Rethinking “planning” in modern business
What does planning really mean?
It’s one of the most overused words in business — and one of the least understood.
At Kaleidoscope, we sat down with six of our in-house planning experts to explore this question. Between them, they bring more than 150 years of experience shaping some of the world’s most trusted planning tools and helping thousands of businesses navigate uncertainty.
What we found is that planning isn’t about making lists or ticking boxes. It’s a cognitive process — a way of thinking — that helps businesses anticipate change, make better decisions, and act with confidence.
In this article, we’ll share what our experts revealed about how planning really works, why it’s so difficult, and how the right tools can transform it from a chore into a strategic advantage.
Meet the experts behind Kaleidoscope
At Kaleidoscope, we spoke with the people who know planning best — the minds shaping how it’s done.
Michael, our CEO and founder (and previously the founder of Anaplan), has spent decades building planning software that helps businesses make better decisions.
He’s joined by Kat, who leads product strategy. A former accountant turned product leader (and ex-Anaplan), she bridges financial logic with modern product design.
David and Dorian, both ex-Anaplan and ex-accountants, bring deep expertise in how planning actually happens. David architects solutions that turn complex business logic into clear, actionable models, while Dorian applies his decades of experience to how users think and experience the product.
Dafinka, our product lead (also ex-Anaplan), brings operational depth and a focus on turning planning theory into practice.
And Gayathri leads user research, keeping us close to how teams plan and make decisions in the real world.
From shaping some of the world’s leading planning tools — to now, reimagining what planning can be — we've got an expert team powering us.
Planning is decision-making under uncertainty
Every expert we spoke to agreed: planning is fundamentally about making informed decisions when the future is uncertain.
It’s not just about setting targets or allocating budgets — it’s about asking the right questions:
What are we trying to achieve?
What resources and constraints do we have?
What scenarios could unfold next?
As Dorian put it:
“Between evaluation and execution, there’s a form of planning.”
Good planning happens in that in-between space — where insight meets action.
Planning is iterative, not static
Traditional plans are often static: made once, then quickly forgotten. But real-world planning is a living process.
Michael describes it as:
“A loop, not a line — you’re constantly revisiting assumptions as the world changes.”
Our experts talked about planning as a continuous cycle of modelling, testing, and adapting — one that evolves as new data, risks, and opportunities emerge. That means businesses need tools that support iteration, not just documentation.
Effective planning environments allow people to explore what-ifs, update assumptions, and align around new insights — all in real time.
The core components of good planning
Across every conversation, a simple but powerful framework emerged: inputs, activities, outputs.
Inputs
Reliable data (sales history, market trends, benchmarks)
Clear assumptions (growth rates, constraints, resources)
Collaboration from multiple teams (finance, marketing, operations)
Activities
Scenario modelling and what-if analysis
Alignment on key assumptions
Documentation of decisions and rationales
Outputs
Actionable, feasible plans
Clear visibility of progress and variance
Shared understanding of roles and objectives
As David summed it up:
“Planning should turn data into decisions, not dashboards.”
Planning isn’t an isolated task — it’s a shared process of sense-making.
What people expect from modern planning tools
When we asked what makes a great planning platform, one theme stood out:
“It should help me think — not replace me.”
Planning software should enhance human judgment, not automate it away.
The team highlighted that modern tools should be:
Visual and intuitive — not buried in dense spreadsheets
Scenario-driven — enabling what-if exploration
Connected — integrating live data from across the business
Collaborative — supporting comments, discussion, and shared decisions
Reliable and fast — building trust through performance
Smart — guiding users through AI-powered prompts and insights
As Michael noted:
“A great planning platform should act like a thinking partner, not a black box.”
The tensions shaping the future of planning
Tension | What it means | What businesses need |
|---|---|---|
Flexibility vs. structure | Freedom to model ideas, but with guardrails for coherence | Structured templates with room for creativity |
Spreadsheet familiarity vs. modern UX | Comfort vs. capability | Blend spreadsheet logic with visual workflows |
Human judgment vs. AI guidance | Insight vs. automation | AI as a co-pilot, not an autopilot |
Short-term agility vs. long-term strategy | Tactical action vs. strategic direction | Tools that span both horizons |
These tensions reveal why so many planning tools fall short — and why a new approach is needed.
Planning is about thinking, not just doing
If there’s one message that came through in every conversation, it’s this:
“Planning is not a single activity — it’s a cognitive process of foresight,” says Dorian.
That means successful planning isn’t about completing tasks. It’s about making assumptions visible, linking decisions to outcomes, and building shared understanding across a business.
A well-designed planning platform bridges human intuition with computational clarity — helping people see, test, and trust their decisions.
The future of planning technology
Our experts see a clear opportunity: to build tools that support how people actually think.
That means:
Flexibility without chaos — adaptable models that still hold together
Rigor without rigidity — accurate, structured insights without friction
Collaboration without confusion — shared context that keeps everyone aligned
As David put it:
“The best planning systems don’t just give you answers — they help you ask better questions.”
At Kaleidoscope, this philosophy drives our vision for the next generation of planning tech — one that connects a business into a single source of clarity. Because when planning works, it doesn’t just predict the future — it helps shape it.
Conclusion: Planning as a competitive advantage
Planning is more than spreadsheets and strategy documents. It’s how businesses think, decide, and adapt.
The stronger your planning process, the faster you can respond to change — and the more confident your decisions become.
At Kaleidoscope, we believe the future of planning lies in connected, collaborative, and intelligent platforms that make foresight accessible to everyone.
If you’re ready to rethink how your business plans, explore what we’re building at Kaleidoscope.