What do Decisions, Rollercoasters and Cereal all have in Common?

_{Day 16/100 Hey, my lucky number}

I have a confession to make. I love loops.

• I love rollercoaster loops that make my stomach do backflips.

• I love Fruit Loops that turn my milk into a sugary rainbow potion.

• I even have a whole content theory on the art of opening and closing narrative loops

But today, I'm obsessed with a different kind of loop - one that might just save your marketing career when you're staring at 37 open browser tabs and still can't decide which direction to take your campaign.

It's decision-making time, and we rarely have all the data we need. Ever launched a campaign while thinking "I'm about 62% sure this is the right move"? Same. Welcome to marketing in 2025, where waiting for perfect information is like waiting for LinkedIn to stop changing its algorithm – an exercise in disappointment.

How to Make Better Decisions When You Don't Have All the Facts

In marketing, we rarely have all the information we need to make the perfect decision. But waiting for perfect data is like waiting for perfect weather in London—it's going to be a long wait, and you're probably missing opportunities.

Enter the OODA Loop—a decision-making framework that helps you act quickly and adapt in fast-changing environments.

What is the OODA Loop?

OODA stands for Observe, Orient, Decide, Act. It was developed by Colonel John Boyd, a military strategist, to help fighter pilots make split-second decisions in combat. But it turns out, this framework is just as useful for marketers trying to navigate the battlefield of digital content.

Here's how it breaks down:

Observe: Gather available data and information about your situation.

Orient: Analyze this information through the lens of your experience and knowledge.

Decide: Choose a course of action based on your analysis.

Act: Implement your decision and see what happens.

The good shit comes from not going through these steps just once, but cycling through them continuously.

Using OODA in Marketing Decisions

Imagine this: Your competitor just launched a feature that's getting traction. You don't have time for three weeks of market research. What do you do?

Observe: Check social mentions, monitor forums, use AI to analyze sentiment around the new feature.

Orient: How does this affect your positioning? What resources do you have to respond? What have similar situations taught you?

Decide: Will you match the feature? Pivot to highlight your different strengths? Reposition your messaging?

Act: Launch your response—whether it's a counter-campaign, a product update announcement, or a new content strategy.

Then, critically, you run the loop again based on the results. See feedback, adjust, repeat.

We Live in 2025, Just Do It All With AI

All of this is good, but understanding the process can take as long as doing it, so I made it easy for you.

I built a whole ass prompt to do the entire thing, because if you’re anything like me, you need 8 hours sleep to think properly, and who is getting that in this economy?

It can help you cycle through OODA loops faster by:

1. Automating observation: Monitor competitors, track market shifts, and alert you to changes

2. Enhancing orientation: Analyze patterns in data you might miss

3. Testing decisions: Run simulations or A/B tests quickly

4. Accelerating actions: Deploy content, campaigns, or communications faster

Try This AI Prompt for Quick Decision Support

I've created a prompt template to help you use the OODA framework with your AI of choice.

All you need to add is your TARGET, GOAL, SITUATION and DATA. Can be as much, or little (usually this is the case) as you have.

Just copy, paste, and customize:

VARIABLES (Edit these before using)

TARGET: [Your target audience and content type (e.g., "B2B SaaS companies via newsletter")]

GOAL: [Primary business objective (e.g., "Increase trial signups by addressing pain points")]

SITUATION: [Current market conditions or competitor actions to respond to]

DATA: [Key metrics, feedback, or insights you currently have]

ROLE
Adopt the role of a strategic content marketing director with expertise in rapid decision-making and market adaptation. You excel at analyzing incomplete information, identifying patterns, and creating content strategies that outmaneuver competitors. You have deep experience in applying military strategy concepts like the OODA loop to content marketing situations.
TASK
Analyze the current content marketing situation using the OODA (Observe, Orient, Decide, Act) framework and develop a comprehensive content strategy that allows us to adapt quickly to market conditions and gain competitive advantage for {TARGET}.
STEPS

OBSERVE: Thoroughly analyze all available data, market trends, and competitor actions
ORIENT: Synthesize this information with past experiences to identify opportunities
DECIDE: Determine the optimal content approach based on analysis
ACT: Outline specific, actionable steps for implementation
FEEDBACK LOOP: Establish metrics and feedback mechanisms for continuous improvement

CONTEXT/CONSTRAINTS

Target audience and content type: {TARGET}
Business objective: {GOAL}
Current market situation: {SITUATION}
Available data and insights: {DATA}
Time and resource constraints will be identified in the Observe phase

GOAL
Create a nimble, adaptive content strategy that allows us to move faster than competitors, capitalize on emerging opportunities, and continuously improve our approach through rapid feedback loops and iteration.
FORMAT

Use clear headings for each OODA phase
Include bullet points for key insights and actions
Use tables for comparative analysis
Highlight critical action items and metrics
Include timeline elements where appropriate

OUTPUT
Deliver a complete OODA-based content strategy including:
1. OBSERVE (Current Situation Analysis)

Market dynamics summary (200-300 words)
Competitor landscape analysis with key insights from {SITUATION}
Content performance data interpretation from {DATA}
Environmental factors and resource constraints analysis
Identification of information gaps and assumptions

2. ORIENT (Strategic Context & Opportunities)

Analysis of how current situation relates to past experiences and patterns
Identification of 3-5 key opportunities based on market gaps
Constraints and risk assessment
Competitive advantage analysis considering {BUSINESS_GOAL}
Resource alignment with {AVAILABLE_RESOURCES}

3. DECIDE (Strategic Direction)

Content strategy hypothesis (what we believe will work and why)
Top 3 content priorities with rationale
Resource allocation recommendations
Risk mitigation approaches
Decision criteria and success metrics
Timeline considerations based on {TIME_CONSTRAINT}

4. ACT (Implementation Plan)

Detailed content calendar with specific deliverables
Assignment of responsibilities
Production workflow and approval process
Distribution and promotion tactics
Engagement strategy and audience interaction plan
Contingency options for rapid pivoting if needed

5. FEEDBACK LOOP (Continuous Improvement)

Key performance indicators (KPIs) aligned with {BUSINESS_GOAL}
Data collection methods and schedule
Analysis framework and decision triggers
Timeline for OODA loop repetition
Team learning and adaptation mechanisms

The strategy must address how to outpace competitors through faster OODA loops while maintaining content quality and strategic alignment with {BUSINESS_GOAL}.

If you want to know more about my prompt writing process, holla at me in the replies. I’ve written over 3,000 of them now for Penfriend, and likely another 2k for my own stuff.

Happy Looping

The OODA Loop won't make every decision perfect, but it will help you make better decisions faster—which is often the difference between seizing an opportunity and watching someone else take it.

✌️ Tim "Loop-de-Loop" Hanson
CMO @Penfriend.ai

P.S. I'm writing this from a mountain cabin during a snowstorm, trying to apply the OODA loop to my current situation.
Observe: It's freezing.
Orient: I have no snowshoes.
Decide: Maybe that third cup of coffee will warm me up.
Act: Realize the power might go out and I should probably save my coffee for when I really need it.

If this newsletter suddenly ends mid-sentence, please send a rescue team with Wi-Fi and extra hotspot data.