Reverse Design Thinking for the Future CFO Architect
Start with the DECISION, NOT the DATA, and work backwards.
The Problem: Finance Is Stuck in Time
Despite the shiny dashboards and “Ai-powered” features, the modern finance stack still mimics a 1990s Lego model:
Chart of Accounts → ERP → Reports → Dashboards → Manual Analysis
Rigid systems and analytical structures hamper fast and efficient data insights.
Our UI and UX are either stuck in “spreadsheet hell” or packed into “no-whitespace screens with lots of boxes.”
Finance tools are still centered around structuring data vs. delivering collaborative clarity and influential insights.
CFOs? We are often forced into the role of spreadsheet janitors (“clean up on aisle 6”) vs. being the strategic data insight partners that everyone needs.
The Shift: Reverse the Flow - “Cross the Streams” on Purpose! For those who know me, I use this meme often.
“Strike That. Reverse It!” - ok… guilty, another one of my favorites…
Reverse It!
Start with the desired outputs… then work backwards to create the milestone map.
What’s the strategic north star this decision or desired output points to?
What are the assumptions required to achieve the desired output?
What are the 2-3 milestones that we need to mark on the activity map as we journey from here (today) to there (future desired output)?
From this reverse design thinking, a new finance decision platform can be built to enable CFO’s to:
Ask better and more powerful questions.
Document the answers (the “assumptions”).
Set milestones, metrics, and dates that get us from here (today) to there (future).
Quickly forecast what’s next vs. just reconciling the actuals.
Recommend course-correcting decisions for when the actuals don’t match the forecast (hint - they will!). Set acceptable ranges of the actual results.
If the actual results fall outside these ranges, pre-wire the course-correcting decision upfront to keep the ongoing “activity decisions” aligned to the desired outcome.
Make better strategic decisions based on the risk/reward curve of the business.
Coach other executives, your CEO, and the board on this “Decision System Platform” and on how to ultimately own making better decisions.
It’s not about more tools. It’s about the right decision architecture.
The Real Barrier: Human Adoption, Not Tech
Here’s a bit of brutal honesty. New Ai tech adoption is not the bottleneck for becoming a strategic and insightful CFO for the business. Your willingness to change your classic CFO behaviors is your bottleneck.
Most CFOs are wired to avoid risk, not embrace being only 80% accurate.
CFOs need to embrace their best inner “Product Manager.”
The new “Office of CFO” Ai software being built is still most often focused on features and point solutions, and therefore is also not reimagining what’s needed from the future CFO’s architect of the business.
You, as CFO, will need to lead these new Ai tech stack vendors on what you need, why you need it, and give input on how they need to design it.
This will require a mind shift to become the CFO architect you need to be. This requires keeping the overall map always in mind (by zooming out) while also zooming in on the detailed activities of your finance team to see if those activities align with the future mental map. Then, asking critical questions of how we can do this finance activity faster, easier, and more automatically, and what product architecture is required.
The Opportunity: Build the Virtual CFO Advisor
This is the moonshot:
A “Virtual CFO Advisor”:
Highlights real-time “data stream” variances
Ai Agent that proactively engages the CFO daily
Conversational Ai to help CFOs structure their next insight conversation or presentation
Ai to recommend various course-correcting decision pathways
Creating forward-looking scenarios, impacts, and risk analysis
Strategic conversation coaching cues on how to better communicate with influence as a CFO
It’s a product category that doesn’t exist yet but is being actively attempted in more new “finance stack” software than any of us has seen in the history of finance software.
This ‘Ai CFO Advisor’ will take 3+ years to get right and 5+ years for 50%+ of CFO’s to adopt. In the meantime, we will all need to have the best human CFO architects (or become one!) in order to train this new Ai CFO Advisor Agent. How do I know? Hit my profile pic and see my “activity feed” here on Substack, where I’ve been posting weekly “quick Best Of’s” that I find and curate into the Substack “Notes” feature. One of the recent ones spoke directly to 50%+ historical adoption of technology and my first-hand experience with the DVD player from 1997-2004.
The Human CFO In The Loop Bottom Line: “Human in the Loop” will always be required in the CFO/finance world. The Ai will only be as good as the human who trains it and leads it.
The Build Strategy: Adopt a Product Manager Mentality
Here’s a good “build” path that needs to be embraced today. You don’t need to be a technologist or know how to code. You do need to be curious and willing to start behaving like the best “product manager” you’ve ever known.
Sit side-by-side with the leaders in your finance team regularly. Map their calendars, conversation flows, and deliverables to their respective “customers” inside their organization.
Sit side-by-side with executive leaders receiving today’s financial data. Map their calendars, conversation flows, and what they do with the data your team gives them.
Iterate your new product by delivering what you are hearing both groups “need,” not fixing or patching what they are currently doing. Note: there’s a huge difference between what people currently “do” vs. what they actually are trying to accomplish overall. More often than not, people have chosen sub-optimal activities out of necessity to keep moving forward.
One step at a time. Focus on improving daily, weekly, and certainly monthly. Create real-time feedback loops on every new version launch.
It’s time to build the new operating system for the office of the CFO. We need a whole new finance stack. We need “product manager” style thinking. Start with the end in mind… and start building your mental map backwards… milestone by milestone all the way back to what is happening today. Now start building.
P.S. Not a paid subscriber yet? Paid subscribers get exclusive access to full blog posts, additional blogs in series, summary framework tables, scorecard templates, and paid subscriber AMA’s (Ask Me Anything) to help you implement the strategies discussed in Cook's PlayBooks. Want to become a paid subscriber and unlock these benefits? Click here!
