AMA: Square Director of Outside Sales, Lucy Ye on Sales Interviews

In my experience, the best sales candidates are not necessarily people with the most years of sales experience. I've noticed the best sales candidates all have these qualities in common: Insanely Driven and Hard-Working (folks who are intrinsically motivated to double down on KPIs to exceed their goals if that's what it takes) Adaptable (people who can think on their feet, and adjust their sales motion/process to best hit their sales targets) Inquisitive (excellent salespeople know that the key ...Read More

One of my favorite sales interview questions to ask is "Tell me about a time something did not go according to plan in your personal or professional life. What happened and what would you do differently, if anything?" This one's great because it helps the interviewer see if the interviewee is just as comfortable talking about their failures as they are about their successes. It allows the interviewer to see how the person handles setbacks, what they do when setbacks occur and what their overall ...Read More

I always recommend that candidates study the job description carefully. Take a look at the qualifications and skills/experience that the hiring manager wants. Do your best to come up with examples/stories to showcase those desirable skills/experiences in the interview.  If you have time, it never hurts to connect with someone who is doing the role today and pick their brain on what they like, don't like, and do to succeed in the role. You should be able to find them on LinkedIn. This type of ins ...Read More

I'm going to include some red flags on resumes since I have already talked about common mistakes people make in sales interviews.  Some resume red flags: Resume is multiple pages long (people pay most attention to the first half of the resume so if it's very dense, you will lose your audience) Having every single job the person's ever had listed on there (relevant job experiences only please) Having little-to-no quantitative results (e.g. % attainment, conversion rates, etc.) on the resume, espe ...Read More

Common mistakes include: Focusing on why you want to work at X company, but not why you want Y job (it's arguably more important to show why you're drawn to the role that you will be doing every day rather than just the company you will be joining) Not having any questions whatsoever for your interviewer at the end (it's important to show that you took some time to think through thoughtful questions) Spending more than half the interview going through every single job you've ever had (essentiall ...Read More

I believe you're referring to assessing the level of autonomy you will get in the sales role you're interviewing for. In most instances, autonomy and flexibility are given to top performers who consistently hit or exceed their numbers in Sales. It is expected for a manager to be way more prescriptive if you are underperforming. That said, here are some questions you can ask the hiring manager to assess their management style and to see how much autonomy other top performers are currently getting ...Read More

Some questions I like to ask are: Tell me about a time you missed your goals. What happened? (Answer should explain why the person missed goal, what lessons they learned from it and how they've been performing since) What is a piece of critical feedback you've received from a client, colleague or manager in the past? (Answer should show the person's ability to be coached and take action on feedback) Tell me about a time you had to re-motivate yourself during a difficult time. How did you do it? ...Read More

There are many ways to crush your sales interview, but an excellent sales interview usually comes down to 3 core elements -- #1) Preparation #2) Storytelling 3) Self-Reflection.  The best candidates I've interviewed will always come PREPARED to: Answer why they are interested in the company and the role Answer what they know and don't know about the industry/role (having thoughtful questions for your interviewer shows you're curious and eager to learn) Pitch the service/product you're trying to ...Read More