Over the course of my career I’ve interviewed hundreds of candidates for jobs at all levels of sales teams, from entry level sales reps to senior VPs of sales. I try to keep my questions consistent across a round of interviews for a single role so I can compare candidates fairly, and I’ve learned that certain questions are especially revealing, not just in terms of whether a person is qualified on paper for the job, but also whether they’re a good fit for the team and organization.
The list below includes some of what I consider to be the most important of these questions. I’ve used combinations of them through the years from my experience as True’s special advisor focused on sales and revenue operations, and as a leader of sales teams at organizations ranging from data platform Snowflake, where I’m the VP of global sales development, to Cloudera, where I formerly served as VP of global inside sales.
There are plenty of questions and conversation prompts here to choose from; I recommend picking your favorite 10 based on what qualities you’re looking for and asking them of all of your candidates for a given role. My own managers pick and choose from this list based on the segment, culture, and geographic location. (Note that many of these questions are relevant to different departments as well, far beyond sales.)
Feel free to make a copy of this list so you can refer back to it the next time you list an open role via the True Jobs page or otherwise.
What to ask when you want to know if the candidate is adaptable:
- Tell me about a time when you had to adjust your work style/process?
- Describe a time when you were assigned a new task or asked to change quickly. How did you adapt?
- How would you help your colleagues adjust to company changes?
What to ask when you want to know if the candidate learns quickly:
- From what you know about our company, can you give me an elevator pitch?
- Tell me about a time when you had to learn a new task at work. What did you do to speed up the learning process?
- How do you learn new things?
What to ask when you want to know if the candidate has unwavering drive:
- Why sales?
- What is your proudest accomplishment, and how did you achieve it?
- Tell me about a time when you achieved and surpassed a personal goal.
What to ask when you want to know if the candidate is a team player:
- Tell me about a time when you had to navigate conflict with a fellow team member.
- Have you ever gone out of your way to help someone on your team? What did that look like?
- Can you remember a time when you made a positive impact on your team?
What to ask when you want to know if the candidate can navigate complexity:
- Tell me about a time when you took a complex idea, adapted it, and made it simple and easy to understand.
- What are some examples of instances when you’ve used data to make a decision?
- Tell me about a time when you had multiple deadlines and projects. How did you organize and prioritize?
What to ask when you want to know if the candidate is rigorous in their sales process:
- What’s your response to rejection?
- What are two or three trends in our industry that may disrupt your path to success here? How would you adjust to ensure you’re successful?
- What’s your reaction when you do succeed?
What to ask when you want to know if the candidate is naturally curious:
- Tell me about a time when you asked for feedback from your manager. Why did you want it?
- What interests you most about this position?
- Tell me about a time when you improved a process at work or in school. How did you uncover an area to improve?
What to ask when you want to know if a sales development rep candidate is coachable:
- Think about the last time you needed help at work. What did you need help with, and why did you decide to ask for help?
- Can you describe an area where you’ve identified a need for improvement and how you’ve tried to improve?
- Tell me about a time when a team project yielded unfavorable results. How did you take accountability?
What to ask when you want to get to know the candidate better:
- Tell me about something you’ve gotten better at over the last 12-24 months. How did you go about doing that?
- What do you like to do on the weekend? What are your hobbies?
- What brings you joy and harmony?
If you’re a founder of an enterprise SaaS solution growing your team, also give this article on shaping paths for your first five sales hires a read.
Lars is a special advisor at True, where he helps portfolio founders implement best-of-breed sales technologies and processes that enable efficient revenue operations. Learn more about Lars and how he supports the True community of entrepreneurs.