One of the core responsibilities of a CEO is to make hard decisions that have real consequences for the team and the business. Holding the title does not mean you always know the answer. It simply means you are the one who has to decide.
When I joined the CEO Collective as a member a decade ago, I found the written case process we used in our meetings to be more valuable than I expected. Preparing a case required me to clarify the issue, lay out the relevant context, define real options, and state the direction I was leaning toward.
That exercise alone improved my decisions.
Like most CEOs, I had a lot running through my head. Tradeoffs. Risk to the team. Financial pressure. How it would land with investors. Writing forced me to lay out all the pieces instead ofletting them compete for attention. It allowed me to prioritize and compare ideas to test how strong they were.
Half of the work of making a sound decision is simply getting all the details down in writing.
When a decision stays in conversation or in slides, it can remain vague. Bullet points only skim the surface. They create the appearance of clarity without requiring precision.
Prose forces discipline.
Get a pen and paper, open a blank document on the computer or type it in an email draft you never send. The medium doesn't matter. What matters is that you write in full sentences.
When you write in prose, you're forced to find the words that best describe and define the issue. Gaps in logic surface quickly, assumptions become more visible, and you can’t hide behind formatting or slides.
In the CEO Collective, every case is written in response to five core questions. You can use that same discipline.
Be precise about what you are trying to accomplish.
For example:
“To decide whether we should acquire Company X in the next 90 days to accelerate revenue growth and expand into the Southeast market.”
That statement defines the decision and the intended outcome. It clarifies that this is not about curiosity oroptionality. It is about accelerating growth and entering a new geography.
If you cannot state the purpose clearly, you are not ready to evaluate the opportunity.
Now lay out the context that informs the decision.
· Our revenue growth has slowed to 4 percent over the past three quarters.
· We lack presence in the Southeast,where industry growth is strongest.
· Company X generates $12M in revenue with 18 percent EBITDA margins.
· Our leadership team is already stretched managing two major initiatives.
This is where you separate fact from narrative and prioritize what matters most. You are grounding the decision in data, capacity, and strategic reality.
Spell out the real paths.
· Acquire Company X within 90 days and finance through debt
· Delay six months and revisitvaluation after observing market trends
· Walk away and pursue organic expansion instead
For each option, outline:
· Financial impact and leverage tolerance
· Integration complexity and leadership bandwidth required
· Cultural compatibility between the teams
Seeing the options side by side oftenreveals that the issue is not “Should we acquire?” but “Do we have the capacity to integrate successfully right now?”
Based on what you have written, take a position.
“My plan is to move forward with the acquisition, contingent on securing financing within our leverage threshold and appointing a dedicated integration lead before closing.”
Here you are explicit about both the direction and the conditions. This section is the heart of the work you are doing. Anticipate what needs to happen, what can go wrong, and how you can adjust as you move through the process.
Ask yourself questions that challenge the plan. Questions you would ask if someone brought it to you for feedback.
· Are we overestimating orunderestimating integration complexity?
· What happens if revenue projections fall short by 15 percent?
· How will this affect culture and retention over the next 12 months?
· What will the impact of this integration be on the rest of our business?
· If this fails, where will the failure most likely occur?
By the time you answer these five questions in writing, the issue is no longer a swirl of concerns. It now has shape, logic and visible tradeoffs.
Often, clarity emerges before anyone else weighs in.
If you have trusted peers or advisors, share what you have written. It’s an opportunity to get feedback that mayvalidate your thinking or expose something you’ve missed.
But even if you never bring it to peers, the discipline itself improves the quality of your decision. I have found half of the value of a peer group is this process of writing down the issue and the solution.
You can’t eliminate uncertainty, but you can improve how you think before you act.
In a world increasingly shaped by AI, this discipline matters even more. AI can help you draft faster, organize your thoughts, and polish the language. But it cannot and should not do the core thinking for you. The value of this exercise is not the finished document. It is the process of wrestling with the questions yourself.
As you write and reread what you’ve written, your conviction sharpens and your understanding deepens. That insight is what gives you confidence in the decision. Use AI to refine and extend your ideas, but don’t outsource the thinking itself.
Before you schedule another meeting or replay the issue in your head again, sit down and write it out. In my experience, that alone will move you further than you expect.
