Bob Moesta - Demand Side Sales 101 Book Summary

Book Summary • 10 min read

I've been following Bob Moesta's work for a long time so I'm delighted he formalised his thinking in a book. A great combination of practical Jobs to be Done tools, applied to sales and business growth.

Bob Moesta - Demand Side Sales 101 Book Summary

The summary of this book also draws on the inteview I conducted with Bob, which you can watch here. I reference parts of that conversation in this book summary.

The book in a nutshell

Sales shouldn't be "icky", it should be about helping customers find the right solution for their desired outcome. By applying Jobs to be Done frameworks to sales you can unlock the secrets of growing your business in a natural, human and customer-focused way.


The key goal of Bob's book is to:

“Reframe the way YOU think of sales—to flip your lens and perspective.”

Bob has been thinking about how people behave and buy products for years. He's worked with businesses across many industries including Basecamp, Intercom and Casper. This book is written for salespeople, but the frameworks and lessons are relevant for anyone looking to grow their business. It's great for researchers trying to better understand human behaviour, for product designers looking to create human-centric products and for marketers aiming to maximise the impact of their campaigns.

Bob has been inspired by many great thinkers and professors, but this insight from Peter Drucker was his starting point:

“People rarely buy what the company thinks it’s selling.”

The theories and frameworks set out in this book are a way of explaining the phenomenon Peter Drucker so astutely observed.

Key questions answered in this book:

  • What causes people to behave the way they do?
  • Why is there a huge shortage of sales professors and frameworks to help salespeople sell?
  • How can we apply more rigour and theory to sales to help people be more successful in selling their product?

Key arguments:

  • Supply side thinking is focused on profit. Everything the business and the salespeople talk about is through the lens of the product.
  • Much of marketing is based on correlation. The purpose is to determine which attributes correlate most to people buying a thing. This does not explain why a customer buys that thing. Instead, we need to focus on causation, in order to create products people want and unlock growth.
  • To do this businesses should adopt a "demand side sales" approach. This is about positioning the sales process within the customers struggling moment to help them achieve their desired outcome.
  • There are forces that push and pull the customer towards new solutions when they experience a struggling moment. The goal of demand side sales is to minimise the negative forces while maximising the positive forces to create pull for your product.
  • The sales funnel is supply side focused and needs updating with the timeline of how customers buy. Starting with the first thought, Salespeople should ask good questions before introducing information about what their product offers.
  • Supply side businesses look at marketing, sales and customer servicing as a linear process. Marketing hands off leads to sales, who close the deal and hand over to customer servicing. With demand side sales these business units should provide inputs at every stage of the customer's buying timeline.

Let's go into a bit more detail...

The problem with sales

Speaking to Bob added a lot of context to his motivations for writing this book. His aim for the book was to use the theory of Jobs to be Done as a frame for teaching sales. Techstars and Y Combinator teach founders of new startups how to raise capital but not to sell. Selling is seen as something everyone should pick up through experience, but sales is part of so many areas of business. Before startups even have a product to sell they have to sell the vision to investors, co-founders and employees.

"You ask startups about what's the hardest part - they say sales. And no one wants to talk about sales, there's no theory behind sales so maybe people need help with sales."

Bigger companies have more formalised sales teams but there is still no theory or frameworks to help salespeople sell. If you have 20 years experience selling then you've probably figured it out. But for those with more limited experience or when it's not part of their day job, selling can feel daunting. Bob aims to wrap a framework around sales to make it more accessible and to shift businesses away from supply side thinking. Bob said in my interview with him:

"If you flip the question from how do we build product to how do we help customers make progress it actually makes it easier to sell"

Supply Side vs Demand Side Sales

Supply-side selling is focused on pushing lots of products, features and technology onto customers without understanding their need. They use lots of correlative tools to find their customers. Tools like personas, market segmentation and prospect lists. Whilst these are very common tools in the business world they don't tell you why customers buy. When speaking to Bob about this he said:

"We know who they are and how to get their attention but what we don't really study much is what causes them to buy?"

Demand side selling is about listening to, and understanding why, the customer wants to hire the product.

Sidebar: the term "hire" is commonly used in Jobs to be Done instead of buy or use. The term reflects the belief that people pull different products into their lives to help them make progress. Customers hire and fire solutions as their struggle changes or better products become available.

The focus on demand side selling is on the process the customer follows to buy (pull a product in their lives) rather than the process the business goes through to sell a product (pushing products onto customers).

“Buying is very different than selling. The best sales process mimics the progress that people are trying to make in their lives.”

In the book, Bob gives an example of working with Casper, a challenger in the market of selling mattresses. Casper's key insight was that they weren't selling mattresses they were selling sleep. They examined the key success factors for achieving sleep and then identified the constraints of buying a mattress. The result was a very different experience to the incumbent mattress providers. Casper...

  • Made buying easy (online with free delivery and returns)
  • Offered fewer options (removing the complexity of choice)
  • Had no pushy salesmen (a big pain point with incumbent providers)
  • Removed the complexity of mattress technology and matched the mattresses to the progress customers sought

In just 5 years Casper had a valuation of $1 billion, with over a million customers, 3.2% of the market and sales of over $400 million. This kind of success is repeatable if you follow the frameworks for demand side selling.

Frameworks for demand side selling

Bob contends that the struggling moment is the foundation of every sale.

"The struggling moment is the seed for all new sales"

The picture below illustrates the progress the customer is trying to make. They have a problem and they have an idea of what their desired outcome looks like. The solution they end up hiring is the one that will help them make this progress. This is the customer's Job to be Done.

Bob has created two key frameworks to help us understand the journey the customer makes from their current state to their desired state.

The four forces

There are positive and negative forces to the customer making progress and finding a new solution to their struggling moment.

F1: Push - What's happening today that's causing them to look for something new? What struggle or pain are they experiencing?

F2: Pull - What's the attraction of the new? What's the desired outcome customers are looking to make progress towards?

F3: Habit - What's in the present that is holding people back?

F4: Anxiety - What's the customer's concern about adopting something new?

The push and pull forces are the positive forces motivating the customer to seek a new solution. The habit and anxiety forces are negative forces creating blockers to change.

The push and habit forces are based in the present and are working against each other. The push forces are problems they are experiencing with their current product. These negative experiences are making them look for something new. Yet, habits are forces of routine and behaviours that create apathy. Sticking with the current solution is perceived as the simplest option.

The pull and anxiety forces are based in the future and projections of positive and negative outcomes. Pull forces are the desired outcomes customers are seeking and other solutions that may help the customer make progress. Anxieties are the imagined events that could go wrong in making that change. These are worrying moments and are a force against change.

“In business school we are taught to add more features and benefits, which would create more magnetism, pushing people to buy our product. It’s not true! We’ve got to reduce their anxiety.”

Understanding the motivations for progress. The key to trigging behaviour change is not more features, it's about selecting the features that will strengthen the driving forces while minimising the negative forces of progress. By speaking to customers and asking good questions (we'll come to this below) you can start to map out the four forces. When doing this you need to understand how the forces for progress break down into functional, emotional and social motivations.

The functional motivations are the easiest to spot, for example, this mattress is uncomfortable. But by uncovering more emotional and social motivations you will have a much greater chance of customers pulling your product into their lives.

The timeline for progress

The four forces and motivations for progress can be plotted on the customer's timeline for progress. Bob structures his customer interviews around the timeline, applying criminal interrogation questioning techniques to help the customer recall the details. When it comes to interviewing Bob says:

“It starts with listening to your customer and truly understanding their needs. It’s not only what they say, but how they say it, what they don’t say, and what they eliminate.”

This is the timeline for progress.

  1. First thought. This is all about making space in the customer's mind for solutions to fall into. When I interviewed Bob, he said Clayton Christensen said it best: "questions make space in the brain for solutions to fall into". Bob builds on this by suggesting the best way to help people is ask them questions and not answer them. Instead, tell them stories or state the obvious truths.
  2. Passive looking. When passively looking the customer is "learning, framing, and prioritizing to know what to do next." At this stage, customers are receptive to learning about new things because they have space in their mind. Everyone is exposed to tons of information so if the customer doesn't have space it just bounces off.
  3. Active looking. Active looking is about seeing possibilities. The customer is, "seeing possibilities, framing trade-offs, and ruling things both in and out - inclusion and exclusion". Customers start connecting the dots between the struggle they're experiencing and what they're learning. This is when new solutions start to stand out.
  4. Deciding. This is where the final trade-offs are made. A key part of this is framing certain things and being able to let go of others. Satisfaction with the purchase comes when there's lots of detail in the deciding part. When I spoke to Bob he linked back to the motivations for progress: "The thing that helps us make the decision is the emotion, not the function"
  5. Onboarding. - This is the first use of the product. This is when the customer first experiences the product helping them make the progress they set out to achieve.
  6. Ongoing use. The deciding and first use phases are the "big hire". As the customer continues to use the product, Bob calls these little hires that help form new habits for the customer. As time goes on, new struggling moments arise which can be a rich source of inspiration for ongoing development.

Top tip: I highly recommend reading chapter 4 of the book. Bob lays out lots of interview techniques and shows real-world examples of real interviews in practice. If you want to become good at this technique this chapter is a must-read, several times!

While the four forces and the timeline are key frameworks for research and understanding the customer, they are also key to a customer-focused sales process.

A demand side focused business

Every business has some form of sales funnel. Sales teams manage customers through that funnel from first enquiry to closing the deal. Bob argues that using only a sales funnel is a supply side approach to sales. The process is around how you sell not how the customer buys. The sales funnel needs to be respectful of and aligned with the customer's timeline for progress. Different stages of the buying process require different messages and information. To bring the sales funnel and the customer's timeline for progress together, businesses need to:

“Sales, marketing, and customer support must learn to play together! Most organizations treat them as three separate entities, but they’re not.”

Bob urges businesses not to think in a linear way where marketing hands off prospects to sales, who close deals and hand customers off to client servicing teams. Instead, he advocates working together, providing inputs at each stage of the timeline.

The typical pitfall businesses fall into is having one presentation (or a demo video for digital products). The trick is uncovering where in the timeline customers are by structuring the conversation around key questions. That means there will be multiple starting positions. Importantly, effectiveness in sales is serving people at the point of need. This is where sales, marketing and customer servicing can work together.

To maximise the impact, the marketing team need to position their message at the point of need. But if there is a steep learning curve around using the product for the first time then the marketing money is wasted.

Instead, salespeople can handhold the customer through the onboarding phase and ensure the customer is well equipped to get started. If it is a digital tool, then onboarding videos and proactive customer servicing agents should reach out via instant messaging to ease the customer past these moments of friction.

The book provides more examples like this throughout the timeline.

In conclusion

The three principles for success Bob leaves us with is:

  1. People buy for their own reasons
  2. Nothing is random; everything is caused
  3. The struggle creates demand

There's also a lot of myth-busting, how to get started guides, lists of great questions to ask and lots more hands-on tools. I thoroughly recommend digging deeper into Bob's book (this is not an affiliate link, just a genuine recommendation).

← Humanising and disrupting the email market - Issue #004
Interview with Bob Moesta about his book Demand Side Sales →

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