Outbound rarely fails because reps are lazy. It fails because nobody told them who to target, what to say, or how often to say it. Will Aitken ran this one solo, walking through the outbound system he builds for teams. Almost every broken outbound motion fails at one of three points: weak messaging, targeting that is far too broad, and execution with no system behind it. Your buyer never asked what you do Ninety-five percent of the market is not buying right now, so leading with your product lands on nobody. Will's fix is to work out the buyer's status quo first. Competitor, doing it themselves, spreadsheet, or outsourced? Each breaks differently, and those breakages are what you reach out about. His shortcut for any role: every function exists to make the company money or protect the company's money. Work out which, then how that person is measured. The problem identification chart Will's core tool, borrowed from Gap Selling, which he notes he can use since he wrote the sequel. Three columns: the business problem, its impact, the root cause. You fill it in by asking what goes wrong next, repeatedly. His worked example ran from nobody trained to handle a mental health incident, through someone getting hurt, litigation, a PR problem, employees leaving, being unable to hire, to lost revenue. That last link is what a buyer actually cares about. Three kinds of signal, and they are not the same thing Catalysts are events that create the problem. Layoffs mean the remaining team cannot maintain policies across twenty systems. An acquisition means two IT environments getting blended into more chaos. Symptoms are observable directly. A job posting mentioning policy updates across networks tells you they have a capacity problem today. Intent is someone showing interest, in you or a competitor. Downloads, profile views, an old deal cycle, site visits. Start with the people who already half know you Will ranks prospects by familiarity, not fit alone: past users who changed companies, old deal cycles, webinar attendees, anyone connected to your executives or customers. The version that scales is building your list from lookalikes of existing customers. Reach out to Coca-Cola on the back of your PepsiCo work and they do not know you, but they know PepsiCo. He caps research at five minutes for mid-market, and is blunt about personalisation theatre. You cannot connect someone's interest in hiking to a cybersecurity audit. One good business reason beats a full account brief. Know your math before you change anything His example chain: two hundred calls, twenty connects, ten conversations lasting over thirty seconds, three meetings booked, two that showed up qualified. Each gap points somewhere different. Few connects means contact data, call timing, or spam flagging. Connecting but not converting means your opener is not creating curiosity. Conversations that do not become meetings means the problems you raise are not the ones they have. Resources mentioned GAP ProspectingProblem Identification Chart Template The Speakers: Will Aitken, Host, Sell Better Catch The Daily Sales Show live Follow Sell Better Explore our YouTube Channel Watch the replay Thank you to our sponsor: Outbound Sales Pro, First Orion, Replay, ZoomInfo
