What happens when legal pros think around a problem instead of on it?
I know this probably sounds like the start of some insufferable motivational post on LinkedIn, but hear me out. Lateral thinking is a real thing, and its unique intersection of logic and creativity is perfect for legal teams.
Legal Data Intelligence projects often follow a similar framework of challenges and conditions: they’re data-intensive, time-short, resource-strapped. While the systems, workflows, and models we have in place to manage them are essential to repeatability and defensibility, sometimes, they box us into a habit of repetitious thinking.
Lateral thinking presents an option for zooming out of that cycle, looking at challenges from new angles, and finding solutions, workarounds, and proof points you might be missing.
What Is Lateral Thinking?
Lateral thinking involves solving problems through indirect and creative approaches, often by viewing the problem in a new way.
While linear thinking helps you find a route from Point A to Point B within an existing framework or set of rules, lateral thinking asks you to start with a blank slate—no maps involved.
Think of it like walking around or over a maze instead of through it to reach the other side. Or like the legend of the Gordian Knot: When Alexander the Great heard that whoever could free the complex knot holding an oxcart would be destined to rule all of Asia, he didn’t try unraveling it by hand; he simply sliced through it.
Now, you’re probably thinking: No rules? No frameworks? Do you even do law?
It’s a fair point. Certainly, legal teams must operate in a defensible, compliant, and secure manner at all times. These are non-negotiable requirements, and they do necessitate the use of approved systems and workflows in many contexts. Your legal and ethical obligations must always be top of mind.
At the same time, trustworthy systems and workflows aren’t used in precisely the same way for every organization, team, or project. When legal data platforms are extensible and customizable, workflows can be more versatile than you’d think. Fundamentally, the practice of law is a human undertaking. It includes automatable tasks, and human effort can certainly be augmented by accelerative and even transformative technologies. But there’s a finesse, a creativity, undergirding it all—and, in fact, that creative, strategic component is what drew many of us to this industry in the first place.
So, while the law itself is structured, the work around it (ops, workflows, data pipelines) isn’t always linear. Bullishly sticking to conventional thinking leads to frustration and inefficiencies when the nature of our matters changes. Lateral thinking will help you open doors to innovation on issues like resource allocation, cross-functional collaboration, and technology adoption. And all this adaptation will help you better handle that next gigantic data dump and equip your team to thrive in the era of AI.
Logic and Creativity: The Perfect Pair
Across all the projects, events, interviews, and simple conversations I’ve collaborated on with folks from the legal industry over the last 14 years, what I’ve loved most is witnessing the brilliance and creativity of this community.
You are smart. You are also imaginative and resourceful. And when you face a tough project or a roadblock at work, you can put all of these skills together to take a lateral approach and come up with a solution worth your experimentation and time.
Both logical (analytical) and lateral (creative) thinking are necessary in legal work; they help your team understand and work within the merits of a case, while building the arguments and storytelling strategies that can help you win that case. You need both, because:
- Analytical thinking structures an argument and defends your position using available data, requirements, and conditions.
- Lateral thinking reshapes context, reframes problems, and finds new answers and solutions.
It’s like the PB&J of this profession. Odds are, you and your team are already pretty good at striking this balance without even knowing it. Working through the exercise of lateral thinking more intentionally can simply help you improve your skills, come up with new ideas, and innovate rapidly in this every-day-is-different legal landscape.
Exercises to Kickstart Lateral Thinking
Sounds great. But how?
Below is a list of exercises to get you started. Whether you try them on your own (great!) or with your team (even better!), they should help you start forming new paths of thought that will take you around or over a new problem—confronting it in ways that might be unexpected, and unexpectedly effective.
Give these a try and let us know what you think.
1. The “Wrong Question” Exercise
Purpose: Surface hidden assumptions by intentionally asking the incorrect question.
How it Works
- Write down the problem as you currently understand it: “We want to reduce review time by 20 percent.”
- Now, deliberately ask the wrong question:
- “How do we make review take longer?”
- “How do we make this process more complicated?”
- “How do we ensure no one ever adopts this new tool that could help us?”
- List your answers honestly and with detail. The more specific you are about your organization’s habits and realities, the better.
- Then, flip them around: what’s the opposite of the worst idea you have?
Why it Works
When you describe how to make something worse than it currently is, you may reveal the impediments, behaviors, and assumptions that are creeping into your systems. Mirroring them back shifts your perspective and helps you spot those assumptions in new ways.
2. The “Remove the Middle” Method
Purpose: Spotlight and break your dependency on “the way we’ve always done it.”
How it Works
- Map your process for a particularly challenging or troublesome recurring task in 5–7 steps.
- Remove the middle step—just pretend it’s not an option anymore.
- Ask yourself: “If this step disappeared tomorrow, what impact would that have? What would we do instead?”
Why it Works
Corporate workflows often calcify around legacy steps. Removing one forces creative substitution, which may make your current workflows more efficient—or reveal entirely new workflows that can change the game for your team.
3. The “Perspective Jump” Drill
Purpose: Expand the way you frame a problem by the changing vantage point from which you view it.
How it Works
Take your issue—say, “we don’t feel properly prepared to manage a data breach, should the worst happen”—and answer it from three perspectives:
- A first-year associate
- A CEO
- A client under pressure from a tight deadline or pressing privacy concern
Write down and compare your answers. You should ask questions like:
- How do they differ? Why?
- What are the strengths and weaknesses of each perspective?
- What motivations do they each have, and how do those priorities change their answers?
- What frustrates them most about our current process and each option on the table?
Why it Works
Lateral thinking often emerges when you leave your own incentives at the door—but it’s hard to forget or set aside what you know so deeply. Taking on a new persona and really noodling on a problem from that viewpoint can help you loosen your paradigms.
4. The 10 Percent Rule
Purpose: Because thinking outside the box can be scary and fear inhibits creativity, focus on encouraging incremental creative shifts that feel safe enough to try while initiating slow but steady progress.
How it Works
Starting with a question like “How do we redesign this entire system?” is … tough. In my experience, it’s a great way to usher in an awkward silence in a group setting and accomplish much less than you’d hoped.
So instead, schedule regular check-ins—a great first step to overcoming the brainstorming learning curve. Every time, begin those brainstorming exercises with: “What’s a 10 percent improvement we could test this month?”
Rather than putting a single issue in the hotseat, talking about huge change, and frightening everyone into implementing it immediately, you’ll invite yourself and your colleagues to voice the small challenges that are nagging at them every day. Incremental improvements to these issues build invaluable trust, motivation, and momentum.
Once you’re just a few rounds deep and this process comes more naturally, you end up somewhere surprisingly different.
Why it Works
So many things about corporate and legal environments will resist sweeping change. Small, iterative reframes can grow into serious improvement; over time, you’ll look back and see the transformation you’ve been hoping for.
5. The “Constraint Swap” Challenge
Purpose: Break rigidity by reimagining the operational rules you’ve previously seen as non-negotiable.
How it Works
Choose one real, persistent constraint on your team. Examples could include:
- Budget
- Headcount
- Timeline
- Legacy technology
Now, change that script for a moment. You might restrict it even further, or you could pretend that the opposite is true. Envision:
- Unlimited budget
- Only one team member
- 24-hour deadlines
- No familiar tools allowed
If this were your reality, how would you adjust? Ask questions like:
- “What would we do first?”
- “What tools would we prioritize?”
- “What assumptions would disappear?”
Then, return to reality and extract usable insights.
Why it Works
Constraints shape thinking more than we realize. Contracting or expanding them can reveal new takes on stubborn challenges, help you better prioritize the resources you do have, and think big, aspirational thoughts to identify your best path forward with skill development.
Optimize Thinking to Maximize Impact
In legal (and especially in Legal Data Intelligence), you train for precision. You train for speed and risk mitigation and defensibility. All the strategic corners of this training also help you train the way you think. Thinking skills, like anything else, grow with practice. So take some time to be more intentional about it in the coming month.
Lateral thinking won’t replace disciplined analysis, and it absolutely should not. Linear reasoning is crucial to this profession. But when you’re staring down a stubborn workflow issue, a team bottleneck, or mounting external pressure, sometimes the breakthrough is hiding in a question you haven’t asked yet.
If structured conversation feels safer, that’s great! Keep it structured. Lateral thinking can work really well with realistic, grounded guardrails:
- Start with a clear objective. Inviting an open-ended, creative conversation doesn’t mean it should be poorly defined. Spell out what you’re doing and why.
- Anchor to data. Establish a few meaningful checkpoints that tie directly to the challenge at hand. Measure what matters. Really give that some thought; don’t just stick with what’s convenient.
- Test your ideas. Every time you come up with a new approach, treat it like a hypothesis. Run small experiments so you can adjust quickly to keep what works and boot what doesn’t.
- Name the process. Make it explicit to your team: this is more about guided exploration than chaos. You may diverge from expectations and established norms, but then you’ll converge to validate before forging ahead on anything new.
The goal is to expand your range. The broader that range is, the more options you have when complexity hits—and you know it absolutely will. Ten focused minutes in your next meeting is enough to start practicing.
So next time a problem refuses to budge, resist the instinct to press harder in the same direction. Move sideways instead. Ask the inconvenient or bizarre questions. See where they lead you.
Sam Bock is a member of the marketing team at Relativity, and serves as editor of The Relativity Blog.
