The first step in the process of doing informational interviews is to actually having someone to do an informational with. Generally the CEO of Microsoft isn’t cold-calling you asking: “Would you like to grab coffee with me, I’d love to hear about what you are up to these days.” It just doesn’t happen. You are the one who has to reach out to them. Most people are incredibly willing to talk with you (given proper context, time constraints, and setting), but are not going to fall into your lap. In this chapter, we find someone to talk with.
First and foremost, we need to change your definition of who “anyone” is. I already know what you are thinking (I thought the same as you): CEO’s, Founders, Investors, Wall Streeters, Doctors, etc. While you may meet these types over the course of your career, I wouldn’t start there. The likelihood is high that you will be turned down and get discouraged if you swing for the fences when you’re just getting started. My recommendation is to always start with someone you already know and ask them: “Do you know someone I should talk with?”
Who You Should Talk To
You should do your first informational interviews with people you already know well: your family, friends, coworkers, and social circles. Examples include:
Family: Your parents, siblings, aunts, uncles, grandparents.
Friends: Personal friends or partners and their families
Work: Colleagues, administration, your boss, senior management.
School: Classmates, professors, administration, staff, alumni
Social Circles: Gym, co-ed teams, church, yoga group, Meetups
Online:LinkedIn / Facebook / Twitter friends
Some of the most productive informationals I’ve had were with people I knew my whole life, but never really talked to about their life or business. I am advocating having an informational interview with your mom or dad. I’ve personally done informationals with my parents, my grandparents, my in-laws, my best friend, my buddy at work, my boss, my boss’s boss, my high-school math teacher, my college real estate professor, and a dude from the gym. They were all productive and helpful.
For example, my parents had family friends who came over to our annual parties about once a year. I had met them (or been introduced to them) many times and quickly forgot about them. Towards the end of college during my job search, I asked my parents if they knew anyone I should talk with. These people came up and I reached out to them. Little did I know, they were one of the largest real estate developers in my town. They had invaluable connections, not only in my job search, but later in my career when I needed people to talk with. Often we know very little about familiar people and the informational interview is a great medium to learn more.
I believe in meeting with everyone. Every different career stage has something unique to offer an informational interview. I have benefitted from meeting high school kids all the way up to CEOs. This means you cannot be picky about who you meet with. If you request or they request, take them up on it.
In an informational I believed I did not have time for, but accepted anyways, a younger college student wanted to grab coffee with me to talk about his career choices. In the meeting, we talked through his options and the discussion turned to his background and family. He nonchalantly let me know his father and uncles owned some of the largest real estate holdings in Downtown Los Angeles. He later was able to connect me with them. Even college (or high school) freshman have things to offer you.
Stages of a Career
To further extend your reach, I’ve identified people you can talk to in five different career stages. Look for them in your industry and in your network.
The Junior: Still in school or working
Young, confused, but honest, Juniors often don’t know everything, but are eager to learn. Often they come to you looking for advice and connections, which is good! They are often in school or working that first job, looking to expand their opportunities or figure out what they are going to do. They can be helpful with learning a new industry, giving back and making connections.
The Starter: 1-5 years of their career
Hard working, at the bottom, and insiders, Starters are early in their career, but often offer great insider perspectives on their industries and companies. Starters are great at telling you how to land that first job, who to talk with and can help make connections further up within their company.
The Trailblazer: 5-10 years of their career
Experienced, educated, and savvy, Trailblazers are turning their experience and hard work into value. No longer grunts within their organizations, they are often go-to, trusted people for their Vice Presidents and Officers. Trailblazers are great for learning how to succeed in an organization, self-improvement and soft skill development, and can become future colleagues and mentors.
The Mentor: 10-20 years of their career
Seasoned leaders and influencers, Mentors are well respected within their fields. They are often leading or nearly leading companies, have seen it all, and yet are still approachable. My favorite to talk to, Mentors are great at career development, connections for jobs, advice, industry insider information and job opportunities.
The Legend: +20 years of their career
Rich, powerful and connected, Legends are C-Suite, business owners and renown in their fields. Usually they have little time and are the hardest to talk to. While fun to say “I’ve met with so and so,” these interviews are generally short, difficult to carry, and intense. That said, Legends are helpful with connecting you with people who hire, giving recommendations and offering sage advice.
Talk to Everyone
Reach out to anyone and everyone you can find. Find familiar people who know and like you to introduce you to people you haven’t met before and to learn from them. Any time you go to an event, sit down in class, get a business card, buy something, or grab coffee, there are people around who are opportunities to meet with. Again, you cannot be picky. You should try to meet them all.
Now is also a good time to set up a system for tracking your contacts. This can be an excel spreadsheet, tagging emails, or using contact cards to keep track of info. Once you get going, it can be tricky to keep track of who you’ve met with, who you’ve been referred to, and who you’ve reached out to. When I first started, I used Excel to keep track of names, emails, phone numbers, companies and notes. As I evolved, I started tracking within a CRM called Contactually, logged contacts with Evercontact, and tagged emails within Gmail. Use what works for you.