3 Common Pipeline & Performance Management Problems (& How to Fix Them)

May 18, 2023

Did you know that companies with a defined sales process won 53% of their forecasted deals compared to only 43% of their peers with ‘ad hoc’ processes, according CSO Insights. That’s 23% more output with a defined sales process.


As Executive Sales Leaders, it’s up to us to define a common sales process and language that is shared across the organization. However, despite our best efforts, pipeline problems and performance challenges can still pop up.


These challenges often come from getting caught up in managing the pipeline from the back-end vs. managing from the front-end. As a result, sales teams experience ups and downs. Good month. Bad month. Good quarter. Bad quarter. And so on.


If this sounds familiar, here’s a quick challenge for you to try today: Pull up the pipeline for one person in your sales organization and think about these questions:


  • What is the criteria for each sales stage that you see? Is there a common language across all departments/areas as to what a 50% opportunity looks like?
  • Do all opportunities need to have a confirmed next appointment with the prospect to stay active?
  • How many first appointments are scheduled for the next two weeks for this person?


These questions apply no matter how you’re managing your pipeline, whether that’s a robust CRM you’ve used for years, are just rolling out a CRM for the first time, or you’re using some form of home-grown system.


Now, let’s look at three common problems we’ve heard a variety of companies say are most troubling and tips for what you can do to fix them: 


#1. Lack of a common language and criteria for each stage of the pipeline.


If you had a probability to close stage of 50%, would every person on your sales and leadership team define a “50%” probability the same way? Even across business units there can truly be a common language for what your team considers the halfway point to getting to yes. 


Without a common language and shared criteria for each stage, Sales Leaders and the Sales Team get tricked into thinking we are further along in the sales process than we really are. If we do guess wrong, it can negatively impact a busy Sales Leader’s ability to make timely decisions and forecast with accuracy. 


One way to fix this: Clarify the criteria for each sales stage and what it takes to move from stage 1 to 2, stage 2 to 3, and so on. Create a simple cheat sheet with the definitions of each stage and share it with your team.


#2. Inflated pipelines and “hopium” are a result of counting opportunities as active that should not be active.


When we assume we have more opportunities than we do or that we’re further along in the sales process than we really are, it results in a lack of urgency to prospect, a decline in overall activity, and missed steps within the sales process. 


For Sales Professionals, it’s important to be optimistic; however, hope can cloud reality. The result of hopium is overestimating pipeline values, over-forecasting and unintentionally allowing time to kill deals. 


One way to fix this: For every opportunity in the pipeline, ask your rep: when are you meeting again? This simple question can help determine whether an opportunity should be active or not active. (We like to call this type of opportunity “parked”). Opportunities that are not tied to mutually agreed appointments can’t be counted on for income and forecasts.


Note: For Salesforce users out there, a task is a “to do'' and not a mutually agreed upon appointment. “Events Scheduled” will be tied more closely to appointments depending on the definitions for events in your company.


#3. Sales Managers leading ineffective 1 on 1’s and team meetings.


When done right, 1 on 1s and team meetings make your team stronger and help you build better relationships. However, the challenge Sales Managers have to overcome is establishing a regular cadence and running meetings that deliver better outcomes.


There is tremendous value in having a regular cadence of scheduled 1 on 1s. This is even if you talk all the time or can easily walk into their office or call to ask a question.


Having regular 1 on 1s communicate, by evidence of your time, that the person on your team is important to you. Relationships, whether personal or professional, take intentionality.


The same is true for team pipeline meetings. Managers must be intentional by having a framework for a clearly defined pipeline meeting. This means leading the conversation with key questions and building accountability by following up on what was covered during the meeting. 


What challenge or actions did you give your team last time and how did you follow up on that?


One way to fix this: Always include agenda items in the body of the invite. This will give your team members an idea of what you want to talk about, the questions you’ll ask, and will serve as a reminder for you about what you promised to follow up on.


Bring a Common Language & Criteria to Your Team’s Pipeline


Now, you may be thinking about some people on your team who are process adverse but are brilliant conversationalists and natural at selling. Or, vice versa.


Process will out-sell just personality every time. It’s process plus a dynamic personality that will kill it in the field and on the phones time after time.


Strike the right balance between process and art form (personality) to keep your Dealership on track for growth now and in the future.


If you’re not sure how or where to start, one of our core strengths is helping Sales Leaders and Sales Teams create criteria so everyone shares the same pipeline view. Let us know if we can help and good selling out there! 

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.