20 Killer Questions When Interviewing Sales Leaders

Finding the right person at the right time has always been difficult, especially when it comes to who will lead your sales department. It is a notoriously difficult position to hire for. The very best candidates are difficult to dislodge from their current roles, and once you get their interest, they are masters of ‘selling themselves’.

Whether you are a seasoned CxO or founding your first tech company, the risks are equally high. This is why, when you are interviewing these very capable people you need to cut through the noise and ask questions that will separate the good from the great.

These questions should form the base of your conversations with Sales Leaders. Here are 20 killer questions that will help you find the person that best suits your needs.

Hiring junior salespeople? Here are some killer questions for you too.

Leadership:

Leadership plays a critical role in how the sales team operates and the level of success it can achieve. Effective leadership can ensure that the team is motivated, productive, and working towards the established objectives. While also considering the well-being of each team member.

1. Can you give us a specific example of how you have developed and mentored a high-performing sales team?
2. Can you give an example of a situation where you had to adapt your leadership style to accommodate different sales team members, and what impact it had on the team's performance?
3. How do you approach creating a sales culture that emphasizes innovation, risk-taking, and accountability?
4. Can you give an example of how you have effectively dealt with a sales team that was underperforming?
5. How have you built and maintained a top-performing sales team in a highly competitive market?

Selling:

It is one thing to be a great leader, but can they sell? Do they have the right methodology and experience to lead your sales team to success? The goal is to increase customer satisfaction and loyalty, drive sales and revenue, and be more efficient in the process.

1. How do you build trust and credibility with customers, particularly in complex or long-term sales cycles?
2. Can you tell us about a time when you had to negotiate a challenging deal and what strategies you used to reach a successful outcome?
3. Can you give an example of a sales campaign that you planned and executed that delivered exceptional results?
4. Can you give us an example of how you have effectively introduced a new product to the market?
5. Can you give an example of how you have successfully disrupted a traditional sales market and created new opportunities?

Strategy:

A well-defined sales strategy helps sales teams focus their efforts and resources on the most important activities, leading to increased revenue and overall business success.

1. How do you stay on top of industry trends and how do you stay ahead of the competition?
2. How do you approach sales forecasting and what methods have you found to be most accurate?
3. Can you describe a time when you had to pivot your sales strategy and what factors influenced your decision?
4. Can you describe a time when you had to make a significant investment in sales resources, and what factors you considered in your decision-making process?
5. How do you effectively manage and mitigate sales risks?

Personality:

Asking questions based on personality traits can help determine the best candidate for a sales leadership role. Such questions provide valuable insights into a candidate's ability to lead a team, connect with customers, and adapt to changing environments. By assessing these traits, organisations can choose the best candidate to drive business success.

1. How do you maintain a positive and optimistic outlook, even in the face of adversity?
2. Can you describe a situation in which you had to work outside your comfort zone, and how you approached it?
3. Can you describe a situation in which you had to navigate a complex political landscape and what steps you took to maintain your team's success?
4. Can you describe a time when you had to make a decision that involved a trade-off between hitting your sales target and doing what was best for the customer?
5. How do you maintain a high level of ethical standards in your sales practices?

I hope you found this guide to interview questions for sales leaders useful. What do you think about my questions? Also, if you have a killer question of your own, please leave a comment below. 

Darren Timmins is the CEO of the Technology Talent Management company Animate. He has spent the last 20 years supporting the hiring of senior leaders and critical teams for some of the most exciting technology companies on the planet.