Prospecting in Sales Requires Relationship Building. Does Your Team Know How?

Prospecting in Sales Requires Relationship Building. Does Your Team Know How?

Managing a sales team has its own unique set of challenges when it comes to selling and building customer relationships — especially when prospecting over the phone. Even the most well-meaning sales reps might be unsuccessful when encountering certain obstacles in the prospecting process. 

So, how do you handle the challenges that arise when prospecting in sales? 

The goal of this guide is to help you respond to areas that are inhibiting the performance of your sales organization and identify seven common barriers that stand in the way. In addition, we will also cover the approach, methods, and tools that will help you successfully overcome these barriers. 

Barrier #1: Establishing Relationships During the Prospecting Process

Relationships determine influence. This principle remains true regardless of your selling environment, but developing a relationship over the phone instead of face-to-face requires an advanced skill set. 

There is a barrier that exists when prospecting over the phone. Decision makers do not feel as vulnerable, as if they were anonymous and not accountable for their actions. They will return emails, work on other documents, and flat out be rude when talking over the phone. This almost never occurs when a rep is in a decision maker’s office! 

The distance barrier that exists over the phone is similar to the one that exists while you are driving a car. If you were standing in line with a stranger, you wouldn’t try to cut in front of them or get right behind them so they will move faster. But in a car, because other drivers don’t really know who you are, you may feel you have the freedom to behave completely differently.

Prospecting Tips: How to Overcome the Distance Barrier

Since the distance barrier exists, successful sales reps have mastered the ability to create the same intimacy over the phone as would exist face-to-face. They understand that the decision maker has criteria they use to quickly determine, sometimes in the first 10 seconds, whether they are willing to engage, reveal needs, and embrace the rep’s recommendation.

Research shows that to effectively build a relationship over the phone, reps must learn to establish this foundation of trust, credibility, and rapport (TCR). The ability to establish trust, credibility, and rapport over the phone requires a unique skill set that can be applied to the prospecting process.

To assess your team’s ability to establish relationships with their customers based on a foundation of TCR, ask the following questions:

  • Does your team understand how to approach the decision maker as a peer by gaining insight into their role, business objectives, and decision drivers? (If your reps are generically calling to discuss product or services or touching base, they aren’t leveraging their true ability to connect as peers.)

Barrier #2: Gaining access to a decision maker or key influencer.

Face-to-face selling usually begins with a meeting with a decision maker or key influencer. Over the phone, you are required to navigate the multiple screens the organization has set up to keep you from accessing the decision makers. From the receptionist to the decision maker’s personal assistant, gaining access is not easy and to be successful you must find your way in. 

Assess Your Own Organization 

Depending on what you sell, you may face different types of accessibility issues when it comes to speaking with decision makers. 

To assess your team’s ability to gain access, ask yourself:

  • Do your reps fully exploit the opportunity to speak with the receptionist to gain insight on key players?
  • Do your reps leave multiple voicemails or send several emails without response when prospecting new customers?
  • When working with the evaluator, are your reps prohibited from reaching out to the higher-level influencers?
  • Do your reps often work with the buyer or evaluator at the last stages of the customer’s buying process instead of consulting with the decision maker early in the planning process?  

When prospecting new customers, successful sales reps actually don’t see the screen as a barrier, but as an incredible resource. They value the fact that there is someone who is consistently available to set up meetings with a person who is very difficult to reach, as well as someone who can provide helpful information.

Learn more about stacking your prospecting pipeline here >> 

Navigating the Barriers: Receptionists, Personal Assistants, and Voicemail 

To ensure your reps are equipped to gain access, here are some sales prospecting techniques and key ways to help them successfully navigate the barriers and get higher within the organization.


It’s amazing how often reps will bypass the one person in the organization who is paid to talk to everyone and has a list of the names of all the key players, their titles, direct numbers, and email addresses. 

The receptionist can play a critical role in helping you determine your customer’s organizational structure, as well as providing you with information that can help you connect with all the players.

Here’s how to prospect and work with receptionists to be a high-performing sales rep:

  • If you have a name, ask the receptionist for their title. If the title seems unqualified, ask for their boss, and then their boss, until you have determined the organizational structure (i.e., Data Manager reports to the Director of IT who reports to the VP of Operations, who reports to the CIO). It may take several calls, but it’s much better than getting stuck at a lower level or calling the wrong contact for weeks.
  • To determine email or direct phone number, offer your best guess and have the receptionist correct you (i.e., “I have John Williams as; is that correct?”)
  • Always assume that any name given to you by the receptionist is wrong. In our experience, we have never met a decision maker who tells the receptionist to give their name out when sales reps call. Receptionists are given a predetermined name to route all sales calls. Don’t fall into that trap. Again, ask polite but direct questions about the person’s title. If unqualified, ask for the head of the relevant department (“I’m not sure that is the right person. Can you tell me who is over your IT department?”). Again, assume that it will be the wrong contact. Just keep asking who they report to until you have all the players.
  • If the receptionist is unable or unwilling to help, look for a coach, someone in the organization who has an understanding of the key players or organization with whom you are trying to connect, but will not assume the role of decision maker. Instead, try sales prospecting techniques like picking a role that will not draw suspicion of the receptionist, such as a customer service or sales rep. 

Personal Assistants, Screens, and Gatekeepers

Most reps view the toughest barrier to reaching the decision maker is the personal assistant or screen. Why? Their primary job is to manage the calendar and act as a filter to determine who gets access. But the best sales prospecting methods involve tapping into these people as an important resource.

Here are some keys to working with a personal assistant or screen:

  • To build a relationship with the screen, help them do their job. Work with them to determine if you can provide a relevant solution. By doing this, you will build a positive relationship with them and improve your chances of getting them to sponsor a meeting, and perhaps even provide you with valuable information along the way to appropriately position your solution.
  • Treat the screen as the decision maker. Communicate that you would like to ask them questions about their company to determine if your solution is a fit. Once you go through the preliminary discovery meeting with the screen, you can then provide relevant benefits of your solution, which could improve the odds that the screen will sponsor or set up a meeting with the decision maker. 


Once you have the right phone number, you may still need to leave a voicemail. Often, most reps say they don’t leave voicemails when prospecting new customers. But the successful ones do — and here’s why. 

On average, someone will call you back four percent of the time. More importantly, if you leave a good voicemail, you are establishing a positive relationship with the decision maker. In doing so, they will be much more likely to respond positively when they answer the phone or respond to an email from you.

Here are a few tips for leaving an effective voicemail message that will sometimes get returned while also warming up the decision maker: 

  • When approaching strategic decision makers, do the necessary research to ensure that you gain insight on their specific objectives before leaving a voicemail. The more specifically you address their problem the more likely the call will be returned. A rep from a high-tech firm gained access to the CEO of a $2.5 billion company by communicating that he was calling about a specific problem they had with system integration. He got a returned phone call and a $3 million deal.
  • Make the most of the brief time you have to gain the decision maker’s attention.
  • Communicate the problems you address instead of focusing on what your product or solution does. 
  • Provide relevant examples/success stories that will create interest and establish credibility (i.e., “We have been very successful working with companies like yours — XYZ, ABC, and 123 – to address the challenges of _________.”). People are focused on their challenges, goals, and barriers to success. If you address those, I promise they will listen. Maybe they won’t call you back, but chances are they will be immediately receptive if you finally connect live.

Learn more about sales prospecting by listening to our podcast, sALES with ASLAN®, here.

Barrier #3: Engaging the actual decision maker

The first 15 to 30 seconds of the prospecting phone call — also known as engaging — is where most “B” and “C” grade reps fail. Even seasoned sales pros are uncomfortable making that introductory call to a new decision maker. Why? Because the key to being successful in the first fifteen seconds of the call is counter-intuitive to what most reps naturally want to do or have been taught. 

To be successful at initiating new relationships, reps first need to understand the psychology of selling over the phone. Since 1996, we have been studying customer’s buying habits when being approached via the phone. Our research has shown that when called by a sales rep, decision makers are unreceptive or emotionally closed 80 percent of the time. 

Understanding the emotional state of the customer is essential to engaging the decision maker when prospecting. Why? Because when people are emotionally closed, and you try to persuade them with logical arguments (i.e., Here’s why my product or service is right for you), they become even more closed.

Decision makers reject sales calls, not solutions. 

The decision makers you deal with are not rejecting a product, service, or solution. They are rejecting a sales call. Therefore, you need to change your approach from selling to creating an environment where you reduce the customer’s anxiety and ensure the customer is open and receptive. 

Here are three simple steps to tripling your success rate in initiating relationships with decision makers when prospecting: 

1. Don’t sell 

Nearly 80 percent of decision makers are emotionally closed because they, like us, have experienced pushy, confrontational sales reps. Therefore, the key to connecting with them is to act the opposite. 

So instead of pulling the rope and trying to force the decision maker in your direction, Drop the Rope®. Communicate that you are not sure if what you offer is a fit, ask permission, complement their current supplier, and speak in a relaxed, non-threatening tone. All these behaviors communicate that you have Dropped the Rope, and the customer has the freedom to choose.

2. Ask to learn more about them. 

Secondly, high-performing sales reps focus on getting agreement to the most natural next step a prospect can make: a discovery meeting. 

Many reps make the mistake of asking the decision maker if there is a need at this early stage. Instead, Drop the Rope by asking for an opportunity to learn about their key objectives, and then they can decide if it makes sense to move to the next step.

3. Do your homework and let them know.

When asking for the opportunity to discuss and learn about the decision maker you are prospecting, it’s important to demonstrate that you have done your homework and that you have some understanding of what’s necessary to the decision maker. This not only ensures instant credibility with the decision maker, but it also demonstrates that you have an Other-Centered® objective instead of trying to sell your product or service.

When asking for the opportunity to discuss and learn about them, demonstrate that you have done your homework and that you have some understanding of what’s crucial to the decision maker.

Learn more about making outbound sales easier here >> 

Barrier #4: Moving up the prospecting sales pipeline

When prospecting by phone, reps do not have the luxury of walking around the prospect’s facilities, and therefore do not have the face-to-face opportunities to expand their relationships within an account. They often are stuck with the person who they initially contacted, who is often more of an evaluator or buyer than the decision maker. This leads to a Catch-22 situation. 

If you try to go around your existing contact and go higher up in the organization, you risk hurting your relationship with the one connection you do have. But if you stay at the lower level, you could lose the account/opportunity altogether. At a minimum, you are at risk. 

Here are some simple tactics that successful sales reps use to advance higher-ups in the organization.

If calling the account for the first time,  determine all the key players. 

Contact the highest-ranking decision maker first. Whether you connect with them or not, you can establish your connection at the higher level (i.e., “Bob, I was referred to Judy Smith, and I’m in the process of setting up a meeting, but I wanted to connect with you as well to get a better understanding of ____ ”). 

By first establishing a relationship at the higher level, it removes the roadblock, “Please do not contact Judy Smith” or “my boss.” You are already there. Even if you don’t need to connect at that level, you have established credibility with the lower-level contact and demonstrated that you belong at that level. 

Gain sponsorship by demonstrating credibility. 

There is only one reason that a lower-level contact will agree to sponsor you to a higher-level decision maker. It will improve their political clout within the organization. So to gain sponsorship, you must demonstrate that you have the expertise to provide a solution at a higher level. To show expertise, ask questions that can only be answered at a higher level or creatively look for ways to demonstrate how your solution will provide value at higher levels in the organization. 

Gain access. 

This is important: Gain access by creating a process or event that will include introductions to key players and be perceived by the customer as a needed step in evaluating your solution/product. For example, you could offer an assessment of their existing organization and then ask to present the assessment findings to the key stakeholders.

Other ideas include: 

  • Setting up best-practice meetings where you organize a meeting with leaders in the same industry (non-competing). 
  • Coordinating an event as part of the initial phase of working together where your executives meet with their executives to determine needs.

Learn more about sales prospecting strategies >> 

Barrier #5: Discovering Honest Needs

There are multiple barriers to conducting a successful discovery meeting over the phone:

  • The ability to demonstrate that you are listening is greatly diminished. 

But because discovering exact needs is the most critical step in selling, developing this competency is vital. 

Reps who have not developed the skills to conduct a discovery meeting over the phone will struggle with uncovering the honest, unrestricted information that reveals the real decision drivers and the needs/challenges at the core of the organization. Discovering these will ultimately determine the success of the rep’s sales efforts or at least ensure that they are not wasting their time on unqualified accounts. 

Successful sales organizations have learned to address this unique skill set and have equipped their reps to lead a successful discovery meeting where precise needs and challenges are revealed. 

To improve the level of information captured during discovery, consider these common challenges to discovering honest needs:

1. Reps are uncertain as to how to ask questions that effectively initiate development. 

All too often, reps are so focused on their prospecting agenda when initiating a discovery meeting that they forget the customer altogether and resort to asking close-ended questions to check-off the information they are looking for. Reps who fail to ask open-ended questions will find the customer very resistant to investing in the discovery process, and the reps will be unsuccessful in discovering the customer’s exact needs:

Don’t ask closed-ended questions like: 

  • “How many _____ do you have/need?”
  • “What suppliers are you using?”
  • “Who’s in charge of ___?”
  • “How long have you ____?”

Do ask open-ended questions like: 

  • “Susan, I know you are currently heading up _____. Can you tell me more about your key objectives for this year, and where are you in accomplishing those objectives?”

If you focus your questions on learning about the customer and where they are heading instead of what you would like to know or what’s on your screen/questionnaire, you will significantly enhance your chances of success.

2. The customer assumption that all sales reps are self-serving.

Something particularly challenging during discovery is the fact that customers assume that sales reps’ motives are self-serving. So when they don’t know why you are asking specific questions, they will assume the worst and likely not offer any valuable information. Therefore, reps must take every opportunity to communicate the opposite. One way to do this is by asking questions in a way that demonstrates your Other-Centered reason for asking it.  

The key is to prime the question by providing a customer-focused reason for your question. For example, instead of asking, “Where are you currently buying ___?” say this: “So that I can make sure to connect the dots about what’s important to you, where are you currently buying ___?”

3. Rep’s lack of knowledge.

If a decision maker has to spend time getting you up to speed on the basic facts about their business, their interest in discovery dramatically diminishes. The rule of thumb is don’t ask the decision maker for any information you can quickly get from some other source. 

By conducting some initial research on the business, you will be able to build instant credibility with the decision maker by asking relevant, insightful questions. For example, “I know you are currently reorganizing your processes to improve ___. How will this affect your operation in ____?”

4. Rep’s temptation to begin selling during discovery.

As we began to dive into the customer’s world, we hear things that cause us to want to jump right into selling. We often hear negative information that could ultimately affect our chances of winning the deal (i.e., likes current supplier, tried your product before and it didn’t work, really doesn’t require ___). The natural reaction is to begin defending your position and try your best to change the prospect’s mind. Although this is a very natural response, it shuts down discovery. 

Our only hope for ultimately influencing the customer’s decisions is to thoroughly complete discovery and gain the necessary information to position your solution in a relevant way. Remember, until you can validate the customer’s perspective, opinions, and concerns, they will never listen to your viewpoint. Also, you greatly enhance the relationship by listening to the customer and creating an environment where the customer is comfortable to reveal honest needs.

5. Rep’s inability to truly listen. 

The typical rep has a difficult time genuinely listening to the customer. The opposite of listening is ignoring. Because you are not present when you interact over the phone, the customer is unaware of your facial expressions, and they can often feel as if they are talking to dead air or being ignored. Or when they do try to explain their point of view, a typical failing is that your response doesn’t demonstrate that you understand what they are saying. 

To demonstrate that you care about the customer and what is important to them, acknowledge not only what the customer is saying, but also what is being implied. For example, if the customer says, “This year seems to be going better.” Instead of saying, “Great.” Ask, “What happened last year?” 

Our only hope for influencing how a customer decides is to thoroughly complete discovery and gain the necessary information to position your solution in a relevant way.

Barrier #6: Validating Payoff

When reps have the opportunity to sit across the desk from a decision maker or make a sales presentation, there are multiple props they utilize to ensure the audience understands, visualizes, and embraces the point. But over the phone, your options are limited. 

To be effective at executing prospecting strategies, reps must be able to communicate in a way that ensures the customer emotionally experiences the benefits. Top prospectors have learned two techniques for building value over the phone and validating the payoff of their recommended solution: 

Word pictures and strong statements.

Word Pictures 

Reps are often faced with addressing a specific challenge or communicating a message that may be difficult for the customer to grasp or comprehend its significance. For example, a customer may be able to find a cheaper solution that appears to have similar value but be unaware of the consequences of purchasing an inferior product. Word pictures are an effective way to ensure the customer fully understands your point. 

Word pictures help the customer get emotionally involved and comprehend the weight of your recommendation. 

Let’s say you are competing with a company that offers multiple solutions and you only offer one. You want to demonstrate the importance of being focused. Here’s how a word picture can help: 

Take a 100-watt incandescent light bulb: When you turn it on, what does it do? It lights up a small room. The 100 watts of light are scattered about, as designed, and it illuminates a small room. But what if you were to take that same 100 watts of light and concentrate it through a very small hole in a device known as a laser? Now, with the same 100 watts of light, instead of lighting a room, you burn a hole through a metal wall. That is the power of focus.

Now you can connect your firm’s focus on a particular discipline to the power of a laser. The key is creating word pictures for those specific situations where an important concept is difficult for the customer to grasp.

Strong Statements

Another sales presentation technique to ensure the customer embraces your recommendation and sees the importance of the message is using strong statements. Often reps use weak language to describe a benefit of their solution or the solution provider, and this greatly diminishes the effectiveness of the message. 

In a face-to-face meeting, the decision maker can see your facial expressions, your gesticulations, and your posture. Over the phone, you only have your words. The words you choose will determine if the customer believes you and will follow your leadership. 

There are two aspects of strong statements. 

The first eliminates the competition by using words like “first” and “only.” Here, you use words that communicate to the customer that no one in the market place has more, better, higher quality, etc. For example, if you say, “Our customer service is very responsive,” it doesn’t have near the impact as, “No one in the market responds quicker to a customer issue than we do.”

Secondly, strong statements can be used to communicate your expertise and instill confidence in the audience. I recently had the opportunity to sit with a color sports analyst for ESPN. He explained that producers always remind guests to use definitive statements when providing opinions about a team or player. Why? The audience doesn’t care about anything else. 

When customers are unsure what to do and you use weak language like maybe, could, or probably, it appears that you are just as confused as they are. Customers need and want to be led, but they will not follow if you are not sure where you are going. 

Effective reps speak with confidence when communicating those key sales presentation points that are important for the customer to understand. They say, “If you do this, this will happen.” They leave no room for doubt.

Barrier #7: Advancing the Relationship 

If reps have made little investment in meeting with a decision maker, they will likely miss the importance of ending every call with a commitment to the next step. 

A sales rep’s only resource is time. It is their only currency, and how they invest that currency will ultimately determine their success. Because reps don’t typically take the time to define the most logical next step with each customer interaction, they not only miss the opportunity to advance that customer relationship, they also end up wasting a lot of time chasing down unqualified prospects which in turn limits the amount of time they have to spend with qualified customers and the downward spiral continues. 

Productive reps are intentional about determining the steps that are critical to advancing the relationship and ensuring those steps help distinguish their solution in the marketplace. Here are some mistakes most often made by junior reps:

Beginning the call without determining what they want to happen at the end of the call. 

It is critical to think through the possible next steps based on where the decision maker most likely is in their buying process. If you wait until the end of the call to determine the next steps, it will probably end with a fuzzy next step like, “Well, just let me know how the meeting went.” Or “That sounds great! Why don’t I give you a call in a month?” 

Top reps always assume that they will most likely never connect with the decision maker again, so they know if they can gain a verbal agreement to a defined next step, the chances of keeping the process moving forward increase exponentially.

Choosing the wrong event or next step. 

The events that you want the decision maker to agree to should be based on two factors: 

1. What is most helpful for the customer in making a decision? What should always be communicated as the purpose of proposing the next step?

2. What event or events will ensure that your product or solution will be viewed as best and unique and give you a competitive advantage?

Often reps put little thought into the method they want the customer to walk through, a process that will ultimately determine if the customer realizes the benefit of the product/ solution and sees it as the best solution.

If you can develop a creative customer development process, it becomes much easier to close business and gain commitment. Your focus shifts from selling a product to selling your process, which will lead to an easier sale for you and a more manageable commitment for the customer.

Being afraid of creating a fork in the road. 

Some reps are so afraid of discovering that the prospect may not be that interested in the product or solution that they avoid asking for a commitment that might expose that truth. 

As a result, they end the call with zero commitment but feel a lot better.

Highly productive reps create a fork in the road. They realize that every time they are working on a deal, they are losing a deal. They don’t have the luxury of hoping Bob’s going to buy. 

So they expose reality by asking for a commitment that will either advance the sale or reveal the customer’s honest concerns: “Bob, it sounds like you are serious about evaluating this solution. Here’s what I recommend as a next step. Allow us to assess your current _____, and then set up a meeting with you and your team to discuss our recommendations. With whom do we need to meet with to get that process started? Great, it should take us several days to ___. Can you meet on the 15th to review our recommendations?” 

Bob now has to respond to this offer, and regardless of his response, you are getting closer to a resolution. You are either helping Bob by addressing his barriers to moving forward or moving on to a more qualified buyer. It is much better than following up for months only to find out you have been wasting your time.

A sales rep’s only resource is time. It is their only currency, and how they invest that currency will ultimately determine their success.

By overcoming these seven barriers to successful prospecting, you and your team will connect more completely with your clients and ultimately increase your overall sales performance.

As you apply the information in this guide, be aware that becoming skilled at overcoming these barriers is an ongoing process. No matter how successful you are, you can improve your game by continuously developing the skills and behaviors highlighted herein. Let us know if you have any questions about what you’ve read here, or if you need continued training and development. We’ve been one of the nation’s leading development training programs for over two decades, and we’d be happy to help.  

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7 Barriers to Sales Prospecting

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