Interview guides

Sales Professionals and Sales Managers

Find persuasive, data-savvy sales talent who drive results.

Customer Retention
  • How did you measure customer retention or loyalty?
  • What steps did you take to retain clients?
  • Describe a serious client issue and how you handled it. Did the client return?
  • How important was the relationship vs. the product/service itself?
  • Did you build relationships with clients through lunches, events, or networking activities?
Inbound Sales
  • What was the nature of the inbound calls you handled? How many did you respond to per hour?
  • How often did you convert an inquiry into a sale? Were scripts provided?
  • If you received 10 inbound calls, how many would you typically convert?
  • Were calls recorded? What feedback did you receive?
  • What follow-up process did you use after inbound calls?
  • How did you handle language barriers or difficult callers?
  • What sales and customer service training were you provided?
  • How was success measured and rewarded?
Outbound Sales
  • How did you choose which customers to cold call?
  • What was your reach ratio?
  • Did you leave messages, and did you rehearse scripts before leaving them?
  • How did you determine who to call (directories, business lists, social media, referrals, CRM)?
  • Were you given a lead list or expected to create your own?
  • What percentage of calls resulted in meetings?
  • Describe a typical meeting (duration, questions, objections, closing, follow-up).
  • What objections did you routinely handle?
  • How did you handle discouragement from lack of reach or interest?
  • After an initial meeting, how did you nurture relationships? How many leads converted to clients?
  • How did you overcome the feeling you were “bothering” people?
Product Sales
  • Tell me about the product you sold. What features did you promote?
  • What objections did you face about the product?
  • Did you believe in the product enough to sell it effectively?
  • Did you compare your product to competitors? How well did you know their offerings?
  • Was price or product features most critical to your clients?
  • Did you provide customer feedback to management? How, and how often?
Quotas & Compensation
  • What was the average size of a sale in your last role? How many were you expected to close weekly, monthly, annually?
  • How were quotas set in your role? Did you agree with the targets? Were they reviewed weekly, monthly, or annually?
  • Were sales staff ranked? Where did you rank?
  • What was your total annual compensation in your most recent sales role? What is the most you’ve earned in one year?
  • How was your base salary, commission, or bonus structured? Were there other incentives (trips, hybrid work, recognition)?
  • Did you use a T-2200 for expenses (Canadian sales tax form)? What expenses were covered by your employer vs. out-of-pocket?
  • How much time did you invest in networking/outside events? Which types were most effective?
  • Describe the compensation plan you’re seeking now (minimum and ideal base).
  • Please rank your top motivators: compensation, recognition, autonomy, training, prestige, job title, work-life balance, remote work.
Sales Approach & Negotiation
  • How would you describe your sales style?
  • Think of a stapler. How would you sell it to me?
  • Describe a contract you negotiated. What hurdles did you face and how did you overcome them?
  • What top five questions did you routinely ask prospects to assess their needs?
  • What steps did you take to close a sale?
  • When did you know to walk away from a prospect?
  • Did you give presentations? For what audiences? How long? Did you use PowerPoint or other tools?
  • If not, who handled presentations in your firm?
Sales Managers

Initial Leadership Questions

  • Describe the last sales force you managed. How many reps? Senior vs. junior?
  • Did you hire the team? How did you locate, evaluate, and onboard them?
  • What made your hiring decisions successful—or unsuccessful?
  • In your opinion, what makes it difficult to hire the ideal salesperson?
  • What does a typical day look like for you as a Sales Manager? (Desk work vs. client meetings).

Coaching & Performance Management

  • How do you praise or recognize top performers?
  • How do you help weaker performers grow?
  • How did you coach your best vs. weakest reps? Were they receptive?
  • Have you terminated a low performer? How did you prepare and communicate the decision?
  • Have you lost a top performer? Did you see it coming? Did you counter-offer?
  • What was your turnover rate? How did you address it?
  • Did you do formal performance reviews, or manage performance daily?
  • Did you collaborate with HR on performance issues or manage independently?

Change & Resilience

  • Have you managed sales through a recession? How did you keep morale and results up?
  • Have you led through major organizational changes (product redesign, compensation restructuring, M&A)? How did you manage disruption?
  • What reports and data did you use to guide your team? What data were you missing?
  • What do you worry about most as a Sales Manager? How do you address those concerns?

Leadership & Strategy

  • Some say great salespeople don’t always make great managers. Do you agree?
  • When you transitioned from selling to managing, did you struggle with giving up the spotlight?
  • What are your views on internal competition within the sales force? Helpful or harmful?
  • Who was your sales mentor? What lessons did you carry forward?
  • How did your team collaborate with marketing? With production/manufacturing? What issues arose?
  • In your roles as a manager, who did you report to, and what was their style?
  • Individual contributors sometimes earn more than managers. Why did you choose leadership?
  • Do you have experience managing client contracts? What about large account losses?
  • Who handled pricing and high-level negotiations—yourself, lawyers, senior execs?
  • How did you deal with the loss of a major client?
  • What metrics or reports did you use to increase sales?
Service Sales
  • How is selling a service different from selling a product?
  • Tell me about the last service you sold. How did you describe it to clients?
  • Did you position it as a service or a solution?
  • What aspects were negotiable with prospective clients?
  • Do you believe services are commoditized, making prices more negotiable? Why or why not?
Sales Professionals & Sales Managers Initial Questions
  • What has motivated you to build a career in sales (business development)?
  • Tell me about a sales professional you know. What do they sell, and what have you observed about their style, personality, and results? Are you like or unlike this person?
  • Describe the sales cycle, from cold call to close, in your current or former role.
  • What supports are available to you in your role to help you create the lead or make the sale?
  • What customer databases/CRMs have you used? What information was crucial to gather and record? How was the information used to generate reports and drive sales?
  • What type of sales leader inspires you to perform at your best?
  • When you leave a client’s office (or virtual meeting), what do you think they say about you and your approach? What would be their one complaint, if any?
  • Have you ever quit a sales job? If yes, why?
  • Looking ahead, what outcomes are you hoping for in terms of role, autonomy, and earnings?
Soft Skills in Sales
  • How do you build trust quickly with a prospect?
  • Describe a time you dealt with rejection. How did you bounce back?
  • What motivates you when results are slow?
  • Describe a time you had conflict with a client or teammate. How did you resolve it?
  • How do you balance persistence with respect for the customer’s boundaries?
  • What’s your approach to active listening during sales conversations?
  • Tell me about a time you had to adapt your style to a very different personality type.
Technology & AI in Sales
  • What sales enablement platforms or CRMs (Salesforce, HubSpot, Dynamics, Zoho, etc.) have you used?
  • How have you used LinkedIn Sales Navigator or similar prospecting tools?
  • What analytics dashboards or BI tools (Tableau, Power BI) have you used to track sales metrics?
  • Have you used AI-powered lead scoring or pipeline forecasting? Did it improve conversion?
  • Have you used AI-driven chatbots or assistants to qualify leads? What results did you see?
  • How do you use generative AI to draft outreach messages, proposals, or contracts?
  • Have you integrated sales automation tools (Outreach, Gong, Apollo, Salesloft) into your workflow?
  • How do you ensure personalization while still leveraging automation?
  • How do you stay ahead of emerging digital sales tools?

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