Rational thinking might drive economics, but emotional behavior drives decisions. And no one understands that better than Dan Ariely, author of Predictably Irrational, a book that’s reshaped our assumptions about how people make decisions.

In this episode, we’re unpacking key lessons from Dan Ariely’s work with the help of our special guest, Leslie Alore, SVP of Marketing at Flexera.

Together, we explore what B2B marketers can learn from setting the right expectations, why fewer choices close more deals, and how the power of “free” and fear of loss can drive serious retention.

About our guest, Leslie Alore

As the SVP of Marketing, Leslie Alore leads Flexera’s marketing strategy with an aim to create great experiences and outcomes for our customers.

Her passion for people and technology—combined with more than 15 years of marketing leadership in the tech space—has established her as a successful, results-driven executive who enables teams to do their best work.

Prior to joining Flexera, Leslie served as the Global SVP of Lifecycle Marketing at Ivanti. Before that, she held various marketing, operations and GTM strategy roles at Iron Mountain. Leslie is an active speaker and mentor in the GTM community, and has been recognized among “Top Women in Marketing” by Ragan Communications and “Women of the Channel” by CRN.

Leslie holds a BBA in Management, and an MBA with a concentration in Strategic Leadership from Walsh College of Accountancy and Business Administration.

• ‍Set expectations to shape reality. Great marketing doesn’t just reflect value, it creates the conditions for it. Leslie highlights how expectations shape reality. When buyers believe something is good, they interpret every detail through that lens. This isn’t about manipulation, it’s about clarity and consistency. Leslie says, “The effect of expectations… believing beforehand something is good, therefore it will be or the reverse.” So stop hoping your audience connects the dots. Tell them what to expect, then deliver on it. Perception isn’t a bonus, it’s the foundation.‍
• Shrink your options to speed the decision. Too many options stall progress. The paradox of choice tells us more isn’t better, it’s paralyzing. Leslie urges marketers to curate the path forward: “You actually want to give people fewer options and take control of the options that they see.” Don’t just join the shortlist, define it. When you narrow the frame, you speed up the decision for your customers. ‍
• Turn “free” into staying power with loss aversion. There’s magic in “free,” but the real power lies in what people fear losing. Once someone uses your product, whether it’s a freemium tool or an ungated resource, they’ve invested. Now there’s skin in the game. Leslie puts it simply, “People will overvalue something that's free and ignore kind of the trade-off costs associated. And loss is psychologically painful. We don't want to lose that, which we already have.” Whether you offer software, content, or services, create early wins. Then make the cost of leaving feel higher than the cost of staying.

*“ There's many organizations that lean into that power of positivity…What's very interesting is that consumer brands do this a lot very, very well. B2B organizations tend to do almost the opposite. They tend to lean more into FUD. And that's a harder road to tread.”

*“ If you’re an organization that is selling software, the software is designed to provide a business outcome. It's designed to solve a business problem. Instead of focusing on, here's the business problem. Doesn't that suck for you? You can say, ‘here's the solution.

*“You have the power, you can feel confident about your ability to achieve X, Y, Z because you've solved this problem.’ It's saying the same thing, but orienting it in a positive way and being very, very, very consistent in that message. Beat that drum over and over and over again.”

*“ Narrow down the competitive options for them. Your sales process will move faster. You will be able to take better control of the narrative if you say, ‘this is us and these are the two other vendors that look like us. And here's why we are different and better, and here's what you can expect from these guys.’ And that doesn't mean saying negative things about them.  It's just highlighting your strengths and your virtues.”

*“People are willing to accept trade-offs for something that is perceived to be free…This is the exact reason that PLG, product-led growth, is so powerful. Because if you can get people in the door with some sort of freemium offering, people will actually work harder to do the legwork to get a free product to work and interact with it, than they might be willing to put in for something that they have to go pay for. And then once they have it and they've put in the work, they don't wanna lose it.”

Links

Connect with Leslie on LinkedIn

Learn more about Flexera

About Remarkable!

Remarkable! is created by the team at Caspian Studios, the premier B2B Podcast-as-a-Service company. Caspian creates both nonfiction and fiction series for B2B companies. If you want a fiction series check out our new offering - The Business Thriller - Hollywood style storytelling for B2B. Learn more at CaspianStudios.com. 

In today’s episode, you heard from Ian Faison (CEO of Caspian Studios) and Meredith Gooderham (Head of Production). Remarkable was produced this week by Jess Avellino, mixed by Scott Goodrich, and our theme song is “Solomon” by FALAK. 

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