Several years ago, while serving as a board member advising a company that was struggling to meet its operating plan, I came across a framework by Gabriele Oettingen called WOOP, which she discusses in her book “Rethinking Positive Thinking: Inside The New Science of Motivation.” WOOP stands for a simple, four-step self-regulation tool.
- Wish: Identify a clear, concrete wish or goal you want to achieve.
- Outcome: Envision and name the best possible result of fulfilling that wish.
- Obstacle: Pinpoint the main inner obstacle holding you back (like a habit, emotion or thought).
- Plan: Create an “if-then” plan specifying what you will do when that obstacle appears.
What got my attention was O, or identifying the main inner obstacle holding us back. The leadership team did a nice job with strategic planning and built a budget with clear assumptions. But the team had spent too little time identifying what within the company or the team would prevent the desired results. A budget describes the destination. It does not expose the behavior standing in the way or the obstacles.
Dr. Oettingen suggests a method called mental contrasting to address these inner obstacles. The mental contrasting methodology begins by imagining a desired outcome, then deliberately bringing the central inner obstacle into view. Her research suggests that positive fantasies alone can reduce the energy available for action. Mental contrasting connects the desired future to the reality that must change.
That distinction matters. A team may want to increase EBITDA by three points. The external obstacles are easy to name: pricing pressure, labor costs, competitors and uncertain demand. But, the more useful obstacles are internal behaviors — say, a Director of Sales who has an innate need to be liked and cannot exit an unprofitable customer relationship that may cause the company to miss budget, or a CFO who is an insightful, gifted analyst but awkward at building relationships with lenders during a capital raise.
Those obstacles rarely appear on a strategy slide because each one carries a difficult conversation. That is precisely why they matter. To implement the WOOP framework, start with one important wish you can reasonably achieve. Describe the best result in concrete terms. Then ask each leader to identify their strongest internal obstacle. Keep working until the obstacle becomes a behavior, assumption, incentive or fear that someone in the room can address.
Next, turn the obstacle into an if-then plan. The trigger should be observable, and the response should have an owner. To create an effective “If [obstacle], then I will [action]” plan, first identify a specific, effective response — either a concrete action we can take or a helpful thought we can tell ourselves — to address the obstacle. This response is called the action. When we embed this action in the structure “If [obstacle], then I will [action],” it becomes the plan.
Finally, run a 30-day test. Choose one measure to determine whether the obstacle is weakening. Review the evidence, not the intention. If nothing changes, the team may have named a symptom or protected the real issue.
This practice also reveals goals that should be abandoned. When the outcome has little chance of success, increased enthusiasm is a poor substitute for sound judgment. Resources can be redirected to a goal the company can credibly pursue.
Optimism has a place in leadership. It helps people envision a future worth building. Execution begins when leaders are equally willing to recognize obstacles they must confront to achieve it. A goal becomes useful when the obstacle enters the framework. ●
Sanjay Singh is a Board Advisor and Private Investor
