Not all business problems are created equal. Time savings often translate to five-figure cost savings, which may not be compelling. The most powerful executive problems are "six-figure problems"—major risk mitigation (avoiding lawsuits), significant revenue generation, or replacing other large costs.
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Executives don't care about tactical benefits like 'five fewer clicks'. A crucial skill for modern sellers is to extrapolate that tactical user-level gain into a strategic business outcome. You must translate efficiency into revenue, connecting the dots from a daily task to the company's bottom line.
Firing decisions should be a function of both incompetence and business constraint. Not all underperformers are equal priorities. Some are like a "trash can on fire in the driveway"—a problem, but not the company's main bottleneck. Focus firing efforts on roles that are the direct constraint to growth.
Focus on the root cause (the "first-order issue") rather than symptoms or a long to-do list. Solving this core problem, like fixing website technology instead of cutting content, often resolves multiple downstream issues simultaneously.
The "Discovery Tree" maps problems in three layers: Situation (how they do it today), Operational Problem (daily annoyance), and Executive Problem (C-level risk, e.g., getting sued). Focusing only on operational issues leads to small deals; connecting them to executive-level risks is necessary to justify a large investment.
Jacobs's team uses the acronym WOTWOM—Waste Of Time, Waste Of Money—as a rapid check on new ideas. Any suggestion can be challenged with this label if it doesn't clearly contribute to organic revenue growth or margin expansion. This simple tool creates a culture focused on high-leverage activities.
To justify a high price, connect a low-level operational issue (e.g., billing inefficiencies) to an executive-level P&L problem (e.g., revenue leakage) and finally to a critical C-suite metric. This transforms a minor annoyance into a must-solve business problem.
When solving a critical bottleneck, founders should choose the most direct action with the highest probability of success. Instead of indirect methods like content marketing for leads, choose actions so direct it would be 'weird not to work'—such as immediately flying to a customer's office to sign a critical contract instead of waiting for an email.
Don't try to fix everything at once. Inspired by the Theory of Constraints, identify the single biggest bottleneck in your revenue engine and dedicate 80% of your energy to solving it each quarter. Once unblocked, the system will reveal a new constraint to tackle next, creating a sustainable rhythm.
To capture an executive's attention, connect operational-level problems to their strategic business impact. A slow development cycle isn't just a process issue; explain how it directly causes delayed time-to-market, higher costs, and lost market share to competitors, which are the metrics an economic buyer truly cares about.
Getting approval for an operations hire is difficult because they aren't directly tied to new revenue. Instead of a vague promise of "efficiency," build a business case by quantifying the cost of a broken process—like a high lead disqualification rate—and show how the hire will unlock that hidden pipeline.
