Cook’s Startup Planning System: Part 1 of 2

3 CFO Frameworks by Audience; 3 Planning Pillars

Feb 12, 2026

This post is the result of a deep dive working session with one of my clients who provided permission for me to share this. While I’ve discussed how to design and implement a startup planning system dozens of time in my career with dozens of teams and clients, this particular session was worthy of “writing it down” to create this post.

For full transparency, Ai wrote most of it down by transcribing our zoom session. I asked Gemini to review the Fathom Notes transcript to organize my verbals into a better structured post. Then I spent a few hours cleaning it all up. The result is what follows below.

Assumptions → Decisions → Spend Control → Course Corrections

Your core thesis:

Assumptions: The numbers are simply reporting the underlying activity. Planning should start - end - and course correct based on the assumptions behind the numbers - not the numbers themselves. And yet, FP&A teams do a poor job leading with the assumptions when doing variance analyze. Cart - Horse is backwards.
Spend Control: Budgets don’t authorize spending. Budgets should be communicated as planned $ and absolutely not an authorization to start spending to this plan. The company and especially the CFO/Head of Finance reserves the right to revalidate assumptions before the actual spending occurs and should set up key systems to cross check the assumptions before writing the checks.
Course-corrections required for any plan: If the actuals don’t validate the underlying assumptions, the future period’s budgets (plans) must change. As CFO/Head of Finance, you must communicate that we will be modifying the board approved plan at least twice and likely every quarter as we validate our assumptions that created our original plan.

The 3 Key CFO Frameworks (by audience)

A CFO’s Planning System has 3 different audiences with 3 key “Planning Pillars”. Communicating properly to each audience is critical and emphasizing the planning pillars 7 times 7 different ways is critical before your leaders “own” their portion of the plan.

1) CEO + Board Audience:

“Buckets of Money” and “Use of Funds”

Purpose: secure alignment and funding at the CEO and Board (strategic level).

Language Used: runway, risk, priorities, tradeoffs, outcomes.

Output: the board-grade “money allocation philosophy.”

What the Board actually approves:

A set of strategic bets
A set of budget buckets (R&D / GTM / G&A)
A set of assumptions that justify the bets
A right to change the plan when assumptions change

What the Board and CEO should not do:

Dive into the line item details - they aren’t qualified operationally to do so

Key lines you coach and ask your clients to communicate:

“We need to approve key investments against our strategy.”
“We are doing so with key ROI assumptions against our key initiatives.”
“We will have our hands on the money wheel and will course correct based on investment assumptions.”

2) Exec Peers Framework:

“Mini Business Plans”

Purpose: translate the Board/CEO buckets of money into functional operating line item plans with accountable owners (the execs)

Language Used: “Let’s review the use of funds with the $ allocated to you”

Output: department plans with headcount + vendor spending justified

This is the missing middle layer you called out:

The Board/CEO “Investment Buckets” are too abstract for exec execution but are the proper guardrails for the mini-business plan executive layer of plan ownership
Execs don’t get to say “The Board gave me 15% of revenue, leave me alone.”
Execs must justify their own use of funds allocated to them with clear ROI’s for new headcount and vendor spending and clearly documenting the underlying assumptions at a line item level.

Your role as CFO/Head of Finance becomes their “board” - pitching you to properly spend the money they’ve been allocated. Your role is to partner with them to fine tune their assumptions by asking questions and highlighting trade-offs or alternatives they may not have considered.

3) Operational Staff Framework:

“Spend Approval System”

Purpose: govern where money actually leaves the building.

Language Used: clarity, speed, guardrails, approval systems.

Outputs: a lightweight procurement/intake/spending documentation and approval system.

This is where most startups get it wrong:

Execs and boards agree on a plan.
Directors/managers spend money based on short term incentives vs longer term plans
The original assumptions silently drift.
Finance “discovers” drift after the fact.

A proper spending approval system:

Captures spending assumptions before the spending occurs as the quick “cross check” of the original assumptions many times created months before.
Make the company create an “assumptions of record” database to enable faster spending course corrections and faster future spending approvals.

The 3 Planning Pillars (by audience)

Pillar 1 — Allocation (Board Level)

“How do we allocate money across bets?”

This is your “buckets of money” system.

Implementation steps:

Define the strategic bets (what we’re trying to win at).
Allocate dollars into buckets (R&D/GTM/G&A + optional “strategic reserve”).
Tie each bucket to the assumptions that justify it (not just the dollars).
Publish the operating principle:
- Budgets are plans, not entitlements.
- Assumptions are the truth.
- We reserve the right to reallocate when assumptions change.
Deliverables:

Board allocation slide (one page)
Top assumptions list (the “why” behind the plan)
Runway/risk ROI statements on use of funds

Pillar 2 — Budget Build (Exec Level)

“How do we turn buckets into mini business plans?”

The structure:

High-level allocation (buckets)
Then: build department budgets with line-item logic
Headcount is ~70–80%, vendors ~20–30%
Separate logic and question sets for headcount vs vendors

Implementation steps:

For each exec, build a mini business plan:
- Goals, initiatives, owner, milestones
Convert into a department budget:
- Headcount plan (roles, timing, location, fully-loaded cost)
- Vendor/tooling plan (purpose, ROI hypothesis, dependencies)
Document the assumptions behind each line item:
- “If we spend this, what does success look like?”
CFO challenge stance:
- Execs tend to hire people to go faster
- Finance tends to prefer systems and automations and variable costs vs people
- Meet in the middle with explicit people vs software tradeoffs
Deliverables:

Department plan template (initiative → resourcing → assumptions)
Headcount plan (roles + timing + success definition)
Vendor plan (tool → purpose → success definition)

Pillar 3 — Spend Control (Operational Level)

“How do we approve spending in a way that validates our assumptions?”

This is where your “intake system” and the “same questions every time” becomes the playbook.

Implementation steps:

Install a fast and easy purchase request intake workflow
Requiring “assumptions of record” on every meaningful spend.
Separate two motions:
- Budget approval (planning)
- Spend approval (execution control)
Require at least two approvals on spend over a certain $ amount (guardrails).
Build the cadence loop:
- compare actual outcomes vs stated assumptions
- course correct during the year (not annually)
Deliverables:

Spend request form (the questions)
Approval matrix (who signs what)
Spend review cadence + variance playbook
“Assumptions of record” repository (even if it’s a doc + sheet to start)

The Engine Underneath: “Assumptions of Record”

Most companies have:

A system of record for dollars (P&L)
A system of record for headcount (HRIS)

I’ve seen very few who have:

A system of record for spending assumptions

How it works:

Each spend / hire is approved based on underlying assumptions.
One of the best assumptions for new hires is defining the role’s success after 90/180 days. If it’s a new vendor spend, then defining the success of that vendor’s activity after 90/180 days.
Then compare the actual new hire or vendor results to the original assumptions not just the dollars/expense line.
Now shift more dollars to what’s working and fewer dollars to what’s not.

The Question Architecture

You started to define the “universal” question set:

The universal question frames

Who / What / Why / Where / When / How

Every spend request is just a structured version of these questions.

You don’t say no. You simply ask questions to:

Define the real problem
Expose assumptions
Create alignment on true buy-build investment partnerships
Document decisions
Build a database that becomes the company’s assumptions of record

Critical design rule

The system must “write it down”. It must capture the underlying assumptions at the line time level. If these assumptions stay verbal, it doesn’t scale.

Your “Decision Tree”

You have two branches you’ll formalize in the module:

Branch A: In-budget spend

Goal: validate original assumptions are still true.

“Remind me what assumptions we approved for this line item.”
“What changed since we set the plan?”
“Are we still solving the same problem?”
“How will we measure success/failure?”

Branch B: Out-of-budget (incremental) spend

Goal: force tradeoffs and reprioritization.

“What are you trading off to fund this?”
“Where does this rank vs your other priorities?”
“What risk do we take if we say no?”
“What risk do we take if we say yes?”

You also gave the best example of how to avoid gaming spending based on dollars vs activity assumptions. Don’t fall into the classic planning or spending request trap from your executives of “I can use the same dollars with different activity assumptions”:

“Instead of 1 support rep in the US, I’ll hire 3 in Singapore.”

This is gold because it proves:

Budgets don’t protect you
Assumptions drift even when dollars don’t change
I hope everyone sees the core problem with this logic. It suggests that the original plan assumptions of only needing 1 rep to complete the activity, that 3 reps are now better at completing the activity? This is simply spending the same dollar with lower productivity and lower efficiency. Small teams win and allowing more activity for the same dollars eventually results in more overhead, more management and more inefficiency.

Confidence + Risk Ratings

Your CFO coaching framework:

Force confidence/risk scoring as part of the planning conversation
Document the narratives around their confidence and risk scores.
The system creates future pattern recognition.

Assumptions don’t have to be numeric.

“Success = launch by X date” as a valid assumption.
“Failure = If we miss the launch and downstream revenue slips” is a valid risk and would suggest delaying new sales and customer support reps and marketing launch dollars.

Systems and Tools

You name-checked the best systems and today’s market map:

BizTerra (an early internal-derived prototype) - I helped build this with my good friend Delly 10+ years ago at Mozilla
Tropic
Brex partners with Zip to deliver this functionality
Ramp has built their own