Your Checklist for Pipeline Momentum & Game-Changing Results

April 15, 2025

Imagine a pilot preparing for takeoff. They don’t just hope the plane has enough fuel or assume the weather will cooperate or all the gears and instruments are fine. Instead, they follow a checklist—a precise, deliberate process that ensures a successful flight.


Similarly, just as a pilot’s checklist guides them through critical pre-flight preparations, you need your own checklist to navigate the sales process effectively. Whether you’re selling supplies with a monthly or weekly reorder pattern or you have a longer sales process, intentional conversations and smart questions ensure your opportunities move toward closure with fewer surprises. 


This excerpt, from our upcoming book Pipeline Momentum for Game-Changing Results by Marisa Pensa and Stacia Skinner, highlights the importance of building and using a “questions bank” to uncover critical information. Let’s dive into how you can use this tool to evaluate the Four R’s: Right Person, Right Value, Right Timing, and Right Pricing.


Why Questions Matter


We all need a bank of qualifying questions to ensure we have the necessary information to advance the sale. For example, consider the “Right Person.” While no one intentionally sets a meeting with someone who can’t make a decision, today’s sales environment can involve multiple decision-makers - especially when expanding beyond general supplies. If you bluntly ask, “Are you the decision maker?” the answer is unlikely to be revealing. Instead, you need to approach with more nuanced questions that get to the heart of decision-making dynamics.


Let’s explore some examples for each of the Four R’s. These questions serve as your pre-flight checklist to avoid shortcuts that can derail your progress later. They’ll help you stay on course and provide clarity when things start to stall.


Questions Bank for the Four R’s


Right Person

Questions for Self-Assessment: 

  • Who am I talking to, and why that person? 
  • In addition to this contact, who else will be involved in the decision-making process?
  • Have I invited the people with the right responsibilities into the conversation (e.g., technical leads, financial approvers, operational stakeholders)?


Questions for Your Contact: 

  • In addition to yourself, who else typically likes to have their input considered? Should we include anyone else in our next call or meeting? 


Right Value

Questions for Self-Assessment: 

  • Who will be better at their job because of how we approach deliveries, service, etc? 
  • Will my solution enable the customer to control costs, elevate employee morale (For example coffee brewers!), impact office culture, or put time back into their day? 
  • Can I confidently detail the impact I will bring to the customer’s business?


Question for Your Contact: 

  • Based on our discussion, what do you think would benefit you most—finding ways to save time in your day or eliminating the hassle of __________?


Right Timing

Questions for Self-Assessment: 

  • What factors suggest this customer has a genuine, significant need that can be addressed with our Dealership? 
  • Do I know when they placed their last order and their typical order cycle?
  • When they place their next order, will it be from us?
  • Do you have a commitment that they will in fact order with you next time they order? 


Questions for Your Contact: 

  • When was your last order? (whether supplies, coffee, cleaning supplies, etc)
  • How often do you typically order those products? 
  • Can you see yourself placing your next order with me or on our website?  


Right Pricing

Questions for Self-Assessment: 

  • For new investments like a coffee brewer, furniture, or technology, has the customer allocated the necessary funds, and do I clearly understand their funding process?
  • Do I understand the customer’s budget constraints and how this purchase fits into their financial priorities?
  • Have I addressed potential objections related to price and justified the ROI of this investment?


Question for Your Contact:

  • If we’re in the ballpark of what you’re currently paying and can provide even better service, would you place your next order with us?


Similar to a pilot’s pre-flight checklist, these questions guide you through the complexities of the sales process, helping you avoid costly missteps and maintain momentum. If you’re unsure about any aspect of the sale, revisit this list, identify the gaps, and ask yourself what question will bring the clarity you need.


Remember, every flight needs a checklist, and every sale deserves one too. By consistently focusing on the 4R’s—identifying the right person, delivering the right value, aligning with the right timing, and ensuring the right pricing—you’ll navigate your sales journey with precision and purpose. With these qualifying questions in your toolkit, you’ll be well-equipped to land the right results every time.

August 12, 2026
AI has changed how sales professionals prepare. In minutes, industry specific AI tools can help you research a company, understand an industry, organize your thoughts, and generate questions for an upcoming meeting including targeted categories. That is a real advantage. But it can also create a dangerous feeling: I already know this customer. You read the website. You scan recent news. You review a few LinkedIn profiles. You uncover lease renewal or contract renewal dates. And then, AI gives you a polished summary of the company’s likely priorities and challenges. The problem? “Likely” can quickly start to feel like “true.” AI should prepare you for discovery. It should never do the discovering for you. Here are five ways to use AI without losing the curiosity that makes great selling work. 1. Use AI to Prepare AI is excellent at helping you get ready. Use it to research companies and industries, brainstorm questions, organize your thoughts, identify possible decision-makers, and spot blind spots. Used well, AI saves time and helps you enter the conversation more informed. Try this prompt: “I’m preparing for a first meeting with [company name]. Using publicly available information, give me a brief overview of the business, three possible priorities or challenges, and three thoughtful discovery questions.” But preparation is only the starting point. The goal is not to prove how much you know. It is to learn what you do not know.  2. Watch Where AI Can Fool You AI can make assumptions sound like facts. It can also be incomplete, outdated, or simply wrong. Even accurate information can lead to the wrong conclusion. A company may be expanding, but growth may not be the customer’s biggest concern. The real issue could be staffing, service, cost control, or the time lost managing too many vendors. The danger is not using AI. The danger is believing you have learned everything before meeting the customer. Preparation should increase your curiosity, not replace it. 3. Remember: Curiosity Cannot Be Automated AI can tell you what a company does, what happened recently, and what trends may affect its industry. Only a real conversation can uncover why the customer is considering a change now, what is frustrating them, what success looks like, and what they are worried could go wrong. Use your research to open the conversation, not control it. 4. Ask the Questions AI Cannot Answer AI can suggest questions. The art of selling is knowing what to ask next. Try: “How did you decide on ….?” “Had we not called, what were you already planning to do about ______?” “What have you already tried?” “If you were sitting in a review six months from now, having personally made a significant impact on the business, what would success look like for you?” “What happens if nothing changes?” These questions move the conversation beyond surface-level pain. They also help you avoid pouncing too quickly. Whether the customer mentions delivery, cost, service, or vendor consolidation, slow down. The first answer is rarely the full answer. Ask one more question before offering one more solution. 5. Do Not Outsource Your Curiosity Everyone has access to similar AI tools. Not everyone listens well. Not everyone notices hesitation, follows an unexpected comment, or stays with an issue long enough to uncover what really matters. That is still your competitive advantage. Use AI to prepare, broaden your thinking, and identify what you may be missing. Then put it away and be fully present. Before your next customer conversation, challenge yourself to do three things: Prepare with AI. Verify with the customer. Ask one more question before offering a solution. Do not simply work through a list of AI-generated questions. Listen to the answer and follow where it leads. The question you did not plan to ask may be the one that uncovers the real opportunity. The more powerful AI becomes, the more valuable human curiosity becomes. AI can help you enter the conversation more informed. Your next move is to stay curious long enough to leave the conversation with a better understanding.
Sell like a Chameleon
May 24, 2026
Here’s a simple guide to recognizing four common customer speeds and how to adjust your approach.