ClickCease 75 Strategic Sales Approach Assessment Questions - Stealth Agents
75 Strategic Sales Approach Assessment Questions

75 Strategic Sales Approach Assessment Questions

75 Strategic Sales Approach Assessment Questions



In the wild and sometimes wacky world of sales, there’s a method to the madness. Those who consistently crush their quotas and carve out a corner of the market for themselves aren’t just riding on luck’s coattails; they’re harnessing the power of a strategic sales approach.


But let’s step back for a quick sec. What is this enigmatic “strategic sales approach,” and why should you give a hoot? Well, sit down, my friends, because we’re diving into the sales world where understanding your game plan can turn you from a salesperson to a sales legend.


Introduction: Unraveling Strategic Sales Approach

Are you a sales superstar looking for that extra oomph to escalate your deals from promising to profitable? Or perhaps you’re an eager bean, fresh out of the sales boot camp, eager to learn the ropes.


You see, a strategic sales approach isn’t some kind of mystical sales spell. It’s about combining your company’s goals and mission with tactical activity that ensures you’re hitting the right notes with your prospects at the right time.


Sound good? Let’s dive into 75 strategic sales approach assessment questions that can help you sharpen your skills, make your closes a little bit tighter, and sling that product or service with the killer instinct of a cheetah in a Hail Mary dash.


List: 75 Strategic Sales Approach Assessment Questions

Ready to blow the roof off your numbers this quarter? Here are 75 questions to consider when assessing your strategic sales approach. These will help you dissect, analyze, and fortify your sales strategy like a pro.


  1. What are your top three priorities as a salesperson this quarter?

  2. Are there any gaps in the market you could exploit with your product?

  3. How many of your recent sales were to new customers versus repeat customers?

  4. Do you have an onboarding process for new customers after the sale?

  5. What’s your customer retention rate and how can you improve it?

  6. Are you leveraging social selling to build your brand and connect with prospects?

  7. How often does your sales team update their skills and on what areas do they most need development?

  8. Do you have a clear sales process in place, from lead to close, and does it need adjusting?

  9. What tools or software are you using to manage your sales pipeline?

  10. How do you measure the success of your sales efforts?

  11. Is your pricing strategy competitive and does it reflect the product’s value?

  12. Does your sales team have good relationships with key decision-makers?

  13. What are the most common objections your sales team faces, and how do they handle them?

  14. Are there any products or services in your portfolio that are underperforming, and why?

  15. How can you upsell to existing customers and increase the lifetime value of your accounts?

  16. What’s your sales conversion rate, and how does it compare to industry standards?

  17. How do you qualify your leads effectively?

  18. Do you have a strategy for nurturing leads that aren’t ready to buy yet?

  19. What is the feedback loop like between your sales and marketing teams?

  20. Do you have a process for gathering feedback from customers post-sale?

  21. How do you incorporate storytelling into your sales presentations?

  22. Which customer segments are most and least profitable for you?

  23. Are your sales team’s goals aligned with the broader company objectives?

  24. What percentage of your time do you spend with high-value customers versus low-value ones?

  25. Do you utilize customer relationship management (CRM) effectively?

  26. How do you handle long sales cycles, and are there ways to shorten the process?

  27. What is your ideal customer profile, and how do you match your pitch to their needs?

  28. Do you have customer case studies and testimonials readily available to address customer concerns?

  29. How often do you review and update your sales collateral and presentations?

  30. Do you personalize your outreach and content to different industries and customers?

  31. Do you use data analytics to inform your sales strategies and tactics?

  32. Are there any trends in the data that can help predict future sales patterns?

  33. How do you manage the distribution of leads among your sales team?

  34. What are the commonalities between your most successful sales?

  35. What’s your average deal size, and how can you increase it?

  36. Do you encourage your sales team to work together to learn from each other’s experiences?

  37. How do you handle the competition, and do you keep a close eye on their moves?

  38. Are there any partnerships you can form to increase your reach and effectiveness?

  39. What metrics do you use to measure the health of your sales pipeline?

  40. Do you conduct win/loss analysis for insights into your sales performance?

  41. How often do you review and update your ideal customer profile?

  42. What’s your response time to customer queries and how could you make it faster?

  43. Do you segment your leads and customers for a more targeted approach?

  44. What’s the technology adoption rate like among your customers, and how does it affect your sales process?

  45. How do you educate your buyers and provide value throughout their purchasing journey?

  46. Do you conduct team-based selling for big-ticket deals?

  47. What’s your follow-up strategy after a sales meeting?

  48. How do you make use of content marketing to support your sales process?

  49. How do you incorporate buyer personas into your sales approach?

  50. What’s your strategy for re-engaging with old leads?

  51. Are you seen as a trusted advisor by your customers?

  52. What’s your process for setting and following up on sales meeting agendas?

  53. How do you handle customer objections to price or cost?

  54. Do you use social proof in your sales process effectively?

  55. What’s your sales team culture like, and how does it support strategic selling?

  56. Are there any incentives or bonuses that could improve your sales team’s performance?

  57. How do you incorporate the concept of urgency into your pitch without being pushy?

  58. Do you measure and optimize the performance of your sales team on a regular basis?

  59. How do you balance formal sales targets with long-term relationship building?

  60. What’s your process for asking for referrals from satisfied customers?

  61. Do you use account-based marketing to focus your efforts on high-value prospects?

  62. What’s your approach to continuous learning and staying ahead of the curve in your industry?

  63. Do you pay attention to the emotional needs of your customers in addition to the logical ones?

  64. How do you handle rejection, and what strategies do you use to bounce back?

  65. What’s your strategy for building credibility with a new prospect?

  66. Do you set clear next steps after any interaction with a prospect?

  67. Do you ask for the sale, and do you know how to effectively close it?

  68. How do you use testimonials and case studies in your sales process?

  69. Do you have a clear understanding of your customer’s decision-making process?

  70. Are there any psychological triggers you can use in your sales approach?

  71. What are your prospect’s biggest pain points, and how does your offering solve them?

  72. Do you align your sales strategy with both the current and future needs of the marketplace?

  73. How do you handle objections from a customer who is not the decision-maker?

  74. Do you have a multichannel sales approach to reach your customers where they are?

  75. What’s your long-term plan for managing relationships with customers after the sale?







There you have it, 75 questions to ignite the flames of strategic selling in your soul. So what’s the takeaway? A successful strategic sales approach is less about what you sell and more about how you sell. It’s a dance, a tango, a back-and-forth with potential clients where you’re taking the lead and they’re swooning over your every well-thought-out step.


So take these questions, ponder over them, and update your strategic playbook. Sales isn’t a sprint; it’s a marathon. And with the right strategies in place, you’ll not just finish — you’ll win the whole darn thing.

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