The Informational Interview That Changed My Life

When clients reach a career ­crossroad, I often suggest informational interviewing to scope out a prospective new role, firm, ­industry or career path. That suggestion is almost always met with resistance. The most ­frequently voiced objection is not wanting to bother a busy person. When that is overcome, a trove of information, insight and inspiration can be uncovered.

An informational interview is defined as “a meeting in which a potential job seeker seeks advice on their career, the industry, and the corporate culture of a potential future workplace … They use the interview to gather information on the field and on specific companies where they might want to work. They can find employment leads, and expand their professional network.”

In addition to getting information about a role or firm, you may gain perspective beyond job titles, allowing you to see not only what skills are required but also how you could fit into that work setting. It is also an opportunity to gain insight into the hidden job market. Research brings information; interviews provide insight, details and nuances. This creates a clearer ­understanding of what you’ll be getting yourself into and will lead to a better, more informed decision. It has worked that way for me and my clients.

My career could be described as ­nonlinear. I did not follow a well-tread path and chose to reinvent myself several times as a lawyer before ultimately becoming a professional coach. With each transition, I used ­informational interviewing to help steer me toward good choices.

In 2008, I reached my 20-year mark as a lawyer and was looking for a change. While I had a great legal career, I wanted to write a second act that would be different, interesting, and, most importantly, to offer a service that would really benefit people in a meaningful way. And, I wanted to be able to envision myself doing it for the next 20 years.

It was during this time that a conversation with a stranger planted the seed in my mind with his simple words “you would make a really great coach.” Because I was in a searching mode, I began to explore that field. When you are at a ­crossroad, pay attention to what people say about what you’re good at doing.

Reading about coaching convinced me it was a strong possibility, and now I had to find people to talk with about it.

The informational interview that changed everything was with Sheila Kutner, a ­professional coach and teacher. I had only met her in passing as the wife of a lawyer I had worked for in private practice many years earlier.

My ask of Sheila was a brief telephone conversation, but she invited me to visit her home office, located in a beautiful suburban neighborhood. The front door opened into a living room on one side and a kitchen on the other. A flight of stairs led to Sheila’s office where we spent a few hours together. She described her coaching experiences and the types of things her clients had accomplished with the structure of coaching. And, she showed me the business side too. A major takeaway from our conversation were her words, “This is an entrepreneurial profession.”

Uh oh. Up until then, it had all sounded perfect. The activities and responsibilities of a coach perfectly aligned with my ­talents, personality, interests, values, ­motives, preferences and skills. But now, Sheila was telling me that I’d have to generate a continuous flow of new business to take the place of clients who achieved their coaching goals. I had spent the last 15 years of my legal career as a government lawyer and marketing was something I had not done for a long time.

Or hadn’t I? At that time, I was chief counsel to a new commonwealth agency in dire need of funding. Part of my job was lobbying lawmakers, giving speeches, delivering training, arguing in appellate courts, and testifying in Senate hearings. I was in the persuasion business. Realizing that marketing for clients required strengths I already had made it seem a bit less daunting to join “an entrepreneurial profession.” This often ­happens with clients I coach—they feel completely unprepared for a challenge until we create awareness that they already have experience to tap into.

Sheila illuminated a crucial side of ­coaching I had never thought about. That bit of information made me better prepared when I finally made the switch. Since then, I have met many coaches who were surprised by the reality that getting clients is part and parcel of doing the work they love. I enjoy marketing and now help my clients embrace it as well.

When we were finished, Sheila paused slightly before exiting her office, and then firmly and with a bit of a flourish, closed the door and made a remark about now ­stepping back into her home life. She showed me what my life could be if I prepared and dedicated myself to it.

A good informational interview is an ­opportunity to envision, which feeds the ability to create. There would be many hurdles to overcome, but I now believed I could do it. Before I talked with Sheila, coaching was a vague idea that she animated and brought into living color.

While many professionals will not do what Sheila did in opening her home and office for several hours, most are willing to take 15 minutes to talk about their field and role and you can learn much from that.

Tips for Having an Informational Interview

When you contact the interview subject, be clear and concise about what you want, which is 15 minutes to talk about their role, experience in the field, and any guidance they might have for someone interested in a similar career path. During the interview, be mindful of the time and only go over after checking with the other person.

Here are some sample questions:

  • How did you get your start in this field?
  • What’s it like working at your firm/company/agency?
  • How did you choose this firm or ­position over others in your field?
  • What is the most rewarding aspect of working in your field? The most challenging?
  • How can I best leverage my previous experience for this field?
  • What experiences, skills or personality traits does your firm look for when hiring?
  • What do you wish you had done differently when you first started?
  • What are you glad you did?
  • What job search advice would you give to someone in my situation?
  • Can you suggest two or three people who would be good to meet as I continue networking?

Tips for Giving an Informational Interview

  • Consider what you know about your role, field and industry that someone just entering it would not know;
  • Keep in mind that the person will be minding the time, so if you can spare more, give more, as Sheila did;
  • They will want to know about your ­day-to-day, so give that some thought prior to the call. Perhaps you’re having an ­atypical day or week. Think about ­percentages and what you spend the highest and lowest doing and what comes in between.
  • What do you like about your role? The field?
  • What are some downsides? Every job has them and choosing well includes ­discerning if the negatives are deal-breakers.

Sadly, Sheila Kutner passed away in 2014, but her legacy lives on in the coaches she trained, the clients she coached, and her unbridled energy, enthusiasm and passion for both. I am grateful for the gift of time she gave that helped me make an informed career decision that has been so fulfilling, enriching and changed my life.

Reprinted with permission from the Sept 20, 2017 edition of “The Legal Intelligencer” © 2017 ALM Media Properties, LLC. All rights reserved. Further duplication without permission is prohibited. For information, contact 877-257-3382, or visit