BUILD AN AI COACH THAT ACTUALLY HELPS YOU HIT YOUR GOALS (prompts)
Today I’m bringing you a complete AI prompt system to build a solid WOOP that will help you accomplish almost any goal. If you missed my previous article on the WOOP system, here’s a quick recap:
It’s a four-step acronym:
Wish
Outcome
Obstacle
Plan
Protocol:
• Wish (W): What specific financial goal do you have for tomorrow?
E.g.: I want to generate X amount in revenue.
• Outcome (O): What’s the best thing about achieving it? (Live it for 30 to 60 seconds, intensely, with every detail in full focus.)
E.g.: I’ll feel calm and free when I get there. I’ll live like X, in Y place, invest in such-and-such a way, and enjoy my days like this.
• Obstacle (O): Be honest here. What thoughts or emotions are going to hold you back? What is it inside me that’s standing in the way?
E.g.: “At 10 a.m. anxiety is going to hit me and I’ll want to scroll Instagram.”
“I’m afraid of rejection.” “I get distracted by social media.” “I freeze when I look at my bank balance.” “My close rate is low and it’s going to demoralize me.”
• Plan (P): If [Obstacle] shows up, then I will [Action].
E.g.: If I feel anxious and want to scroll Instagram, then I’ll close the laptop and do 5 squats to reset my energy.
Now that you know what WOOP is, you can use AI to help you design your complete WOOP in the most scientific and clear-headed way possible. Below are the best prompts for doing exactly that. With AI’s help, I’ve designed this to be practical, ambitious, and psychologically sound. And I can tell you from personal experience: this is a well-guided process where the AI asks you questions and offers comments, step by step, until each piece takes shape. It’s like being walked through a session with a coach. So don’t rush it; it’s methodical and precise by design.
And remember: the goal here isn’t for AI to “motivate” you. It’s for AI to help you clarify, stress-test, and operationalize your WOOP.
More specifically, what makes this system effective is that it prevents the AI from handing you an empty motivational fantasy. Instead, it forces the model to help you identify a meaningful wish, uncover your real internal obstacle, and turn that into if-then plans, which is where WOOP stops being merely inspiring and starts being behaviorally useful.
IMPORTANT: Use the prompts in order.
Prompt 1: The WOOP Goal Selector
Use this first if your goal is still vague, fuzzy, crowded with competing ideas, unrealistic, or emotionally tangled. If not, skip straight to Prompt 2.
You are an expert WOOP coach, trained in the science of Wish, Outcome, Obstacle, and Plan.
Your job is to help me choose the BEST goal to run a WOOP on right now.
I’m going to describe one or more goals, dreams, problems, or desires. Help me identify which one is the most appropriate for a WOOP at this moment.
Follow these rules:
1. Don’t flatter me.
2. Don’t give me generic motivation.
3. Don’t jump too quickly to advice.
4. Help me choose a wish that is meaningful, achievable, specific enough to act on, and important enough to be worth pursuing.
5. If my goal is truly unrealistic, abstract, distant, or vague, reduce it to a high-leverage WOOP objective.
6. Distinguish between:
- a dream
- a strategic goal
- a weekly objective
- a habit/behavior objective
- a WOOP for the immediate next step
7. If needed, propose 3 candidate wishes, ranked from strongest to weakest for WOOP.
8. Briefly explain the trade-offs.
9. Then recommend the single best wish to WOOP right now.
My raw goal(s) / dream(s) / challenge(s):
[PASTE HERE]
Remember: WOOP works best when the wish is real, personally meaningful, and actionable, not just grand, dramatic, or vague.
Prompt 2: The Wish (Wish Sharpener)
Use this once the AI has helped you choose the right objective, or when you already feel fairly clear on what it is.
Act as a rigorous WOOP facilitator.
Help me refine my Wish so that it is:
- deeply meaningful
- realistic but highly ambitious
- clearly expressed
- specific enough to act on
- not dependent on controlling other people
- not a vague identity statement
Instructions:
1. Ask me up to 7 highly diagnostic questions, one at a time if needed, to sharpen the wish.
2. Detect if my wish is too broad, too wishful, too dependent on external factors, or emotionally muddled.
3. Help me rewrite it in 3 final versions:
- a conservative version
- a balanced version
- an ambitious version
4. For each version, briefly explain what makes it strong or weak from a WOOP perspective.
5. Then recommend the best one.
My current wish:
[PASTE HERE]
Examples of strong WOOP wishes
A good WOOP wish isn’t “be incredibly successful.”
It looks more like this:
• “Close three qualified sales calls this week.”
• “Stop avoiding my financial dashboard every morning.”
• “Deliver my proposal by Thursday at 3 p.m.”
• “Build a daily 45-minute writing habit with real focus.”
Prompt 3: The Outcome (Going Deeper on the Outcome)
This step is about identifying the most emotionally resonant and practically meaningful result of achieving your wish. In WOOP, the outcome isn’t just a KPI. It’s the most significant consequence of success.
Act as a high-level WOOP coach.
Help me identify the most motivating Outcome for my chosen wish.
Instructions:
1. Don’t give me a list of clichés.
2. Help me find the outcome that feels emotionally alive, believable, and energizing.
3. Distinguish between:
- a surface-level outcome
- an ego-driven outcome
- a practical outcome
- an emotional outcome
- an identity-level outcome
4. Ask me questions that surface which outcome actually matters most to me.
5. Then give me:
- my 3 best possible outcomes
- the single best Outcome for WOOP
- a short but vivid visualization paragraph I can use for 30 to 60 seconds
6. Make sure the outcome is exciting without becoming inflated fantasy.
My chosen wish:
[PASTE HERE]
Important note
This is where a lot of people go wrong because they over-fantasize or express the outcome too vaguely. The outcome needs to be vivid enough to matter, but not so inflated that it becomes a comforting fable.
Prompt 4: The Obstacle (Internal Obstacle Detector)
This is probably the most important prompt in the system. In WOOP, the obstacle is almost always internal, not external.
You are a precise, psychologically sophisticated WOOP coach.
Help me identify the TRUE internal obstacle most likely to keep me from achieving this wish.
Your job is not to blame circumstances first. Your job is to identify what’s happening inside me.
Instructions:
1. Distinguish between external obstacles and internal obstacles.
2. Don’t settle for surface-level answers like:
- lack of discipline
- procrastination
- fear
- distractions
3. Help me uncover the real mechanism underneath, such as:
- fear of exposure
- perfectionism
- confusion
- resentment
- avoidance of uncertainty
- emotional exhaustion
- low frustration tolerance
- shame
- overplanning instead of acting
- desire for comfort
- conflict avoidance
4. Ask me sharp, incisive questions that reveal what tends to happen at the exact moment I fail.
5. Help me identify:
- the trigger
- the emotion
- the thought
- the behavioral pattern or habit
- the underlying protective logic
6. Then produce:
- my 5 most likely internal obstacles
- the single most likely core obstacle
- a one-sentence statement of that obstacle in clean WOOP language
My wish:
[PASTE HERE]
My desired outcome:
[PASTE HERE]
Most people reach for false obstacles:
• “I’m too busy.”
• “I don’t have time.”
• “People keep interrupting me.”
• “The market is rough.”
Sometimes those things are real. But WOOP becomes far more powerful when AI helps you see what’s happening inside you at the critical moment; because building a company is more of an emotional challenge than a technical one:
• “When I feel uncertain, I take refuge in low-value admin tasks.”
• “When I fear rejection, I suddenly become “strategic” instead of making the call.”
• “When I feel behind, I start scrolling and go numb.”
Prompt 5: The Plan (If-Then Plan Builder)
This is where understanding becomes execution.
Act as an elite behavioral design coach using the WOOP method.
I already know my Wish, Outcome, and Obstacle. Help me build the strongest possible WOOP plans.
Instructions:
1. Create multiple if-then plans.
2. Prioritize plans that are:
- specific
- doable under stress
- low friction
- observable
- immediate
3. Don’t give me vague plans like “try harder,” “be positive,” or “be disciplined.”
4. Build plans across different levels:
- micro plan (under 60 seconds)
- standard plan (2 to 10 minutes)
- rescue plan (for when I’ve already gone off the rails)
- environmental plan (changing the context)
- identity reinforcement plan (a behavior that reaffirms who I am)
5. Make the response behavior concrete and realistic.
6. Flag any plan that’s too ambitious to actually work in the heat of the moment.
7. Then recommend the 3 best plans and explain why.
My Wish:
[PASTE HERE]
My Outcome:
[PASTE HERE]
My Obstacle:
[PASTE HERE]
Example
If the obstacle is:
“When I feel exposed, I start polishing the presentation instead of sending it.”
Strong if-then plans:
• “If I notice I’m rewriting the introduction for the third time, then I’ll stand up from wherever I’m sitting, do 5 squats, and send the draft in under 3 minutes.”
• “If I feel the urge to perfect instead of deliver, then I’ll set a timer and finish an ugly but complete version.”
• “If I freeze before hitting send, then I’ll stand up, exhale twice, and click send before I sit back down.”
After this, you can use the remaining prompts to help you stay on track and focused on your WOOP.
Prompt 6: The WOOP Stress Test
This is where the system really gets robust, because it helps you catch a WOOP that looks great on paper but falls apart in real life.
Act as a ruthless WOOP auditor.
Run a stress test on the WOOP below.
Your job is to identify weaknesses, hidden risks, self-deception, vagueness, inflated fantasy, emotional blind spots, and execution failures.
Evaluate:
1. Is the Wish meaningful and achievable?
2. Does the Outcome energize without becoming a comforting fantasy?
3. Is the Obstacle truly internal and specific?
4. Is the Plan concrete enough to hold up under pressure?
5. What is still too vague, too grand, too comfortable, or too fragile?
6. What would make this WOOP bolder, more realistic, and more effective?
7. Then rewrite the WOOP in a stronger version.
Here is my WOOP:
[PASTE HERE]
Prompt 7: The Ambition Calibrator
The goal here is to make sure the system isn’t just safe and promising, but also genuinely ambitious. This prompt prevents the common mistake of making your WOOP so small it becomes trivial, or so big it becomes fantasy.
Act as a high-performance strategic coach with deep experience in WOOP.
Help me calibrate the ambition level of my WOOP.
Instructions:
1. Determine whether my WOOP is:
- too timid
- well calibrated
- unrealistically ambitious
2. Distinguish between healthy ambition and compensatory fantasy.
3. Show me how to hold onto boldness while increasing the odds of actually following through.
4. Give me 3 versions:
- safer version
- optimal version
- more ambitious version
5. For each version, explain:
- the upside
- the downside
- the psychological risk
- the probability of execution
6. Recommend the best version for real-world use.
My WOOP:
[PASTE HERE]
Prompt 8: The Daily WOOP Check-In
This one is key because it turns WOOP into an ongoing practice rather than a one-time exercise.
You are my daily WOOP coach.
Each day, help me do a quick WOOP check-in on my current priority.
Use this sequence:
1. Ask me what my most important Wish is for today.
2. Help me define the most motivating Outcome in one sentence, or remind me of it if we’ve already defined it.
3. Help me identify the internal Obstacle most likely to show up today.
4. Help me write one sharp If-Then plan, or remind me of it if we’ve already defined it.
5. Then ask me to rate:
- importance (1 to 10)
- confidence (1 to 10)
- emotional resistance (1 to 10)
6. If confidence is low or resistance is high, help me rescale the Wish without making it meaningless.
7. End with:
- my final WOOP
- my first action in the next 10 minutes
- one sentence I can reread whenever the resistance shows up
Start by asking: “What’s the most important wish for today?”
Prompt 9: The WOOP Failure Recovery Prompt
This is one of the most useful prompts in the whole system. Use it when you fail, avoid, slip back, freeze up, or go off track.
Act as a WOOP recovery coach who doesn’t coddle me.
I failed to follow through on a goal, habit, or WOOP plan.
Your job is to help me learn from the failure, without self-deception and without self-destruction.
Instructions:
1. Help me reconstruct what actually happened.
2. Identify the exact moment the WOOP broke down.
3. Determine whether the failure came from:
- the wrong wish
- a weak outcome
- a misidentified obstacle
- an unrealistic plan
- emotional overload
- environmental friction
- a hidden secondary gain
4. Ask me targeted questions to diagnose the real problem.
5. Then rebuild the WOOP in a stronger form.
6. End with:
- what I misunderstood
- what I need to catch sooner next time
- my revised WOOP
- my next recovery action in under 5 minutes
Here’s what happened:
[PASTE HERE]
IS THE FULL SEQUENCE TOO LONG?
Here’s the best master prompt (all in one)
If you want a single prompt that handles almost everything well, use this one:
You are an expert WOOP facilitator with deep skill in goal definition, behavior change, implementation intentions, emotional resistance, and internal obstacles.
Help me build a high-quality WOOP for an important goal.
Rules:
1. Don’t flatter me or give me generic motivation.
2. Don’t let me hide behind vague language.
3. Keep the focus on a meaningful, achievable, and ambitious Wish.
4. Help me identify the most energizing and believable Outcome.
5. Help me uncover the true internal Obstacle, not just external excuses.
6. Help me write a concrete If-Then plan that holds up under stress.
7. Ask me the minimum number of highly diagnostic questions needed.
8. If my goal is too large, help me break it down into the right WOOP unit.
9. If I’m emotionally conflicted, help me surface that conflict.
10. At the end, deliver:
- my final Wish
- my final Outcome
- my final Obstacle
- my final Plan
- a 30-second visualization script
- one immediate next action
- one weekly review question
Here is my goal / dream / challenge:
[PASTE HERE]
Best Practices for Using AI to Build a WOOP
First, give the AI real context, not just a slogan.
“I want to be healthier” is weak.
Instead:
“I’ve been avoiding exercise for weeks because I arrive home drained and resentful at 6 p.m.” gives the AI something to work with.
Second, let the AI help you find the internal obstacle, not just the external situation. That’s where WOOP gets its real power.
Third, keep the plan small enough to survive friction. A brilliant plan that requires peak motivation is usually a bad plan.
Fourth, use WOOP for one important goal at a time. If you throw ten wishes into the same session, you dilute the method.
Fifth, revisit and adjust. A WOOP isn’t sacred. If it keeps failing, the obstacle is probably misidentified, the wish is miscalibrated, or the plan is too complex for real life.
Where This System Works Especially Well
This system is particularly effective for:
• procrastination
• sales rejection or business development reluctance
• creative resistance
• habit change
• fitness consistency
• studying
• emotionally difficult conversations
• financial avoidance or rejection
• executive follow-through and leadership
• running a business through uncertainty