Working Through Hard Problems
Joe Elmendorf
Strategy Consultant & Mapper
For problems so interconnected they feel impossible to start.
You have the kind of problem that doesn't fit on one whiteboard. A product that's pushing a decade. A website with thousands of pages nobody can account for. Another re-org. Another re-platform. A strategy that is different in each deck and person's head.
Most of these things became the way they are innocently. They grew one right-at-the-time decision after another, and now everything touches everything else. Every conversation about it circles.
Maybe you've tried stepping back to map it, but the diagram went to spaghetti before it made any sense. Maybe you gave your AI every document and got back a confident summary that misses the complexity. The tools keep making it easier to produce more, but none of them help you decide what matters.
What you’ll learn
An effective pattern that turns a problem too big to make sense of into a regular-sized problem, what you're already good at solving.
Walk the edges of the situation: finding what's locked, what's movable, and where you stand within it.
Spot the signs that a problem is not one thing, but many tangled together.
Before you start, choose one piece of the tangle and document what “figured out” will look like.
Put the rest on hold (on purpose), with a reason ready when someone asks why.
Leave with a one-card framing tool you can reuse on any hard problem in the future.
Make maps that answer your question in minutes, with just a pen and a notecard.
Keep your maps rough on purpose, so they remain fast to make and painless to throw away.
Read a finished map twice: once for the answer, once for the new problems it reveals.
Look up after each map. Re-check where you are. Choose the next piece.
Scale the same loop from a small decision to a decade-old tangle.
Put rough thinking in front of other people without flinching.
Workshop agenda
Everything Is Connected to Everything Else: The Paradox of Hard Problems
The best way to work on a hard problem is to purposefully ignore most of it; yet the better you understand the whole of a problem, the harder it is to ignore any part.
Orient: Find Where You Are
Look around before deciding anything. Understand the edges, the fixed points, the areas of flex, and your own position inside the problem.
Frame: Pick One Part
Choose the part worth figuring out now and how you'll know you're done with it. You'll fill out a one-card framing you can reuse on every problem after this.
Resolve: Make a Map
Make a map that answers the question you gave it. Then read it for what it revealed: smaller problems inside the part, or new ones next to it.
Step Back and Go Again
Re-orient, pick the next part, and run the loop again until the hard problem is a pile of smaller, solved problems.
Peer Learning
See how your peers made maps along the way, all focused on the same thing. We'll learn from how others framed a problem space and what each framing revealed.
Learn directly from Joe
Joe Elmendorf
Ten years teaching people to draw ugly and think clearly
Who this workshop is for
Technical, Content, and Information Architects working to bring intentionality to a system that grew organically for years beforehand.
Designers, researchers, and product managers whose hardest problems can't be seen yet.
Engineers, strategists, and consultants whose job is getting a dozen other people to see the same invisible thing.
What's included
Live sessions
Learn directly from Joe Elmendorf in a real-time, interactive format.
Lifetime access
Go back to course content and recordings whenever you need to.
Community of peers
Stay accountable and share insights with like-minded professionals.
Certificate of completion
Share your new skills with your employer or on LinkedIn.
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Frequently asked questions
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USD
2–3:30pm EDT