Sales Tales - A podcast sharing epic stories that get you through your sales adventure.

In April 2020, Quibi launched with $1.75 billion raised, Jeffrey Katzenberg (Disney, DreamWorks) as founder, Meg Whitman (eBay) as CEO, and a lineup of short, Hollywood-produced shows built for your phone. Six months later, Katzenberg and Whitman announced they were shutting it down. By December, the service was gone.

On paper, Quibi had everything a strong deal in your pipeline seems to have: money, executive sponsorship, a firm deadline, and plenty of activity. We use this example to break down why opportunities like that still fall apart, starting with a LinkedIn poll Josh ran asking sellers why their last deal didn’t close. 47% said they had the wrong person in the room. 33% said the timeline was never real. Only 13% lost to a competitor. Everything else traced back to qualification.

Dave brings four questions that tell you whether you actually have a deal:

• What happens if you do nothing? A gut check for pain, and how to tell real consequences apart from interest and curiosity
• What are the consequences of missing your deadline? Why “sometime in Q4” is a non-answer, why the date has to come from the buyer, and the follow-up question that tests it
• If you had to find it, is there money available to solve this? What to do when the answer is “I don’t know,” and how a price range opens the conversation
• If you decided to move forward, what would actually have to happen on your side? Why asking about the process gets you further than asking who the decision maker is

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

On January 28, 1986, Space Shuttle Challenger sat on the launch pad at Kennedy Space Center on a cold January morning. The people closest to the problem had already raised the alarm. Engineers at contractor Morton Thiokol had seen O-ring erosion on earlier flights, testing showed the seals got worse in the cold, and they recommended against launching below 53 degrees. NASA managers pushed back, Thiokol management reversed its position, and the Rogers Commission later found that the engineers' continuing objections never reached the senior people who made the launch decision. Earlier missions had come home safely, so a known problem had slowly become acceptable.

Sales leaders fall into the same pattern. The warning signs are usually there, and your reps often see them first. A process that keeps producing results is easy to excuse, and an answer you don't like is easy to wave off. In this episode, we cover four brutal truths that sales managers can see coming and would rather not face and unpack each one.

In this episode you'll learn:

• Your best rep is going to leave. Most managers know it could happen and plan for nothing. The episode covers why a client should belong to the company and not to one rep, how to build bench strength, and why "always be recruiting" beats writing a job posting after the resignation.
  
• Your forecast is probably telling you what your reps think you want to hear. This is the O-ring problem in your pipeline. The close date slides to October, nobody asks why, and the bad news arrives in December. We cover the questions that test whether a deal is real.
  
• The problem you keep coaching might actually be you. When several reps keep struggling with the same thing, that's a signal about leadership. This covers supervising versus coaching, promoting your best seller with no leadership training.
  
• Eventually you have to let someone fail. Stepping in to fix things keeps this quarter's results looking fine while your team stops growing. Failure is where the learning happens and how to start with low-stakes situations.

Three questions to take back to your team: If your number one rep left on Friday, what breaks on Monday? Have you created a culture where it's easier to move the close date than kill the deal? Are you coaching your reps, or becoming their best sales rep?

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

🎙️ Hosted by Josh Shirley with co-host Dave Doherty🔗 Listen on Spotify and Apple Podcasts

On January 15, 2009, US Airways Flight 1549 hit a flock of Canada geese minutes after leaving LaGuardia and lost both engines. Captain Chesley "Sully" Sullenberger and First Officer Jeff Skiles had about three and a half minutes to get 155 people on the ground somewhere over New York City. Skiles worked the engine restart checklist. Sully worked the question no checklist could answer: where can this plane actually land? He chose the Hudson River, and everyone on board survived.

Years of practiced procedures handled everything predictable, which freed Sully to focus on the one thing nobody could have planned for. Sales communication works the same way. Every time you rewrite the same pre-call email, referral intro, or meeting recap, you spend brainpower your customer conversations need.

On this episode, Josh reads four short emails he actually sends:

• The meeting confirmation, which gives the buyer an easy out days ahead and doubles as an upfront contract for the call
• The referral introduction, a template his referral sources personalize and send on his behalf
• The meeting recap, which confirms the next meeting and gives the buyer a reason to show up
• The breakup email, the "have you found another way?" message most sequences save for last, sent earlier

He walks through why each one works and how to write your own versions, so you can prepare the predictable and save your attention for the unpredictable.

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

In 1975, a Kodak engineer built the first digital camera. Kodak had the invention, the knowledge, and the cash, and still shelved it because it threatened the film business that was making them so profitable. This leads to a hard question in sales: which deals in your pipeline are you refusing to see clearly?

In this episode, we walk through four signs it's time to let a deal go:

• pain that never gets past surface-level interest
• a champion who can't get you access to the people who can say yes
• no believable path to funding
• a buyer who isn't taking any steps on their own

We'll discuss why you should stop asking "Are you the decision maker?", how to tell an unfunded problem from an unfundable one, and why a deal with no pain belongs back at the qualify stage. The episode closes with a simple four-point scorecard for deciding whether to work a deal, diagnose it, stop forecasting it, or let it go.

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

Some sales emails are bad because they're too long. Others are bad because they're too salesy. And some are bad because they act like you and the prospect are old friends—even though you've never met.

In this episode of Sales Tales, Josh and Dave break down four real sales emails that landed in Josh's inbox and diagnose exactly where they went wrong.

You'll meet The Pitch, The Novel, The Fake Friend, and The Ransom Note—four common approaches that sellers use every day, often with the best of intentions.

In this episode, you'll learn:

• Why leading with your product and value proposition can make an email all about you

• Why cold emails should usually stay around 75 words

• The difference between professional rapport and pretending you already have a relationship

• Why researching a prospect doesn't give you permission to diagnose their problems

• How third-party stories can surface pain without telling a prospect what's wrong with them

• Why relevance matters more than friendliness

• What to do when you've sent five emails and find yourself writing, "Just following up..."

Plus, Josh tells the bizarre story of Notre Dame linebacker Manti Te'o and the girlfriend who didn't exist—and explains why some prospecting emails can feel a little like getting catfished.

If your prospecting emails aren't getting responses, don't just send more of them. Take a look at what you're actually putting in their inbox.

Sales Tales shares epic stories that get salespeople talking.

In 1970, Apollo 13 was heading home with a problem. To re-enter the atmosphere, the crew had to power the command module back up, but they had an extremely limited electrical budget. Flip the wrong switches in the wrong order, and they'd blow it before they ever made it back.

Every cold call has the same problem. A prospect who doesn't know you has an extremely limited attention budget, and most sellers try to flip every switch at once: who they are, what they do, why they're calling, all in the first ten seconds. The system shuts down before it ever gets a chance to work.

Josh and Dave break down the sequence that keeps a prospect's attention budget intact instead of spending it all at once. It starts with a pattern interrupt that tells the truth instead of following the script the prospect is bracing for, moves into a mini upfront contract that stops the clock the prospect is silently running, and lands on a 30-second commercial that's about the prospect's world instead of a features-and-benefits dump. In this episode, we cover how to find a reason to keep the conversation going without going into full sales mode too early, and how to recognize the exact moment to stop talking and book the next meeting before the energy runs out.

By the end, you'll have a three-part way to earn the right to a real conversation instead of hoping one of your words happens to land.

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

In 2008, Domino's had a problem. Customers kept calling to ask where their pizza was. The obvious fix was answering the phone faster. Instead, Domino's asked a different question: what if the customer never had to call in the first place? They built the Pizza Tracker. Within two months, a million people used it.

Six months ago, Josh asked himself the same question about his sales process: what would I do differently if I could never follow up again? On this episode, he and Dave break down the five things that changed.

They cover why most upfront contracts sound professional but don't actually define what gets decided, what separates a real clear future commitment from a polite "let's stay in touch," why BAMFAM (book a meeting from a meeting) has to happen before you hang up or it doesn't happen at all, how a quick post-sell step after every yes keeps a deal from quietly unraveling, and why the most successful email in most sequences is usually the last one, and what happens when you send it first.

By the end, you'll have a five-step way to build follow-up out of your process instead of getting better at doing it.

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

In 1961, President Kennedy didn't tell the nation he'd like to try to get to the moon sometime. He said the country would land a man on the moon before the decade was out. A deadline. A commitment. And on a hallway visit to the Space Center, he asked a janitor what he was doing. The man didn't say he was mopping the floor. He said he was putting a man on the moon.

That's the difference between a maybe and a clear future commitment, and it's the whole subject of this episode.

Josh and Dave break down why phrases like "we're ready to move forward" or "we'll circle back after we talk internally" feel like agreement but carry almost no information. They bring in Robert Cialdini's research on restaurant no-shows: when reservation lines changed one question, from "call us if you need to cancel" to "will you call us if something comes up?", show-up rates jumped, because one is a passive request and the other is an actual commitment the person has to agree to out loud.

We dive into SVIC, a four-step tool for turning vague buying signals into commitments you can actually build a forecast on:

1. Summarize what you heard
2. Validate it with the buyer
3. Identify how important it really is to them
4. Capture the specific next step.

By the end, you'll know exactly what to listen for to tell a real commitment from a polite maybe, and a simple mechanism to make sure the ones you get actually stick.

Sales Tales is the sales training podcast built on real stories, real tactics, and zero fluff. New episode every week.

In 1985, Coca-Cola had the data. Thousands of blind taste tests, all pointing in the same direction: people preferred the sweeter formula over both Pepsi and classic Coke. So they made the switch. New Coke launched, and it became one of the biggest marketing failures in business history. Seventy-nine days later, Coca-Cola Classic was back on shelves.

Coke optimized for taste. Customers weren't buying taste. They were buying nostalgia, identity, the memory of what a Coke was supposed to feel like. Coke measured the wrong outcome and paid for it.

In this episode, you'll learn:

• Why the business outcome the customer cares about is often not the one you're tracking, and how that gap opens without anyone noticing
• Why adoption problems are rarely about the product, and what "people don't like change" actually means for your onboarding and training plan
• The difference between a commercial relationship and a day-to-day usage relationship, and why losing touch with the person who bought from you is what quietly turns an account reactive
• How a clean handoff between sales and account management protects retention, including the shift from briefing the incoming team to certifying them on it
• Why setting up quarterly business reviews at the start of the relationship, before anyone's uncomfortable asking for one, changes the entire tone of the account

This episode is for account executives, account managers, and customer success or client success professionals who own an existing book of business and want a system for keeping it, not just servicing it.

Sales Tales is the sales training podcast built on real sales stories, real tactics, and zero fluff. If you want to know how to close deals, retain accounts, and think like a top performer, you're in the right place.

In 1998 a Navy captain named David Marquette got his dream assignment pulled out from under him. He'd spent six months studying every wire on what he thought was the best submarine in the fleet, and the day he showed up to take command, it sailed off without him. His new ship, the Santa Fe, was the worst in the Navy, the one other crews used as a cautionary tale. Marquette didn't know the vessel. He couldn't lean on expertise. He had to lean on his people instead, and that's what turned him from a boss into a leader.

Josh and Dave use that story to break down three pillars that separate a boss from a leader in sales management, with real signs for each one.

In this episode, you'll learn:

• Pillar one: bosses sell, leaders build sellers. The specific habits, writing the deck, taking over the meeting, being the one customers call, that quietly train a team not to think for itself
• Pillar two: bosses create pressure, leaders create purpose.
• Pillar three: bosses build dependency, leaders build legacy. The one question that tells you which one you are: if you left tomorrow, would the business still run?

Dave shares a story from his own career about a client account he took back from a rep every single year instead of coaching them to hold on to it, and what changed once he started handing over real authority rather than just responsibility.

If you've ever wondered why your best people wait for your approval instead of bringing you a plan, this one's for you.

This episode is about: sales leadership, sales management, coaching sales reps, delegation in sales, sales team development, sales manager mistakes, building a sales culture, sales coaching framework, leadership vs management, empowering sales teams, sales team accountability, and developing sales talent.