Toolbox of Questions

September 15, 2021
BY: Adam Kent

ALL The Question’s You’ll Ever Need
Have you ever experienced that situation where a sale was all but finalized, only to fall apart at the last minute? Or you thought everything was going great only to get that email or call that your soon to be client decided to go with someone else? Maybe you’ve been in that situation where your potential client told you they weren’t interested right now but instead, you to find out they just weren’t interested in you and went with someone else?

One of the biggest myths is that a price objection is the real reason why they didn’t go with you. What they were more than likely objecting to, was the value. As in, what you communicated wasn’t worth what you were asking for. So how do you communicate the value then? It’s actually a rhetorical question, because the answer is in asking more questions. Relevant and powerful questions.

This doesn’t just apply in the professional world. Think about those moments when you’re having a chat and all the sudden, it goes awkwardly silent… You’re just standing there trying to figure out what to say next. In the professional world, those awkward moments can make anybody feel nervous. What if I say the wrong thing, get an answer i don’t want to hear, or, what if they aren’t interested anymore? what if! what if! what if! It is more important now than ever to accept that people no longer like to be “sold”. The preference is to make our own decisions. Everyone knows they are being sold but ironically, nobody wants to know they are being sold to.

Consider this; The one asking questions, controls the conversation. That’s right! It shows confidence, posture, professionalism, a genuine interest, and it can drastically increase the likelihood of you winning a brand new, happy client. Yet, as known as this may be, it is still not a commonly applied practice.
If you truly want to stand out above and beyond the average, dig deeper, ask more questions!
Enjoy over 130 different questions you can apply today!

Warm Things Up
• If we asked your best customers why they love doing business with you, what do you think they would say?
• What are you currently doing about {blank}?
• What motivated you to start/work for your company?
• What were your original expectations going into the business?
• Have any of those expectations changed at all?
• What are some of the things you like in your line of work?
• What are some of the things you dislike In your line of work?
• What are the biggest challenges you’ve had to overcome?
• What are the biggest challenges you are currently facing?
• What’s your best memory so far?
• How has your role in the company and what you do evolved over the years?
• What’s your (least) favourite thing about what you do?
• How would you describe your business in 10 words or less?
• How would your (team, boss, customers, vendors etc.) (pick a word they used: {word} is a great one. Would you mind elaborating on that a bit?)
• How many {blank} are you currently producing?
• How do you use this product, service, application in your business right now?
• Who are you using now?
• What do you like about {blank}?

• What are the ideal qualities you look for in a…
• How is your ideal different from right now?
• If you don’t mind me asking, what didn’t I do, or say that had you go with {blank} instead?
• If it’s ok with you, I would love to know what I could have done differently to earn your business?
• You mentioned that {blank} was important to you. Is there anything else missing that’s important to you right now?
• I respect loyalty, and I’m sure we can both agree that needs do evolve over time. Would you be open to sharing what your current needs are, and if we’re able to take care of them?
• If there was one thing that could change your mind right now, what might that be?
• If there was one thing we could do to {blank}, what might that be?
• How would you rate {blank} on a scale of 1 to 10? (no matter the number you’re given, ask them to elaborate)

Making Stronger Relationships
• Is there anything that I/we could be doing for you (differently, better, more, etc.) to ensure you are getting what you expect from us?
• What you do feel like we are doing well for you? Knowing what’s working for you will help us continue to do it. Or possibly find creative ways to do it better!
• Is there anything you feel we could do more of, or less of to support/help/take care of you?
• If you could change one thing about our business relationship, what might that be?
• How can I make life easier for you?
• If a potential client was to ask why you choose to do business with us, do you mind sharing how you would respond?

Uncovering Challenges
• What are your challenges?
• What’s your biggest challenge right now?
• If you could change one thing right now, what would that be?
• What would you change right now if you could?
• What would make the biggest difference to your business right now? (why/how)
• Have you identified the challenge?
• What’s causing the issue?
• Could you share an example?
• How long has {blank} been going on?
• If nothing changes, what’s the consequence?
• What barriers stand in your way?
• What are the obstacles?
• What have you already tried?
• What’s working/not working? )ask why/how)
• On a scale from 1 to 10, how satisfied are you with {blank}? (ask: What would you like to see the {blank} do/accomplish to be a 10?)

Explore the Past & Future
• Think back to when you first implemented {blank}…
• What did you think would change?
• What results were you expecting?
• What result are you seeing now?
• What kind of result do you want to see in the future?
• Is {blank} meeting your expectations?
• So how does right now compare to what you want?
• What does {blank} look like 12 months from now, three years from now? As in, what would you like to be doing more of…? Less of…?
• What action/s do you have to take in order to achieve/reach/get {blank}?
• What needs to change in order to make that happen?
• How will you know you achieved {blank}?
• Do you know what the milestones are?
Your Customers Customer’s
• Who are your most valuable customers?
• Have you identified your ‘AAA’ client?
• Do you have an ideal client profile?
• What’s your target market?
• What does your typical client look/sound/act like?
• What do clients expect from you?
• What’s the difference between your best client, and an average client?
• Have your customers shared why they chose you over a competitor?
• Have your customers evolved over the lifetime of your business?
• Do you see customer expectations changing over the next 3 to 5 years?
• What do customers like most about doing business with you? What do they least like?
• What steps are you taking to improve in {blank}?
• Could you explain the difference between a profitable customer and an unprofitable one?

Uncover Hidden Needs
• So, what got you interested in {blank}?
• Do you know what caused {blank}?
• What motivated the need for {blank}?
• What led you to {blank} decision?
• Do you mind explaining what led to {blank} conclusion?
• What do you hope to accomplish by {blank}?
• What is motivating your decision to {blank}?
• Why is {blank} important to you?
• How much longer are you prepared to deal with {blank} before taking action?
• When are you planning to take action?
• By doing {blank} what do you think will change?
• If you decided to work together, what would you expect?
• If you can achieve {blank} result, what will it mean to you?
• How important is it that {blank} changes?
• What’s the consequence if nothing changes? What concerns do you have if you can’t achieve {blank}?
• What’s the impact of not {blank}?

Who Else Is Involved?
• If you don’t mind me asking, what can I do to help you move forward with {blank}
• Is there a specific decision-making process I need to be aware of in order to win your business?
• Is there anybody else we need to communicate with to move ahead?
• Has {blank} shared their thoughts on {blank}?
• How do they feel about {blank}?
• Are you and {blank} in agreement on {blank}
• Are you and {blank} on the same page with {blank}?
• In what way does {blank} look at this differently to you?
• When making a decision like this, are there any specific steps we need to take with you?
• How would you like us to present {blank} so everyone will see it’s a winning solution?
• How can we best present this solution so that everyone will see it as a win instead of a loss? Can you walk me through your decision-making process?
• How do you feel about {blank} as a solution?
• Do you anticipate any resistance to us doing {blank}?
• Does your team have a tendency to resist change, or embrace it?
• How do you currently introduce changes in your business?

Communicating Value
• How do you measure a successful relationship with your vendor/supplier/team etc.?
• Have you considered any alternatives?
• How important is price compared to service? (quality, deadline, delivery, availability, support, ease of use, customer support)
• What’s most important to you out of price, quality, service, etc? (when they say all of that, agree, and ask in which order or which is most/least important)
• How would you define the quality you’re looking for?
• What’s the impact to your business when the quality drops?
• How do your team feel about {blank}
• Can you afford to/not to take this risk?

Competition & Opportunities
• What makes you different from your competition?
• What is it that makes you successful?
• Have you noticed any trends that could support/impact your market share?
• How do measure progress?
• What do you want to be different about {blank} by the end of the year? (next year, 3 years, 5 years)
• How do you see us helping you achieve {blank}?
• What is it that you hope we can do for you?
• What do you need to change to {blank}?
• How do you plan to stay in front of your competitors?
• What can you/we do to mitigate the risk?
• What product/service strengths differentiate you from {blank}?
• Any plans to integrate new {blank}?

Impact & Implication
• How much longer are you prepared to continue like this?
• What do you think is going to happen if {blank} doesn’t change?
• What’s the one thing you could do differently right now?
• What’s the one t
• What’s impacting your sales?
• How is {blank} affecting your business right now?
• How does this problem affect sales? Profitability? Scheduling? On-time deliveries? Quality? Production?
• What do you think these problems are costing you?
• How is this problem impacting the bottom line?
• Let’s assume you decide not to address this problem immediately. What will that cost you this year?
• If you don’t fix this problem, what is the potential impact on your business? Can you afford to take that risk?
• If we could eliminate that problem you are currently experiencing—for instance, that problem that’s costing you $1 million per year — what benefit do you think that would have on your company?
• If we could implement that change, what would that enable you to do or achieve?
• How would implementing this change affect you personally?
• What would you be able to do differently?
• If those changes could get implemented, how do you think your job (or career) would look 5 years from now?

1. Select 5 – 10 questions that resonate with your business.
2. Modify them in whatever way you require so that it matches how you communicate.
3. Record yourself sharing the questions
4. Practice these questions until you are able to share them authentically and flawlessly.
5. Repeat steps 1 – 5.

Download Toolbox of Questions PDF