Thoughts on Selling - Value Selling, Sales Leadership, Sales Enablement Insights

Tim Ohai thinks change management is a scam. He's got receipts — he used to be the guy they put on stage to sell it.

His argument is simple and it stings: change management is written from the organization's point of view, never the individual's. So I stopped him and asked him to swap in two different words. Sales enablement. He didn't hesitate. Same thing. We're just going to shove it onto people and hope they like it.

That's the conversation. Three disciplines, one mistake — we keep building for the org and delivering to a human being who never got asked.

Tim wrote Sales Chaos in 2011, before most of the industry had settled on what to call any of this. He's since walked away from the enablement label entirely for strategic execution, which he'll tell you is the thing nobody was ever formally taught. He asks rooms full of leaders who was trained to execute strategy. Crickets. Every time.

We get into why 95% of AI initiatives produce nothing measurable and why that's not the AI's fault. Why most pipeline reviews inspect the deal instead of the customer. And the UK team that nearly doubled its win rate off one conversation their reps didn't want to have — because a GM refused to move on to the next idea for three straight quarters.

The line that stuck with me: if I don't have clarity and I don't have empowerment, coaching is just a nice hug.

Tim's at timohai.com, and he's very active on LinkedIn.

A deal stalls. The buyer goes quiet. And the industry has one answer: more. More sequences, more touches, more tooling. Then somebody says the rep needs to want it more.

The rep is almost never the problem.

In this episode, Lee reads Chapter One of The Second Meeting, the first book in the Acelera Sales Fables. Before the reading, he tells the origin story. Alex Mercer started as Stacy, a brief appearance in a nonfiction manuscript. Following her career from bank teller to VP of Sales selling fintech took more room than a few sentences, so she jumped ship and took a novel with her.

He also talks about Max, the cavachon who spent fifteen years teaching him presence and is still teaching him two years after his passing, and about what presence looks like on a Tuesday: in a room with ten people, on a video call, at a checkout counter, on the phone with your mother.

Have the conversation with Alex: https://thesecondmeeting.com Buy the book, or a stack for the team:https://books.acelera.group Lee on Amazon: https://amazon.com/author/leelevitt Work with Lee: https://acelera.group

Together We Win, the nonfiction book Stacy walked out of, is out on Amazon now.

Cory Dunham failed the same calculus class twice — for the same reason both times. He wouldn't ask for help.

That story sits at the center of this conversation. Cory is an executive coach, keynote speaker, business strategist, and private pilot who's spent 40 years in business learning that the voice telling you not to raise your hand is not you. It's a recording from years ago, and it only shows up when it doesn't serve you.

We get into what that costs a salesperson. If you walk into a meeting carrying "I'm not worthy to be here," you cannot simultaneously help a customer transform their results. Those two things are in direct conflict.

Cory's traffic metaphor is the one that stays with you: when you keep switching who you are — pumping the brakes on your authentic self — the people behind you honk, pull back, or run into you. None of that builds a relationship.

We also dig into what real listening actually is. Cory thought it was shutting his mouth. Then he became a pilot, where you repeat back the controller's instruction word for word or somebody gets hurt. Different stakes than a sales call. Same discipline.

Plus: the four-step path to earning the helm, why The Four Agreements is the book I'd hand every salesperson, ADHD and hyperfocus, improv as listening practice, and what the word "sell" originally meant before we ruined it.

Connect with Cory:

LinkedIn — Cory Dunham

Email — [email protected]

Podcast — unapologeticleadershippodcast.com

Most companies believe revenue growth solves everything. Doug C. Brown has spent three decades proving otherwise.

Doug is CEO of CEO Sales Strategies, and his work starts from an uncomfortable premise: the money you're looking for is already inside your business. You've paid to acquire it. It's sitting in underpricing, in proposals nobody followed up on, in a fulfillment process that takes eight weeks when it should take one. It just never made it to the bank.

In this conversation, Doug walks through the diagnostic he uses — 21 EBITDA drivers, each with five or six sub-points — and shares what it turned up: a $2.4M HVAC company that grew to $4.96M with EBITDA moving from 13% to 28%, and a valuation that climbed $7 million. A $772,000 plumbing company sitting on $226,000 in unclaimed EBITDA, found in two hours. A billion-dollar company losing $72 million a year and still describing itself by its top line.

Lee and Doug also get into why choice paralysis kills deals, why "being customer-centric" quietly becomes scope creep, and how a realtor cost herself an $80,000 commission by handing a hesitant buyer a way out.

The throughline: none of this is about squeezing customers. It's about running a business that can afford to serve them well.

In this episode:

• Why revenue growth without margin discipline is just expensive motion
• The 21 EBITDA drivers and how the 15-minute diagnostic works
• What too many SKUs does to your salespeople and your buyers
• Business ROI vs. personal ROI — and why missing the second one loses deals
• Where AI genuinely elevates the customer experience, and where it doesn't

Find Doug: [email protected] | LinkedIn: dougbrown123

Find Lee: podcast.thoughtsonselling.com | meet.acelera.group

Thoughts on Selling — Serve Customers. Not Quotas.

Michael Skriver started in finance and IT, then — as he puts it — upgraded to sales. He's spent his career leading complex B2B organizations across Europe and Asia, and he came into this conversation with a line his CEO once dropped on three thousand people: you have no clue how to sell, you're a bunch of traders.

That CEO was right. And what he taught Michael next is the through-line of this episode: if you say you're customer-centric, show me in your decisions, otherwise it's a slogan.

We get into what that looks like when it's real. Executive sponsors who put their own credibility at stake instead of approving account plans from a desk. KPIs that measure when a shipment leaves your factory instead of whether it arrived usable. Technical and commercial sellers working as a pair, with the person in the white coat doing the digging — because everyone knows the guy in the tie is dangerous, especially if his title is long.

The middle of the conversation is a masterclass in cross-cultural selling. A Japanese general manager telling Lee three times "I want you to do a good job," and what he was actually protecting. A boss who couldn't sit through 45 minutes of small talk and killed the relationship in seven. Twelve Japanese executives across the table. And the karaoke moment that wasn't an invitation — it was a test.

They close on the thing every seller hears in every market on earth: our market is different. Michael's read on what that sentence is really asking for is worth the listen on its own.

Also in here: the $700 shoes, why interrogation shuts buyers down, intrinsic versus extrinsic motivation, and a CEO's advice to stop doing more with less and start doing less with less.

Guest: Michael Skriver — futuresalesglobal.com

Host: Lee Levitt — sales coach, podcast host, and author of The Second Meeting and Together We Win, both available at books.acelera.group

Questions or comments? Use the contact form at podcast.thoughtsonselling.com, or grab time to talk at meet.acelera.group.

If this conversation was useful, share it with a coworker or two.

Buyer confidence is at an all-time low — and more data isn't fixing it. In this episode, Lee sits down with Tom Pisello (The ROI Guy), value-selling pioneer and founder of GeniusDrive, to unpack why B2B deals stall even when the numbers are solid.

Tom and Lee explore Aristotle's three buy buttons, the shift from FOMO to fear of messing up, why trust now drives 50% of the purchase decision, and what vendors need to do differently in an era of AI-accelerated complexity.

Topics covered:

• High-performance driving as a sales metaphor: your car goes where your eyes go
• Why emotional connection precedes logical justification in every buying decision
• The confidence gap: why two-thirds of buyers regret purchases shortly after signing
• Collective buying committees, compromise, and eroded confidence
• AI's role in accelerating value frameworks — from six months to six days
• The outcome economy and why token-maxing is the wrong metric
• Leadership in an era of rapid, disorienting change

References and further reading:

• Frugalnomics Survival Guide by Tom Pisello — Tom's foundational work on value selling and the three buy buttons that drive every B2B purchase decision
• The Art of Racing in the Rain by Garth Stein — the book (and film) behind Tom's keynote framework, and the source of the episode's central metaphor
• The Challenger Sale by Matthew Dixon and Brent Adamson — foundational work on the role of emotion in B2B purchase decisions
• Todd Caponi — trust and transparency expert, author of The Transparency Sale; recommended by Tom as essential listening on the trust dimension of selling
• Lee's forthcoming books: The Second Meeting and Together We Win

Connect with Tom Pisello:

• LinkedIn: Tom Pisello (The ROI Guy)
• Podcast: Value Coffee Talk
• Website: geniusdrive.com/community

Chris Carter has been in the SAP ecosystem for decades — and he's watched AI go from expert systems on a Commodore VIC-20 to a tool that's genuinely changing how enterprise companies forecast, plan, and sell. He's not impressed by the hype. He's impressed by the people who actually use it well.

In this episode, Chris and Lee cover what separates the sellers who are winning right now from the ones firing off AI-generated emails into the void. Spoiler: it's preparation. It's curiosity. It's doing the work before you walk in the door.

Chris shares how he uses Google Gemini to simulate industry-specific discovery — getting the AI to ask him questions one at a time before a customer call, so he shows up already thinking in their world. He breaks down the Gartner analytics maturity curve and why most companies are still stuck at "here's what happened" when the real opportunity is "here's how we change what's going to happen."

He also tells the story of Shea — an SDR who cold-called Lee with bad CRM data, pivoted beautifully when challenged, and ended up as a coaching client who finished last year as number two on his team. The lesson? Stop selling the meeting. Sell the reason to show up.

And then there's the question that anchors the whole conversation: if sales is a game, who makes the rules? For Chris, the answer is simple — and it changes everything about how he competes.

What you'll hear:

• Why consumer-grade AI is not the same as enterprise AI — and why both matter
• How to use AI for preparation, not just production
• The Peloton analogy that scared a room full of Oracle salespeople
• Why a 0% response rate on a million AI emails is just laziness
• The "stop selling the meeting" coaching insight that took Shea to #2
• What it means to make your own rules of engagement

Connect with Chris Carter:LinkedIn: Christopher M. Carter (Wisconsin)Speaker inquiries: christophermcarter.com

Connect with Lee:Contact form: podcast.thoughtsonselling.comSchedule time: meet.acelera.group

Gina Smith spent 27 years selling medical devices into hospital operating rooms — and she got there entirely by accident. No role models. No sales background. A career in HR she was tired of.

One conversation with a sales manager who couldn't fill a role. And a "mercy interview" she then went out and won.

In this episode, Gina and Lee dig into what actually drives sales performance in high-stakes, complex environments — and why it has almost nothing to do with product knowledge or closing technique.

What we cover:

• How Gina went from HR to 27 years in medical device sales — and why she was skeptical of salespeople herself
• Why the best salespeople are introverts who learn to act like extroverts — not the other way around
• The shift from OR presence to supply chain gatekeeping, and what it costs sellers who can't adapt
• The "painful truth" principle: why telling customers what they don't want to hear builds more trust than protecting the relationship
• "Who are you being?" — the question that reveals everything about a salesperson's intent
• Why mapping out a sales process on the CFO's whiteboard won't fix the real problem
• The difference between selling to people and serving them — and why buyers can always tell which one you're doing

Gina now coaches founders and small sales teams through her practice at ginarsmith.com.

Connect with Gina:LinkedIn: Gina R. SmithWebsite: ginarsmith.com

Connect with Lee:podcast.thoughtsonselling.comLet's Talk: meet.acelera.group

Danny Bobrow has spent 36 years in marketing and communications. He discovered a hard truth about sales effectiveness: getting the phone to ring is only half the battle. What happens after it rings—how calls are handled, how trust is built, how resistance is navigated—determines everything.

That discovery led him to create the Persuasion Blueprint, a framework built on brain science, first impression research, and hard-won lessons from mountaineering expeditions and adventure racing. His core insight: before you can persuade others, you have to persuade yourself.

What we cover:

• The three C's of persuasion: Caring, Connection, Collaboration—and why sequence matters
• Mehrabian's research: why words account for only 7% of effective communication
• The brain science of resistance: amygdala, limbic system, and why facts trigger fight-or-flight
• The health club saleswoman who outsold everyone by letting prospects stay in control
• "If you want to go fast, go alone. If you want to go far, go together."
• Why the best salespeople are "patiently persistent and respectfully resilient"
• The Sherpa model for coaching: running the race at your client's pace
• How political polarization and fragmentation make persuasion skills more critical than ever

Key insight: "People don't care how much you know until they know how much you care. And if you feel pressure, so will they."

Connect with Danny:

• Website: DannyBobrow.com
• Complimentary Persuasion Scorecard available

Kris Rudeegraap is the co-founder and co-CEO of Sendoso, the largest direct mail and gifting platform in the world. Before building a company with global warehouses, a drop-ship network across continents, and $150 million in funding, Kris was a top seller who got creative when email stopped working.

This conversation covers the origin story of Sendoso, the psychology of reciprocity, and why dimensional mail is the channel that never stopped delivering—even when everyone forgot about it.

What we cover:

• From mail merge to direct mail: how Kris went from 90% email response rates to running a mini mail room
• The dog bark moment: hearing a pet on a sales call, sending a dog toy from Amazon, and booking the meeting
• Curiosity as the single most important attribute of a salesperson
• "The open rate of a FedEx box is 100%" — why scarcity and tangibility still work
• Email was the cheap drug—easy but not effective anymore
• Building Sendoso: software + warehouses + drop-ship + AI recommendations
• The Kansas City ribs story: prospect broke a rib skiing, so they sent BBQ ribs
• The pizza box campaign: "Hungry for a new solution? Let's chat."
• Customer delight vs. door opening: 50%+ is top of funnel, but land-and-expand is huge
• AI/data layer: pulling interests from Gong calls to recommend gifts six months later
• Secret sauce: tenacity to win + creating wow experiences + bridging the gap for human connection
• "People buy from people they trust" — and trust comes from deposits in the relationship bank account
• What's next: AI agents, autonomous workflows, and doubling down on data

Key insight: "We're selling the emotional connection that comes from getting something delivered to your doorstep. That's the surprise and delight moment. That's the pattern disruption. That's the relationship."

Connect with Kris:

• LinkedIn: Kris Rudeegraap
• Email: [email protected]
• Website: sendoso.com