🌊 Deep Dive: How I Created My 2026 Strategy (With AI’s Help)... The Honest Playbook
Why I stopped winging it, how Claude helped me consolidate a year’s worth of chaos, and the critical mistakes you need to avoid when using AI for strategic planning
Welcome back to Inside Small Giants for 2026! I hope you had a restful break and are ready for another year of honest insights into building a business that's great instead of just big. This is our first deep dive of the year, and I'm kicking things off with something timely: how I actually planned 2026. If you're still figuring out your strategy for the year (or if you created one but aren't sure it's realistic), this one's for you. At the end of this post, paid subscribers will find 3x downloadable resources: the exact AI prompts I used, a strategy document template you can customise, and a checklist to catch hallucinated numbers before they make it into your plan. Let's dive in.
Let me be honest: I find strategic planning painful.
Not because I don’t value strategy — I do. But because most strategy documents feel like a performance designed to impress board members and investors rather than tools that actually help you run your business.
You know the ones I’m talking about. Twenty slides of market sizing and TAM calculations. Ambitious revenue projections that ignore operational reality. Lofty mission statements that have nothing to do with what you’re actually building day-to-day.
That wasn’t going to work for Mane Hook-Up.
After a chaotic 2025 where we tried to do too much — spreading ourselves thin across product development, events, community building, and partnerships without the team or runway to support it all—I needed a different approach to planning 2026.
I needed a strategy document that would actually help me make decisions, not just look impressive in a pitch deck.
So I used Claude (Anthropic’s AI) to help me create it. The entire process took about an hour, and the result is a 10-page strategic plan that I actually reference weekly rather than filing away and forgetting.
Here’s exactly how I did it, what worked, what didn’t, and the reusable templates and prompts you can use to do the same.
The Situation: Why I Needed Strategy Help
At the end of 2025, we had done a lot in comparison to 2024. By traditional metrics, the growth looked incredible.
But here’s what those numbers didn’t show:
We’d set wildly ambitious goals for 2025 that we didn’t hit
We generated revenue from multiple streams but had no clear prioritisation between them
We built community, launched events, onboarded stylists to the platform, and published podcast episodes—but it felt scattered
I was exhausted from trying to do everything at once
The biggest lesson from 2025 was brutally simple: we tried to do too much, too fast.
I needed a 2026 strategy that would force focus. Three clear priorities. Realistic targets. Measurable outcomes. And most importantly, a plan I could actually execute without burning out.
But I didn’t have weeks to spend on strategic planning. I needed something that would help me consolidate all the learnings from 2025, synthesise data from multiple documents (pitch deck, event calendars, revenue reports), and create a coherent plan quickly.
That’s where AI came in.
How I Used Claude: The Actual Process
The entire strategic planning process took about an hour of focused work. Here’s exactly what I did:
Step 1: Gathered All Relevant Documents
Before touching AI, I collected everything that would inform my 2026 strategy:
2025 revenue breakdown and performance data
Our pitch deck (containing market analysis and positioning)
2026 events calendar (we’d already planned major events)
Platform user data and metrics
Community metrics and engagement data
Podcast performance data
Having this data ready was crucial. AI can synthesise information brilliantly, but only if you give it the right inputs.
Step 2: The Initial Prompt
Here’s the structure of the prompt I used (without my specific business details):
Initial Prompt Structure:
I need to create the 2026 strategy for [MY COMPANY] taking the following into consideration:
FOCUS AREAS:
There will be a focus on [NUMBER] things:
1. [Priority 1 - for me, this was educational events]
2. [Priority 2 - for me, this was growing the platform]
3. [Priority 3 - for me, this was building community]
REVENUE STREAMS:
- [Stream 1] = [how it generates revenue]
- [Stream 2] = [how it generates revenue]
- [Stream 3] = [how it generates revenue]
KEY CHALLENGES:
- [Challenge 1]: [what you need to figure out]
- [Challenge 2]: [what you learned and need to apply]
- [Challenge 3]: [what decision needs to be made]
STRUCTURE:
We want to create some sections similar to last year's strategy:
- Summary on [LAST YEAR]
- [COMPANY] in 5 years
- [COMPANY] in 2 years
- The rest is up for consideration
Please review all attached documents to make sure you have all relevant information needed. Let me know if you need me to answer any questions before you start drafting the strategy.
The key here was being specific about focus areas while leaving room for AI to ask clarifying questions. I didn’t try to provide everything upfront—I let the AI tell me what information it needed.
Step 3: Answering Claude’s Follow-Up Questions
Claude came back with about 15 clarifying questions organised by category. This was actually one of the most valuable parts of the process—the questions forced me to think through details I hadn’t fully considered.
Here were the question categories Claude asked:
