Enterprise Sales Interview Screening Questions

Screening Enterprise, Digital and Top Salespeople: Questions to Ask


In screening Enterprise Sales and Digital Reps it's super important to be able to get very granular in a selected core group of areas. You need to know that reps. have the ability to attain strong results and connect with prospects, sponsors, and stakeholders all the way up the chain. 

It's also important to know the "how" or (process) defining their way of getting results. Next, it's important to understand their attitude and relationship building skills showing that they grow, keep and manifest long term solid fruitful connections. They've got to have the energy and poise to light up the room every time in the C suite. Asking the right questions is also key, many fail at this juncture as they don't elicit the proper emotional responses in the customers nervous system. Pre closing and closing is at the end of the process however humanity showcasing has to be present on the front, mid or back end of the process. 


In this article we will begin to bring you closer to some of the many power questions we've developed to get the needed information. We will also start to teach you about: honesty questions. This will help you get to the truth quickly. 


We want to know about results, not skills. If you have results, you possess skills. 


Being able to measure Sales people in the following areas is so important: 

  • Results

  • Energy

  • Attitude

  • Processes

  • Relationships

  • Interview the Customer

  • Close Them

  • Humanity

There are specific questions I ask based on the Reaprich science that "truth tell" in all these areas. I began to develop these questions as I became Oracle's #1 Sales Recruiter, won their "Best Recruiter" award, and three outstanding achievement awards. I was fortunate to repeat this success in many tier 2's and 3's and multiple Unicorns. 


Defining results begins to be outlined into the categories of what did you achieve against a goal, was it singular or team goals, did you win the business cold, or was it already warm? 

We also measure timeline and deal size, however the best salespeople often go outside the norm to help the customer meet their goals, connect with them, along with studying and preparing. How many deals were needed to meet the sales goal? How much of your quota was new business? When a sales candidate states a strong sale or result, we ask them to bring us close to the names, people and specifics within the timeline of that deal. This is the first way to validate whether it is real or not. 


We also ask lots of reversal psychology questions which ask candidates to describe 3 words that others would use to describe them, or how other people saw them with a deal. Many people have already made up prescribed answers about themselves but only the best can quickly reference with specifics how others see them. Our team has multiple questions in each area of Reaprich and then templates for the hiring manager. This training allows us to get to the facts quickly. 

Below and throughout this article are some of the questions we use. We also included a few extra tips at the end. 


Results Questions: 

1.Tell me about the two deals your most proud of that your sourced yourself and closed: 


2. What are the names of the people at the customer during key junctures in the deal that helped you forward it along each step to close? 


(If team selling)

1. Walk me through your two top deals. Name the people that initiated, grew, and closed the deal. 

2. What was your contribution in each part of the deal? 

Who did you influence internally and externally to get this done? 


Continuous Result Focused Relationships: 

3. What clients have you closed multiple times? At multiple companies? 

4.  At what clients could you get a walk the hall key pass if you visited them in person? 


In the early days the questions were centered around: how much was your quota and how much did you exceed it by? That's very important to know. It's part of every strong screen. The best co's also want to know if you created walk the hall relationships, even when working remote. This means you can place a call to anyone in your PO process and they will already know who you are. The very best salespeople often get committed to what the customer is committed to. Find out what matters to the customer. Get behind the company volunteer cause. Care about what they care about. If they feel you're genuine they will like you more. In asking people to describe their top deals I love stories where they went outside the box to get it done. 

The best software salesperson in NY that closed multiple 100m deals knew everyone in the deals, including family members. He would show up and run barbecues and be a resource and true friend. He would pass out cigars at 3AM to the forgotten people running the servers and monitoring everything. He would also sit in the lobby an hour and a half before his mtgs. and see everyone who was coming and going. He was so connected he would get 40- to 100 of Wall Sts. top people to go to Atlantic City with him. His Processes and Relationships were deeply extensive and impeccable. He started with nothing in NY City as a young boy. This same man connected me with 3 top C level CTO's in one day.


A Process Question:

Tell me about the Processes you used, learned or developed to continuously get to these top results your describing: 


Some Relationship Questions: 

1. Give me two examples of the long term business relationships your most proud of and what results were caused from them: 


2. How do you build new relationships quickly? What is your process? 


Honesty Questions: 

1. Please give me the 1st 4 descriptive words that come to mind that a customer would use to describe working with you: 

Note: can they easily reference words others would use? 

The brain can only reference how others see us smoothly and quickly if it's authentic and in our memory. 

2. What 3 words would a co worker use to describe you? 


Notice whether they generally can answer this, do at least the correct amount of words, do they tell stories instead? A little delay is fine, but can they complete the exercise? 


Extra tips: 

1. Notice how any potential hire treats the people scheduling them. Ask for feedback. When not under a mandate for good behavior important things are often revealed. 


2. Do they put attention into the small details in the interview process? Even in casual dressing do they appear ironed, shined shoes, and someone you can put in front of a customer?


Success leaves clues.


With Awardhire we develop deep screening processes to adjust to each company's needs. In doing this we have many achieve a 93% long term success rate and retention in their sales hires. 


Reach out to our leader: evan.pellett@awardhire.com.

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