
Interviewing and assessing
Interview Question Guide
Interview questions for individual contributors and for sales leaders, each with the reason to ask it and what to listen for in the answer, grouped by hard, soft and fit indicators.
Interview Question Guide
Interview questions for individual contributors and for sales leaders, each with the reason to ask it and what to listen for in the answer, grouped by hard, soft and fit indicators.
Questions to put to a candidate, each with the reason it's worth asking. The first set is for individual contributors, the second for general and sales leadership.
Individual contributor questions
Hard indicators
- How do you keep up to date on your target market?
- Even if the target market of their last job is totally different from the one they’re interviewing for, this will show their ability to find and keep up with relevant trade publications and blogs.
- Tell me about your background?
- Can they draw parallels between their experience and how that ties into this role? Manage time wisely? Engage your attention?
- How has technology made you a better/more successful salesperson? Give me an example.
- Are they leveraging technology to strike a balance between human touch & technology?
- Based on what you understand about this role, how good of a fit do you think you are?
- For one, it reveals how much they know about the role, which clues you in to how well they’ve prepared. Secondly, it allows them the chance to showcase their relevant strengths in: environment, similar customers, products, etc.
- Walk me through your performance metrics for the last few years.
- They should be able to articulate & provide this data easily. If not, then it’s not important to them, and if it’s not important to them, then they probably aren’t the right fit.
Soft indicators
- What’s the biggest misperception people have about you?
- A good measure of EQ.
- What has been your most significant professional accomplishment?
- You’re looking to see WHY they attach value to it. Is it because they received formal recognition either through an award or financial gain? (all about them). Or because it benefited the customer/patient or organization? (good indicator they're built for impact). It's good to ask follow-up questions, for example: Why was it significant to you? What did you learn from it? What was the outcome?
- Tell me about one of the biggest mistakes you’ve made (professionally).
- Do they self-reflect in order to always be improving? What would they do differently? What does the mistake reveal about them?
- Have you ever had a losing streak? Tell me about it.
- Everyone has bad spells, so beware of someone who claims they’ve never experienced a downturn. Nothing’s wrong with a temporary slump as long as the candidate learned from it.
Fit indicators
- What about this opportunity appeals to you?
- You're seeking to determine “why” they're interested in this role. Are they running away from a collapsing company? Are they bored? Wanting more $$? Ideally, you’re looking for some non-monetary reasons that supersede the quick pop of a better income/quality of life. (meaningful work, purpose, mission-oriented, etc)
- Which company culture have you thrived in best? Why?
- They're drawing from personal experiences, instead of giving you an abstract answer.
- What’s your approach to handling customer objections?
- Preparing to deal with objections instead of winging it's critical. Listen for evidence of a process.
- Tell me about the best boss you’ve ever had. What makes him/her so memorable to you?
- As they describe this person’s leadership style, listen to see if it’s similar to yours, or quite different. This is a big one for cultural fit, at least at the most basic level.
- What do you think our organization could do better?
- It shows how much research the candidate did before meeting with you, and it demonstrates their creative thinking and entrepreneurial capabilities.
General and sales leadership questions
Hard indicators
- Tell me about how your team has performed. Please provide some specific examples of accomplishments.
- A manager’s success is measured through the performance of his/her team.
- How do you incorporate technology within your team?
- Reveals where & how often they're leveraging tech to build more efficient teams.
- Describe how/when you use Data Analytics to lead your team.
- Beware of candidates that express active revulsion for data analysis. It doesn’t have to be a passion, but it should be an important part of their sales forecasting/tracking.
Soft indicators
- What do you think makes for a successful rep coaching session?
- Their idea of a coaching session should include actual coaching, not just a dry discussion of the numbers. Listen for responses that include mentions of career development, goals, skill-building, and problem-solving.
- What do you think it takes to be a great leader?
- The guide asks this without giving a reason to listen for.
Fit indicators
- What attributes do you look for when you hire someone for your team?
- Do the attributes they value line up with the company’s values?
Keep going.

Candidate Submission Checklist
Fifteen things to ask your recruiter to send with every resume, from travel and non-compete status to their own opinion of the candidate, so each submission arrives complete.

Interview Scorecard
A weighted scorecard for rating a candidate on sixteen hard, soft and fit indicators across two interviews, with importance values, a worked example and a score key to read the result.
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