Millennials: How to Interview Anyone With Confidence

I challenged my university-aged son to create a plan to visit 10 business leaders and learn from them. He accepted! This project turned into leadership lessons, including how to interview anyone with confidence.

The idea was for Benjamin (19 years-old) to make appointments with business leaders and interview them at their offices. He had a number of purposes for doing these informational interviews:

  • Increase his confidence in the interviewing process.
  • Gain an ability to build rapport with a variety of people, including those much older than himself.
  • Identify what leaders look for in new hires.
  • Network long before it’s time to find a job.
  • Identify what jobs and careers best match him, and what it takes to get them.

He developed a process for these interviews, which he shares below. But first, here are a few lessons that made the experience exceptional.

Giving Versus Taking

In an early draft of Benjamin’s cover letter, he used a common phrase found in informational interview guidelines: “I want to explore if a career in this field interests me.” One point of informational interviews is to explore career interests, but as he shared it with me, the phrase “interests me” rubbed me the wrong way.

We discussed giving versus taking.

“Exploring careers that interest me,” is taking. Instead, he wrote, “I want to explore careers where I could make a contribution,” which is giving. This is more than just word choice, it communicates your mindset.

Here are a few examples of giving versus taking:

  • Take: talking about yourself and your interests.
    Give: asking questions so the other person talks.
  • Take: focusing on a job you want and networking toward it.
    Give: focusing on learning from the other person.
  • Take: “how much could I make in this career?”
    Give: “what do I have to contribute to this field?”

Being Interested Versus Being Interesting

“Why would they want to meet with me?” Benjamin asked when I proposed the plan. I told him they don’t want anything from him. They will meet with him to be nice, give back, or as a favor to me. It’s not about Benjamin, it’s about the leaders. The key, I told Benjamin, is to not try to be interesting, instead be interested in the leader.

Asking questions is essential to communicating interest in the other person. “All I do is ask questions,” Benjamin says. “I’ve heard their advice on choosing a major, how to approach a job interview, and offers to look at my marketing portfolio.”

“I make 30-minute appointments with each person. But not one of them has actually been under and hour. I say, ‘I don’t want to take more of your time,’ but the person says ‘no problem, I’m enjoying this!,’ and keeps talking.”

Benjamin discovered how people love to mentor those open to receiving it. When someone shows interest in us, we are happy to help. 

Margin Versus Excuses

On his way to meet the CEO of a large nonprofit in downtown Seattle, Benjamin missed the entrance to the parking garage. With only 10 minutes until the appointment, he was stuck in traffic trying to get around the block and back to the garage.

By the time he got to the receptionist, he was 15 minutes late for his 30-minute appointment. The CEO came out. Benjamin apologized for being late. The CEO said, “We don’t have enough time today. Make an appointment with my Assistant and we’ll try this again.” Benjamin went home embarrassed.

This CEO is a friend of mine. I thanked him for meeting with Benjamin and apologized for him being late for the appointment. My friend shared with me, “I could have rearranged my schedule and met with him that day. But I remembered a potential vendor who did the same thing with me. We never let him reschedule and he didn’t get our business. It’s a hard lesson, but better for Ben to learn it now than when a job or sale is on the line.”

I later shared this conversation with Benjamin, who was quite sobered by hearing it.

We talked about what happened. He realized he needed to let go of trying to be time efficient or save a few dollars on parking. Next time, he would make sure he left himself more margin, even if he waited 15-20 minutes in the lobby.

Benjamin’s next interview was at the Starbucks headquarters. He left earlier this time and arrived at the Starbucks headquarters with 25 minutes to spare. That day was a rare 90-degree Summer day – and the air conditioner in his car was broken! Because of this, he arrived sweaty in his jacket and tie.

In the Starbucks headquarters lobby, not only was there air conditioning and iced coffee, a live jazz band played. He cooled down with cool Jazz while he waited for his appointment with a Starbucks executive, which was one of his favorite interviews to date. Lesson learned.

Benjamin’s Informational Interview Process

Here is Benjamin’s informational interview process from start to finish. Let’s hear it from him in his own words:

  1. Identify people I want to interview. My Dad introduced me to friends of his and I’ve met some through events at my University. I’m not focused on just one field or position. I’ve interviewed CEOs, managers, and employees, both young & old. I can learn from anyone.
  2. Email the person. I created a cover letter template that says what I’m is asking for and why. I change it each time to match the person I’m writing. I also attach a resume that mentions my work experience and what I’m studying.
  3. Prepare good questions. I researched good informational interview questions. I made my own list of questions and tried them out on my Dad. The two keys to a good question are: 1) it gets the person talking, and 2) it uncovers their values and thinking. For example, rather than asking “Do you use social media in your marketing?” I ask, “What are the key things that make your marketing effective?”
  4. Meet the person. I wear a suit and tie and bring a copy of my resume to every interview. During the interview I listen and ask questions. I focus on being curious and digging deeper. I’m also ready to answer any questions they have for me. But after answering I redirect the conversation back to them by asking another question.
  5. Email a thank you. I email a thank you note that includes something I learned or found interesting from the interview. I have a template I customize for each interview.

The ability to meet someone for the first time and carry on an engaging conversation is a critical skill for everyone.

These days Benjamin is interviewing for internships. It’s fantastic to see him confidently approach the application and interview process. He’s getting an education, and it not just from classes at his university.

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    Keith is an author, speaker and Professional Certified Coach. He helps on-the-go leaders multiply their impact. Keith is the author of several books including The COACH Model for Christian Leaders.

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    • Gill Vriend

      Thank you for this inspiring post. Much food for thought here, not least because my own son, aged 17, will be graduating high school shortly with an unusual personal history: an MK, with an English mother (me) and Canadian father, brought up in Asia, educated by life and American system mission schools, on his way to the UK next year to study ‘Politics and international relations’. Whom should he interview, I wonder?

      • Gil, that’s the thing, “Who” isn’t the most important thing. The connecting skills develop as your son prepares for and does the interviews. Then, he can choose people who’ve made some aspect of the transition he’s interested in. Assuming he’s still living in Asia, could be British expats, or a local political leader, or one of his friend’s parents he things is interesting. My son, Benjamin, grew up in Indonesia and Singapore.

    • A number of parents have written me saying they want to encourage their kids to do this. That’s fine, but look for what would be helpful for your child AND fit their personality and interests. Benjamin is interested in business and has the ability to chat with anyone, so this interview project built on his strengths to developed him further. For your kid, it could be a research project, or making something, writing code for an app, volunteering for a nonprofit, etc. The point is working with them to find a creative opportunity, and then coaching them through the implementation – and more importantly the learning from it.