Your 2026 AI Strategy Offsite (Agenda inside)

Welcome back to Watch Me AI

We are currently in that strange, hazy week between Christmas and New Year’s. You rarely know what day of the week it is, there is lots of cheese involved, and you have a moment to breathe.

I love using this quiet time to think about the year ahead.

Usually, this involves a blank notebook and a lot of staring at the ceiling. But this year, I’m running a Personal AI Offsite.

Here is the agenda for my AI Planning Session (and how you can do it too).

Reminder: Early bird pricing for The AI Business Playbook ends Wednesday night.

The Playbook is my entire AI operating system. All the prompts, automations, and workflows I use to run my business.

Early bird pricing ($247) ends December 31st. After that, the price goes up to $497.

Get it here 👉 The AI Business Playbook

1. The “Data-Driven” Look Back

We often rely on vibes to judge how our year went.

If you’ve been using AI tools this year, you have a goldmine of real, personal data. Let's hold up that mirror and get to the juicy insights.

(Note: I’m referencing specific tools I use, but you can do all of this with your go-to AI tools. It works best with the tool(s) that know you best.)

How to do it: If you use Granola (or any meeting recorder that allows you to query bulk transcripts), or if you have ChatGPT Memory enabled, run these prompts to get the truth about your year:

The Time Audit: “Looking at my meetings/chats from 2025, what 3 topics consumed the most time? Did these align with my stated goals, or was I getting pulled into the weeds?”
The Impact Audit: “What activities or decisions actually moved the needle on my [Revenue/Project Goals]? Contrast this with the activities that felt urgent but produced little result.”
The Energy Audit: “Analyze the sentiment of my voice/text. When did I sound the most excited and confident? When did I sound the most drained, frustrated, or repetitive?”
The “Blocker” Audit: “What recurring problems or ‘fires’ did I spend the most time fighting? Is there a pattern to what keeps distracting me?”

You can go even deeper by querying your Google Drive, Calendar, or LinkedIn data. I walk through how to do this in the 2026 AI Strategy Planning Template — one of the early bird bonuses for the AI Business Playbook.

2. The “Coach” (Strategic Planning)

Once I have the data, I switch to planning.

1. Start Without AI

Grab a notebook (or a blank doc) and brainstorm your goals for 2026. What do you want? What does success look like for you come December 2026? Write it down in your own words first. AI is great at refining, but only you know what your hopes and dreams are.

2. Go Deeper with AI

Now bring in the AI. Share what you wrote and let it help you expand and clarify.

“Here are my goals for 2026: [paste your notes]. Help me go deeper. Ask me questions to clarify my vision and surface anything I might be missing.”

I don’t like typing out long brain dumps, so I use Whispr Flow to dictate. I ramble about what I want, and let the AI structure it.

3. The Values Check

Before you go further, make sure your goals actually make sense together:

“Based on what I’ve told you, do my goals actually align with what I say matters most to me? Call out any contradictions or tensions.”

4. Narrow, Focus, and Get Specific

If you’re like me, you’ll have too many goals at this point. This is where AI really shines — helping you narrow down and get tactical.

I like asking: “Which 20% of these goals would likely yield 80% of the impact? What should I actually prioritize?”

Once you've narrowed, have it help you focus and plan. For example:

If you run a business: “My most important goal is [X revenue / X customers / X launches]. Help me reverse-engineer this into monthly and weekly targets. What specific activities need to happen each week to hit that number?”
If you work in a company: “My most important goal is [promotion / launching X initiative / hitting X metric]. What are the key milestones I need to hit each quarter? What will my stakeholders actually care about?”

I ended up spending several hours on this part. The forced focusing and detailed planning was extremely helpful.

5. The Reality Check

Before you call it done, stress-test the plan:

“What needs to be true for this plan to work? What am I assuming that might not hold?”
“Imagine it’s December 2026 and this plan failed. What went wrong?” (The Pre-Mortem)

You can then ask the AI for ideas on how to mitigate the risks (see number 4 below).

3. Make It Visual

Resolutions are words. It helps to create a visual asset to make your goals more tangible and easier to track.

Here are three ways to make it real:

The Visual Roadmap: “Create a visual roadmap for my 2026. Style it like a clean, modern infographic. Show quarterly milestones for [Goal A], [Goal B], and [Goal C] leading to my end-of-year vision.”
The Weekly Scorecard: “Based on my plan, create a simple weekly scorecard I can use to track whether I’m on pace. Include the 3-5 leading indicators that matter most, with specific target numbers. Make it something I could print and post on my wall.”
The Magazine Cover: “Generate a photorealistic image of me on the cover of Forbes Magazine in December 2026, having achieved [Big Goal].” It sounds silly, but can be great motivation and inspire clarity.

I'm mainly using Nano Banana or ChatGPT’s image generator for these.

4. The Accountability System

A plan is useless if you forget it by February 1st.

You need systems that put your goals in front of your face and keep you on track.

Option 1: The Automated Check-In

Set up a simple automation to force a monthly review. You can use ChatGPT, Relay, or even a recurring calendar event with an AI link.

The Prompt (to draft your check-in agenda): “Create a 15-minute monthly strategy review agenda. Include: (1) scorecard review — am I hitting my weekly targets? (2) what worked vs. what didn’t, (3) what’s the one thing to focus on next month, (4) do I need to adjust the plan?”

Option 2: The Weekly 5-Minute Pulse

Block 5 minutes every Friday. Open your scorecard and answer three questions:

Did I hit my numbers this week?
What’s the one thing that moved the needle most?
What’s the one thing I’m avoiding?

Log it somewhere — a note, a spreadsheet, a voice memo. The ritual matters more than the format.

Option 3: The “Back on Track” Prompt

You will fall off in February. Expect it. When it happens, use this:

“I set these goals in January: [paste goals]. It’s now [Month] and I’ve fallen off track. Help me identify the smallest possible action I can take today to restart momentum.”

Option 4: The Accountability Partner

AI is great, but sometimes you need a human. Find one person — a friend, a colleague, a coach — and share your scorecard with them. Set a 15-minute monthly call. The social pressure is worth more than any app.

That's the agenda for your 2026 AI Strategy Offsite. By the end of this session, you should have:

Insights: A data-backed view of how you spent 2025 (and what you need to stop doing).
Vision: A clear picture of what success looks like in December 2026.
The Plan: Specific weekly and monthly targets to get there.
The System: A built-in accountability loop so you don’t lose the plot by Valentine’s Day.

Bonus Round: 3 More Ways to Use AI for a Reset

Once the big strategy is done, here are three lighter ways to use AI to set yourself up for success.

1. The “Gratitude” Audit

It’s easy to let relationships slip when you’re busy. Use AI to surface the people you need to thank.

The Prompt: Ask Granola (or whichever AI knows your collaborators best), “Who did I meet with this year who gave me great advice or energy, whose worthy of a gratitude note?”
The Action: Ask AI to draft a template, but you write the actual note. Send 5 of these before next week. It starts your year on a high note of connection.

2. The “Systems” Reset

Reduce decision fatigue by templatizing the recurring stuff you do every week.

The Prompt: “I write a weekly status update for my team every Friday. Based on what makes a good status update, create a reusable template I can fill in each week in under 5 minutes. Include sections for: wins, blockers, priorities for next week, and any asks.”
Bonus: Do the same for meeting agendas, project kickoffs, or 1:1 prep docs. Build the templates once, reuse forever.

3. The Learning List

Instead of doom-scrolling, curate your input for the new year.

The Prompt: “I want to get smarter about [Topic A] and [Topic B] this year. Curate a syllabus of 6 newsletters and 6 podcasts that will teach me and keep my interest. Explain why each is worth my time.”

I hope these ideas set you up for your most successful, fulfilling year yet.

If this was helpful, forward it to a friend who’s also planning their year.

Wishing you a wonderful 2026!

Mollie

P.S. Final reminder, early bird pricing ends December 31st.

The AI Business Playbook is my full operating system for using AI at work.

This includes the exact prompts, automations, and workflows I use to run my business (including how I set up systems like the ones above).

Early bird pricing ($247) ends December 31st. That’s in 2 days. After that, the price goes up to $497.

Get it here 👉 The AI Business Playbook