10 Interview Questions to Ask Sales Executive Candidates

Hiring a dedicated sales executive is a big step for a startup. Choosing the wrong candidate can keep your new business from meeting sales goals and growth expectations. To help ensure you find a good fit for your business, we have compiled a list of interview questions targeted to a startup sales executive position.  

  • In your last sales role, how much of your time was spent cultivating current customer relationships versus finding new clients?

Large established organizations can have sales executives that are more focused on one than the other. As a startup, you don’t have that luxury. The few sales executives that you hire need to be able to spend time cultivating current relationships and finding new clients equally well.

  • What is the best way to establish a relationship with a prospect?

People often choose to do business with people they like and trust. This is what gets a sales executive in the door. Listen for signs of genuineness, empathy, and adaptability. If the sales candidate can’t communicate these traits to you during the interview, then he or she will not be able to convey them to your customers.    

  • How do you research prospects before a call or meeting? What information do you look for?

Good sales executives can connect the dots between the client’s business objectives, pain points, and the product or service they are selling. At the very least, the candidate should be reviewing their customers’ website and LinkedIn information. Facebook and Twitter can also be utilized to provide personal information that can help in relationship building.

  • If you were hired for this position, what would you do in your first month?

When hiring a sales executive, it’s important to find a self-starter that is willing to take initiative. This is especially true for a startup organization! The candidate should be able to communicate some form of an action plan while demonstrating an interest in learning about your organization and how you currently operate.       

  • How does your currentor most recent companybring value to the customer?

This question gives you the ability to hear the candidate’s sales pitch at their current company. Listen for differentiators and how the sales executive leverages competitor information. How does he or she demonstrate and communicate value to the customer?

  • Walk me through the most successful steps you took to land your most successful sale.

The candidate should be able to communicate the step-by-step process he or she used to close the sale. This will help you gauge his or her thought process using a real-life example. Listen for any challenges that had to be overcome to ensure success.  

  • Describe a time when you had a difficult prospect, and how you handled that situation to win the sale. 

How did the candidate approach the difficult prospect? Conflict is inevitable—what matters most is how it’s managed. Listen for a clear explanation of the circumstances, the steps the candidate had to take to turn the situation around, and the results of these actions.

  • How do you keep up to date on your target market?

The target market of your business may be very different than the candidate’s previous sales position but this question will help you gauge the amount of effort put forth to keep up to date. Websites such as Built in Chicago, business development software like Talent Ticker, conferences, and webinars are good examples. As a follow-up question, ask about something specific the candidate has learned recently about their target market and the source of the information.

  • When do you stop pursuing a client?

The right answer to this question will depend on your organization’s process and sales cycle. However, 80 percent of sales require five follow-up calls so the more persistent the executive, the better. There’s also no such thing as a 9-to-5 salesperson, so the right candidate needs to be available to their customers.

  • Have you ever turned away from a prospect or client? If so, why?

Walking away is never easy—especially after spending time and energy fostering a relationship with the client. Sales executives must have the ability to know when to walk away from a deal that’s not a good fit. Every minute wasted chasing a difficult or low-value deal is time that could have been spent closing a more profitable one. Listen for signs that the candidate doesn’t try to force every deal and can recognize when a client is a poor fit. Sometimes it makes sense to walk away from a current client. If your selling consulting services—how easy is the client to work with? Sometimes sales executives hold on to difficult clients at low rates rather than using that time to pursue better clients that are easier to work with at higher profit margins.


Early-stage companies need executives that are willing to help create the sales process and can deal with whatever is thrown their way. Sales executives are naturally persuasive and good communicators— so as the interviewer—it’s important to ask detailed questions to uncover the sales candidate’s personality and probe beyond memorized answers. Hiring a sales candidate that may look the part—but ultimately can’t perform the job—could be a very costly mistake for a startup.  

The blog was written by Viaduct Senior Account Executive Roger Naglewski.

Explore More Blogs

Explore all Blogs

Should You Hire Fractional Executives at Your Startup?

Should You Hire Fractional Executives at Your Startup?

In the startup arena, limited resources combined with dwindling capital can make it challenging to gain a competitive...

Learn More

How to Create a Recession-Ready Talent Strategy

How to Create a Recession-Ready Talent Strategy

Economists put the chance of a recession in 2023 at 63 percent. In response, 72 percent of leaders...

Learn More

The 5 Soft Skills You Need to Succeed in a Startup Environment

The 5 Soft Skills You Need to Succeed in a Startup Environment

When you think of a startup environment, there are a few images that might come to mind: A tiny...

Learn More

3 Interview Questions to Ask Chief Growth Officer (CGO) Candidates

3 Interview Questions to Ask Chief Growth Officer (CGO) Candidates

A C-suite interview has a much different dynamic than a standard mid-level management interview. The stakes are higher...

Learn More

Join Us For One of Our Upcoming Events