The Outbound Playbook: Problems, Signals, Execution

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.