Skip to main content
Professional DevelopmentRandom Thoughts On Business

76 Killer Questions for Your Sales Team

By November 5, 2021December 3rd, 2021No Comments
wilderness questions for your sales team

Smart questions equal smart answers. We’ve compiled a (very long) list of top questions for your sales team to ensure:

  1. They get the information they need to provide solutions to the client’s problems.
  2. They develop a rapport that leads to a beneficial relationship.
  3. They find areas of opportunity to discuss in the future.
  4. They improve their fact-finding, deal-closing missions.

Your salesmen and women have stressful jobs. They are a driving force in the success of your business and often act as the face of your brand. Have you equipped them with the tools to succeed? Are you encouraging professional development?

Here are 76 questions for your sales team, designed to build relationships, encourage creativity, provoke thoughts, and ultimately, make that sale (with a few of our favorite quotes for inspiration).

Questions For Your Sales Team

For Bonding and Rapport

Success isn’t about how much money you make; it’s about the difference you make in people’s lives. +Michelle Obama

  1. Can you tell me more about that?
  2. How do you feel about that?
  3. Have you given up trying to deal with the problem?
  4. What are your assumptions concerning…?
  5. How should we plan to stay top of mind with each other?
  6. What type of relationship do you want to have with a provider of…?
  7. How did you hear about us?
  8. How do you see your business grow, and your needs changing over the next one to two years?
  9. What are other products/solutions you’re currently using that our software has to integrate with?
  10. What kind of support/service/help do you need to become insanely successful?
  11. How do you implement it?

For Up-Front Contracts

Either run the day or the day runs you. +Jim Rohn

  1. How will you define success for our time together today?
  2. For what are you listening for today in our meeting?
  3. Was there a compelling event that caused you to reach out to us?
  4. Are there any surprises we should be prepared for?
  5. If this were just you and me, how excited would you be to move ahead on a scale of 0-10?

For Discussing Painpoints

I thrive on obstacles. If I’m told that it can’t be done, then I push harder. +Issa Rae

  1. Can you tell me more about that?
  2. Can you be more specific? Give me an example.
  3. How long has that been a problem?
  4. What have you tried to do about that?
  5. And did that work?
  6. How much do you think that has cost you?
  7. How do you feel about that?
  8. Have you given up trying to deal with the problem?
  9. What are your satisfiers/dissatisfiers with…?
  10. Other than price, what are the top 3 – 5 pass/fail requirements for…?
  11. What are the top 3 – 5 risks you feel when…?
  12. Is there anything that could stop this deal from happening?
  13. What’s missing or what should we add?
  14. Are “they” going to like it?
  15. What are they going to like?
  16. What are they going to push back on?
  17. What else is going to be in our way?

For No One’s Favorite (Budget)

Never ever chase money. You should chase success, because with success money follows. +Wilfred Emmanuel-Jones

  1. What’s your budget?
  2. When was the last time you made a purchasing decision for a solution like ours?
  3. If you were to decide this is a good idea, how do you buy things like this?
  4. Can I help put together some numbers?
  5. Do you have some numbers I should include?
  6. When do you budget for things like this?
  7. Have you given some thought to how much you’ll need to invest into…?
  8. I don’t suppose you’ve put a budget aside for this project yet, have you?
  9. Have you come up with a monthly allocation for this purchase?

For Decision-Making

The way to get started is to quit talking and begin doing. +Walt Disney

  1. Under what circumstances would you/your company…?
  2. How will you define success for our time together today?
  3. How is this decision made? Hint: Who, When, Where, Why, & What
  4. What do you wish to accomplish while attending this Trade Show/ Conference?
  5. What are your must-haves, should-haves, and could-haves?
  6. What’s your decision-making process like?
  7. Who are all the stakeholders involved in this deal?
  8. Who else are you comparing us with?
  9. What’s the timeline for making a decision?
  10. What’s your budget?
  11. When was the last time you made a purchasing decision for a solution like ours?
  12. What will it take to win your business?
  13. What should I know about your timing? Signoffs?
  14. Who would you like to meet while attending this trade show/conference?
  15. Do you think this deal is going to work?
  16. Are you going to pitch it?
  17. What else do you need to see from me?
  18. Who else besides you will be making this decision?
  19. How would YOU respond to that?
  20. What answers do you need from me so you’re prepared to answer their questions?
  21. How much detail do YOU want?
  22. How much detail will THEY want?

For Personal Review

Don’t settle for average. Bring your best to the moment. Then, whether it fails or succeeds, at least you know you gave all you had. We need to live the best that’s in us. +Angela Bassett

Here is an opportunity for an internal review of your role and your team’s role in the outcome – whether positive or negative. Remember, growth doesn’t happen without introspection.

  1. What were the outcomes? (Make a list, likely several will surface when thoughtfully considered).
  2. What did I/We do/or ask that made that happen?
  3. What went well and why?
  4. What did not go well and why?
  5. What should I have done/asked?
  6. What should I not have done?
  7. What did I learn about what to do, that I will try again?
  8. What questions did the Prospect ask and why? (Think buyer’s instincts).
  9. What statements did the Prospect make and why? (Think buyer’s instincts).
  10. What was effective and ineffective relevant to developing a referral?
  11. For what was I listening for and did I hear it?
  12. What value did my colleague provide to improve effectiveness?

Welcoming Creative Problem Solvers

Wilderness Agency is a team comprised of both full-time and freelance employees that push creative limits daily. More than anything, we value adaptability and education for all team members. If you are willing to step out of your comfort zone and create incredible work with the support of our team, then you will fit right in!

Check out our open positions today, and connect with us on LinkedIn!

Richard Kaiser

Richard Kaiser

Some of my fondest memories from my formative years were from Boy Scout camps sitting on rough, wooden logs that encircled a crackling fire sharing stories with the other boys. I believe in my heart that it is a human need to be told stories. We crave stories much in the same way we crave love. The work we do at Wilderness Agency is based upon this primal need. We bring together some of the best creative talent from around the world to tell our client’s stories, to share their passion with the world.