People Hire Products: Bob Moesta on Struggling Moments, Context and the Real Jobs to Be Done

Moesta, an electrical engineer who has built products for nearly 30 years, says he was told growing up that if you build it, they will come. It didn't work for him. Jobs to Be Done starts from the premise that people hire products to make progress, and that this happens in some context with some desired outcome.

He illustrates with candy bars. A Snickers is typically eaten when someone has missed a meal and needs energy to get back to work, so it competes with a protein drink, Red Bull or coffee. A Milky Way is usually eaten alone after an emotional experience, so it competes with wine, a brownie or even a run.

This reveals the demand-side competitive set instead of the supply-side one defined by technology and business model. Moesta adds that supply and demand are less connected than most people assume, and that the causal chain runs from a struggling moment to demand.

Moesta's example is Southern New Hampshire University. In 2010 the school noticed some 50 or 60 students who paid full price but never came to class and just watched online. They were older adults who had tried college before or already held a degree, and who now had responsibilities and a reason to change. The university studied them and found a huge underserved group, and today it has over 200,000 students.

Moesta says companies such as Intercom and Basecamp use struggling moments as their roadmap. He argues that a roadmap of features can be undone by surprises like ChatGPT, whereas a list of struggling moments stays valid because there are many ways to solve each one. His rule of thumb is to talk features for the first 90 to 120 days and struggling moments after that.

Lenny Rachitsky objects that founders will say they already look for pain. Moesta replies that business school taught pain and gain, but what matters is context: the missed lunch, the pile of work, the podcast in progress. Framing it as context and outcome creates a vector of intention that you can then wrap technology around. He cites QuickBooks, which he says had half the features and twice the price.

At a whiteboard he lays out the forces. A push, which he calls F1, is the situation that makes someone decide today is the day to change. The pull of a new outcome is F2. Against them are the anxiety of the new, F3, and the habit of the present, F4. If F1 and F2 don't exceed F3 and F4, nobody moves.

Because more features add anxiety, he often reduces friction. When he built condos for downsizers, buyers cancelled because they couldn't deal with their belongings. So he raised the price, bundled the move and two years of storage, and sales rose by over 30%. His book Demand Side Sales argues that sales processes should follow how customers want to buy.

Moesta describes Autobooks, a Detroit company that helps banks offer invoicing and payments. Its sales team aimed every conversation at a demo followed by a close. He asked where the customer sits in their buying timeline and split the demo into three: one telling the problem story, one showing alternatives, and one helping buyers choose between paths forward.

He says this almost halved the sales cycle and quadrupled conversion. He divides buying into six phases: first thought, passive looking, active looking, deciding, first use and ongoing use. He also stresses that what people say they want differs from what they buy. In his surveys, 93% of homebuyers wanted an Energy Star house, yet nobody bought it and everyone paid for the finished basement instead.

That is why he rejects traditional market research and compares his method to interrogation: ask people to tell the story of how they decided that today was the day. Because purchases are not random, he asks how many buyers are actually ready, rather than relying on funnel probabilities.

Moesta says he has worked on around 3,500 products and services. He can't read or write because of childhood head injuries, which made vague research terms like fast and easy useless to him. The process starts by framing a question about what makes people say today is the day, finding people who recently bought, and extracting their stories. From these he pulls the pushes, pulls, anxieties, habits and what he calls hire and fire criteria.

Rather than segmenting, he clusters stories into pathways, since sets of pushes go with sets of pulls. Most products are hired for three to five conflicting jobs, such as speed versus thoroughness. Intercom found four reasons people hired it and, instead of building four products, switched off irrelevant features per pathway. One pathway competed with HubSpot, another with Zendesk, and pricing was matched to each.

Moesta ties the dyslexia into his craft. He says it taught him to see patterns, and Rachitsky is amazed he writes books at all. Moesta explains that his company Scribe Media runs recorded conversations that are transcribed so the books sound like him, and he can produce one in three and a half to four months.

Moesta has spent about a decade studying why people move between companies, on the idea that employees hire companies more than companies hire employees. He is writing a book on it with Michael Horn and Ethan Bernstein. The phrase he hears most is "I was so lucky", but unpacking the story always reveals preparation, pushes, pulls and anxieties.

He says over 50% of people who got new jobs didn't get more money. They wanted skills, balance, challenge, or to be around smarter people before founding something. When people do mention money, it often stands for respect, responsibility or a measure of progress.

His first tip is to read Chris Voss's Never Split the Difference. Moesta deliberately plays things back incorrectly because people say no, then explain further, while a yes ends the conversation. His second is to talk only to people who already tried to make the progress, even for new products. A social media company that wanted a marketplace studied eBay and Etsy sellers and buyers, and he says it built a marketplace worth almost $3 billion.

On sample size, he says the patterns of pushes, pulls, anxieties and habits begin to repeat around seven or eight interviews. He usually does ten and no more than twelve, preferring two rounds of twelve to one of twenty-four. Statistical significance matters only if sampling is random, and he uses design experiments to cover the range of the market.

His third tip is to skip the discussion guide, because identical questions stop you from following the most meaningful threads. Instead he asks "tell me more" and "give me an example" until the interviewee reaches the edge of language, then brackets with options he knows are wrong so they elaborate.

To start, Moesta suggests finding ten recent customers and asking not about the product but about why they bought it: what they hoped for, feared, gave up, and how they convinced others. He describes three kinds of energy, functional, emotional and social, behind every decision. He also recommends interviewing churned users, since they are still making progress in their own way.

He distrusts predictions: "Bitchin' ain't switchin'." At Basecamp, people said they'd leave without Gantt charts, yet they didn't. Following your best users up-market can wreck the simplicity that attracted everyone else. Moesta adds that value depends on where someone starts as well as where they end, and overshooting the outcome makes customers want a discount.

He describes layers of language. First comes the pablum layer, such as "it was good". Next is the fantasy and nightmare layer of exaggeration, and below that is what actually happened. One interviewee took 18 months to buy a $137 coat rack, though he believed it took a week.

Lenny relays the most-liked LinkedIn question, a skeptical challenge asking for a zero-to-one product built with Jobs to Be Done that achieved broad adoption. Moesta points to Autobooks and to Techstars companies such as Nutrisense and Havoc Shield. He says the method helps decide what not to build, and calls it hypothesis-building research, in contrast to the hypothesis-testing that dominates large organizations. He quotes Drucker's line that what a business thinks it sells is not what customers buy.

For new products he asks what people will stop using when yours launches, and interviews those people. He believes there are no truly new jobs, only better ways of delivering them. When Lenny raises Twitter's attempt, Moesta separates a supply-side flavor with hundreds of prescriptive steps from his own qualitative method of process, practice and skills. He says the most dangerous move is to sit in a room and guess the jobs, since you will be 100% wrong.

He explains the irrational detail behind Snickers: its peanuts and nougat mash into a ball that absorbs stomach acid, while a Milky Way's caramel melts like a drink. His point is to connect supply and demand but start from demand, since struggling moments exist before any product does.

Moesta says he met quarterly with Clay Christensen for 27 years, and that Christensen wanted the technique turned into a theory. Christensen's version is a thinking framework, while Moesta's is a tactical method. He contrasts both with Tony Ulwick's approach, which is function-focused and asks what jobs a product can do, whereas he holds that only people have jobs. He grants that Ulwick's step-heavy method suits risky, regulated environments if the organization is disciplined. He recommends Demand Side Sales as the first book.

It doesn't work when there is no real choice, such as employer-provided health insurance, or when people want the choice to be obvious. In those cases he uses ethnography, spots friction, prototypes, and studies how people use the thing rather than why they bought. The same applies to habits: people can recall when they chewed gum, but not when they bought it, and someone who has used Tide for 20 years will make up a reason. A switch to Gain, by contrast, produces a detailed story.

Asked about misconceptions, he says the biggest is thinking it's pain and gain rather than context and outcome. Another is focusing only on outcomes, and the worst mistake is skipping interviews. Stories that seem irrational usually just lack their context, and innovation happens when people change direction.

Moesta closes with three takeaways. Struggling moments are everywhere, but people act on them only in certain contexts, so study the ones people act on. Think about the progress people want by their standard, not yours. And choose what to be bad at, since most failed products made a trade-off the customer disagreed with.

In the lightning round he recommends Shape Up by Ryan Singer and The End of Average by Todd Rose. His favorite interview question asks for the top three struggles that, if solved, would change the business. He credits Intercom's success partly to its founders bringing the whole executive team into the interviews.

His dining-room-table story shows the method at work. Downsizing buyers insisted they didn't want a dining table, but they wouldn't move until they knew where theirs would go, because it held decades of family memory. He sacrificed the second bedroom suite to add a symbolic space for a table, and sales rose 22%.