Yesterday, I met with a CTO I am coaching. His firm underwent a Tech Due Diligence (Tech DD) with us last year, where we identified several areas needing improvement across the entire tech function.
When the investors learned of these issues, they decided to pull out of the deal. While this was a tough moment for management, it became a valuable opportunity for growth.
Since then, we have been working together—me providing part-time advisory and direction while the CTO and his team put in the hard work. I am pleased to say that they are making meaningful and sometimes significant progress with each weekly meeting.
One key lesson the CTO has embraced is the power of writing—for clarity, direction, and capturing key successes and value. When I say ‘writing,’ I don’t mean endless documentation but meaningful and practical habits that help structure tech delivery and team progress.
The Three Core Writing Habits:
- Daily Journaling
- Daily Recording of Results and Decision-Making
- Monthly Reflection
These three skills are ones I have developed both as a long-term consultant and as a screenwriter. As a consultant and business owner, I’ve learned that people often forget the decisions they make and fail to celebrate their wins.
As a screenwriter, I’ve learned that daily writing brings absolute clarity to your thinking. Journaling is like having a conversation with yourself—it answers even the most challenging questions.
And in my role as a due diligence expert for VC and PE firms, I know the power of presenting a well-documented journal of events to demonstrate the VALUE a tech team provides.
Simple Actions to Implement:
- Morning Journaling: Before reading anything or speaking to anyone, write three A4 pages as a stream of consciousness. I learned this over 20 years ago from Julia Cameron, the goddess of this art.
- Evening Reflection: Before wrapping up the day, list the lessons learned and decisions made. Record what was agreed upon.
- Monthly Report: At the end of the month, write a board-level report outlining what the team worked on, key challenges, and wins. Keep it both technical and commercial.
During our meeting yesterday, my mentee surpassed my expectations—he presented a monthly report for January that was clear and commercially insightful. We agreed that after compiling 12 such reports, he would be able to look back on the year with pride. Not only that, but the tech team and CEO would have a concrete record of their progress and value creation. His team was so inspired by his output that they are now considering adopting the practice themselves.
Why Are We Doing This?
To produce continual EVIDENCE OF VALUE.
The most common issue I see is tech leaders / CTOs don’t record anything about what value they bring to the business and my strong opinion is that everytime you release a new feature/update it quickly becomes the new normal, part of the furniture, taken for granted.
And the only person who can change that is you.
