Over the years I’ve done a LOT of hiring and interviewing for Box. Fun fact: My boss, Jim Priestley, calls me the “VP of Interviews”. So, recently I went back and tallied up just how much. I was astonished at the volume! For each of the the past 4 years I have interviewed around 100 people per year. At first (2011,2012) it was mainly under the tutelage of one of my mentors Jerry Clarno as we worked tirelessly to scale an enterprise sales team. (His insights on talent have been invaluable). Over time I proved myself and began to be trusted with interviewing folks for other departments like customer support, legal, marketing, product and even in a select few instances Executives.
I’m grateful for the opportunities I was given to meet so many wonderful people! This volume of experience has come in quite handy! Not only do I have a broader network than I had before but I also have a better sense of what I’m looking for when I step into an interview room. I’ve learned a ton about what to look for in a resume, what questions to ask to get deeper insights and ways to make the process more fun. At various points during our massive growth from 50 employees to 1,300 I would do 5-7 interviews in a row so I had to find ways to make sure the 7th person had the same positive experience as the 1st!
Working for a high profile company like Box and being on the Faculty @ Alchemist Accelerator has allowed me to use a very particular set of skills when I speak to VCs and founders about how to scale a business. In nearly every conversation we talk about recruiting and hiring. Finding and hiring the right talent for your team is just as critical as having a great product so it makes sense they would be curious how we did it so successfully.
The question I often hear is a version of: “What is the single thing you look for when interviewing sales candidates?” Earlier in my career I probably would have answered this with 2 simple things like “Likeability and energy” or “self starter and track record of success”. Over time I have a better sense of what I’m looking for and have honed in on what I look for in folks as indicators that they will be successful in a high growth environment. Provided they meet all the standard criteria to get to an interview (education, job experience, past success) I generally will look for these 7 things:
1) Natural Curiosity – I’m not talking about asking a list of generic questions about the company here or what the territory looks like etc. What I’m looking for is insightful questions that get my gears going too. I want to feel like the candidate is generally a curious person that is thinking deeply about the “why” behind things. Some of the most successful people I’ve hired asked me questions in the interview about product direction, segmentation, competitive positioning etc that were right on target with the things we were talking about privately behind closed doors. These types of folks are going to ask better questions in sales cycles and uncover more information about their prospects. In sales, gathering relevant information is critical.
2) Self Awareness/Attempts at Self Improvement – This is uber important to me! I’m looking for the person to have confidence to admit where their strengths end and also show me where/what they have implemented to offload those things or improve upon them. One of the most natural ways to get at this is to talk about the deals you have lost, why you lost them and what you would have done differently or the things you do differently now to shore up that previous type of miss.
3) Adaptability/Positivity – I’m looking for people who have shown an ability to roll with the punches and keep on chugging with confidence in a tense and at times uncertain environment. I’m ideally looking for people that are going to stay with the company for 4+ years and grow into hopefully more significant roles, so adaptability and positive outlook will help them push through those inevitable territory segmentation exercises, product launches, opportunity holdout conversations that come as you take a company from some small number of employees/ revenue to a larger number of employees/revenue.
4) Likeable-ness. Some folks call this rapport building. My friend Andrew Smith asks himself something like: “Could I spend time with this person on a long road trip and enjoy it?” The idea here has 3 simple reasons. I believe buyers buy from people they like. They tell people they like more information. I believe teams perform at an optimal level in stressful situations like hyper growth when they generally trust one another and like one another. They learn more when they are open vs closed off. If I don’t like you. I’m probably going to be less inclined to share my secrets of success or listen to yours.
5) Honesty/Integrity – Not all sales leaders or companies value this but it is critical to me. As you scale a company you need to be able to be honest with customers about product limitations be truthful about roadmap and build trust internally. I have seen some sales folks close deals and hit quota with less than honest tactics but it puts the team and company in unnecessary jeopardy and should not be tolerated. No slime balls for me!
6) Creativity – What I’m talking about here is the ability to see problems from different angles and to see what is possible vs what is the present. The most successful sales folks I know are able to take impossible situations and come up with creative solutions that help the customer accomplish their goals in ways they (at times even the company the rep works for) had never considered before. This could be creative contract structures, payment structures or creative business cases.
7) Drive/Ambition – Some people call this hunger. This is likely the most sought after sales skill. If you don’t have an inner motor that pushes you past constant rejections you won’t be an elite sales rep. At the end of the day, you can be curious, likeable, adaptable, creative and self aware but if you aren’t naturally hungry it won’t be possible for you to wake up every morning and ask people to part with their money.
*Bonus: I also look for candidates that will add something to the current squad. Whether a technical skill, broad network, relevant thought ledaership, unique creativity etc..I’ve found that team building and scaling rapidly are much like creating new recipes. There are lots of ingredients to a successful organization. Hiring new talent to join to an existing high performance team in is an incredible way to amplify existing strengths while adding new skills to the mix.*
In an interview I’m looking for it to be a as much like a natural conversation as possible. I have various questions I ask to dive into each of these areas. Generally speaking I’m also looking for depth to answers. Its amazing how many people aren’t able to dive into detail when asked follow up questions on a particular topic. I hope you find this post useful!
* You can learn more about me on Linkedin or on Twitter *
Building, Growing, & Fine Tuning High Performance Sales Teams 
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