For the last few years, my work has felt easy. Most of what I did every day as an interim CEO and advisor is what I’ve spent 20 years learning how to do, and I didn’t have to think too hard about it.
I’ve loved working with this ease - it felt like something I earned after decades of navigating punishing learning curves and startup chaos.
It’s also a common theme across the dozens of solo founders we’ve talked to - they hung out their shingle because they’re great at their craft - the hard parts about running their business are everything outside of the craft (business development, LinkedIN posting, SF city taxes, etc.).
And over the last two years, Claude and ChatGPT have been my brilliant, scattered, and unstructured buddies - need an edit? Ask Claude. Want quick market research? Chat away. It felt like pure enhancement to my already-easy work life.
But then I heard there might be a better way
A phrase that kept on coming up in the Twittersphere and on podcasts was that the way to get the most out of these tools was to move from conversation into automation.
Give me the operations or marketing function at a company, and I know what this means. But in terms of my day to day, my reaction when I heard this was, "Do I even have workflows?”
I follow my instinct. I do what I know how to do when it needs to be done.
Turns out, that’s the definition of a workflow.
Here's what experience does to workflows
What I thought was "just doing stuff" was actually living and breathing workflows all day, every day. I just knew how to do them so well I didn't even think about the steps.
A coaching call - that’s a workflow. Running a successful conference - that requires about 30 well executed workflows. Closing a sales deal - it’s all internalized workflows.
Experience makes workflows invisible.
Every "easy" thing I do is actually an invisible workflow:
Schedule call with prospect → Talk → Take notes → Summarize goals → Develop pricing POV → Update proposal template → Proofread → PDF → Email → Follow up
Provide client a template for financial data collection → Check if it's complete → Remind them to complete it → Review the completed workbook → Distill key insights and open questions → Prepare a discussion guide for a client meeting to discuss the insights and questions
Receive data request → Clarify metrics needed → Pull raw data → Clean and format → Create visualizations → Double-check → Package and send
The power in making invisible work visible
At first I resisted. Translating my intuition into a spreadsheet felt so reductive. Even offensive at times. But something happened when I saw all that intuition spread across a seemingly endless amount of rows. I started to see how much I was actually carrying. I started to question where and how I was spending my time. I started to feel powerful at the idea of giving a lot of those cells away to a machine.
Once you illuminate the invisible, you can plug in AI in intentional, repeatable ways instead of constantly starting from scratch.
You move from "How could I make this proposal better?" to "Complete this proposal template based on these call notes and my pricing sheet (plus clear guidance on perspective, tone, style and pitfalls to avoid, etc).”
And investing in this translation once allows you to do it 10 more times. When you prompt AI for support in predictable, consistent ways you get predictable, consistent results. Intuition turns into leverage.
And that’s just Step One (but it’s the most important leap)
Defining the workflow, and practicing consistent prompting, is just step one toward more rewarding work.
For a financial analysis workflow, using well crafted, highly structured prompts offers more comprehensive and insightful analysis (yep, you heard that right) and hours of time back. You know what I like more than doing easeful work? Time with my daughter.
There are a whole bunch of steps from here that we’re mucking through right now – moving from copying and pasting to running workflows that are triggered by the click of a button. And then there’s the workflow running without your involvement at all, except as management and quality control.
We’ll keep sharing what we’re learning.
Your challenge: List 5 workflows
This week pay attention to the workflows you’re doing without even thinking. Make a list.
Next up: Pick one workflow and systematically incorporate AI
In an upcoming post, we’ll walk you step by step through our experience crafting a repeatable series of prompts for one workflow.
Our challenge - can you improve the quality of your output and get time back?
Let’s find out!