A common leadership mistake is setting impossible goals. This often stems from a flawed planning process that doesn't clearly distinguish between aspirational "stretch" goals and committed "planned" goals. Without this clarity, especially in financial planning, teams are set up for failure.

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A significant gap exists between leadership's strategic decisions and the team's ability to implement them. Leaders assume that mission statements or strategic pillars are self-explanatory, but frontline workers often lack clarity on how these goals translate into daily tasks, leading to wasted effort and misalignment.

Ambitious leaders are often "time optimists," underestimating constraints. This leads to frustration. The 'realistic optimist' framework resolves this tension by holding two ideas at once: an optimistic, forward-looking vision for the future, and a realistic, grounded assessment of present-day constraints like time and resources. Your vision guides you, while reality grounds your plan.

Setting a specific, achievable goal can inadvertently cap your potential. Once hit, momentum can stall. A better approach is to set directional, almost unachievable goals that act as a persistent motivator, ensuring you're always pushing beyond perceived limits and never feel like you've arrived.

Vague revenue targets are ineffective. To make a goal achievable, you must deconstruct it into specific revenue-generating activities, like individual launches, and assign a monetary target to each. Without this detailed plan, a financial goal is just a wish that is unlikely to be realized.

When founders define success by external metrics like net worth or exit size, the target constantly shifts upward upon achievement. A $1 million goal becomes $10 million, and a single exit becomes a need for multiple. This creates a perpetual cycle of striving without ever feeling successful.

Contrary to keeping targets private to avoid failure, entrepreneur Mark Laurie advocates for announcing huge goals publicly. This act forces the team to reverse-engineer a plan, aligns stakeholders on the ultimate prize, and increases the probability of achievement—making the risk of public failure worth it.

Many sales plans fail because they focus only on the end goal, like a revenue target. A more effective approach is to plan the specific, repeatable behaviors required to achieve that outcome, such as identifying a list of target conquest accounts. This turns a 'vision board' into a concrete action plan.

Pursuing huge, multi-year goals creates a constant anxiety of not doing "enough." To combat this, break the grand vision into smaller, concrete milestones (e.g., "what does a win look like in 12 months?"). This makes progress measurable and shifts the guiding question from the paralyzing "Am I doing enough?" to the strategic "Is my work aligned with the long-term goal?"

Teams often self-limit output because they know overperformance will simply raise future targets to unsustainable levels. This "prison of expectations" incentivizes predictable mediocrity over breakthrough results, as employees actively manage goals to avoid future failure.

Bilyeu calls 'under promise, over deliver' a failure mindset focused on managing expectations. True high-achievers set impossibly high goals—so high they're almost embarrassing—and then work relentlessly to surpass them, aiming for extraordinary capability, not just safe delivery.