Questions to Ask in Each Stage of the Buying Cycle

Ask prospects these critical questions at each sales stage to position your solution as the perfect fit.


In sales, we often think our role is to give the buyer all the information about our product and let them decide whether or not to make the purchase.

However, wise salespeople understand the importance of listening to the buyer throughout the process. Without understanding their needs, pain points, and goals, how can you provide the right information to convince them that your solution is the perfect fit?

Asking the right questions and actively listening throughout the buying process allows you to customize your pitch, address objections head-on, and position your offering as the ideal solution to their problems. Let’s discuss what those right questions are.

What’s the Buying Cycle?

Questions to Ask in Each Stage of the Buying Cycle, What’s the Buying Cycle?

The buying cycle is the series of steps a potential customer goes through before making a purchase decision. When reflected in your CRM, the process can include a Meeting Set, an Initial Pitch Demo, Reaching All Decision Makers, Proposal Presentation, and so on. 

However, these stages may look different for every business. The customer has different needs, concerns, and questions at each stage. 

For example, at the meeting set stage, you'll want to provide an agenda or overview for the meeting invitation, so prospects know what to expect. At the initial pitch demo, you'll likely share marketing one-sheets, testimonials, and case studies to show how your solution shines.

To smoothly guide prospects through each stage, you should map out three crucial elements:

1. Information to Get from the Prospect 

At every stop, you want to gather specific details about the prospect's situation, goals, potential roadblocks, etc. Getting this info allows you to customize your approach just for them.

2. Content to Share 

You'll also need marketing materials, sales decks, case studies — whatever resources will be most relevant and helpful for that specific stage of educating the prospect.

3. Questions to Ask 

Most importantly, you need to know the right questions to ask the prospect, depending on where they are in the cycle. The questions will reveal their needs, priorities, and buying process.

Why Do You Need to Gather Information at Each Stage of the Buying Cycle?

Imagine you're trying to sell someone a new car but don't know if they're looking for a family vehicle, a sports car, or an eco-friendly option. Without knowing their specific needs and preferences, you're shooting in the dark.

By asking the right questions at each stage of the buying cycle, you can:

  • Understand the customer's pain points and what they're looking to achieve
  • Tailor your messaging and solutions to their specific needs
  • Address any concerns or objections they might have
  • Build trust and rapport by showing that you're listening and trying to help

It's about gathering the information you need to provide the best possible solution for that customer. And when you do that effectively, you're much more likely to close the deal.

The Buying Cycle: What to Ask at Each Stage

Questions to Ask in Each Stage of the Buying Cycle, The Buying Cycle: What to Ask at Each Stage

Buyers' needs evolve as they progress through each stage of the buying cycle. If you launch into your generic sales script without understanding where they are in that cycle, you'll likely miss the mark.

Effective salespeople know that asking intelligent, purposeful questions sheds light on the buyer's motivations. Then, you can tailor your message to resonate with the buyer’s goals and overcome any potential roadblocks.

Let's look at what to ask at each stage and why it matters:

1. Meeting Set

At this initial point, you piqued the prospect's interest enough for them to agree to an introductory meeting or call. Your primary goals are to understand if they’re a qualified opportunity and give an overview of their needs and backgrounds.

You'll want to get clarity on basics like:

  • Who should we invite to the meeting?
  • Did you agree to the meeting for information purposes, or are you interested in considering a solution like ours?

These questions help set expectations upfront. If it's just an educational chat, you know to scale back your sales pitch. If they're already considering you, you can start digging into their needs sooner.

Getting this context early helps you make the most of the initial meeting. It also avoids awkward guesswork and wasting time going down the wrong path.

2. Initial Pitch Demo

Once interest and fit have been established, the next step is the initial pitch demo. This is where you'll give your first formal walkthrough of your product/service's features, capabilities and value proposition

It's also a critical time to extract more details about their current challenges, goals, and buying process:

  • What are your goals around X?
  • What are you using today to solve that challenge/reach that goal?
  • What, if anything, would prevent you from using a platform like ours?
  • Who else do we need to bring into the conversation?
  • What is your candid feedback? Are there any objections we should know about?
  • Does this fit into your current priorities?
  • Can we take X next step?

These open-ended questions help you understand their situation holistically, including their goals, current workarounds, potential roadblocks, other stakeholders involved, and whether your solution aligns with their priorities. 

With this context, you can quickly validate whether you have a viable opportunity. You can also tailor your demo to address their biggest pain points and priorities.

It lets you put your best foot forward by positioning your offering's most relevant capabilities. The prospect's responses will shape how you craft the next steps, such as proposals, calls, and additional demos.

3. Reaching All Decision Makers

Questions to Ask in Each Stage of the Buying Cycle, Reaching All Decision Makers

You've had initial conversations and made some discovery calls, but you may need to involve other important people before closing the deal. 

Maybe it's the team who would use your product day-to-day or the person controlling the budget. Getting all the right decision-makers aligned prevents blockages later.

You’ll want to ask them the same questions you asked in the initial pitch. Aside from that, you'll also want to ask:

  • What is your buying process?
  • What can you share with us in terms of budget?
  • Do you have the budget/When is your budget cycle?

Understanding their formal buying process ensures you don't miss any crucial steps or stakeholders. Getting a sense of budgets/cycles helps you gauge how qualified the opportunity is and how to strategize the next steps. 

You don't want to put tons of effort into an opportunity with no allocated budget.

4. Proposal Presented

Once you've gathered all the requirements and stakeholders are on the same page, it's time to put together a formal proposal laying out precisely what you'd deliver and how much it would cost. Then, you'll reconvene with the prospect to present it and get their reaction while it's fresh.

When you reconvene, ask:

  • Is this offer in line with what you thought we'd submit?
  • Anything missing?
  • How can we make this a no-brainer for you?

You want to confirm the proposal meets their expectations, uncover any gaps or remaining objections, and determine what it will take for them to move forward confidently. This feedback will shape your best and final offer.

5. Assessment

After seeing your proposal, the prospect will go through their internal vetting process. This is when they'll pick your offer apart, compare it to alternatives, and identify any concerns or areas of misalignment.

This is your chance to reconfirm fit by asking:

  • Are you evaluating alternatives?
  • Are there any features you don't see yourself using?
  • Are any parts most useful?
  • What would make these even more valuable?
  • Does this solve your problem?

You can directly address any concerns about competitors or underutilized features. More importantly, you can surface the biggest areas of value that tip the scales in your favor. If there are still gaps, you may need to revisit the offering.

Continually validate that your solution is the best fit at every stage before the prospect makes their final decision. These checkpoints ensure you submit an airtight proposal that checks all their boxes.

6. Negotiation

Questions to Ask in Each Stage of the Buying Cycle, Negotiation

If the prospect has remaining objections keeping them from saying "yes" to your proposal, you'll enter the negotiation phase. 

This is the time for give-and-take discussions about pricing, timelines, and services — anything needed to get them over the finish line while preserving a fair deal for both sides.

Ask them:

  • Do we need to make revisions to our initial proposal?
  • Are you interested in adding X feature/service after testing?
  • When are you looking to make a decision?
  • Can we provide our MSA/SOW?

You'll want to understand exactly what changes should be made to close the deal. Offering additional services, proof-of-concepts, or flexible timelines can help overcome final hurdles. Discussed decision deadlines also create urgency.

7. Contract Sent

Once negotiations are complete, you'll send the final contract for signature. The paperwork must be squared away before the deal is closed.

At this point, ask:

  • When do you think we should aim to kick off to prepare for onboarding?
  • Is there anything else we should prepare for regarding your contract process or timeline?

Getting their hoped-for start date lets you resource and plan for a smooth onboarding experience. Uncovering any remaining contract process steps avoids surprises or delays.

8. Closed Won

Congratulations — you made it! Once the contract is signed, it's time to discuss:

  • Who do we need to invite for kick-off/onboarding?
  • What key metrics/expectations should we know about in the first few months?

Loop in all relevant players on both sides for kickoff meetings and training. More importantly, set clear expectations around success metrics and timelines. This gets everyone aligned before onboarding begins.

Asking the right questions in these final stages ensures any outstanding barriers are cleared and all logistics are squared before officially launching your new customer engagement on the right foot.

The Power of Asking the Right Questions

Purposeful, tailored questions let you extract critical insights into the buyer's needs, potential roadblocks, and decision criteria. 

Then, you can position your solution in the most compelling way and proactively address objections. You reinforce your role as a trusted advisor, not just another salesperson.

Buyers these days are more informed and have higher expectations than ever before. They want partners who genuinely understand their reality. Meeting that bar increases your chances of closing.

So start mapping out the right questions to ask at each stage of your sales cycle, listen intently to the answers, and evolve your strategy and messaging accordingly. 

With this buyer-focused philosophy, you'll be better equipped to navigate each opportunity productively and meaningfully.

Level Up Your Sales Process

Are you inspired to use smarter techniques to improve your sales process? Lunas has expert resources that can help you become a master of navigating the sales cycle:

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