How to Sell Better By Helping People Make Progress

Vlad Malik
7 min readOct 20, 2020

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This is a hypothetical interview, where I ask questions and quote answers from Bob Moesta’s book, Demand-Side Sales 101 (Buy it on Amazon).

What it means to be a sales person

Vlad: How would you define the job of a sales person?

Bob Moesta: “Your job as a salesperson is to help people make progress on their terms… Salespeople don’t convince people to buy, people convince themselves. They buy for their own reasons. The customer defines the value. You need understand them first, and then your product and how it fits into their lives.”

Vlad: At one point the book, you say to provide the customer with options. Don’t try to define value for the customer.

Bob Moesta: “Sales is about managing and packing the tradeoffs the consumer is willing to make…. As the salesperson you should be asking questions to frame out [the customer’s] definition of value…”

Vlad: Frame the value. Not define value.

Bob Moesta: “You educate them on their options, specific to their needs only…”

Vlad: Asking questions is integral to your approach. You write that you ask questions to create space in your customer’s mind for answers, for change. But you first ask questions to get at the cause of a decision. How did your focus on causation come about?

Bob Moesta: “The idea of having a cold lead, where I pitched a preplanned presentation of features and benefits to a persona and not a real buyer, frustrated me to no end. A sales funnel based on the probability someone will buy, without understanding what causes them to buy, made no sense to me.”

Vlad: Do you have a piece of advice for getting at the cause during an interview?

Bob Moesta: “We truly do not bring a list of questions… When interviewing, we continue until we can imagine the dominoes in their life tipping over.”

Differentiation and trust

Vlad: Most companies focus on what they call “features” or “benefits”. Your work focuses on “the struggling moment”. Tell me about that.

Bob Moesta: “It’s the progress that matters, not your features and benefits… Most real growth… comes from truly understanding the problem your customer is trying to solve and focusing on helping them. By doing this, you reach people who wouldn’t even enter the marketplace to begin with. This is where most real growth comes from-the struggling moment!… Instead, the focus of sales tends to be on the point of differentiation from competitors.”

Vlad: That’s true. You can often do more with less. A sophisticated CRM solution with many features that competitors lack might not alleviate the struggling moment for a person in particular circumstances. People are so often fed up despite having a lot of choice of tools. It’s just that none scratches their particular itch. What would you advise startups?

Bob Moesta: “Choose what to suck at… You’re better off with a kick-ass half than a half-assed whole.” (quote from Jason Fried)

Vlad: Many startups are also concerned about building credibility with customers. In the book, you write that to gain credibility, you have to “speak to their situation”. In your podcasts and the book, you also talk a lot about trust. You write “Trust is caused”. What causes trust?

Bob Moesta: “Most salespeople try to never say no, but that’s a bad approach. They should assemble their house of cards on trust.”

Vlad: There’s a good example of this in the book. The conversation where the customer hires a bank that comes ready to listen instead of presenting something. To build credibility, they might have decided to prepare a detailed slide deck. But they didn’t do that, did they?

Bob Moesta: “[E]ven knowing them very well, they still came in with a blank sheet versus a Power Point.”

Vlad: And then later said “No” to a request?

Bob Moesta: “Delivering the bad news in a straight-forward way he earned [them] trust, because the other guys waffled on it.”

Aligning sales to the customer’s decision-making timeline

Vlad: What is a key thing sales organizations can do to get more effective?

Bob Moesta: “Align sales and marketing to a timeline of the users decision. Make each phase of the timeline a component of the sales process… As a salesperson, your job is to meet the buyer in each of the six stages-first thought, passive looking, active looking, deciding, and ownership-with an input… Take each phase of the timeline and make it a sub-system of the bigger process.”

Vlad: Let’s walk through the customer’s timeline. What’s step 1?

Bob Moesta: “Create the first thought… I might need to do something about this; what if I’m missing something?… Help people see their process in a new way, get them to question what they are doing and realize it’s not working, make them curious about a better way… You want the buyer to question what they are doing and realize it’s not working… opening the buyer’s brain, so they are looking for a solution.”

Vlad: Next is passive looking. What is passive looking?

Bob Moesta: “You want buyers to repeatedly see your product or services popping up in their daily life, especially in places where they’re struggling the most… Speak to those not ready to buy or those who are not even sure what a possible solution might be, speak to their situation to gain credibility, start connecting their first thought to your solution.” (customers are also learning the language of the solution, what the things they care about are called)

Vlad: You also write that you can create pushes by helping the customer see what life will be like if they keep their existing solution. To push them into active looking…

Bob Moesta: “Think of active looking as going deeper… The buyer is trying to figure out how this is going to fit into their life… I have to do something about this now… Active looking is accumulating facts, but they don’t have enough information to decide.”

Vlad: You write that at this point, you should “work with customer as they imagine their ideal solution”. But as you said earlier, you’re not persuading per se, right? You’re just framing and helping, so in the end it’s their decision. What should a sales person do at this stage?

Bob Moesta: “When somebody transitions to active looking and asks for a quote say, ‘I need thirty minutes to an hour of your time to understand your business before I can give you a quote.’ In that meeting set the expectations, “I’ll come back with three alternatives that will help you frame your situation better. From there we will morph a fourth option by merging the best of three… Then set the tone, ‘I’m a straight shooter. If it’s a no, I’ll tell you no’.”

Vlad: At that point, how do you close a sale?

Bob Moesta: “[B]y giving them three well-designed options that frame the tradeoffs that they’re willing to make… three different options with different sets of tradeoffs but the same price tag. Without these comparisons, people struggle to buy. People need to reject something before they can buy something else…. Realizing what people are willing to give up in order to make progress is the most powerful part…. The traditional notion of a tradeoff is a set of ‘compromises’. But in the setting of sales that’s not how we would define a tradeoff.”

Vlad: You often say “contrast creates meaning”. What happens when people are ready to make a decision?

Bob Moesta: “The moment they commit, buyers adjust their reference point of what better means. Better doesn’t mean better than everything they’ve looked at. It means better than the old product they fired… Here is where value, satisfaction, and expectations are locked in… The key is the word “commitment” versus “transaction,” because there are exceptions where people are committed to doing something, but they are not able to follow through.”

Vlad: That’s very true. I’ve often found that the end result of a lot of product research is I’ve learned enough to realize what I want, but I can’t have it… I can’t afford it, or it doesn’t exist, or I need much more help… I’m not able to make the tradeoffs or take the risk of choosing the worse “better”. So I choose to wait. Let’s talk about what happens when a sale is successful. What happens then?

Bob Moesta: “Most people stop selling once someone’s made a purchase. But progress is about making sure you deliver on the expectations that were set… Ongoing use is where the jobs get done and the progress is achieved… How do you build a habit? That’s the goal in ongoing use.”

Vlad: You also talk about retention in the book or not getting fired.

Bob Moesta: “Remember, the most vulnerable people in your portfolio are your current clients because you’ve learned to ignore them… Chad switched for one reason but he’s going to stay for a whole bunch of other reasons. The bank needs to know what they are. And, it’s not about pushing services Chad doesn’t need; it’s about understanding where the struggling moments… Are there things that Rachel could be using the computer for that she hasn’t even thought of?”

This is a hypothetical interview where all of the answers are quoted direct from Bob Moesta’s book, Demand-Side Sales 101 (Buy it on Amazon). There is a great diagram in the book and lots of practical tips for interviewing customers with scripts of real conversations.

You can follow Bob Moesta on Twitter @bmoesta

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