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Finding the Buyer’s “Pain”

What are Pain Points?

Pain points are unmet needs waiting to be satisfied. The persistent problems inconvenience prospects (or many people in the prospect organization). Or, they want and conditions – or possibilities – the option is trying to achieve but don’t know precisely how.

Any prospect or customer can have pain points.

These pain points represent two areas of emphasis either:

  1. problems to solve, or
  2. possibilities to make a reality.

“Pain” is the first thing top salespeople look for in their prospects because pain often starts with opportunities on a buying journey. In addition, pain (making possibilities a reality or solving problems) are the driving force for navigating a customer’s problem-solving process.

If you can’t identify a pain point the prospect is willing to pursue, you won’t have a sale. When that happens, remember the possibility isn’t clear enough or the problem isn’t worth solving.

Pain Point Examples

A typical pain point could be something like:

  • A customer wants a solution that costs more than what’s budgeted: Financial limitations stop prospects from working efficiently and lead them to search for more cost-effective alternatives.
  • A team with too many redundant steps in its execution approach can slow down the company’s ability to scale: Too much process lead time costs money and reveals a need to reduce it.
  • The prospect sees the vision and the desired end state but has no idea how to get started.
  • Communication is unclear between leaders and departments: Teams struggle to find a way to communicate more quickly while receiving the correct information to reduce errors in the process.
  • These are all situations that cause “pain” or stifle productivity. The first step in addressing these pains is identifying and eliminating them, so let’s discuss how to do it for your customers.

People-Oriented Pain Points

  • Whether it’s a complaint about customer service, dissatisfaction with a product or service, or an idea for an innovation that has yet to be uncovered — your customer can fill you in if you ask the right questions. There are many different ways to identify and treat customer pain points; the best way to do it is to hear what they have to say.
  • Remember, prospects are your bread and butter. They’re a priority whether they purchase a subscription or a service to help their people run their IT operations better.

Organization-Oriented Pain Points

  • Organizational pain points are problems that need to be solved in an organization. In many cases, corporate pain points create barriers to performance. These are often environmental factors that people believe they have no control over (which usually is not the case).
  • Organizational pain points can keep the company from functioning and are often considered “root cause” problems.
  • The challenge with organizational pain points is that people in lower altitude levels believe they should “only focus on what they can control” or “focus on what is in scope.” As a result, you often need to work with leaders and executives to overcome organizational-oriented pain points.
  • If your prospects say they’re experiencing employee dissatisfaction and retention issues impacting their productivity and hiring, customer churn moving their revenue, or a severe lack of leads that make it impossible to hit their revenue goals, you’ve hit on business pain points.

Pain: Problem or Possibility? Let Your Prospects Decide

It’s human nature to approach a challenge with varying excitement or anxiety — depending on how you look at it—the same with your prospects.

Think about it. Do you view it as a problem or a possibility when facing a massive change, such as moving from farming to hunting or moving from inbound to outbound? If someone were to help you, would you want them to talk about tackling all the problems? Or would you want them to help you shape a vision for what’s possible?

Like all humans, your mindset dictates your willingness to take action — and your preferred approach.

  1. So, what’s the “pain” you experience? Do you want to move towards it? Or do you want to get away from it?
  2. Is that pain related to a problem (move away from it), or is it related to pursuing a possibility (move toward it)?

What is the problem?

  • A thing that is difficult to achieve or accomplish
  • For example: “getting developer and architecture teams on the same page is a problem.”
  • A problem is a cause for anxiety. It’s a source of angst and a source of discomfort.
  • Champions can get fed up with problems and drive problem-solving internally.
  • People who focus on problems seek to move away from them. They want them resolved.
  • The challenge: Getting everyone to agree on the problem and see the problem, so they take unified action
  • That’s why salespeople are valuable. They help unify action toward solving problems.

What is a possibility?

  • A possibility is a thing that may be chosen or done out of several possible alternatives.
  • For example: “one possibility is to allow all people to participate.”
  • A possibility is exciting. It’s forward-leaning. It’s about creating the future.
  • Champions can have a vision and drive possibilities internally.
  • People who focus on possibilities move toward them.
  • The challenge: Getting everyone to agree on what’s possible and see the possibility so they take unified action.
  • That’s why salespeople are valuable. They help unify action toward possibilities.

Ask questions to understand the “pain.” For example, are people moving toward or away? Explore that with them.

Messaging to Pain Points

In times of change, people may “feel” something isn’t quite right and want to do something different, but they may not have the words to explain it. Believe it or not, times are so turbulent that intelligent people may not have the same language for a pain (problem or possibility) and may not have words at all!

For example, what company doesn’t need to acquire more or better business? However, why is it so hard to get everyone to agree on a course of action? Why is it challenging to clarify the end goal and unify the movement to pursue it? Leaders may understand — or think they know — what’s holding the team back, but other leaders may disagree. Team members may believe leaders are over-stretching, and team leaders may believe their people lack skills. Yet, they disagree on how to proceed because they can’t get “on the same page.” Or, they “miss each other in translation.”

Here are some examples of what you might hear from prospects who have messaging pains:

  • “No one knows what our company sell
  • “We see what is happening but can’t help others to see it as well.”
  • “Our Leaders don’t have a strategy for driving action.”
  • “We think there are conflicting priorities, but when we talk to leaders, they say it’s all related to the strategy.”
  • “The vision of the executive team isn’t translating into execution.”
  • “The messaging used by the board of directors doesn’t represent how people talk internally.”
  • “The IT team sets a course, only to find out that the business is going in a different direction.”
  • “Our competitors are outspending and outmaneuvering
  • “The market is changing, and we aren’t keeping up.
  • “Until now, we haven’t considered a more sales-driven approach, and now we’re struggling to figure it out.
  • “Our competitor has more green space than we do in our market.

Because change initiatives are often closely aligned with driving revenue or cutting costs, successfully identifying a message (problem or possibility)while recommending a path forward or a solution is a great way to communicate value in prospect conversations.

Financial Pain Points

Investments and resourcing are often big topics across the leadership team. A lack of resources causes many business pains (problems or possibilities). Many pains can be solved by having suitable investments aligned with the right priorities. Every organization benefits from improving its financial standing. That financial standing is the definition of “growth” from the investor’s perspective.

Here are some examples of critical financial pain points that require solutions:

  • “Our strategy doesn’t have enough action to back it up.”
  • “We don’t have the resources we need to delivery on the promises we are making.”
  • “We’re not selling enough to keep the lights on.”
  • “I’m not sure we’re investing for the future.”
  • “We seem to have more investment in engineering than in sales teams.”
  • “Revenue is up, but profitability is continuing to decrease
  • “We don’t have enough visibility to know if we’re making good financial decisions.”
  • “We may be overpaying for equipment and tools, but we don’t know what to cut.”
  • “We have cloud trials, but they don’t convert into annual subscriptions
  • Your offerings might help businesses that want to reduce spending or manage cash flow.

People Pain Points

People are at the heart of every digital business. They create intellectual property and innovate new ideas to advance the organization. People often constitute a tremendous expense in an organization and the most significant asset. Together, they can achieve incredible things. Divided, they can drag down productivity and morale.

If there are people problems such as the following, it can cause problems in other areas of the business:

  • “We can’t keep our best people.”
  • “I need team A and team B to get along.”
  • “We can’t find enough high-quality talent.”
  • “We struggle to get everyone working together to achieve shared goals.”
  • “We seem to focus more on what individuals need than on what’s best for the company.”
  • “Employee morale is low.”
  • “We have a lot of unplanned turnovers.”
  • “We lose our best people to higher-paying positions elsewhere.”
  • “Our lack of diversity, and thinking, leads to a lack of innovation.
  • “We can’t trust our middle managers to train and motivate.
  • “Our actual company culture doesn’t align with what we say in our corporate values.

Process Pain Points

In many fast-growing companies, operational problems create barriers to execution. Your prospects know implementing repeatable processes is the best way to succeed. The question is, “how?”

They may be facing hurdles such as:

  • “Our hiring process is unwieldy, and we struggle with finding highly qualified candidates.”
  • “Our SCRUM and AGILE processes don’t scale to other groups.”
  • “We don’t have a way to prioritize what we’re doing, when we’re doing it, or why we’re doing it.”
  • “When we have an issue between teams, the escalation paths aren’t clear.
  • “Customer churn is high because our service department is inundated and can’t keep up.”
  • “We have no system in place to qualify leads.”
  • “There are inconsistencies in each employee’s workflow, which leads to disorganization and varying performance.”
  • “The current software we operate in is outdated, but we fear transitioning to a new one will be hard.”

As you unearth process pain points, ask your prospect to envision a smooth-running company, department, or process and what kind of difference it would make to their business. This will help you understand if they’re moving towards what’s possible or away from problems.

Productivity Pain Points

A team leader’s job is to remove team members’ roadblocks so things get done as efficiently and effectively as possible. That said, it’s easy for leaders to get pulled down into the weeds of the business and become reactive to requests or spin their wheels wasting significant time.

Here are some examples of productivity pain points in business:

  • “We keep re-working the same things over and over again.”
  • “We keep dropping data on the floor and have gaps in our reporting.”
  • “We can’t seem to get people on the same page when it comes to taking action.”
  • “We can’t answer questions from business unit leaders or executives.”
  • “Our priorities don’t line up across the organization.”
  • “We keep missing client deadlines.”
  • “It’s too hard to migrate data across clouds.”
  • “We spend way too much time in meetings.”
  • “Our administrative workload is out of hand.”
  • “We can’t coordinate all the people we need in a complex solution sale.”
  • “We can’t seem to implement our solutions as effectively as we would like.”
  • “Quality issues with our product has led to costly recalls and/or customer churn.”
  • “Our employees aren’t supported enough to complete their assigned tasks.”

If something prohibits a company and its employees from working efficiently and effectively, you can position our capabilities solution that saves time, decreases costs, or decreases angst.

Cross-Functional Pain Points (Friction)

Pain points left unsolved can potentially work altogether. It would be best if you asked questions that address the many tasks a team has to complete with the help of others. These are pain points that “no one” owns outright, and no “one group” can take direct control over. These are probably the most common pain points in most organizations, and where your role as a seller can help them by getting everyone “see” the same problem or possibility.

Cross-functional pain points can be across the board, such as:

  • “Onboarding new people is disjointed and inconsistent.”
  • “Marketing and sales leads don’t result in closed deals.”
  • “Internal teams don’t use the applications we build as we expected.”
  • “Internal IT teams don’t have the same definition of security.”
  • “We can’t seem to prioritize all the work we need to do in a month or quarter.”
  • “Orders consistently ship late, and our team is stressed trying to keep up.”
  • “Sourcing talent best fit for the business hasn’t been easy.”
  • Reporting across all of our business units and systems is tedious.”
  • “In my department, managing a team towards the same goal is intimidating because I already wear many hats.”
  • “Keeping up with operational needs as teh company grows becomes more complicated as time progresses.”

Many of these issues can be addressed with a product or service offering grounded in current technology and consulting. In addition, small businesses could benefit from workflow automation and proper guidance from experienced professionals.

Four Tips for Exploring Pain

Once you identify pain (problem or possibility), you can determine how to solve it with your prospect. That’s right, solve it “with” your potential, not solve it “for” them. You can rarely make the possibility a reality with their help. Likewise, solving root-cause problems requires a lot of people to bring their skills and expertise to the party.

Think about doing “with” them, not “to” them. This incredible approach helps you become a trusted advisor rather than a product-pusher

Here are four tips to start exploring possibilities and problems in this way:

1. Use your prospect’s language when talking about issues or possibilities

  • This psychological technique can go a long way in building trust with your option. Instead of trying to appear impressive by relying on jargon only your colleagues would understand, show your chance you take them seriously using their language and terminology.

2. Find out who’s empowered to solve the problem or make the possibility a reality.

  • Find the economic buyer as quickly as possible. Ask your prospect whose budget a purchase would come out of and what teams need to be involved in a buying decision. There’s little point in spending hours with someone who can’t ink a deal.

3. Identify additional vital stakeholders as early as possible.

  • If you’re selling to multiple teams and one team has completely different priorities than another, you need to know before. If you have to go through a two-month legal review process before you can close a deal, you need to know early.
  • Prospects are sometimes worried they’ll appear less authoritative if they tell you they’re not the sole decision-maker, so I like to use the following questions to avoid that impression:
    1. Who besides yourself needs to be involved in this decision?
    2. Who else would want to know that we had this conversation?

4. Frame your capabilities and solutions to reflect the prospect’s dilemma

  • As you build trust with the opportunity and listen to different perspectives, you must personalize your solution to their specific needs. If your key serves multiple purposes, tell them which features speak to their use case
  • Listen and affirm your prospect’s pain points while asking for information; making your pitch meet everybody’s requirements will be easier.
  • Remember, sales is all about empathy. Taking the time to explore possibilities and problems helps you land our value proposition. Make sure y you take this approach with every stakeholder you encounter.

Do All Pains Have a Budget?

Sometimes people need help. And sometimes that help doesn’t have funding. That’s more common than you realize. When you’re talking about making a possibility a reality or solving complex, root-cause problems, you’re also talking about what you need to establish a business case for action. The more solid and precise the business case, the easier it is for your prospect to get the funding they need.

In some instances, have a budget. That budget came from a desire to have-to-get-it-solved. Or maybe even the pain was discussed at the board level. When that’s the case, you’re probably up against two or three competitors.


  1. Do not only focus on the “sales process” – that’s too focused on you.
  2. Do not only focus on the “buying process” – that assumes prospects know what they’re buying and that they already have a budget.
  3. Instead, focus on the customer’s “problem-solving process” to help them uncover latent pains. Help them give an identity to root cause problems so they become champions willing to sell for you when you’re not there.
Updated on June 27, 2023

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