Getting The Right People With The Right Sales Interview Questions

When you’re looking to welcome the right sales rep to your team, you need to use every tool at your disposal. A precise and specific job listing is critical, but so is knowing the questions to ask to make sure that they are the right fit for the team. 

It’s crucial that you take the time to evaluate whether or not they will thrive in the workplace environment you’ve established. Do they have the basic technical and situational sales skills that are needed to succeed? Will they be able to grow under company policy? Most importantly, would hiring them be consistent with your diversity & inclusion goals, and do they share the same vision that your team is moving toward?

Here, we’re going to look at a few examples of the sales interview questions that you should be asking and why you should be asking them.

Related: 5 Reasons Tech Sales Is a Rewarding Career Move

Be Sure to Ask Enough Technical Questions

We are going to look more closely at some of the more complex questions, the motivations behind them, and what you should expect from the candidate answering them. For many recruiters, up to 67% of those surveyed, a percieved lack of talent is the most consistent problem when going through hires. As such, you want to start with the questions that will make it crystal clear as to whether or not they have the skills that you need for the company. 

Such questions to ask include:

  • How do you stay updated on target markets?
  • How did you cultivate customer relationships?
  • How do you handle customer objections?
  • How do you use social media and content marketing in your sales process?
  • How do you qualify prospects before getting in touch?

The answers to these questions don’t have to be perfect or be identical to your company’s practices. Instead, this question is specifically to show that the applicant does bring some relevant experience with them. If they can’t answer these questions and you’re only looking for experienced hires, it gives you a flag, which signifies that you need to move on to another potential candidate.

Looking for an individual with strong sales skills? Check out what re:work training has to offer!

Walk Me Through a Past Successful Sale

There is a range of technical sales questions you will need to ask. However, one of the most important ones is about when they have closed a sale. 

It gives you a good understanding of their experience, and if the employee answers in a satisfactory way, it shows their proficiency at handling tricky situations. You’re looking for thoughtful & passionate answers about their sales, and a demonstration of the candidates ability to overcome challenges. They should be able to demonstrate some problem-solving skills, but also have a greater understanding of how their colleagues and training supported them in the sales process. You don’t want them to only talk about themselves; they should show that they’re a team player, too.

Have You Consistently Met Past Sales Goals?

While sales reps can certainly develop and become more competent at their role, increasing their chances of meeting future sales goals, you should always look at their past work for an indication of how they might perform in the future. You should encourage them to get into detail about specific accounts of how they have performed in the past. You don’t necessarily need a perfect answer for this either (few people can honestly provide one), but you do want a sense of how they will perform.

Tell Me About Times That You Have Lost Sales.

The interview is the candidate’s opportunity to put themselves in the best light. As such, it might seem like a question that focuses on the negative aspect of their job, and it may seem like an attempt to trick and throw them off-track. However, that’s not the intention at all, or at least it shouldn’t be. 

All salespeople have lost sales. By asking them about how it happened, you’re allowing them to show some self-awareness and how they have grown from past failures. If they blame lost sales purely on circumstances outside of themselves, there’s a good chance they’re not the kind of person to take responsibility and criticism well.

How Do You Regroup From a Bad Day?

The previous question addresses how an individual has learned from failure. However, this one will give you a good understanding of whether or not they can manage to maintain the right attitude towards rejection and failure at the moment. If they answer that they need some time or to perform a therapeutic ritual (like a self-affirmation technique) to get themselves back at the optimal level, that’s not a bad answer! You want to see that they have strategies to cope with the emotional stress that often comes with the job.

Can You Think of Any Ways We Can Improve Our Sales Process?

You want your candidates to show that they are, in fact, familiar with the company. 47% of interviewers won’t offer a job to those who don’t know anything about the company and for a good reason. 

Aside from simply asking, “what do you know about what we do?” let them acknowledge specific parts of the business and their opinions of it. Only ask them public information regarding the business.

If they have no reasonable ability to understand how the company sales process works without being a customer themselves, then this question doesn’t work. But there are other questions you can use to test their research skills.

Sell Me This Pen

woman with long sleeve shirt holding a pen

This is a classic tactic. In fact, “sell me this pen” is such a common sales interview strategy that you may want to change it up. Another variation could be “sell me what you had for lunch today” or “sell me on one item that you use regularly.” 

It gives the candidate the opportunity to show their selling skills, but it also shows if the individual can sell to the individual, not focus too much onthe product. A really savvy salesperson will ask about your needs, your pain points, and other specific details before they go into why the product they have is the right one for you.

Related: Sales Techniques: 5 tips for Remote Learning 

Tell Me About Sales Targets You Have Hit

Once again, you’re giving the candidate the opportunity to sell themselves to you by providing more details on the success of their work. But how they answer the question is just as important as what the answer is.

Sales is, above all else, a numbers game. They should be talking about specific quotas, goals, and numbers, as well as where they fit within the context of the team’s achievements. If they are answering too vaguely, you can ask them to be more specific. If they’re unable to show any numbers, then it shows a lack of detail for the measurable achievements that are so crucial to the success of the sales team.

Why Work in Sales Over Another Customer-facing Role?

If you ask an individual why they want to work in sales, they will most likely answer that they like working directly with people, that they are a people person, and they want a role that takes advantage of that. It might be true, but it’s an easy and common answer. 

Find out why they want to work in sales and get the easy stuff out of the way. Sales relies on more than people skills; it requires attention to detail, independence, problem-solving, and a growth mindset. You want to make sure that the individual is actually motivated to be in sales, and this question gives them the chance to show that off.

Have You Had a Manager That You Didn’t Like? Why Didn’t You Like Them?

In most cases, you want the candidate to be focused on showing self-awareness, rather than measuring the skills of others. However, they also need to be aware of the roles their colleagues play, including their manager. 

As such, this shows what they focus on in professional relationships. 

If they focus on personal and subjective opinions, such as laziness, annoying habits, or any other purely emotional response, that’s not a good answer. 

Instead, you want to hear about how the manager’s decisions and behaviors affected the overall working environment. For instance, if they were disorganized, leading to miscommunication, or if they are negative, severely affecting the workplace culture. Asking people to highlight the negative traits of someone they have worked with will help rule out a lot of potential toxicity.

Are you interested in a career in sales? Contact re:work and they will give you all the skill necessary to ace your interview!

Nail The Interview, and Get The Right Sales Reps

man and woman shaking hands near the table

With the sales interview, you are allowing the applicants to sell themselves to you. The right candidate might not always say the right thing; however, they should be able to engage you, display a willingness to grow, and show that they are able to think from the perspective of the company.

Hopefully, the above tips help you construct your sales interviews in a way that will ensure you hire the best candidate possible! Don’t be afraid to change it up, but always keep in mind what the ultimate goal of the interview process is: to find & employ people who will improve your team.

Related: Career Advancement as a Sales Underdog: 3 Tips

Job Boards Perfect for Diversity Recruiting Compliance Efforts

Hiring from a diverse talent pool is incredibly beneficial for a company or business – scientifically confirmed by a 2017 Harvard Business Review article. Finding these employees is simple if you know how and where to look. Outlining alternative experiences, mindsets, and cultures can be the key to your company’s future. Need some more help? re:work makes it easy!

Related:  Diversity in the Workplace as an Employee Benefit can’t claim any of the shiny bells and whistles of a more modern website, but it’s been the leading job board for diversity recruiting for over 20 years. Trusted and renowned, this website holds some of the best job opportunities you will find on the market. For companies, this platform is ideal for hiring minority talents.

Some of the benefits of this platform for employers include the possibility to advertise the job for any timeframe, hire in multiple locations, and select automatic posting renewal. 

Entirely owned by African American families, this website truly understands the needs of employers and minorities, creating the perfect match! Additionally, the expert staff behind the platform will help you craft the ideal profile to attract the best candidates.

Cost for employers: $220 for a standard package of 30 days.


If you wish to implement your team with the best talents from the Latinx community, iHispano is the best job board for recruiting. Hosted by The Professional Diversity Network (PDN), this platform allows recruiters to find over 350,000 new members monthly and can be connected to your LinkedIn profile. 

One of the unique features you will find on this platform is the highly engaging and energetic theme that is difficult to find on standard job boards. Among the qualities that make iHispano unique is the fact that the website uses advanced matching features and state-of-the-art networking opportunities.

Cost for employers: $50 per job posting. 

Black Career Network

Black Career Network is a platform dedicated to matching employers with untapped talent in the African-American community. Hosted by The Professional Diversity Network, this platform boasts all the excellent features of iHispano, but with a focus to attract diversity-driven companies and professionals.

By posting your job here, you will be able to access all the talented individuals subscribing to the Professional Diversity Network (which can be as high as 350,000 per month). You can benefit from other features such as recruitment advertising and networking events, all on the same platforms. 

Cost for employers: $50 per job posting.

PDN Recruits

The Professional Diversity Network Recruits job board is much more than it seems. Here, employers can connect with talents from several minority communities and select the best candidate among thousands of subscribers per month. Due to the endless opportunities for networking, learning, and marketing, this platform has become one of the most regarded in the sector – simultaneously attracting the best employers and employees out there. 

Among the features that make this platform unique, employers can leverage the power of the innovative matching technology developed by The Professional Diversity Network. Additionally, several outreach programs and mechanisms ensure that your job posting is seen by the best candidates worldwide. 

Cost for employers: There are several packages to choose from, starting at $495.

Black Jobs

Black Jobs is one of the best platforms to check out if you are seriously looking to include African American professionals and enrich your team. This job board does not focus on selected industries or jobs, but it makes sure the candidates are the most driven and talented you will find. Leading employers such as Amazon and Netflix have chosen this platform to hire talent and create diversity in their teams. All the jobs posted on this platform are well-payed and offered by culturally-diverse employers and companies who understand the benefits of diversified groups.

Cost for employers: There are several packages to choose from, but the basic one starts at $197 for a 60-day long listing.

Related: Talk Less, Read More: Book Recs from a Female CEO

Whether you are a corporate recruiter or a small business looking for a talented individual to include in the team, WorkplaceDiversity has the right match. This platform covers a broad range of groups with various backgrounds, offering some of the best-performing professionals and employees out there. The website has over 160,000 Unique Monthly Visitors.

However, if you prefer precise types of skill sets, opt for one of the websites that make up this job board’s curriculum. Some of these include platforms dedicated to veterans, Hispanic and African American professionals, and professionals with disabilities.

Cost for employers: A 60-day posting costs $149.

Hispanic/Latino Professionals Association (HLPA)

Another excellent platform for scouting professionals in the Latinx and the Hispanic community is the HLPA. What sets this job board apart from others like it is its status as the official job board for Latinx professionals. The subscribers to this board are more likely to be motivated, driven and very seriously looking at taking their careers to the next level. Aside from the usual features that you will find in most boards, this one boasts sections with top-rated employers, so it can better match talents to companies.

Cost for employers: Packages start at $199.

Career Contessa

An alternative to classic job boards is Career Contessa. This website focuses on women who are interested in career development and even boasts a 1-month coaching plan for candidates to get started in their dream career. The jobs posted here are specifically aimed at professional women across the world, with several features that better target their needs.

Cost for employers: It is free to post your job, but any offer will be reviewed by the team of Career Contessa and needs to be accepted before candidates can see it.

Female Executive Search

Perfect if you’re endeavoring to improve your team with female leadership!

Cost for employers: Unlike other boards, FES works a little differently. After submitting your job posting, the team behind Female Executive Search will get in touch with the talents selected for you!

Pink Jobs

This is the leading job board for employers looking to hire talent specifically in the LGBTQ+ community.

Cost for employers: Free.

Related: Careers at re:work


Several other job boards can be ideal for your company and its goals, and the number of these platforms are growing by the minute. Ready to diversify your business? Get in touch with re:work today!

FAQ: What makes re:work training different from other non-profits?

Have you ever volunteered for, donated to or seen an advertisement from a non-profit? If so, you may have formed a blanket opinion about what they do, how they’re run and who they serve. Here are 5 key reasons why re:work doesn’t fall under that blanket:

The Mutual Benefit Principle

Many nonprofits use imagery and language that appeals to “supporter sympathy”, painting a picture of “underserved” individuals who cannot rise above their circumstances without the help of selfless outsiders. 

While this approach may work for some organizations, it can create a power imbalance between those helping and those being helped. re:work is not a charity case, and neither are our candidates.

We firmly believe in and abide by the principle of mutual benefit: individuals broadening their horizons by creating relationships with those who come from different communities, backgrounds, and perspectives. To that end, we encourage our volunteers to view our candidates as colleagues, because that’s exactly what they’re going to be.

The result? Implicit biases are dismantled, growth is experienced on both sides of the table, and we move closer to the greater goal of bridging the gap between our untapped communities and good jobs. 

Working from within the Community

The majority of our core team are from the exact communities we serve, including our CEO Shelton Banks who hails from Chicago’s Michigan and 103rd St. 

Allyship is necessary and important, but we believe that the story of systemic oppression will only end when power is put in the hands of those affected.

Practicing what we preach, we make it a priority to involve alumni in our business decisions as the company continues to grow and expand. As of this writing, two of our six core team members are former re:work candidates. 

We work from within the community we serve, so our business belongs just as much to our alumni as it does to us.

Proof in the Pudding

Did we mention that we practice what we preach?

Represented in our small organization are college graduates, re:work program graduates, and high school drop-outs; self-taught entrepreneurs and corporate trained professionals; CEOs and newly minted SDRs; White, Black, Latinx, Asian, multi-racial, generation X, Y, & Z – and the list goes on. 

 Every member of our community has unique and valuable input, and this is where our small but mighty team gets its strength to be so high impact. 

We are the living embodiment of the truth behind our mission. 

When we say no-cost, we actually mean we’ll pay you

Not only is the program completely free, but we offer our candidates an hourly pay for their time – as long as they meet re:work’s expectations to get this work! 

We pay our candidates so they never have to choose between income they need to live and investing in their professional futures.

We exist to give people the freedom to see – and dream – beyond the day-to-day grind. Our candidates work hard, and they should be paid for it!

Life-long Support System

Once a part of re:work, always a part of re:work. 

Our relationship with candidates does not end after they get a good job. With over 150 graduates served, we have recently rolled out our Alumni Association. The self-run organization provides graduates with additional employment, career development, and wellness resources that support them long after they land their first sales role. 

On the flipside, re:work doesn’t engage volunteers who only want to show up for one event to check the “giving back” box. 

Our community of candidates, alumni, volunteers, corporate partners, and supporters of all kinds are driven – both personally and professionally – to champion diversity and inclusion in and outside of the office. 

There is power in numbers, and we are building a network of re:thinkers from all different backgrounds, perspectives, and zip codes to create workplaces that are as diverse as our neighborhoods. 

Learn More

Really curious about what makes re:work training different? There’s no better way to find out than to get involved. Sign up as a candidate or volunteer, attend a workshop, or follow us on our social media pages to learn more!