The Sensemaker’s Guide to Arguing

You know that moment when you have a brilliant idea for fixing something that’s clearly broken, but then you realize the hard part isn’t figuring out the solution—it’s getting everyone else to see it too?

Welcome to the real work of sensemaking. The messy, human part where good ideas go to die unless you know how to argue for them properly.

Most people think arguing is about winning or being stubborn. But for sensemakers, arguing is how we turn individual insights into shared understanding. It’s how we test ideas against reality before they get expensive.

This article covers:

Why is there Arguing in Sensemaking?

When you’re trying to make sense of complex problems, you need ways to pressure test your thinking. Not because you enjoy conflict, but because untested ideas become expensive mistakes.

Think about it: every structural change, every new process, every “better way of doing things” has to survive contact with real people, real constraints, and real trade-offs. Arguing early helps you find the weak spots before they find you.

Good arguing helps you:

• Surface hidden assumptions before they derail your proposal
• Build empathy for the people who have to live with your solution
• Get clearer on scope, risks, and what success actually looks like
• Turn resistance into collaboration by addressing concerns head-on

Reasons to Argue

When you argue properly, you’re essentially stress-testing your thinking before it hits reality. You’re creating what I call “comparability” or a level(er) playing field where you can honestly evaluate different approaches against each other. This process forces hidden assumptions into the open and makes trade-offs visible before they bite you.

But arguing isn’t just about finding flaws. It’s about building confidence that your proposal can survive contact with the real world. If your idea crumbles under friendly questioning, imagine what happens when it meets actual users, tight deadlines, and budget constraints.

Most importantly, arguing keeps you from falling in love with your first idea. That initial solution that feels so obvious? It’s usually not your best work. The discipline of considering alternatives—even if you end up sticking with your original approach—makes your final proposal stronger and your reasoning clearer.

Common Use Cases for Arguing in Sensemaking

Structural changes: When proposing new ways to organize information, processes, or teams. Challenge your classification rules, question your content strategy, and stress-test your curation plans.

Resource requests: Before asking for budget, time, or people, argue through the real costs and benefits. Include the hidden costs like training, migration, and ongoing maintenance.

Priority decisions: When everything feels urgent, arguing helps you surface the real criteria for what matters most. Question timelines, challenge scope, and get clear on trade-offs.

Process improvements: Before proposing a new workflow, argue through who gets impacted and how. Consider the people who have to live with your process every day.

System design: Challenge your mental models. Question whether your structure will make sense to users. Test your assumptions about how people will actually behave.

Types of Arguments

Not all arguments are created equal. Here are five forms that reliably strengthen your work.

Evidence-based arguments: Ground your thinking in real data about real users.

Example: “Our content audit shows 40% of pages haven’t been updated in two years” is stronger than “I think our content is stale.”

Structural arguments: These examine how well a proposed structure serves its intended purpose. Question classification rules, content lifecycle, and curation requirements.

Example: “Putting product specs in the same category as marketing pages makes the structure harder to maintain long-term” is stronger than “I don’t like where those pages are.”

Trade-off arguments: These make the costs visible.

Example: “This approach requires hiring two people and six months of data cleaning” is stronger than “this might be expensive.”

Constraint arguments: These test proposals against real limits.

Example: “What if we only had half the timeline?” or “What if our main content creator leaves?” is better than “let’s cross that bridge when we get to it”

User mental model arguments: These focus on how people will actually interpret and use your structure.

Example: “Users think of pricing as part of the buying decision, not a buried FAQ item.” is stronger than “Users can’t find pricing”

Approaches to Arguments

Create an Alternative Structure Never argue for just one approach. Create at least two different structures that could meet your goals. This forces you to think harder about why one is better.

Run a Structural Argument Check Evaluate proposals against intention, information, content, facets, classification, curation, and trade-offs. If any component feels weak, dig deeper. I wrote a lengthy article on Structural Arguments that should serve as a helpful guide if you take this approach on.

Take on the Implementation Reality Test Ask “What would it actually take to build and maintain this?” Include all the unglamorous stuff like data migration, training, and ongoing updates.

Dig into the User Interpretation Challenge Test whether your structure makes sense to the people who have to use it. Don’t just ask if they like it—watch how they actually interpret it.

Go into Failure Mode Ask “What could break this?” Think about edge cases, unusual content, and situations where your rules don’t apply clearly.

Tips for Getting Started with Arguing

Document your thinking Don’t just have opinions—show your work. Write down your assumptions, your reasoning, and your evidence.

Start with intention Always connect your proposal back to the larger “why.” If you can’t explain how your structure serves the real goals, it’s not ready.

Get specific about content Vague ideas fall apart when they meet real content. Know what you’re organizing, who creates it, and how it changes over time.

Name the trade-offs Every good proposal involves giving up something to get something else. If you can’t find any downsides, you haven’t thought hard enough.

Test with real scenarios Don’t just theorize—walk through actual use cases. What happens when someone uploads something that doesn’t fit your categories?

Plan for maintenance How will your structure stay healthy over time? Who will keep it updated? What happens when priorities shift?

Arguing Hot Takes

Hot take #1: If you can’t argue against your own proposal, it’s not ready The best way to strengthen an idea is to attack it yourself first. Find the weak spots before someone else does.

Hot take #2: Most structures fail because of content, not concepts Beautiful organizational schemes collapse when they meet real content with all its messy inconsistencies and edge cases.

Hot take #3: Your users don’t care about your mental model They have their own way of thinking about things. Your structure needs to match their expectations, not your internal logic.

Hot take #4: Implementation is where good ideas go to die The best structural proposal is worthless if you can’t execute it with real people, real budgets, and real timelines.

Hot take #5: Second solutions are usually better than first solutions Your initial idea might be good, but the alternative you create to argue against it is often simpler and stronger.

Frequently Asked Questions

Q: How do I argue for changes when stakeholders seem happy with the status quo? A: Make the hidden costs of the current approach visible. Show what’s breaking, what’s inefficient, and what opportunities are being missed.

Q: What if my proposal requires resources we don’t have? A: That’s valuable information. Either scope down your proposal or make the case for why the resources are worth it. Don’t pretend expensive things are cheap.

Q: How detailed should my arguments be? A: Detailed enough to be credible, simple enough to be understood. If you’re losing people in the details, you need clearer main points.

Q: What if stakeholders focus on parts of my proposal I think are minor? A: Those parts probably aren’t as minor as you think. Pay attention to what people care about—it tells you something important about their mental models.

Q: How do I argue without seeming negative or difficult? A: I hear this a lot when people talk about argument. In trying not to seem “argumentative,” we forget that change only happens if we argue for it. The key is framing position arguments as ways to make a proposal stronger, not as ways to tear it down. Saying “Let’s pressure test this so it succeeds” lands far better than “Here’s what’s wrong with this.”

Q: Should I present multiple options to stakeholders? A: Sometimes. It can lead to better discussions, but it can also create decision paralysis. Use your judgment about whether comparison helps or hurts.

Remember: the goal isn’t to win arguments. The goal is to build better solutions. When you argue well, everyone wins because the ideas get stronger and the implementation gets smoother.

The real work of sensemaking isn’t coming up with solutions. It’s doing the hard thinking to turn those solutions into reality.

If you want to learn more about my approach to structural argumentation, consider attending my workshop on September 19th from 12 PM to 2 PM ET. How to Argue (for IA) Better — this workshop is free to premium members of the Sensemakers Club along with a new workshop each month.

Thanks for reading, and stay tuned for our focus area in October — Proving a Return on Investment.