Same Side Selling Academy with Ian Altman

09/01/2026

Some of the most common questions in B2B sales may actually be hurting your conversations.

“Just checking in.”
“What keeps you up at night?”
“Who’s the decision maker?”

They’re familiar questions, but each can create a problem.

In episode 393 of the Same Side Selling Podcast, Ian Altman breaks down why these questions fall short and what sellers can ask instead to keep conversations focused on the buyer’s challenges, desired outcomes, and key stakeholders.

Better sales conversations don’t come from asking more questions. They come from asking questions that help both sides determine whether there’s a problem worth solving.

Watch the full episode here: https://youtu.be/5PF7SBRsxOE

Which sales question would you add to the list?

08/26/2026

Discovery is where sales opportunities are either strengthened or weakened.

Many discovery conversations focus on gathering facts:

- How many employees do you have?
- What's your budget?
- What's your timeline?

Those questions have their place, but they rarely explain why a buyer would choose to make a change.

The conversations that move opportunities forward uncover a different set of answers:

- What outcome is the buyer trying to achieve?
- Why is that outcome important to the business?
- What happens if nothing changes?
- How will they know they've made the right decision?

Those answers shape every conversation that follows. They influence urgency, differentiation, internal alignment, and whether the opportunity is a good fit in the first place.

A strong discovery call leaves you with more than information. It gives both the buyer and the seller a clearer understanding of the problem they're trying to solve.

What's one discovery question that's consistently led to better sales conversations for you?

08/20/2026

Could a company stuck at $100 million grow to $600 million with a change in focus and positioning?

That's exactly what happened at Dome Construction.

On the Same Side Selling Podcast, CEO Rob Lynch shares how his team broke through a long-standing growth plateau by getting crystal clear on three things:

- What they do exceptionally well.
- The unique value they bring to clients.
- Which opportunities are the right fit.

That clarity transformed the way they engaged prospective clients and positioned their business. The result was stronger client relationships, sustained growth, and a business built largely on repeat customers.

Hear the story firsthand from Dome Construction CEO Rob Lynch on the Same Side Selling Podcast:

https://samesidesellingacademy.com/podcast/from-100-million-to-600-million-in-six-years-with-rob-lynch/

understanding value and what differentiates from competitors to grow from $100 million to $600 million in sales revenue in six years. Same side Selling

08/18/2026

AI is changing sales.

The question isn't whether you should use it. It's which AI you're relying on.

Generic AI tools are trained to answer almost anything for almost anyone. That makes them incredibly versatile, but it also means they don't understand your sales methodology, your buyers, or the nuances of a complex B2B conversation.

The result?

Sales emails that sound polished but generic. Discovery questions that lack depth. Objection responses that seem reasonable but miss what the buyer is actually trying to accomplish.

That's why we built Same Side Coach.

Instead of generating generic sales advice, Same Side Coach is trained on thousands of coaching sessions on real deals based on the Same Side Selling methodology. It helps sellers prepare for conversations, think through opportunities, and respond in ways that keep the focus where it belongs: on the buyer's desired business outcomes. And, it's all integrity-based.

AI should help your team make better decisions, not just write faster emails.

Have you noticed a difference between using general AI tools and AI that's built for a specific job? We'd love to hear what you've experienced.

08/13/2026

Many sales teams assume the path to growth is generating more opportunities.

Sometimes the bigger opportunity is improving the conversations you're already having.

One technology company was facing increased competition and growing pricing pressure. Buyers couldn't clearly distinguish the value they offered from lower-cost alternatives, and only 20% of its small business sales team was hitting quota.

By adopting the Same Side Selling methodology across sales, marketing, and customer success, the team shifted the focus from selling products to helping buyers achieve meaningful business outcomes.

Within a year, more than 90% of the small business sales team was hitting quota. Revenue grew, sales cycles shortened, and customers had a much clearer understanding of the value the company delivered.

The biggest transformation wasn't a new product or pricing strategy. It was a new way of thinking about every client conversation.

Want to find out which company it was and how they made the shift? Read the full case study:

https://samesidesellingacademy.com/wp-content/uploads/2022/08/GPS-Case-Study2.pdf

08/11/2026

The idea that sales is a numbers game has been around for decades, and it still shapes how many organizations measure effort and success.

In this video, CEO Ian Altman explains why that mindset often leads teams to prioritize activity over meaningful progress and how it can quietly limit better results.

Instead of focusing solely on increasing calls, meetings, or proposals, Ian shares a more effective approach to building momentum by creating clarity, alignment, and a deeper understanding of the buyer's desired outcomes.

When sellers help buyers think through their decisions rather than simply increasing volume, conversations become more productive and opportunities move forward with greater confidence.

If your team is looking to improve results without relying on more outreach or longer hours, this video offers a practical perspective that's worth a few minutes of your time.

https://www.youtube.com/watch?reload=9&v=FYm4HeY9bwk&list=PLyYKUe7AjE5xjqENcULn9HiFkZs3Jh7BX&index=2

We have all heard the notion that sales is a numbers game. But, is ...

08/05/2026

One of the biggest misconceptions in B2B sales is that a great demo will close the deal.

The reality is that buyers rarely make decisions because they saw more features. Prospects make decisions because they've built a strong business case for solving a meaningful problem.

When sellers rush to the demo, they often skip the most important part of the sales conversation: helping the buyer understand why change is necessary in the first place.

In the latest Same Side Selling Podcast, Ian Altman explains why demos often lead to excitement instead of action and how to structure conversations that help buyers confidently move forward.

The best demos don't showcase everything your product can do. They reinforce the outcomes your buyer has already agreed are worth achieving.

Watch the full episode here: https://youtu.be/2ilyuUcumVw?si=-yeMSAXL-XcKIgmc

In your experience, what usually causes buyers to lose momentum after a great demo?

08/04/2026

The old ABCs of selling were "Always Be Closing."

It's a memorable line from Glengarry Glen Ross. It also shaped how many salespeople approached selling for decades.

The problem is that it assumes the most important conversation happens at the end of the sales process.

In reality, buyers usually reach a decision much earlier.
They decide based on the questions you ask, the trust you build, and whether you've helped them understand the impact of making a change.

That's why we prefer a different definition of ABC: Always Be Confirming.

When every conversation helps buyers evaluate the right decision for their business, the final step isn't about convincing them. It's about confirming a decision they've already become confident making.

Read more about this concept in Ian Altman's past Forbes article, "The ABCs of Selling: Actually, Be Confirming."

https://www.forbes.com/sites/ianaltman/2018/07/20/the-abcs-of-selling-actually-be-confirming/

Looking back on your best sales wins, did they feel more like a "close" or a "confirmation"? What happened earlier in the process?