The Ultimate Questions to Ask When Hiring a Head of Sales

The Ultimate Questions to Ask When Hiring a Head of Sales


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Searching for the best questions to ask when interviewing a head of sales?

Look no further!

This blog post will review the top 10 job interview questions you should use when hiring a head of sales. Asking the right questions can be the difference between finding the perfect candidate and missing out on a great opportunity.

Read on to find out which questions will help you make the best decision for your company.

1) What are your biggest accomplishment in your sales career?

When interviewing a potential Head of Sales, it is important to ask questions that will give you insight into their experience and capabilities. Asking the candidate to talk about their biggest accomplishments can provide valuable information about how successful they have been in the past.

This question will also help to determine if the candidate has the necessary knowledge and skills to be successful in the role. It is also a great way to assess the candidate’s ability to think strategically. It also allows us to understand if they know what it takes to lead a successful sales team.

You can use this question to determine if the candidate can recognize opportunities and take initiative when necessary. Asking this question can also give you an idea of how well the candidate can close deals, negotiate, and create long-term relationships with clients.

Ultimately, understanding the candidate’s past successes (and self-awareness about their failures) can provide insight into how they will perform in the role and whether or not they are the right fit for your team.

2) What was your role in achieving those accomplishments?

Asking this question can help you better understand how the applicant contributed to previous projects or sales goals. This can give you a better idea of the candidate’s:

  • work ethic,
  • communication skills
  • problem-solving skills,
  • and ability to handle pressure.

You’ll also get an insight into the applicant’s ability to:

  • take initiative,
  • be creative
  • and think outside the box.

You will get an idea of the strategies they used to achieve success and how they worked with a team to achieve desired results.

Overall, asking this question can give you a clear picture of what the candidate has achieved in their past roles and how they were involved in the process. It can also show how motivated and ambitious they are. Asking this question during an interview helps you ensure that you’re selecting someone who is experienced, capable and eager to take on new challenges.

3) How have you developed your sales team’s skills and knowledge over time?

Asking this question is a great way to gain insight into their managerial abilities. It shows that the interviewer is interested in learning how the potential hire has been able to create and maintain a high-performing sales team.

A great head of sales will understand the importance of investing in their team’s growth and development. They will not settle. Dive deep to ensure they provide evidence of how they have personally driven the growth and development of their sales team over time.

The best answers will involve a combination of both structured and unstructured activities, such as setting targets and providing ongoing training, as well as holding regular meetings and feedback sessions to ensure their team remains motivated and on track. The head of sales should also be able to explain how they have identified areas where their team could improve, and how they worked to bring out the best in each individual.

By asking this question, you can gain invaluable insight into the leadership style of the potential hire, and whether or not they would be a good fit for your organization. It can also help you assess if their philosophy aligns with your company’s culture and values. Ultimately, it will give you an indication as to whether or not they are the right person for the job.

4) What motivates you in your work?

When it comes to hiring a Head of Sales, it’s essential to get a sense of what drives the candidate and motivates them in their work.

By asking what motivates them, you can learn a great deal about the candidate’s goals and ambitions.

The answer to this question can provide a lot of insight into how successful the candidate might be in their new role. It can also help you gauge how dedicated and passionate the candidate is about their job. You need someone who is driven to succeed and will do whatever it takes to reach those goals.

By asking the candidate what motivates them, you can also determine how well they can handle failure and disappointment. A strong candidate can stay motivated even when faced with setbacks. This is an essential skill for anyone in sales. Additionally, you gain insight into their ability to take responsibility and remain focused on their goals.

Ultimately, asking this question during a job interview can provide valuable information. It will help you make an informed decision when hiring a Head of Sales. It can help you assess whether they have the qualities necessary to succeed in your role.

5) What challenges have you faced in your role as head of sales, and how did you overcome them?

When interviewing a potential head of sales, it is important to ask about the challenges they have faced in their role and how they overcame them. This question can provide invaluable insight into their ability to handle difficult situations. It also reveals their problem-solving skills and decision-making processes.

The candidate’s response will give you an idea of what kind of leadership and management style they prefer. You’ll uncover whether they have the experience and expertise to help your company reach its goals. Additionally, this question helps to reveal the candidate’s motivation, as it provides insight into their drive to face and overcome challenges.

It is also essential to pay attention to how the candidate talks about their success in overcoming these challenges. Look for answers to:

  • How do they frame their accomplishments?
  • Do they take credit for the positive outcomes?
  • Do they focus more on the collective effort it took to achieve the desired result?

Overall, this question can give you a good indication of the candidate’s capacity for strategic thinking and creative problem-solving. It also lets you hear firsthand how the candidate approaches complex issues and works through difficult circumstances. This can be extremely valuable when selecting a head of sales for your organization.

6) What makes you tick away from work?

When interviewing for a head of sales role, it’s essential to ask questions that get to the heart of the candidate and how they think.

One way to gain insight into candidates is by asking them about what makes them tick away from work. This question can help you understand what motivates the candidate, their values, and how they like to spend their free time.

If a candidate has a passion outside of work, such as volunteering or training in specific competitive sports, it can signal who they are. You can uncover strong leadership skills, an entrepreneurial spirit, and even a commitment to making a difference in the world.

Each of these traits can be highly beneficial when leading a sales team and striving to reach higher goals. Additionally, understanding the candidate’s motivations outside of work may give you an indication of more. It will show you how much energy and enthusiasm they will bring to the role.

Asking this can also help you better understand the candidate’s character and how well they might fit into your company culture.

Ultimately, it’s essential to look beyond their industry, sales and technical skills when hiring for a head of sales role. It’s a terrific question to get insight into the person behind the CV.

7) What strategies have you used to manage and motivate your team successfully?

Asking applicants what strategies they have used to successfully manage and motivate their team is a great way to determine their leadership potential. A good leader will be able to motivate and inspire their team members. They’ll also know how to help them reach their full potential.

When asking this question, you can gain insight into the candidate’s ability to create effective strategies for managing their team. You will learn how well they can understand the organisation’s goals and create a plan to achieve them. Additionally, you’ll be able to assess the candidate’s communication and interpersonal skills.

When it comes to motivating their team, you want to know if they have experience motivating various personality types. You’ll be able to see if they can recognize what motivates each individual and create a plan to get the best out of everyone. Asking this question can also give you an idea of how well they can delegate tasks. We should also discover how they provide feedback to ensure the team works together effectively.

The answer to this question can give you valuable insight into the candidate’s ability to manage and motivate a team. Assessing whether they can create an environment where everyone feels valued and motivated to do their best work is vital. By understanding their past strategies and experiences, you’ll be able to better determine if they are the right fit for the role and company.

8) What do you believe is the most important trait for a successful salesperson?

This question allows you to gain insight into the candidate’s knowledge and understanding of the sales profession. Additionally, it can help you determine if their beliefs align with your own and the values of your company.

A successful salesperson must possess various skills and attributes. These include problem-solving and communication skills to working well under pressure and driving results. By asking this question, you can better understand which traits are most important to the candidate. You’ll also learn how they plan to implement them in your company as Head of Sales.

Furthermore, this question will give you an indication of whether or not the candidate is a strategic thinker. It also allows you to explore their values, such as integrity and ethical behaviour, and how they achieve sales goals. The answers provided can be compared with other candidates so you can make an informed decision when selecting the right individual for your company.

Overall, asking this question is a great way to understand the qualities and characteristics that your potential new Head of Sales will bring to the team.

9) Describe your strategy for managing an underperforming salesperson?

Asking about a candidate’s strategy for managing an underperforming salesperson is a critical question. It allows you to evaluate the potential hire’s ability to assess performance, provide constructive feedback, develop action plans and lead sales teams.

An effective head of sales should have a strategy that focuses on developing their sales team, while also holding individuals accountable to meet performance standards. This question can help you determine if the candidate understands how to motivate and build successful teams, and if they are capable of resolving conflicts or challenges in a diplomatic way.

It is crucial to understand how the candidate will handle situations involving sales managers who don’t meet expectations, as this role requires the ability to handle difficult conversations.

Ultimately, you want to ensure the candidate has experience dealing with underperforming sales managers. They must show they can effectively develop and coach their team while holding them accountable. Asking this question provides insight into the potential hire’s leadership style and demonstrates if they have the necessary skill set to lead your sales team successfully.

10) What do you believe is the most critical factor in determining success in sales?

Asking this question can provide a lot of insight into the candidate’s mindset and approach to the position. Knowing what drives success in sales can help you understand how the candidate will lead your team.

A firm answer could include things like:

  • customer service,
  • relationship building,
  • knowledge of the product/services,
  • understanding customer needs,
  • staying organized and motivated,
  • or creating effective sales strategies.

While these qualities are important for any salesperson, a successful head of sales should also have qualities such as:

  • good communication skills,
  • attention to detail,
  • and an ability to identify areas for improvement.

Your ideal candidate should be able to explain how their background and experience have helped them understand what it takes to be successful in sales, and provide examples of how they have put those ideas into practice. They should be able to demonstrate their willingness to keep up with changes in technology, business trends, and customer needs.

Asking this question during the job interview can provide valuable insight into the candidate’s qualifications and capabilities. It will allow you to identify those with the right skills and knowledge to take your sales team to the next level.


To wrap up, choosing the right questions when interviewing a head of sales is important to ensure you make the best decision for your team. Asking thought-provoking questions such as these can help you determine the candidate’s fit for you. When done correctly, interviewing a potential Head of Sales can be an invaluable resource for your company’s success.

Good luck with your search for your perfect Head of Sales!

So, are you ready to start your hiring process with a difference?

If you still need a hand or two, why not have a chat with the team here at Your People Partners? We love helping your business thrive.

Further reading

author avatar
Helen Sanders Managing Director and Chief People Partner
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