Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.
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The AI Tasks You Should Automate First for Maximum Productivity
Published about 1 year ago • 4 min read
How to Start Automating the Right Tasks with AI
Hey there! Welcome back to Founder Mode!This year, I spent more than 10 hours using AI tools to automate my content calendar. In search of the Perfect Day. The tools looked nice and were advanced, but they saved our team no time at all. I still had to schedule meetings, edit documents, and write emails. These tasks could have been automated easily.
I fell into a common founder trap. I automated what was fun, not what mattered. The problem? I aimed to automate fun and interesting tasks, like a really smart calendar. Maybe a throw back to my days building a calendar with Acompli (Peter CMO of Acompli on the podcast this week). However, I should have begun with simple, repetitive tasks that saved me the most time.
Since then, I’ve completely rethought how I automate tasks using AI. The result? I've saved hours each week. Plus, my work output quality has improved. One tool that has been super helpful in this automation journey is Lindy.ai
The key? I developed a clearer process to figure out which tasks to delegate to AI first. Let me try to explain.
The AI Delegation Matrix
Not all tasks are the same when it comes to AI automation. Here's how I break it down:
Time Impact: How much recurring time would you save by automating this task?
Quality Impact: Would AI perform this task better, worse, or the same as you?
I made a simple 2x2 matrix by looking at tasks in two ways. It has four quadrants:
Picking the right things to AI
Quadrant 1: High Time Savings, Better Quality
AUTOMATE THESE FIRST
These are the gold mines for automation. They save a lot of time while also improving quality.
Examples:
Health Optimization
Inbox / research / knowledge management
Code generation / refactor loops
Due diligence & M&A
Customer support triage
Quadrant 2: Low Time Savings, Same Quality
AUTOMATE WHEN CONVENIENT
These tasks may not save much time on their own. A basic automation solution makes it easier to automate tasks.
Examples:
Document formatting
Note organization
Simple data entry
Social media scheduling
Meeting notes (I never take notes much)
I use Fireflies.AI to record my meetings. It saves me about 5 minutes each meeting(as I typically don't take notes). However consistency makes it easier for my remote assistants to stay on track.
Quadrant 3: High Time Savings, Lower Quality
AUGMENT, DON’T AUTOMATE
These tasks can save a lot of time. However, fully automating them might lower quality. Use AI as a helper here.
Examples:
Strategic planning
Investor communications
Complex customer issues
Key hiring decisions
Product roadmapping
For investor updates, I use AI to create the structure based on our metrics and key events. I spend 30 minutes refining it. This cuts prep time from many hours to 45 minutes. Quality stays high.
Quadrant 4: Low Time Savings, Lower Quality
DON’T AUTOMATE
These tasks don’t save much time, and AI would not perform them well.
Examples:
Team motivation
Culture-building activities
Crisis management
Delivering difficult feedback
Core strategic decisions
I tried automating performance reviews. I found that the time saved was small. The results felt generic and impersonal. I’ve moved this into my “don’t automate” category.
Kevin’s 5-Step AI Delegation Process
Once you know which tasks to automate, here’s how I currently use the system:
Step 1: Task Inventory (30 minutes) Make a list of all recurring tasks. Be specific. For instance, "Write weekly team update" is clearer than only saying "communication".
Step 2: Matrix Mapping (20 minutes) Plot each task on the matrix. Focus on time savings and potential quality impact.
Step 3: Rough ROI Calculation (15 minutes)
Think about how much time you spend each week or month.
Add up the setup / build time to automate it and test.
Estimate out the savings you expect.
Step 4: Implementation Plan (45 minutes) Make a plan for each task. List tools, inputs, and timelines.
Here I try to time box the effort and if I can't do it that is an indication the tooling or my approach isn't right just yet.
If I fail I keep them on a list to revisit later as tools improve.
I mentioned Lindy.ai also check out Make.com or a blast from the past Zapier now has lots of AI'ness.
Step 5: Keep Improving (15 minutes weekly) Adjust as needed.
Track time saved.
Measure quality impact.
Some of the automations take maintenance; if, they aren't helping it's fine to kill them.
List of some of the tasks I’ve successfully automated using ChatGPT and AI tools:
Software Engineering & DevOps
Code generation/refactor loops
CI/CD and build pipelines
Automated testing
Code quality and review
Infrastructure helpers
Product & Marketing Workflows
AI-native SaaS builders (MVPs / POCs)
Advertising & Media Creatives
Due diligence & M&A Prep
Personal Productivity & EA
Inbox / research / knowledge management
Task orchestration
Writing & communications (more structure vs content)
Aviation-Specific Automation
Training plans and study buddy for knowledge tests
Flight ops & certification - keeping up with rules / regulations
Health, Wellness, & Quantified Self
Data-driven optimization
Reminders and automated data reporting
Legal / Finance / Admin
Document analysis
Hiring & immigration
Finance reporting and analysis
Real Results: Before and After
Before:
55+ hours worked weekly
30% of the time spent on low-value tasks
Constant context switching.
Frequent bottlenecks when unavailable.
After:
35-40 hours worked weekly (saving 10-15 hours)
50% reduction in low-value tasks
The team can move forward without constant input from me.
Improved consistency in communication.
Surprising benefit: Team satisfaction has improved!
Common Pitfalls to Avoid
Focus on Fun Automation, Not What Matters. Begin with dull, repetitive tasks. Then, tackle the creative and complex ones.
Crisp instructions and clear prompts are essential. Give detailed context for better results.
Skipping the Human Review Step, AI helps, but we still need to review the output. Never stop testing.
Automating Too Much, Too Fast: Start with 2-3 high-ROI tasks. Focus on them first, then expand before you end up with lots of AI helpers generating junk.
What’s one task you could automate this week? Hit reply and let me know—I read every response.
Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.
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