The Sales Evangelist

“It’s too expensive” may be the answer a prospect gives you, but it may not be the reason they are saying no.

The real issue could be that they do not see the value, they already have another solution, or they have another concern they have not told you yet.

In this objection-handling conversation, I break down two ways to get past the surface response, find the real reason behind an objection, and connect your solution to what the prospect actually values.

The Real Reason Behind a Price Objection

• A prospect who says a $100 water bottle is too expensive may not really have a problem with the $100. They may simply be comparing it to a $10 bottle and not seeing what makes the more expensive option worth it.
• The value changes based on the buyer. For someone working outside in South Florida, a bottle that keeps water cold all day, has a built-in filter, and reduces trips away from a job site can solve problems that a cheaper bottle does not.
• That is why dropping the price is not always the answer. If the prospect does not see the value at $100, they may still not see it at a lower price.
• The salesperson's job is to find out what matters to that specific buyer and connect the solution to that need.

Use the Socratic Method to Get to the Root Issue

• The Socratic method uses questions to help prospects think through their own problems and understand why a solution may be in their best interest.
• The questions should not be random. They should focus on the prospect's challenge and help uncover what is behind the first objection.
• A prospect may start with “I can get a water bottle for $10.” Keep asking questions and you may discover that the cheaper bottle means buying more water, buying ice, leaving the job site, and losing time that could have been spent quoting more work.

Thank the Prospect Before You Challenge the Objection

• The first step is to thank the prospect for raising the concern and show genuine empathy. A $100 purchase is a bigger decision than a $10 water bottle, so the concern deserves to be taken seriously.
• From there, ask what they mean when they say it is expensive. Are they comparing it with another product? Have they never paid that much for a water bottle? Or do they simply believe the product is not worth $100?
• Those questions help reveal what the prospect is really thinking instead of forcing the salesperson to guess.
• Once the real concern is clear, the salesperson can educate the prospect around the value they were not seeing.

Turn Lost Time Into a Business Case

• The water bottle example becomes more valuable when the conversation moves from the product itself to the time it can save. A construction worker who has to leave a job site for water or ice is losing working time.
• If that person can get even 30 minutes back in the day, that time could be used to quote more jobs. When one new job is worth thousands of dollars, the value of the solution looks very different.
• The salesperson is no longer selling a water bottle. They are selling convenience, time, and the chance to create more revenue.
• The same principle applies to other products and services: find the business problem behind the feature and show the prospect what solving it is worth.

The Menu Method Gives You a Shortcut

• The second approach is the Menu method. Instead of asking a long series of questions, give the prospect a few common reasons other buyers have raised the same objection and ask if one applies to them.
• The options should come from real sales conversations. For example, the prospect may think the product is too expensive because it will not last, because they already have another solution, or because they are not interested in working with the company.
• This gives the prospect an easier way to explain what is really stopping them without having to come up with the answer from scratch.
• If none of the options apply, that is useful too. Ask them to explain what the real issue is and keep digging.

Make the Prospect Empty Out Every Objection

• A prospect may have more than one concern. They might start with price and then reveal that they also think the product is fragile.
• That is why asking, “Is there anything else?” matters before moving into the solution. The goal is to get every concern on the table.
• Once the prospect has explained everything, you can address each issue instead of solving one objection and discovering another later.
• The approach is simple: find the root cause, explain how your solution addresses it, and then give the prospect a clear reason to believe the result is possible.

Use Proof Before You Ask for the Sale

• After uncovering the objection, the next step is to educate the prospect and use a testimonial or case study from someone with a similar problem.
• One example in the conversation involves a company that bought the bottles for its team because employees were leaving job sites to get water. Those trips were linked to accidents, lost time, and other problems.
• The company saw roughly $300,000 in value from keeping its team on site, reducing accidents, getting more work done, and dealing with fewer health-related problems.
• That kind of proof can change the way a prospect sees the purchase because the conversation is now tied to a result they care about, not just the features of the product.

Start Small Instead of Asking for the Whole Deal

• Once the value has been established, there is no need to ask the prospect to make the biggest possible commitment immediately.
• Instead of asking a company to buy 50 bottles for its entire team, start with one or two and let them see what happens. If the solution produces the result discussed, there is a clear reason to expand the purchase.
• The same approach can work with software, licenses, professional services, and other offers. Give the prospect a way to test the solution instead of asking them to take a large risk.
• The smaller commitment can make it easier for the prospect to move forward while giving you a chance to prove the value.

"You don't need to talk about all the features. If you could just get help them with understand the one feature or one offering, one solution that can best help them, then money in the bank all day long." — Donald C. Kelly

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Nearly half of all B2B sales conversations end with no decision at all, and that number keeps climbing. This solo episode breaks down the discovery call framework built over years of carrying a bag as a software sales rep, now taught to clients to stop deals from going quiet.

The Real Cost of No Decision

• A study of 2.5 million sales conversations by Matthew Dixon and Ted McKenna found that 40 to 60 percent of B2B deals end in no decision, not a loss to a competitor, just silence.
• Of those no-decision deals, 44 percent come from the prospect of sticking with their status quo, while the other 56 percent come down to indecision and analysis paralysis.

Step 1: Build Rapport With Something That Matters to Them

• Small talk gets replaced with something specific and current about the prospect's business, like a recent win or a stat about their market share, so the conversation centers on them, not the seller.
• This shows the prospect that homework was done before the call, and it gets them talking about something they're proud of right from the start.

Step 2: Set the Rules Before You Play the Game

• Early in the call, the prospect hears that the last five minutes are set aside to make a decision together, whether that's moving forward or agreeing it's not a fit.
• The prospect also gets permission to end the call early if it's clear they're not a match, which takes off the pressure and builds trust instead of suspicion.

Step 3: Run Discovery So They Talk More Than You Do

• Before anything gets demoed, the prospect is asked what they want to learn from the call, then asked what else, so the exact proof they need becomes clear.
• Data from Gong backs this up: sellers should talk 30 to 40 percent of the time while buyers talk 60 to 70 percent, and that ratio is what keeps a deal moving instead of stalling.

Step 4: Use the Last Five Minutes to Get a Real Decision

• Every call closes with a menu of next steps for the prospect, like bringing in a technical stakeholder, so there's a clear path forward instead of a vague "let me think about it."
• Getting the prospect's direct cell number and permission to text also gets added in, which makes it much harder for a deal to quietly disappear.

"Set the rules before you play the game." — Donald C. Kelly

Resources

• Learn more about the research behind this episode: jolteffect.com

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Selling a must-have product sounds easier than selling a nice-to-have. But even when your solution is critical to a customer’s business, you still have competitors fighting for the same deal. So, what makes a buyer choose you?

In this episode, I talk with Mark van Oppen, CRO of SecureAuth, to talk about what it takes to sell a must-have solution in a competitive market.

Selling a Must-Have vs. a Nice-to-Have

• Mark explains why sellers should first identify whether their solution is truly critical to their ideal customer.
• A product should solve a real business problem rather than forcing urgency where none exists.
• Finding the right Ideal Customer Profile (ICP) can determine whether a product becomes a must-have.
• Mark prefers selling solutions that are foundational to the customer’s business because they create stronger customer relationships.

• Having a must-have solution does not automatically mean a buyer will choose you.
• When multiple companies can solve the same critical problem, trust becomes a major differentiator.
• Sellers build trust by doing what they say they will do.
• Trust also comes from demonstrating expertise and understanding the customer’s specific business problem.
• Every interaction should reinforce the buyer’s confidence that you can solve the problem.

• Sellers need to understand how a problem appears inside a specific customer’s business.
• Different companies can experience the same technical problem in very different ways.
• Instead of using the same presentation for every prospect, sellers should tailor their conversations to the customer.
• Deep research helps sellers speak directly to the customer’s situation instead of making the customer explain everything from scratch.
• This level of preparation can demonstrate expertise and build credibility.

• It's possible that AI-powered sales tools would simply hide lazy sales behavior.
• He later became a supporter of tools such as Gong, call recording, automated notes, and follow-up summaries.
• These tools can help strong sellers increase their effectiveness while reducing missed details.
• AI should support good selling habits, not replace attention, preparation, or customer empathy.
• Manual note-taking still matters when automated tools are unavailable.

The three qualities Mark considers when hiring:

• Energy: The enthusiasm and commitment someone brings to the work.
• Excellence: A demonstrated history of committing to and delivering high-quality work.
• Experience: Knowledge gained through time and exposure to a specific role or industry.

Mark puts them in that order because he believes experience can be developed, while energy and a demonstrated commitment to excellence are harder to teach.

• According to Mark, the phrase “say-do-say” describes another way of building trust.
• First, clearly explain what you are going to do.
• Then, actually do it.
• Finally, show the customer what you accomplished.
• This creates a clear connection between the customer’s expectations and the outcome you delivered.
• It also helps sellers reinforce their credibility throughout the sales process.

Mark’s team uses a Mutual Action Plan (MAP) during complex sales.

The MAP includes:

• The customer's problem statement and pain points.
• A list of tasks that need to be completed.
• Stakeholders responsible for each task.
• Specific delivery dates.
• Progress updates as tasks are completed.
• A commercial review covering the business side of the deal.

The goal is to create a shared plan where both the buyer and seller understand their responsibilities and can track progress together.

• A seller's job does not stop after making a promise.
• Following through on commitments gives the customer evidence that they can depend on you.
• Documenting agreements makes expectations clear and reduces confusion.
• Consistent execution becomes especially important when your product sits in the customer's critical path.

Popular Quote:

"The buyer ultimately buys trust from their vendor." — Mark van Oppen

Resources

• Learn more about SecureAuth: secureauth.com
• Reach Mark van Oppen: [email protected]

Product-market fit isn't a yes or no question, and treating it like one is what trips up most founders and sales leaders. That's the core idea Collin Stewart, co-founder and CEO of Predictable Revenue and host of the Predictable Revenue Podcast, brought to this episode, and it reshaped how I think about why some go-to-market motions take off and others stall no matter how hard the team works.

Product-Market Fit Isn't Binary, It Has Strength

• Most founders treat product-market fit as something you either have or don't, which makes the conversation almost impossible, because any founder with paying customers can point to that as proof they already have it.
• Instead, Collin described product-market fit as existing on a scale, from barely there to overwhelming, which means two companies can both have "a product in market" while one sells at a fraction of the speed of the other.
• That distinction matters because it shifts the question from a debate over whether fit exists to a real conversation about how strong that fit is and what would make it stronger.

The Uber Eats Story That Proved the Point

• Collin shared that his old cold email agency normally booked around ten meetings a month for a client using the same process and the same team.
• When a former client joined Uber to launch what's now Uber Eats and asked Collin's team to run the exact same playbook, that single campaign of a thousand outreach emails booked 327 meetings in one month.
• The rep running the campaign hadn't changed and the process hadn't changed, so Collin concluded product-market fit acts as a multiplier on go-to-market effort, and Uber's fit was roughly 33 times stronger than anything else his team had worked on.

Strengthening Fit Starts With Customer Development Interviews

• The fastest way to raise the strength of your product-market fit is to run structured customer development interviews with your pipeline, your existing customers, and people in adjacent markets.
• The key question to ask is what problem you'd solve for them if you could solve anything, then follow it with two scoring questions: how satisfied are they with how they currently solve it, and how important is solving it to them.
• The sweet spot is a problem that scores high on importance and low on satisfaction, because a painful, unsolved, high-stakes problem is what founders should build around, not a nice-to-have improvement.

Why Working Harder Without Direction Backfires

• Collin compared weak product-market fit to riding a tricycle with the brakes clamped down, where grinding out more calls and more outreach just burns energy without covering more ground.
• He said the instinct to just work harder is the wrong move, because a founder who pauses to fix the product and the direction first will out-pace a founder who never stops to check if they're racing toward the right finish line.
• For sales leaders specifically, Collin's advice is to track whether a consistent process with consistent inputs is producing results that are out of line with a rep's past performance, because that gap is the signal that the product, not the person, needs the fix.

How to Build a Case When the Founder Isn't Convinced

• If a founder isn't open to hearing that product-market fit is weak, a sales leader should still go run customer development interviews across five or six verticals on their own. Because that data builds the case no argument alone can win.
• He stressed that every customer development call should end with booking the next call while you're still on the phone, since the entire feedback loop breaks down without that habit and waiting to follow up later multiplies the work.
• Collin kept a sticky note on his monitor that read "don't forget to book the meeting" for years, because that one small discipline is what turns a single interview into a repeatable feedback loop with a prospect.

What to Do About Outbound When Fit Is Still Weak

• The first move when fit is weak is to keep sending customer development interview requests instead of sales pitches, because the goal at that stage is learning, not closing.
• He walks prospects through a loop that moves from a discovery interview, to feedback on a paper prototype, to feedback on an MVP, to the question of what it would take for them to pay, and finally what it would take for them to refer three friends.
• Collin was direct that this only works if you book the next touchpoint before the call ends, because without that step you lose the momentum and have to restart the relationship cold every time.

Leadership Advice, Books, and Quotes

Collin Stewart recommends The Terrifying Art of Finding Customers, his book on connecting customer development to sales. Which he describes as part how-to guide and part honest account of the mistakes he made building his own companies.

Resources

• Connect with Collin Stewart on LinkedIn.
• Learn more about Predictable Revenue, the company Collin co-founded and leads as CEO.
• Check out Predictable.ai, Collin's newer tool for running plays like customer development and social listening; it's in beta, and interested listeners can email Collin at his first name at predictablerevenue.com for details.
• Subscribe to Collin's newsletter at foundersed.co for more on the book and his other projects.
• Grab a copy of The Terrifying Art of Finding Customers.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

AI is changing sales fast. But is it actually replacing salespeople, or is it exposing the sellers who never developed real strategy skills? That’s the question I explore in this conversation with John Stopper.

John and I get into the difference between sales tactics and sales strategy, why AI can sometimes give sellers the wrong picture of a buyer, and why getting closer to the people involved in a deal can make the difference between winning and losing.

We also talk about how sales teams can use AI to identify deal risks instead of simply using it to write more emails.

Why AI Makes Sales Strategy More Important

AI can teach people sales tactics, but strategy requires a deeper understanding of the situation.

• Tactics focus on how to sell, while strategy focuses on who, what, when, where, and why.
• AI can help sellers execute many tactical tasks, but sellers still need to decide which approach fits the buyer and the situation.
• Strong sales strategy starts with understanding customers and what will actually compel them to buy.
• The goal is to choose the right strategy based on the conditions of the deal.

Knowing how to throw every pitch does not mean you know which pitch to throw.

• A baseball pitcher may have four or five pitches available.
• The right pitch depends on the batter, pitch count, runners on base, and inning.
• Sales works the same way. The skill is not just knowing the sales playbook but knowing which strategy to use in the moment.
• Choosing the right strategy can improve your position, accelerate velocity, and compress time.

AI can give both buyers and sellers information that does not accurately reflect the current situation.

• Buyers can use AI to research a salesperson or company before the first conversation.
• Sellers can also build their account research around outdated or incomplete information.
• A polished AI summary can create false confidence if it does not reflect what is actually happening.
• Sellers should verify their assumptions instead of treating AI research as unquestionable fact.

The first sales conversation is an opportunity to check whether both sides are working from the right information.

• Ask the buyer what their AI research has shown them about your company, product, or you.
• Share what your research has shown you about their company and ask whether you have it right.
• Use the conversation to identify what is missing from your research.
• Verify the situation before choosing your sales strategy.

The right message depends on the person you are selling to.

• End users often care about doing their jobs faster, better, or cheaper.
• Managers may care more about how a solution affects their team and the risks involved.
• Executives are more likely to focus on strategic growth and business outcomes.
• Sellers need to understand the buyer's role before deciding what value to emphasize.

“Proximity sells” because sellers need to understand the buyer's world deeply enough to bring useful insight.

• Proximity is not about becoming the buyer's friend.
• It means understanding the buyer's business and seeing things from both inside and outside perspectives.
• Sellers should get close to the people who can influence the deal, not only the person who can approve it.
• Outside experience can help sellers bring insights the buyer may not have considered.

A deal can have strong champions and still fail because someone else inside the organization has the power to stop it.

• Identify the people who may resist the purchase.
• Ask your champion who in the organization could have concerns about the solution.
• Reach out to those people directly instead of waiting for their objections to appear later.
• Address potential resistance before it becomes a deal-ending problem.

AI can be useful when it helps sellers think through what could go wrong.

• Ask AI to research the people and roles that may resist a purchase.
• Identify possible objections and resistance points before they appear.
• Continue updating the research as the deal progresses because new risks can emerge.
• Use AI to help build a deal strategy around what could prevent the deal from closing.

One salesperson should not have to carry every relationship in a complex B2B deal.

• Sales managers can connect with the buyer's manager.
• Product leaders can connect with the buyer's technical leaders.
• CEOs can connect with other executives when the situation calls for it.
• Each person can carry a message that matches their role and expertise.
• Multiple relationships can help both companies become more familiar with each other.

Executive involvement can be part of the sales process, especially when selling complex solutions.

• Executives have revenue responsibilities too.
• A salesperson can prepare an executive with the person's profile, the situation, the message to communicate, and the information to bring back.
• AI can take more operational work off the team's plate.
• That creates more room for leaders to spend time with customers and support revenue-generating conversations.

As AI makes more sales information and tactics available, the ability to create useful insight becomes more important.

• AI has reduced the advantage that once came from simply knowing sales tactics.
• Sellers need to know how to use information, not just access it.
• The goal is to tell buyers something they do not already know.
• Strategy determines what insight to deliver, when to deliver it, and who should deliver it.

AI and digital tools should not replace direct conversations with buyers.

• At minimum, sellers should use video calls when meeting in person is not possible.
• Direct conversations can help uncover what digital research misses.
• Meeting a buyer in person can build trust and show a willingness to make an effort.
• Sales still depends on human relationships, especially when decisions are complex.

“AI has commoditized a lot of that advantage. So now to me, selling and strategy is about how can I tell them something they don't know?” — John Stopper

John Stopper: johnstopper.com

John's website also offers a free, no-obligation deal strategy report. Submit a company you are trying to sell to, and he will run it through his COMPASS system and provide a deal strategy report.

Email: J Stopper at Northstore.com

LinkedIn: John Stopper

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Connection rates have dropped roughly five times since before COVID.

If ten percent of your calls used to turn into a conversation, you're probably closer to two now.

David Zeff, CEO of Whistle, runs an agency that makes cold outreach work for 350-plus B2B clients, and he broke down exactly what's changed, what hasn't, and the parts of outbound most people are too embarrassed to actually do.

Why Connection Rates Have Collapsed Since COVID

• David's headline stat: connection rates have dropped roughly five times since the early 2010s. If a rep used to get a conversation on ten percent of calls, that number is closer to two percent now.
• That drops compounds. Fewer conversations means fewer meetings booked from the same amount of effort, cutting a rep's effective output roughly in half even before factoring anything else in.
• He points out that most investors and boards setting revenue benchmarks don't actually understand how much this single number has shifted, which means the targets built on top of it are often unrealistic from the start.

The Four Things Whistle Screens For Before Taking a Client

• Whistle turns away clients the way a lawyer might turn down a case they can't win. David treats a signed client as the start of the real work, not the finish line.
• First: does the founder actually know their ICP? If they're still deciding between multiple very different buyer types, that's a major warning sign.
• Second: is the total addressable market big enough to support a real sales motion, since a market of a few hundred accounts with multi-year sales cycles isn't a fit for most outbound efforts.
• Third and fourth: is there real marketing support behind the sales effort, and does the product have any real moat, since neither one used to be a dealbreaker a decade ago the way they are now.

The New Risk: Can Your Prospect Just Build It Themselves?

• David's newest red flag: prospects increasingly ask themselves whether they could just build a simple version of the product using AI tools instead of buying it.
• His own team has looked at some clients' products recently and had the same reaction: this looks like something built quickly with AI, which means the prospect is likely to think the same thing.
• Sellers need a clear, early answer to that question, since it's showing up at the very top of the funnel now, not just at the negotiation stage.

Why Cold Email Copy Isn't the Real Story

• Prospects often ask David to see a sample of Whistle's email copy, expecting the wording itself to explain the results.
• His answer is always the same: seeing the email is like seeing the cheese and asking how that made the pizza. The copy alone leaves out everything that actually got the message opened and read in the first place.
• Highly personalized details, like referencing someone's favorite sports team, used to work well on their own. David is direct that this stopped being enough years ago, even though it still gets attention on LinkedIn as a screenshot-worthy tactic.

Stop Separating the Brand From the People

• David points to Gong as the company that got this right early: during the shift to remote work, they made individual employees visible instead of hiding behind the company logo, including putting reps on billboards.
• B2C brands have leaned on individual personalities for a long time. B2B is only catching up to that now, and companies that keep everything behind a logo are giving up a real advantage.
• Donald shared a reference point from a past guest at Chili Piper, who said roughly half the deals in their pipeline had some connection to her personal LinkedIn activity, not because she was directly involved in every deal, but because buyers had engaged with her content somewhere along the way.

Build Community Before You Need It

• David's third layer, beyond the basics and personal branding: building some form of community or network around your business, even a small one.
• A simple example from one of his own clients: a marketing VP asked if Whistle could bring their clients together to trade notes, which turned into a referral network of consultants and adjacent service providers.
• It doesn't have to be a massive branded community. Even something as basic as a small referral relationship, a shared cause you donate to together, or a network of people adjacent to your buyer who can talk about your space, counts and compounds over time.

The Free Tactic Nobody Will Actually Do

• David's final, deceptively simple tip: export your personal contacts from WhatsApp or your phone, write one honest message explaining what you do and asking for a referral, and send it to twenty people a day.
• His prediction is that most people won't actually do this, precisely because it's free, easy, and has no clever trick to hide behind if it doesn't work.
• He's currently running an open deal that came directly from this exact method, reaching out to a personal contact who referred him to someone else who's now moving through the sales process.

"We're in sales. You're always desperate. That's the job." — David Zeff

Resources

• Connect with David Zeff on LinkedIn.
• Visit Whistle to learn more about their outsourced sales development services.
• Join our LinkedIn cohort and learn to prospect the right way.
• Visit Blue Mango Studios for help creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Sometimes the best way to close more deals isn't by adding new people to your pipeline (though that's always a good thing.) Instead, the best thing is to address the issues that make a deal fail before they fail.

In today's episode of The Sales Evangelist, I joined the CEO of Challenger, Andee Harris, to get her take on failed deals and how to address those issues directly with our prospects.

Challenger is a sales training company:

• The Challenger Sale by Matthew Dixon and Brent Adamson explains many of the principles Challenger uses in their training.
• Early sellers might be timid, which usually leads to a failure to recognize when a deal isn't moving in the right direction.
• In Andee's experience, continuous feedback is a great way to course-correct throughout the sales process to tailor the experience and selling strategy to the specific prospect.
• Passive selling isn't the best form of selling for either party. Taking control of the purchase and helping the buyer buy the product is your job.

Three ways to notify deals before they go south:

• Integrate an avenue for continuous feedback. If a buyer likes you as a sales rep, they'll want to share methods to improve their experience.
• Realize that one size doesn't fit all. What works for one client might not work for another.
• Constantly be learning. Be curious, and look to understand and be self-aware of your strengths and weaknesses.

Andee's final takeaway? Understand that we're in a complex selling environment. Multiple factors influence the selling process, but it isn't impossible to create wins and do phenomenally well. To get in touch with Andee, visit challengerinc.com or connect with Andee on LinkedIn.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

A former Marine who did eight combat deployments in eight years now spends his time teaching people to stop pitching and start asking better questions.

Keith Gillispie, founder of REI Automated, left the Marines in 2020 to build a real estate investing and coaching business that's helped more than 1,200 people, with close to 580 of them closing their very first deal. He broke down exactly how he qualifies, questions, and consults his way to the close.

Why "Selling" Is the Wrong Mindset (Stop Being House Horny)

• Keith's blunt term for pushy sellers: house horny, chasing the deal so hard that they force the wrong solution onto someone just to close it.
• His fix is simple: stop selling, and start asking great questions that guide the prospect to the answer on their own.
• He reviews sales calls with his own team every week, and the biggest issue he catches with newer reps is a used-car-salesman energy that shows up the moment they stop asking and start pitching.

Qualify for the Right Industry First

• Keith gets over a hundred Facebook messages a day, and his team has to pre-qualify people before he ever gets on a call.
• A recent example: a rep flagged someone as "qualified" who actually wanted coaching on commercial real estate, which Keith doesn't teach at all. Same broad label, completely wrong fit.
• Even inside a niche that sounds close enough, being in the wrong specific industry wastes everyone's time.

Qualify for the Right Problem: Your Core Competency Must Match Their Core Constraint

• Keith's rule: everyone has problems, but that alone doesn't make someone a fit. What he's good at has to be exactly what the prospect is bad at.
• He calls this matching your core competency to their core constraint. If there's no real gap for him to fill, there's no real reason for the two of them to work together.
• This is what separates a win-win engagement from a sale that shouldn't have happened in the first place.

Qualify for the Right Money (Or Every Call Becomes Charity)

• Even with the right industry and the right problem, a prospect still has to be able to afford the solution, or the call turns into free coaching.
• Keith shared a recent example of two prospects who badly wanted to join his program but couldn't spend even $300, when his coaching runs into the thousands.
• He's direct with his own team about this: sending him financially unqualified leads turns every call into charity work, which isn't sustainable as a business, even though he's genuinely happy to hand out free value when it makes sense.

Diagnose Before You Prescribe

• Keith estimates that more than half of the people who come to him think they know what they need, and they're wrong.
• His example: prospects ask for automation when they don't even have leads coming in yet, or don't know how to structure a deal. Automating a broken process just scales the chaos faster.
• He compares it to a patient self-diagnosing before seeing a doctor. The seller's job, like a doctor's, is to ask enough questions to find the real issue before recommending anything.

Get Comfortable Asking Uncomfortable Financial Questions

• Keith walks straight into questions like current income, whether that number is gross or net, and total debt, early in a call, because he can't build a plan without knowing where someone actually stands.
• He compares it to Google Maps: you need a point of origin and a point of destination before you can build the route in between.
• Roughly one in twenty-five or thirty people push back on how direct these questions are. Keith's response is straightforward: if they can't handle these basic questions now, the program itself is going to be a rough fit.

Build Yes Momentum With Small Asks

• Keith structures his qualifying questions to build what he calls yes momentum: each small, reasonable question makes the next one easier to answer.
• He starts broad, what do you do, how long have you done it, before narrowing into income, debt, and financial specifics, so the conversation earns its way to the harder questions instead of opening with them.
• That same sequence doubles as training. The financial questions he asks on a discovery call mirror the exact questions his students will later need to ask sellers and private lenders.

Ask Questions, Don't Make Statements

• Keith's rule for himself: don't make a statement for the first 60 percent of any sales call, aside from short softening statements like "I'm glad you asked that."
• The only exception is a brief acknowledgment before turning right back around and asking another question.
• Whoever is asking the questions is steering the conversation, and Keith treats that as true for the entire first half of every call he runs.

Never Fully Answer a Question Without Asking One Back

• Keith borrows from Socratic questioning: when a prospect asks a direct question, like how fast he can close on a house, answering too quickly and too specifically can blow up the deal in either direction.
• Instead, he gives a partial, honest answer, then asks a question that uncovers the real reason behind their question, like whether they need to move fast or need more time.
• That extra step means his eventual answer is actually calibrated to what the person needs, instead of a generic response that might scare them off or fail to meet an urgent situation.

Become a Lifelong Student of Your Craft

• Keith has taken more than ten thousand sales calls over eleven years and still says the more he learns about sales psychology, the more he realizes he doesn't know.
• His advice for anyone serious about improving: invest in a coach or mentor who can review real calls and point out specific gaps, rather than trying to learn everything for free through trial and error.
• His framing: you'll pay for the lesson either way, either in money to a mentor, or in wasted time and missed opportunity learning the hard way.

"People don't care how much you know until they know how much you care." — Keith Gillispie

Resources

• Connect with Keith Gillispie on LinkedIn.
• Visit REI Automated to learn more about Keith's education, software, and coaching community for real estate investors.
• Join our LinkedIn cohort and learn to prospect the right way.
• Visit Blue Mango Studios for help creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

37 reps who got the least recognition on one 153-person sales team averaged 62 percent quota attainment. The team average was 107 percent. That gap is the whole argument Sindre Haaland, CEO and founder of SalesScreen, makes for why comp plans alone don't explain sales performance.

Why Identical Comp Plans Produce Wildly Different Results

• Sindre's core observation: two reps can work under the exact same comp plan and produce completely different results, which means money alone isn't the daily driver of performance.
• Comp plans set the structure and tell a rep what they need to do to get paid, but engagement is what determines whether they actually do it consistently.
• An engaged rep will outperform a disengaged one with the identical incentive on the table, every time.

Know Your Sales Math

• Sindre's first question to any rep: have you actually broken your quota down into what you need to do today, not just what you need to hit by year end?
• Reps who treat sales as a series of repeatable, data-driven daily activities have a far more predictable path to their number than those relying on charisma alone.
• Even with a full pipeline of data, the numbers only matter if a rep has the motivation to actually execute the plan. That's the gap gamification is built to close.

The Four Player Types on Every Sales Team

• Sindre borrows a framework from game theory to describe four types of sales reps: killers, achievers, explorers, and socialites.
• Killers are driven by being number one and seeing their name at the top of the leaderboard. Achievers care about personal bests, regardless of where they rank against everyone else.
• Explorers enjoy the process itself, testing new tools and new angles. Socialites, the majority of most sales teams, are driven by recognition, visibility, and feeling like their effort is seen.

The TV and Music Moment That Changed Sindre's Career

• Sindre described watching a sales floor the first time his team replaced a whiteboard with TVs that played music and visuals every time a rep closed a deal.
• People were jumping on their desks. That reaction is what convinced him sales motivation itself, not another feature, was the real business to build.
• A rep's win becoming a shared, visible, celebrated moment does something a quiet bank deposit never will.

Three Rules for Running a Contest That Moves the Needle

• Timing matters more than most leaders assume. Contests started on a Wednesday consistently outperform ones started on a Monday, since early-week motivation has usually faded by midweek.
• Shorter is better. Month-long contests tend to create a "valley of disengagement," with excitement in week one, a dead middle, and a scramble at the end. One-day sprints create urgency without the letdown.
• Change the format so more than the top performer has a real shot. A lottery-style contest, where every meeting booked or deal closed earns a ticket, gives the middle of the pack a genuine "I might actually win this time" feeling.

Get Creative: Pairing, Envelopes, and the White Elephant Game

• Pairing a high performer with a lower performer on a team-based contest naturally creates coaching and mentorship, without ever calling it that.
• Simple physical mechanics work too: envelopes on a wall that reps can pick from after hitting an activity, some holding a dollar, some holding a bigger prize.
• Sindre's favorite: a white elephant style game where prizes range from real rewards to silly forfeits, and reps can steal from each other until the contest ends, creating genuinely memorable moments on the floor.

The Recognition Stat That Proves the Point

• Sindre shared data from a 153-person sales team where they measured how often each rep received recognition in a month.
• The 37 reps who received the least recognition averaged 62 percent quota attainment. The team average was 107 percent.
• Recognition and quota attainment move together closely enough that Sindre treats recognition frequency as a leading indicator, not just a nice-to-have.

Where to Start as a New Sales Leader

• Sindre's starting point for anyone new to this: interview your top performers and find out what they actually do every day, not just what the official process says they should do.
• Frequently, top performers are doing things nobody explicitly asked them to do, or doing an already-known behavior far more consistently than everyone else.
• Cross-check those behaviors against the rest of the team. Wherever the gap is real, that's where a leader's next contest or incentive should be aimed.

"A motivated person will do better than a disengaged one, even with the same comp plan." — Sindre Haaland

Resources

• Connect with Sindre Haaland on LinkedIn.
• Visit SalesScreen, the world's leading sales gamification platform.
• Join our LinkedIn cohort and learn to prospect the right way.
• Visit Blue Mango Studios for help creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Only 10 percent of sales messages actually explain why something should matter to the buyer. The other 90 percent are just decoration on a generic pitch.

That stat comes from Leslie Venetz, who audits thousands of sales messages every year and just released her USA Today bestseller, Profit-Generating Pipeline. She broke down what real relevance looks like, and the exact method she uses to build it.

What Relevance Actually Means (And Why Most Sellers Miss It)

• Leslie defines relevance simply: a message has to be relevant to the person receiving it, not to the seller sending it.
• The biggest problem she sees is that most outreach centers on the seller's process, product, and company goals instead of the buyer.
• When she audits sales messaging, and she reviews thousands of messages a year, only about 10 percent actually explain why a piece of information should matter to the prospect.

The Mail Merge Era: When "Fake Personalization" Felt Like Magic

• Back around 2012, Leslie ran a basic mail merge strategy that felt groundbreaking at the time. Prospects were genuinely impressed just to see their name and company pulled into an email.
• That tactic hasn't disappeared. It's evolved into things like mentioning a prospect's new job title or congratulating them on a funding round.
• The problem is the same one it's always been: something can be true about a prospect without being relevant to them right now.

Personalization Versus Relevance

• Leslie draws a clear distinction: personalization is a fact about the prospect. Relevance is why that fact should matter to them today.
• I shared my own experience of digging through my inbox after the pandemic and realizing most pitches weren't even relevant to my actual role, let alone my actual problems.
• The real gap, in Leslie's words, is that most sellers never get into the buyer's emotional state, the specific pressure a person is under right now, not just their job title or industry.

The Earn the Right Philosophy: De-Centering Yourself From the Pitch

• Leslie's core philosophy is called Earn the Right: before asking for a meeting, a call, or a contract, a seller has to earn the right to that person's attention.
• That means shifting language away from "I'm an account executive at [Company] and we sell [Feature]" toward messaging built entirely around the buyer's specific situation and outcome.
• The shift shows up in something as simple as word choice. Leslie says the biggest difference she sees in client messaging is emails that stop being about I, we, and our, and start being about you and your.

The Five-Filter Segmentation Method

• Leslie's starting point for anyone new to territory planning is the five-filter method: four firmographic filters plus one demographic filter, layered together to turn a broad list into a hyper-specific one.
• She recommends starting with the demographic filter first, since narrowing a title, like going from "IT executives" down to just "CIO," forces a seller to ask what that exact role actually cares about.
• That one change alone, narrowing from a broad title to a specific one, has increased reply rates by more than 12 percent for her clients.

A Real Client Example: Narrowing a Healthcare IT List

• Leslie walked through a real example from a global software company: a list originally aimed at "IT executives in healthcare" got narrowed down using all five filters.
• The firmographic filters included US-only, hospitals specifically, revenue between 100 million and a billion dollars, and customer service departments over 100 people.
• They also added a signal: whether the hospital had missed a recent best-of list. That detail alone reframed the entire pitch around better patient outcomes and service rankings, instead of generic product features.

Shorter Emails, Longer Cadences

• A common mistake Leslie sees even after sellers embrace outcome-focused messaging: trying to cram everything they want to say into a single email.
• Her fix is to trust the cadence. Spread the story about a buyer's likely outcomes across multiple touches instead of one dense pitch.
• That shift also means holding off on a hard call to action early in a sequence, and letting later touches carry more of that weight.

Why "More" Isn't a Strategy

• When results slow down, Leslie sees most teams reach for the same lever: hire more reps, send more emails, make more calls.
• Her pushback is direct: more is never the answer on its own, because it skips the harder work of understanding who you're actually talking to.
• Good segmentation is what makes every other activity, calls, emails, cadences, actually worth doing in the first place.

The Marriage of Art and Science in Sales

• Leslie pushes back on using AI as a way to fully remove the seller from the process. If a prospect is expected to give their time and attention to a reply, the seller owes them a message that was actually written with care.
• The science side is the data: confirming you're talking to the right person, at the right account, about the right thing.
• The art side is judgment: knowing that just because something is technically personalized, like mentioning a promotion, doesn't mean it's the most relevant or human thing to say next.

One Thing to Do Right Now to Get More Relevant

• Leslie's starting point for any sales leader: audit your current sales messaging and count how often it uses I, we, my, and our instead of you and your.
• That audit gives you real data on how self-centered your outreach actually is, even if it doesn't feel that way from the inside.
• From there, use AI for research instead of mass automation. Learn what a specific persona at a specific type of account actually cares about, then build that into the message.

"More is not a strategy." — Leslie Venetz

Resources

• Grab Leslie's book, Profit-Generating Pipeline: A Proven Formula to Earn Trust and Drive Revenue.
• Visit Leslie's company, The Sales-Led GTM Agency.
• Connect with Andy Paul, Leslie's mentor and host of The Win Rate Podcast, on LinkedIn.
• Join our LinkedIn cohort and learn to prospect the right way.
• Visit Blue Mango Studios for help creating podcast production content.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.