Sales is the engine that powers the growth of an enterprise. But it's not just about closing deals. Sales opens new revenue opportunities, generates new ideas for growth, fills the pipeline, relays product improvement ideas from customer feedback to the product team, engineering, and other departments, and serves as the first connection many prospects will have with your brand.

Hiring a Director of Sales is a strategic move that will either move the needle toward your organizational growth goals or leave your team fragmented and customers unimpressed. Considering this, the head of sales, sales leader, or director of sales you decide to bring on board will truly shape your company, culture, prospects, customers, and last but not least, your sales team.

Due to the high impact of this hire, the interview preparation required to "get this hire right" is critical. Before we drill down into the candidate's qualifications and potential director of sales interview questions, we need to have a thorough understanding of your company's goals, metrics, sales cycle, culture, and team to ensure the job description and growth metrics are properly communicated to the candidate. This is a foundational step that not only informs the type of leader you're seeking but also ensures alignment between your organizational growth goals and the candidate's capacities.

Beginning with your industry, what experience does this person need to bring to the table to win in your industry? Is it SaaS, manufacturing, Medical/ bio-medical, or HR? This will be key to their onboarding and ramp time. Next consider the size of your sales team, typical sales cycle, average deal size, and style of outreach. These will play heavily into your overall acquisition strategy. Now, take a look at your internal metrics for growth - are you trying to grow by 25% quarter over quarter? Then you'll probably want to look for candidates who've done this in the past.

By evaluating these internal parameters, you'll be ready for the interview with clear goals for the candidate to align their skills, experience, and knowledge. And now, let's dive into some example interview questions for director of sales candidates to help you find the right fit for your organization.

Sales Leader Interview Questions:

1. Can you tell us about a time when you had to develop and implement a new sales strategy? What were the challenges, how did your team respond to them, and what was the outcome?
2. How do you motivate and lead your sales team during challenging times? Give us an example of a situation where you failed and had to let a team member go, and where you succeeded your team thrived.
3. What are your key performance indicators for measuring sales success? How do you use them to drive performance and results?
4. Can you walk us through your process for setting sales goals and targets? How do you ensure they're realistic yet challenging?
5. Describe your approach to managing and coaching underperforming sales team members. How do you handle the balance between supporting and holding them accountable?
6. How do you ensure a strong culture of collaboration and teamwork within your sales team? Give an example of how you've fostered this type of environment in the past.
7. If someone on your sales team were to give their honest feedback on your leadership without fear of repercussions, what do you think they'd say?

The last question is my favorite as it forces the candidate to look retrospectively at how they've handled a leadership position and their response will make it very evident how they lead.

Overall, the key to finding the right Director of Sales for your organization is aligning their experience and skills with your company's goals and culture. Through a thorough understanding of both, along with the strategic interview questions we talked about earlier in this section, you'll be able to make an informed decision and set your sales team up for success.

Pillar's interview intelligence library offers over 1000 tailored interview questions for your key roles. You can easily add these questions to Zoom or Teams before interviews with just a few clicks, streamlining prep times and ensuring an objective hiring process for your candidates.

Director Of Sales Interview Questions And Answers

Now that we've talked about some questions to ask in the interview, let's talk about assessing a candidate's responses. Tough sales manager interview questions should elicit a thoughtful reply.

Director of Sales Interview Questions and Answers Logic

When you're assessing a candidate's skills, look beyond their responses. Check out their track record, how they tackle problems, and most of all how they represent their past employers and team. A top-notch candidate displays sharp strategic thinking and shares real-life examples, focusing on outcomes and numbers that can be verified in reference checks following the interview.

Secondly, evaluate their emotional intelligence and leadership style through their responses to questions about team management and motivation. Pay attention to the language they use when discussing challenges and failures. Do they take accountability, or do they shift blame? A candidate who can talk openly about mistakes and learning opportunities likely has a growth mindset, which is invaluable in a leadership role and how they handle conflicts on a team.

Lastly, notice the questions they ask you. A genuinely interested and savvy candidate will ask insightful questions about your company's leadership, sales strategies, culture, goals, and most of all their future team. Taking this posture in the interview demonstrates their strategic approach to sales and potential fit within your organization. Through careful listening and probing, you can discern whether a candidate aligns with your company's ethos and if they possess the leadership qualities needed to propel your sales team towards greater success.

Tough sales interview questions elicit the best answers. Questions like, "As a whole, how would your last sales team say you handled firing a team member?" give clear insights into how the candidate perceives their impact on their team.

Questions To Ask the Director Of Sales During the Interview

Interview questions are not a game of "more is better." Taking a strategic approach and breaking down your interview into specific segments focusing on leadership, goals, metrics, cultural fit, skills, experience, and other vital components will provide valuable insights into whether a candidate can help you achieve your sales objectives.

10 Great Questions to Ask a Director of Sales in an Interview:

1. Tell me about your last sales team, what do you think their greatest strengths and weaknesses were? How did you encourage their strengths and improve upon their weaknesses?
2. How do you ensure effective communication and collaboration across a remote sales team? Can you share an example of a time when this was particularly challenging and how you overcame it?
3. What would be your strategy for building strong relationships with key clients and maintaining their business? How have you handled challenging client relationships in the past?
4. As a Director of Sales, what metrics do you find most important in measuring sales success? How have you used these metrics to drive performance on your team?
5. Can you walk us through a time when you had to develop and implement a new sales strategy? What were the challenges, how did your team respond to them, and what was the outcome?
6. We've recently seen the impact of societal shifts like COVID-19 and the wars in Ukraine and Israel/Palestine. How do you motivate and lead your sales team during times of change or uncertainty? Can you share a specific example of when this was necessary and how you handled it?
7. What does your process for setting sales goals and targets look like? How do you ensure they are both challenging and achievable for your team?
8. How have you managed underperforming sales team members in the past? Can you give an example of a time when you had to handle this situation and the outcome?
9. How do you keep up with industry trends and changes in the market? Can you share a time when your knowledge or understanding of the market played a critical role in achieving sales success?
10. As a leader, how do you prioritize your own development and growth? What resources or strategies do you use to continually improve your skills and knowledge in sales management?

These are just some of the many questions you can ask a Director of Sales to gain a deeper understanding of their experience, leadership style, and fit within your organization. Most of them are focused on the candidate's leadership style and creating a high-performing team, but these are only two of the key categories to assess an applicant's fit for a role.

An example of this would be if you're promoting a sales manager to director, you'll probably want to focus more on strategy than metrics, if you're in a final interview with a VP of Sales candidate, you'll want to focus less on qualifications and more on how they work with the leadership team, implement sales initiatives, and drive growth.

Every interview should be tailored to the specific role and your company's needs but hopefully, these resources and questions to ask the director of sales during the interview can serve as a starting point for you.

If you're struggling to find the right Director of Sales, chat with someone from our team. We'd love to show you how interview intelligence can uncover candidate insights through the power of AI. With the right questions and the right approach, you can find top talent that drives meaningful results - to see how- Book a demo of Pillar today.