How to Solve a Problem When You Don't Know Where to Start
A simple 4-step project framework
This post is written with startup operators in mind: tackling new challenges is the defining quality of a young company. However, this framework can help with anything from a cross-country move to community organizing.
First, Feel Your Feelings
The sense of panic when facing an overwhelming or impossible-seeming project is real. While working in a growth-stage startup, I was asked to figure out why a segment of the company’s operational costs had spiked and whether that would be an ongoing problem.
I wasn’t an accountant, and I didn’t have the domain expertise to analyze the costs on a meaningful level. I remember staring at a number on our billing dashboard, comparing it to the original budget, and thinking “How did this land on me? I don’t even know where to start.”
Reframe It as Growth
Lean into the panic. It’s a signal that you’re hitting a growth edge, and working through it will increase your resilience.
I did solve that costs issue, and it expanded my expertise in a way that’s transferable to any company at any stage. More importantly, facing a steady stream of challenging projects head-on gave me confidence in my problem-solving skills and dramatically expanded my comfort zone.
Get Organized
I’ve shipped a wide range of projects across my career, from simple 2-person weeklong initiatives to multi-quarter product launches with dozens of stakeholders. Despite the massive difference in scale, the fundamental approach is the same.
You can distill any project into four basic steps:
Create Your Vision
Sketch It Out
Make It Real
Launch & Learn
Let’s walk through each phase, using my operational cost project as an example (I’ll use italics throughout the rest of the piece when using examples from this project).
Step One: Create Your Vision
Understanding exactly what you’re doing, why, and your definition of success sets the tone for the entire project. You might iterate on this after defining it, but a clear starting point is key.
Many people gloss over this step—resist the temptation! Besides the obvious risk of doing work for unclear value, taking the time to think things through will help calm your nervous system.
Guiding Questions for Step One
What do you want to build, fix, improve, or accomplish?
Clear, reliable understanding of a specific segment of the company’s costs on an ongoing basis
What’s at stake if you wait?
Uncertainty about margin
Investor concerns
What does “done” look like?
An explanation for the cost spikes
Future forecast numbers within X% of actuals
A regular cadence for reconciliation and approvals
Step Two: Sketch It Out
This is the brainstorming and research phase: do this in whatever way works for you and your team. I personally ideate across a combination of messy analog notebooks, Gmail drafts, AI agent conversations, and Notion tasks.
The goal is to understand what you’ll need to do to meet your “done” goal, and clarify the resources you’ll need (e.g. $$ and domain experts).
Guiding Questions for Step Two
What’s standing in the way of “done”?
Understanding the cost breakdown at a more granular level
Correlating a subset of costs to the spike
Understanding what changed to create that spike
A reliable method of subdividing the monolithic bill
A method of distributing ownership for future estimates
Where can I get more information?
Recent roadmap updates
Folks closest to the problem
Existing documentation (internal or external)
Broad solicitation of ideas (don’t discount anything until you understand the problem space)
Step Three: Make It Real
As you sketch out the surface area, you’ll get a sense of what needs to happen, what it will take to make that work, who needs to be involved, and how long it will take. You can start to draft a plan and a timeline.
In the case of my costs project, I pinpointed the cause and consulted with relevant leaders on next steps. We agreed to set up a forecast and reconciliation process to prevent future surprises, and a general structure for how that would work and who would be involved.
Guiding Questions for Step Three
What concrete tasks need to happen?
Assign responsibility for segments of the budget at a more granular level
Set expectations that costs can be unpredictable and to review them before making changes
Create a model for estimations, a source of truth for recording and sharing them, and a cadence for reconciling actuals
Designate approvers for the forecasting and reconciliation numbers
Develop training and documentation
What resources are you depending on?
Team members to take on granular budget ownership
Technical changes to make estimations less onerous
Leadership commitment to the new process, including the ongoing work
Note: there were no additional costs in this specific project, but you’ll also want to evaluate that at this stage
How long will the work take? When can it be done?
Who can do the technical work? When are they available? How long will it take?
What should the source of truth look like and who will create it?
When can we start on the training materials?
Are any of the steps dependent on other work?
Cost owners won’t be able to make realistic estimates until the technical changes are in place
Team leads need to select cost owners before we can start the new process
Who’s responsible for making decisions if the team is at an impasse? Does that change depending on the type of decision?
Technical decisions should be made by domain experts
Resourcing decisions for the ongoing process should be made by the relevant people leaders
Use this information to create a task list and timeline, then think of it as a starting point for negotiation. Assume others will disagree on anything from the premise to the proposed solution, then work together until you have buy-in. This will build trust and keep your mind open to new, potentially better approaches instead of being defensive about selling “your” idea.
Doing the Work
All of this up-front work makes execution so much easier. You’re building a shared understanding of what needs to happen and why, and minimizing disagreement by talking it out in advance.
At this point, it’s a matter of doing the work. A couple of tips for the execution phase:
Expect to modify the plan along the way (you can be pleasantly surprised if you don’t have to!)
Communicate your progress on a regular cadence, including any risks you run into
Step Four: Launch & Learn
When you hit the finish line, go through a quick checklist to make sure you’ve wrapped things up neatly:
✅ Review your work against the original definition of “done”
✅ Proactively seek feedback from customers (internal or external) and/or via a project retrospective
✅ Document any recommended follow-on projects
✅ Make an announcement! Thank and acknowledge everyone who participated
✅ Link to any launch announcements on your project doc
✅ Celebrate!
What I Learned
In my operational costs project, we built out a technical solution for cost estimation, created a spreadsheet, and set up a monthly cadence for forecast/reconciliation/approvals. One key lesson: it was important to repeatedly emphasize the why for the new process in a clear, objective manner.
Why This Matters for Startup Operators
In a startup, no matter your role, you’ll likely have to build something from scratch. This could be a new workflow for product launches, a customer support tool rollout, a policy development process, or a prioritization matrix. The ability to break down a problem, explain its significance to others, and align on the way to solve it is a critical skill.
Approaching the unknown requires both systematic thinking and emotional intelligence. You need a strategic framework, and you need to read the room, understand your stakeholders, and manage your own anxiety.
Before You Go
Want to try this framework? Download my free 4-step project template (available on Notion or Google Docs).