Set Tough Goals

March 2026 – Blake Cutler

A goal is something you count in order to track progress toward something you're trying to accomplish. It's a singularly effective management tool for harmonizing the actions of large groups while also encouraging initiative and rapid decision making.

To set a tough goal, use a 50/50 target. This means you have a 50% chance of success, assuming your team executes well. Aggressive targets like this inspire teams to stretch their abilities and enables risk taking. Countless product have met an untimely death while hitting all their goals on the way down. Yahoo did this. Don't be Yahoo.

We want to achieve our goals. But whether we achieve our goals, from a performance standpoint, matters less than:

  1. The importance of goal metric
  2. The difficulty of the target
  3. Progress made against the target, as compared to prior halves

The Two Types of Goals

Metric goals are usually better than milestones goals because they focus work on what matters most, outcomes, and give teams flexibility on how to achieve them. Milestones can be a better choice when you have deliverables with hard to measure outcomes or long development timelines. In such cases, breaking down the project into manageable milestones provides structure and a clear sense of progress.

Criteria for Evaluating a Goal Metric

When choosing a success metric, begin with the simplest thing you can count. Then add complexity, as needed, in order to better fit the evaluation criteria below.

Criteria for Success Metric Criteria for Milestones
A. Easy to understand and explain A. Easy to understand and explain
B. Tied to other valuable outcomes B. Clear success criteria
C. Outwardly focused C. Spaced-out over time
D. Easy to benchmark D. Memorable
E. Hard to game
F. Movable

Example Goals

Goal Status Current Target Expected
Grow DAU 🟢 On Track 45M 50M 60M
Grow MAU 🟡 At Risk 150M 180M 175M
Ad Milestones 🔴 Off Track 1 4 2
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