. It’s very common, and it’s important that you get good at dealing with it. If you let fear of a non-response, or disappointment because of a non-response slow you down, you’re not going to get very far. The number one reason people won’t respond to you is because they are busy and they don’t have time. That’s one reason you need to treat your outreach like a numbers game. Reach out to a higher volume of people and you’ll get the responses you need to move forward in your process.When it comes to reaching out, I like to tell myself it’s my job to send the e-mail, after that it’s up to the universe. Every drop of mental energy you spend perseverating on whether or not someone is going to respond to you is a waste. Of course, this is easier said than done, but something to keep in mind.

2. The informational interview is boring — This may seem like a crummy outcome, but it’s actually great. It's a sign from the universe: don’t go this way! Something is not clicking! This isn’t the right person for you to be following or working with. Or this isn’t the right topic or area for you to pursue. Listen to your boredom.

3. The person you are interviewing is discouraging — This one has happened to me a lot, especially when I’m talking to someone who is working in an environment of scarcity. For example, the New York media scene is a place of significant scarcity. There are not a lot of jobs, or money, or even readers for the stories that get published. So I found that when I was interviewing people in the New York media space they were often giving me what felt like bad news: my pitch ideas weren’t good enough, I just needed to keep pitching, expect rejection, pay my dues, be patient, grind it out. Other people were even more brutally honest with me: a masthead editor at the New York Times told me that the New York Times is not a good place for a young person to build a career and that I should leave. That was tough to hear. It was all tough to hear. I was hoping that these interviews would open doors for me, instead I felt like I kept hearing some version of “no.”When the person you are interviewing is discouraging about the space you are interested in or your potential in that space, it’s important to discern why:

   1. Is it a kind of I-suffered-so-you-should-too kind of situation? This happens a lot in older more traditional industries (like media, finance, advertising, etc…). This is a kind of hazing mentality. These people want you to think it’s hard. They want you to really struggle and endure the way they had to. You should try to discern (perhaps through additional conversations with people in the industry) if they are telling you something true about the industry or if they are telling you something about themselves and their belief in the importance of suffering.

   2. Are they genuinely trying to help you by giving you a hard truth? If so, listen closely. The people at the New York Times who told me it wasn’t a good place for a young person to build a career were correct. Some young people at the New York Times do make it big (good for them!) but for most young people at the New York Times, it's a slow grind. That wasn’t the experience that I was looking for. If someone tries to help you with this kind of tough love, take it in. Ask yourself if you’re willing to tolerate the conditions they are describing. Don’t assume you will be the exceptional person who will somehow have a different, easier, more lucrative, less stressful experience. If it’s worth it to you, keep going in this direction. If it’s not, take their words to heart and look elsewhere for your vocational path.

4. You make a fool of yourself — This one sucks! There is literally nothing I hate more than the feeling of humiliation or shame. I am well acquainted with these feelings (I think most humans are?). It's unavoidable, especially if you’re “taking big swings,” as the startup bros like to say. It’s important to discern though: did you stick your foot in your mouth like I did when I disparaged a former employer to a potential future employer? Or are you just not clicking with the person you are interviewing with? Sometimes you might feel foolish if the person was expecting you to know more, or have more expertise, and you are simply too green to understand much about their role or their industry. In this case, the person may not end up hiring you (or even wanting to talk to you again) but you can still learn a lot from them. This is a find-out-what-you-don’t-know kind of opportunity. If you did genuinely say or do something stupid, then this is just one of those unfortunately painful life experiences. I’m much more careful about how I telegraph the shortcomings of current or past employers now. Regrettably, you sometimes have to learn things the hard way.

5. The person you are interviewing is mean, inappropriate or discriminatory — I once had an interview with a guy who told me I looked like a catalog model (not that this needs saying, but this made me uncomfortable and I was not flattered). Other people have been negative or condescending or otherwise made it clear that they don’t think much of me. Just ignore these people. They are jerks. Why did they agree to a call or coffee date if they aren’t genuinely interested in engaging in a positive manner?

If you feel unsafe (physically or emotionally) you are completely within your rights to cut the interview short, fake an emergency, do whatever you need to do. You do not need to follow up with these people or thank them, or otherwise engage in any kind of niceties. There are toxic, abusive, and dangerous people (of every gender, age, ethnicity, political orientation, etc…) in all industries and professional spaces. Part of your task is identifying these people and avoiding them. A traumatic and abusive professional experience will not get you where you want to go.

Some people will justify abusive behavior by pointing out that some of the most accomplished people in the world are not nice: Steve Jobs, Elon Musk, Travis Kalanick. Okay, I guess…? If you’re the kind of person who would thrive working with a Travis Kalanick-type colleague or boss, you probably already know that. Good for you! I hope you don’t treat your friends and family the way Travis Kalanick reportedly treated people, but you know… different strokes for different folks.

For the rest of us, having grounded, emotionally intelligent, respectful, thoughtful, and affirming colleagues is important. So if you find yourself in an informational interview with a jerk, just do what you need to do to wrap it up, get out of there, vent about it to a friend, and move on.

You should assume that there is a strong possibility you will encounter more than one jerk in your professional life and plan accordingly.

I think that’s pretty much is? Are there other bummer outcomes that I’m not thinking of? Let me know?