Why a ‘Deep Dive’ Interview Identifies A-Player Talent

As a management and operating philosophy, we at Alpine believe that people are truly at the heart of what makes a business thrive. That’s an idea I strongly believe in and get to practice every day in my work as Chief Talent Officer, wherein I hire portfolio executives, support their development (as people and professionals) and partner with them to create cultures where everyone can thrive through our PeopleFirst Leadership Program.

Our hiring process at Alpine begins with creating a job Scorecard—a rubric for what criteria you’re looking for in a candidate in a particular role—which you can learn more about in this explanation from Alpine Managing Partner Matt Moore. After you, the hiring manager, create a Scorecard, you move into interviewing candidates, where you collect as much information as possible to assess against the Scorecard. As you collect data, it’s less about assessing if a candidate’s experience and attributes are good or bad, and more about looking for key elements that are critical to the specific role (and Scorecard) you are hiring.

One of the most famous components of Alpine’s hiring process is our ‘Deep Dive’ interview, which is perhaps also the most unique part of our firm’s data collection interview practices. The Deep Dive interview was created by leadership advisory firm ghSMART, and its founder Geoff Smart. The book Who is a great way to learn more about the practice that I’ll summarize here.

What the Deep Dive Looks Like in Practice

The Deep Dive interview takes an unconventional and highly reliable approach to uncovering the data you need to accurately assess candidates against your Scorecard. There’s a reason why we are so obsessed with this process at Alpine—we’ve found that it truly helps us identify the best person for a role.

The process is straightforward: In the interview, you explore every educational experience — high school, if they went to college, and if they went to grad school– and then unpack in detail every role in every company where they’ve worked. This is not about cherry picking a few relevant experiences, rather it’s about developing a holistic picture about the person, by learning about every educational and professional experience they’ve had.

The key to an effective deep dive is pattern recognition. You’ll look for similar things as the conversation unfolds– their strengths, their weaknesses, how they showed up when things didn’t go well, and what drove their success when it did. Particularly for senior leaders, you look for their ability to build followership in others, and how they’ve managed and developed their teams. Through this, you’ll learn whether people and companies wanted to work with them again, and why.

Setting Expectations Is a Dual Assessment

The Deep Dive interview is perhaps most famous for being (on average) four hours long. That length of time is an interesting litmus test–if you as a hiring manager hear that you must spend that amount of time with a candidate and you’re not looking forward to it, that’s a pretty good sign that you’re not actually excited about them as a candidate. On the other hand, if you enthusiastically anticipate diving in and hearing this person’s story, that gives you good insight into your own interest in this candidate.

The candidate, similarly, is going to get a pulse for their interest in getting into a lengthy conversation with the hiring manager. If they’re really excited about the role, this is going to be a wonderful opportunity to get vulnerable and to really show who they are. If, on the other hand, they too have been skirting through the process, an interview like this is probably going to be the worst use of time they could think of. The Deep Dive’s length of time is a positive thing for the right people.

Why Any Interviewer Should Use the Deep Dive

The good news is that the key elements of the Deep Dive can improve the interview process for any role. As the name implies, the deep dive allows you to go deep into a person’s professional history and helps you create pattern recognition. For example, if someone made a mistake in their first sales role, and then in their second sales role—you should question if that’ll happen in their third sales role with you. On the other hand, if someone really messed up the first time, and then you see them crush it in their next role– that tells you something about their ability to grow and change. Someone who learns from mistakes and can change their behavior has a growth mindset–they’re very coachable and they have a will to win, which are vital strengths in any role.

Something that the deep dive does well is puts a person’s wins and losses in context. For example, if someone has on their resume that they sold $10 million worth of their product, that might sound impressive if your total budget and quota for the year is $10 million. But what if their quota in that role was actually $50 million or $100 million? What if that $10 million came from just one customer that someone had already developed and all they had to do was sign on the dotted line? Spending time asking these questions gives you the context to understand why the wins matter and what the losses were a result of.

This context also helps level the playing field, often leading to more diversity in your candidate pool. For example, let’s say you’re comparing two candidates, both of whom went to the same college with the same major. One candidate has a 4.0 GPA while the other has a 3.2 GPA. It’s tempting to assume the 4.0 GPA candidate is stronger, but when you add in context – let’s say hypothetically the 3.2 GPA candidate is putting themselves through school by working two part time jobs, while also caring for a sick relative – your assessment may broaden or change. This is especially important if, in this example, your scorecard is anchored on agility and resilience, and less focused on IQ or “book smarts”. I’m not saying the 4.0 GPA candidate is lesser, but I am saying that having more context on candidate history and context can significantly enhance your assessment. Given their attributes and personal experience, the 3.2 GPA person may in fact be a better fit for your particular scorecard.

By hearing all of someone’s experiences, the Deep Dive allows you to see the full candidate. At Alpine, we’re interested in hiring people with both strong attributes and experiences and the Deep Dive gives you that unaided data to put those pieces in perspective.

Tal Lee Anderman (left) leading a workshop on Deep Dive interviewing at Alpine’s 2023 Growth Summit, alongside Trucker Tools CEO Kary Jablonski (right) and other Alpine portfolio leaders.

Commit to Taking Action

I often laugh that most of us spend a surprisingly small amount of time interviewing two groups of people who have a very large impact on our lives. The first is roommates, and the second is employees. So many of us have started living with someone after one or two conversations, and then go on to spend every day with those roommates until you eventually move out. The same is true of employees; in the best run interview processes, you might have 4-5 conversations with a candidate before working with them, hopefully for many years. Ideally, leaders should have a chance to go deep with candidates to make sure that you’re uncovering who these people are, and why they’re a good fit.

I encourage any leader to try out the Deep Dive interview to see what kind of insights you uncover before bringing someone into your organization. As we at Alpine strive to build an environment where the best in the business can thrive, we’re confident that our tried-and-true hiring practices like the Deep Dive will continue to help us achieve this.

If you’re interested in a career with Alpine Investors, please visit our careers page to learn more. If you’re interested in joining portfolio leadership, please visit our talent programs page to learn more.