Feeling Stuck on a Difficult Decision? These 10 Questions Will Help You Move Forward.
More is lost by indecision than wrong decision.
— Marcus Tullius Cicero
You’ve probably been there: the pros and cons list isn’t helping, every option comes with tricky tradeoffs, and you're stuck trying to predict the future. When a decision feels especially complex or high-stakes, even small next steps can feel uncertain.
What makes these moments so hard isn’t just the number of choices—it’s the weight behind them. The desire to get it right. To honor your values. To make a decision you won’t regret later.
That’s where better questions—and a few reliable decision-making tools—can be helpful. The 10 questions below are designed to create clarity from the overwhelm. Each one is informed by a different research-backed decision-making model.
Decision-Making Frameworks
While it would be overwhelming to try to use every model listed below, you may find that one or two stand out and offer a clearer way forward.
WRAP Process (from Decisive by Chip & Dan Heath): This four-part process helps you avoid common traps like binary thinking and overconfidence. It stands for: Widen your options, Reality-test your assumptions, Attain distance before deciding, and Prepare to be wrong. It’s especially helpful when you’re stuck toggling between just two choices or overly confident in your assumptions.
OODA Loop (Observe, Orient, Decide, Act): Developed by military strategist John Boyd, this model emphasizes rapid, iterative decision-making. It reminds us that decisions don’t need to be perfect—they need to be responsive. It’s especially helpful when conditions are changing or you feel pressure to act without clarity.
Six Thinking Hats (Edward de Bono): This creative problem-solving tool encourages you to look at a decision through six distinct lenses: facts (white), feelings (red), caution (black), optimism (yellow), creativity (green), and structure (blue). It helps you break out of habitual thinking and examine your decision from all angles. It’s also great for teams to use in decision-making or problem-solving scenarios.
Pre-Mortem Technique (Gary Klein): Instead of asking “What could go wrong?” after deciding, this approach invites you to imagine that your decision has already failed. Then you ask: Why did it fail? It’s a strategic way to uncover risks and hidden flaws before they become real problems.
Regret Minimization Framework (Jeff Bezos): This method asks you to imagine yourself in the distant future, looking back on the decision you’re about to make. Which path would you regret not taking? It helps you shift focus from short-term discomfort to long-term alignment.
10 Coaching Questions for Difficult Decision-Making
Whether you're coaching someone else through a tough choice or facing one yourself, these 10 coaching questions are designed to help you slow down, think deeply, and move forward with more clarity and confidence.
1. What matters most in this decision?
Start here. Ground the decision in your values before you get lost in the options. This question helps you surface the deeper priorities that should drive your choice—like integrity, impact, connection, or well-being.
This reflects Values-Based Decision-Making, which centers decisions around personal or organizational priorities. It also aligns with the “W” in the WRAP process—Widen your options—because knowing what matters most can open up new possibilities beyond the obvious.
2. What do I really want here?
Not what you’re expected to want. Not what looks good on paper. What you want. This question invites you to separate your true desire from external noise.
This ties into the Orient stage of the OODA Loop, where you take time to understand your internal landscape before choosing a course of action. It’s about clarity, not consensus.
3. What’s the worst-case scenario—and how likely is that to happen? If it did, could I handle it?
Fear clouds your judgment. This question lets you name the worry, assess its realism, and begin to separate emotion from probability.
This is the heart of the Pre-Mortem Technique, where you imagine the decision has failed and explore what could have caused it. Pairing this with the WRAP process (specifically, Reality-testing your assumptions) makes your thinking more grounded and less reactive.
4. If I say yes to this, what am I saying no to?
Every “yes” costs something. Time, energy, focus, other opportunities. This question makes the trade-offs visible.
According to Decisive by Chip & Dan Heath, a common trap is ignoring opportunity cost—the things we give up when we choose. Bringing those trade-offs into view helps you make a decision with your eyes wide open.
5. What would I choose if I weren’t worried about disappointing anyone?
This question invites your unfiltered truth to the surface—especially if people-pleasing or external pressure is shaping your decision.
In the Six Thinking Hats model, the “red hat” acknowledges emotional bias, while the “white” and “yellow” hats help you evaluate facts and positives. By noticing where guilt or obligation is driving the choice, you free yourself to decide with integrity.
6. What does my gut say? What does my head say? What does my heart say?
Each voice—instinct, logic, and emotion—has insight to offer. When they align, the path becomes clearer.
This reflective check-in is a simplified version of the Six Thinking Hats model, helping you draw from multiple ways of knowing. By listening to all three, you integrate instinct, reasoning, and values in a grounded way.
7. What would my future self thank me for?
Zoom out. Imagine looking back from five, ten, or fifty years down the road. What decision would you be proud of? What would you regret not doing?
This is the Regret Minimization Framework in action. When you're overwhelmed by short-term uncertainty, this long-range lens helps realign your decision with who you want to become—not just how you want to feel today.
8. What would a trusted mentor or friend ask me to consider?
Sometimes we get so close to a decision that we lose perspective. This question invites you to imagine someone who knows your values and goals offering their honest input. What might they challenge you to see? What would they hope you don’t overlook?
This reflects the “Attain distance” principle in the WRAP process, and draws on research around perspective-taking in behavioral psychology. When you're feeling stuck, stepping outside your own viewpoint—even just imaginatively—can bring fresh clarity.
9. What would the most courageous version of me do?
Courage doesn’t mean certainty—it means choosing what aligns with your values, even if there’s risk. This question helps you bypass perfectionism and act with conviction.
This combines the Attain distance principle from WRAP with the forward-looking courage of the Regret Minimization Framework. By imagining yourself as your boldest, most grounded self, the next step may become clearer.
10. What’s one small step I can take toward clarity?
You don’t have to decide everything today. Sometimes, the first step reveals the second.
The final “A” in the OODA Loop is Act. Even small steps—like journaling, seeking advice, or blocking quiet time—can create the clarity you’ve been waiting for.
Coaching Questions to Inspire New Insights
Find fresh perspectives with these carefully crafted coaching questions designed to spark new insights and drive meaningful change. Whether you're coaching others or reflecting on your own growth, these prompts will challenge your thinking and guide you toward powerful breakthroughs.
