Interview Everyone

A Mostly Serious mini-article


Becoming an Excellent Listener

Tim Ferriss posed a question to Chris Sacca on a recent episode of The Tim Ferriss Show, asking Chris what commonalities are shared among founders where success and massive scale seem predetermined. Using Matt Mullenweg and Ev Williams as examples, Chris’s response is that they are all excellent listeners.

“These guys go out of their way to interview other people. I don’t just mean in casual conversation. If you catch Ev, he’s got a notebook always, and if you ask him to see the last few pages of the notebook, he’s just meeting with other people…from whom he’s learning.” — Chris Sacca

Specifically, Chris mentioned Ev Williams interviewing billionaires in unrelated industries and other highly influential people. Unfortunately, many of us may not be greeted so openly when calling up our friendly neighborhood billionaire to sit down for an interview, but we’re all lucky enough to have a treasure trove of valuable information and insight everywhere around us. Your friends, family, and co-workers all have even more to offer than you may think.


Mostly Serious Interviews

Interviewing people has an incredible way of revealing information that would probably never be disclosed when having a loose conversation that isn’t controlled or focused. It’s easy to allow small talk and recent events to dominate. The interview format structures a conversation to force topics that may be difficult to ask and even more difficult to answer.

We recently held interviews with every member of our team at Mostly Serious. We asked questions about the company, visions, team, and culture. Our team drives our company and its policies, so these topics aren’t outside of what is already on our minds each day. But when put in the context of an interview, things change. Everyone went a little deeper than they do during a typical discussion.

The Mostly Serious company hierarchy as envisioned by four team members. Unfortunately, Merle Waggard only made one diagram.

Here are some example questions we asked:

  1. What did you do before this position?
  2. What will you do after this position?
  3. How will you, personally, define success for the company?
  4. What is missing from the current process at Mostly Serious?
  5. What problems do you face most often?
  6. Coffee or tea or be with me?
  7. If Mostly Serious were an animal, what would it be?

The responses were surprising — not only because no one else said we are an elephant, and clearly we’re an elephant — but because each person went far beyond answering the questions. A response turned into a conversation and the conversation turned into opinions and insights we had never expected to uncover. By the end of the interviews, we had a clear understanding of our business direction from every person on our team. We had unknowingly drafted a roadmap to our future.

Elephant, clearly the correct answer, and my other favorite responses to the animal question.

In many culture-driven organizations, it isn’t surprising to have a team-led vision. What is surprising is how level the playing field becomes when everyone has the same opportunity to voice their opinions. When purposefully and pointedly asked, people seem much more likely to provide their full, uninhibited views on a variety of topics.


Interview Everyone

It wasn’t until after these interviews that I heard Tim’s podcast interview with Chris. Knowing how much we had gained from our company interviews, I wondered how many little nuggets of wisdom I have missed by not interviewing more people. I decided to interview some friends — some who I am very close to and some with whom I haven’t had more than a few disconnected conversations with as we bumped into each other at events.

These questions were different. I wasn’t as concerned with business. Work life is influenced by personal life, and vise versa, so there is plenty to learn without diving into the details of industry. Instead, I asked questions that people typically only answer when having a late night alcohol-induced conversation with close friends.

Some question examples include these:

  1. Where did you grow up?
  2. What is your greatest accomplishment?
  3. Why don’t you live in another city?
  4. Where do you hope to be in 5 years? 10 years?
  5. What is your favorite item or service you wouldn’t give up?
  6. What do you waste the most time on?
  7. If your life was an animal, what would it be?

Again, surprisingly few people view their life as an elephant. They do, however, open up and answer questions with unbelievable transparency and honesty. These aren’t questions that go far beyond what you may ask a new friend as you’re getting to know each other better, but in the context of an interview, you can ask these questions with an entirely different set of expectations. You are using a key that provides access to someone’s mind in a way that is likely not possible otherwise. Unless you have lots of booze.