Wandering down the road, Alice asks the Cheshire Cat, “Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” it responds.
“I don’t much care where—” she says.
“Then it doesn’t matter which way you go,” the cat interjects.
“—so long as I get somewhere,” she finishes.
How many times have you felt like Alice in a presentation or analysis? Lost in a forest of data, walking somewhere, but not moving forward.
Data cannot provide both the question and the answer. It’s a decision-maker’s responsibility to define the problem and figure out how to solve it, using data as evidence. Absent that, you get swirl and slow decisions. Try working backwards instead.
Why start at the end?
Without a clear destination, even the most sophisticated analyses can lead to dead ends and irrelevant conclusions.
When faced with a problem, I often ask teams to first consider the desired outcome. Then I ask them to spend two minutes writing no more than one sentence on 1) the outcome we’re working toward and 2) the decision we need to make.
This exercise kickstarts the working backwards process while revealing gaps in understanding. You want to understand:
- the minimum amount of data required
- the specific analyses needed
- the steps necessary to reach a confident conclusion
If your team members end up re-articulating the problem rather than an outcome, your first problem isn’t a lack of data. It’s a lack of alignment. That’s when it’s time to play the Cheshire Cat and ask: Where do you really want to go? What result would make us all give each other high fives at the end?
Inside-the-box thinking with big-picture benefits
This top-down approach focuses priorities and aligns every action with the ultimate goal. At the same time, the process leaves room for unexpected insights, those “unknown unknowns” that can spark innovation.
This is what we call “inside-the-box thinking.” It’s not about limiting creativity; it’s about channeling it toward solving the right problem. And paradoxically, by narrowing your focus, you often uncover opportunities that would have been missed in a more exploratory approach.
The three steps to working backward
Working backward is more than just a mindset shift. It’s a structured process with three key components:
Step 1: Map Out Your Decision Tree
The first step is to define the potential outcomes of your decision through a decision tree, where each branch represents a possible action based on the results of your analysis.
For example, imagine you’re considering a customer segmentation study. Instead of diving into data collection immediately, start by asking:
- What are the specific decisions this study will inform?
- What actions might we take depending on the findings?
A well-defined decision tree should always have at least two meaningful branches. If there’s only one plausible outcome, then why invest time and resources in analysis?
Here’s a tip: use a sequence of “why” questions to drill down into the core issue. (See: Taiichi Ohno’s Five Whys) For instance:
- Q: Why do we want to conduct a segmentation study?
- A: To better understand our customers.
- Q: Why is that important now?
- A: Because sales have plateaued, and we suspect we’re not meeting customer needs effectively.
- Q: Why do we think that’s happening?
- A: A new competitor seems to be addressing younger consumers more successfully.
By the end of this questioning process, you’ve clarified the decision: Should we adjust our strategy to better serve younger customers?
Step 2: Draft a blueprint for analysis
Once you’ve outlined your decision tree, the next step is to create a detailed plan for your analysis. This involves drafting “dummy” tables or placeholders that outline the specific data and evidence you’ll need to evaluate each branch of your decision tree.
These dummy tables are a roadmap for your data journey. They help you focus on collecting only the information that’s relevant to the decision at hand. For example:
- What metrics will you need to assess each option?
- What level of detail is required to make a confident choice?
Now, you can use the IWIK™ framework to identify the critical unknowns that your dummy tables must address. Populate your IWIK Knowledge Matrix to prioritize essential information and ensures your analysis remains targeted.
By planning your blueprint upfront, you avoid the common pitfall of drowning in irrelevant data. Instead, you’re building a focused, actionable plan that aligns every piece of information with the decision you need to make.
Step 3: Reverse engineer your data needs
With your decision tree and blueprint in place, the final step is to work backward to determine the data and analyses required. Ask yourself:
- What data do I need to populate my dummy tables?
- What analyses will provide the insights necessary to evaluate my options?
From here, you can work with intention to assess available data, collect additional information as needed, perform the analysis, and deliver your findings.
Why isn’t everyone doing this?
Despite its clear advantages, the backward approach is underutilized in business decision-making. Why? Two main reasons:
- Lack of Awareness: Many leaders simply aren’t familiar with the method or its benefits.
- Effort and Risk: The backward approach requires significant upfront involvement from decision-makers. It also forces you to define success and failure early on, which can feel risky compared to the perceived safety of exploratory analysis.
But here’s the reality: avoiding risk doesn’t eliminate it. In fact, failing to define your decision upfront often leads to wasted time, money, and effort. The backward approach may require more discipline, but it ultimately delivers faster, clearer, and more actionable results.
Moving forward by looking back
The backward approach isn’t about skipping steps or rushing to conclusions. It’s about starting with the end in mind and reverse-engineering your way to success. By mapping out your decision tree, drafting a blueprint with IWIKs, and defining your data needs, you can transform even the most complex challenges into manageable decisions.
Sometimes, the best way to move forward is to start at the end.
Christopher Frank, CEO, PSB Insights
