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How to Unlock the Power of Strategic Sales Questioning for Agency Growth

Posted by Mark Duval on Feb 20, 2020 6:44:00 AM
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When it comes to new business and agency growth, questioning skills are everything. Excellent communication skills by themselves aren't enough. Knowing which questions to ask, when, and how to customize and build on them off-the-cuff requires high-level strategy and improvisation ability. It’s an art.

unlock agency growth questions

There are many lists of sales questions available online, and I’ll share some of those below, but I think what you will find is that most of them are variations on the same themes. Some are better than others. But mostly, the best sales questions have been shared across the internet many times over. You may enjoy having hundreds of sales questions at your disposal, but in reality, you will only have time for 10-15 questions—at most—during a conversation. Often, far fewer than that.

So, which handful of questions are the most important ones for you to ask your next prospect? Use the information you have to thoughtfully curate a list of questions that are the most relevant and most critical to explore at that particular moment.

In a consultative sales process, our job is to ask smart questions and listen carefully so that we can ask the right follow-up questions, qualify the opportunity, and ultimately come back with the best solution. Good sales questions can give you a head start, but the heavy lifting comes from having role-played your prospect conversations so often that you know your questions like the back of your hand.

Questioning strategy can be leveraged across the customer lifecycle for upselling opportunities, referrals, customer relationships, and win-back business, in addition to new business. If you hone this skill, you will find it to be a powerful advantage for your agency business. 

“The agencies [that have experienced exponential growth] are the ones who have embraced questioning in every interaction with clients. They excel in the early part of the sales process when first qualifying prospects, but they are also building sales playbooks for upselling and cross-selling new services.”   

— Peter Caputa, CEO of Databox and founder of Hubspot’s agency program (via Costello)

I’ve shared some of my picks for strategic sales questions below. But first, some tips.

Tips for using questioning strategy with your prospects:

  • Consider adopting a sales qualification framework.
  • Customize questions and make them client-centric.
  • Make transitions natural and conversational — it should not appear that you are reading from a list or interrogating your prospect.
  • Know how to leverage open-ended questions to get past one-word responses.
  • Ask follow-up questions until you arrive at the underlying reason(s) “why.”
  • Don’t suggest answers for your prospects — give them time to respond.
  • Read between the lines so that you don’t waste your time with opportunities you’ll never close.
  • If you have determined that there is not a good fit, end the call (respectfully).
  • Practice your sales questions repeatedly so that you are over-prepared.
  • Use personality types to tailor your conversation to the person with whom you are speaking.
  • Don’t rush to provide a solution. Continue the discovery process and take your time to develop an appropriate solution.
  • Avoid getting so caught up in your questions and your goals that you forget to be personable and make a genuine connection. Remember, people do business with people they like, know, and trust.



strategic questions for agencies

Rapport-building questions

  • Thanks for clearing some time for me today. Since we last spoke on the phone, has anything changed?
  • Do we still have 30 minutes to try to understand if we might be a good fit for each other?
  • Help me to see the world through your eyes—what can you tell me about your business to help me get a better feel for it?


Discovery questions

  • What was the impetus for you to look into this service/solution? 
  • What made you consider us? 
  • What do you know about us and our solutions/services? 
  • What are your expectations for our services/solutions? 
  • What would you like to see us accomplish? 


Kick-off questions

  • When we spoke, you mentioned that (X, Y, or Z) is an issue for you. Can you tell me how long you’ve been dealing with that?
  • We spend most of our time helping businesses like yours. Can you tell me a little bit about how you are dealing with (X, Y, or Z) at the moment?
  • What were you hoping that I could do for you?
  • If I don’t think that I can help you, would it be okay if I told you so? And will you please extend me the same courtesy if you ever feel that I’m not the right fit for your needs?
  • If I could help you solve one problem today, what would it be? 


Current provider questions

  • Why did you choose to go with your current provider in the first place? 
  • How long have you been with them? What were you doing before that?
  • What do you most like about your current provider? What don’t you like? 
  • How would you rate things with your current provider on a scale of 1-10 with one being disaster and ten being perfect? Why?
  • Is there any chance you might stay with your current provider or are you definitely moving on? 
  • What concerns do you have about switching providers and pursuing a new solution? 
  • What might cause you to change providers in the future?


Identifying the problem questions 

  • What business problem are you trying to fix with this (service/product/solution)?
  • How long has this been an issue? 
  • What is prompting you to do something about it now?
  • Have you tried to solve this problem in the past? (If so, why didn’t it work? If not, why? Was there something preventing you from trying to address it previously?)
  • How serious would you say the problem is right now, today?
  • What happens if you do nothing about the problem?
  • What do you estimate this issue has cost your business over the last (insert appropriate timeframe)? 
  • Companies similar to yours have discussed issues around (X, Y, and Z) with us. Are those issues currently affecting you and your business? 


Budget clarification questions

  • Do you have a budget allocated for this project? If not, when do you expect that you will? 
  • How much have you invested in fixing this problem to date? What are you currently spending on it? 
  • If not currently spending anything, what is it costing you to not have it resolved?
  • Who controls the budget for this kind of issue, and shouldn’t that person be involved in this process also?
  • How does the budget sign-off process work?

clarification questions

Understand timeframes and urgency

  • Have you seen an increase in (X, Y, or Z challenges) over the last few months? Help me to understand if things are getting worse, and if so, how quickly?
  • When do you need a solution in place by?
  • When, in terms of a date, would you like to start seeing the benefits of implementing a new solution?
  • If you find a provider who offers the perfect solution for your business, what is your timeframe for entering an engagement?
  • How many other providers are you speaking with about possible solutions?


Understanding objections, obstacles, and process

  • On a scale of one to five, with five being “definitely,” how likely are you to engage an agency to address this issue?  
  • How does your company evaluate new products/services before engaging a partner or vendor?
  • What steps do you need to take to make a decision and enter an engagement with your agency partner of choice? 
  • What do you imagine your three biggest internal barriers to securing approval for an engagement might be?


Understanding your prospect’s business: goals

  • What are the biggest priorities for your company this year? 
  • What needs to happen at your business in the next 12 months?
  • What’s standing in the way of you meeting your goals?


Understanding your prospect’s business: competitiveness

  • What are your business’ weaknesses? Do you believe these weaknesses are holding you back from greater success? 
  • What are your company’s strengths? What’s your competitive edge? 
  • What do you consider your most important product or service? 


Understanding your prospect’s business: clients

  • What challenges are your customers trying to solve when they purchase your products/services/solutions? 
  • Can you walk me through how the buyer personas for your products/services/solutions differ in terms of their needs? 
  • What is your customer lifetime value? (See how to calculate it here).
  • What are the factors that stop your customers from using your products or services?


Solution impact questions

  • How much would you guess this problem has cost your business in terms of money, profit, time, resources, energy, people, meetings, remedial action, consultants, and so on over the last year?
  • How critical is it to fix this thing? And how would you rate its importance?
  • What does solving this problem mean to you personally? What do you stand to gain if the issue is solved? What do you stand to lose if it goes unresolved?
  • What does your business stand to gain if this problem is resolved? How does its resolution (or lack thereof) impact your business a year from now? Three years from now?


Defining success questions

  • What does a successful partnership look like for you? 
  • What does success look like to you, both in terms of qualitative and quantitative results? How is that measured?

questions to dig deeper

“Dig deeper” follow-up questions

  • What do other people (in the department/company) say about (X, Y, or Z)?
  • What surprises or upsets you most about this issue?
  • You mentioned frustration around (X). Can you elaborate? 
  • Can you tell me more about (X, Y, or Z)? 
  • Can you give me an example of (X, Y, or Z)?
  • How did that affect you — personally, as a team, and as a business? 
  • Can you help me understand that a little better? 
  • What was the consequence or outcome of (X, Y, or Z)?


“Pulse check” questions

  • Let me summarize what I think I’ve heard so far, and you can tell me if I’m on the right page. Does that sound fair?
  • Do you have any concerns about what I’ve shared so far? 
  • What do you think about (X, Y, or Z) so far? 


Wind-down questions

  • Of all the things we have discussed so far, what am I missing? What have we left out?
  • Do you have any questions that we didn’t touch on yet?
  • Based on what you’ve seen so far, do you think our offering could be a viable solution for your problem?


Next steps

Never conclude a prospect meeting without securing agreement on the next steps. Get a date on the calendar before you part ways. If the prospect is unwilling to agree to a next step, it’s an indication that they aren’t interested in moving forward.

Here are some examples of questions you might use to pin down your next steps:

  • Do you agree that the next step is (X) by (a specific date)? When would be a good time on or around that date to schedule a call or meeting?
  • What’s your preferred mode of communication as we move through this process?
  • What are the best days and times to follow up with you regarding next steps? 


Parting thoughts

Setting aside time for sales questioning skills development is a low-hanging fruit item that you can easily do to support your agency growth and new business outcomes. By casually and strategically sprinkling questions into every point of communication, you can improve prospect qualification, use resources more efficiently, close more new business, strengthen client relationships, and generate follow-on opportunities.

How would you rate yourself, your leadership team, your new business professionals, and your account executives on this right now? Do you already devote time to role-playing prospect scenarios on a regular basis? If not, what’s stopping you?

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Image credits: unlock agency growth questions ©Adobe Stock / Ирина Шатилова; strategic questions for agencies ©Adobe Stock / tostphoto; clarification questions © Adobe Stock / vasekrak; questions to dig deeper © Adobe Stock / Ozgur Coskun

Topics: Agency Sales Tips

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