Good planners obsess over ‘why’
Nowadays, everywhere you go, it’s all about ‘AI.’ Everyone is busy attaching generative AI features. A planner friend from another company I met not long ago sighed, saying that discussions were happening above about whether they needed to add AI features, so they were hastily preparing a plan for an ‘AI chatbot.’
“So, why are you making that chatbot?” I asked, and my friend replied with a wry smile. “Well... because it’s the trend these days... everyone is doing it.”
Doesn’t that sound familiar? There are actually a lot of projects that start with reasons like ‘because the competitors are doing it,’ ‘because it’s trendy,’ or ‘because we were told to do it.’ The planners of these projects are busier than anyone else. They fill out detailed specifications, handle numerous exception cases, and define complex policies, often working late into the night.
But here’s the thing. Is working so *hard* actually doing the job well?
‘Hard work’ and ‘doing well’ are different
To put it bluntly, planners who only think about ‘how’ are hardworking planners, but not necessarily good planners.
Looking back at my junior years, I think I was the same. When I received a planning task, I would get excited and start drawing screens. ‘I’ll put this button here, use this wording, and users should click in this order!’ Thinking about these specific methods is really fun. The visible results come out quickly, so it feels like I’m doing something great.
However, as I’ve gained experience and witnessed the successes and failures of many projects, I’ve come to realize something. Most of the time, the features we worked hard to create are rejected by users or even negatively impact the business because we didn’t properly consider the ‘how.’ The ‘why’ was missing from the beginning.
There’s a famous piece of data from CB Insights analyzing the reasons why startups fail, and the overwhelming number one reason (38%) was ‘No Market Need.’ Isn’t that a painfully striking result? It means that products created with the sweat and effort of countless people disappear because no one wants them.
Source: The Top 12 Reasons Startups Fail (CB Insights)
This is the reality that planning without ‘why’ faces.
What’s different about planning that starts with ‘why’?
Let’s take a look at a hypothetical situation to see how planning that starts with ‘how’ and ‘why’ leads to different results.
Situation: The CEO suggested, “Let’s introduce a ‘customer tier system’ for user lock-in!”
1) The hardworking planner's approach
Junior Planner: (as soon as receiving the task) “Yes, I understand! I’ll prepare the customer tier plan!”
(Returning to his desk)
How many tiers should there be? Bronze, Silver, Gold... maybe 4 including VIP?
What benefits should we offer for each tier? Discount coupons? Higher rewards?
What should the advancement criteria be? Recent 3 months of payment? Cumulative payment?
... Oh, this is more complicated than I thought. There’s a lot to develop. First, let’s check what the competitors did.
The ‘how’ planner immediately focuses on the implementation method of the tier system. They research competitors, define complex policies, and draft lengthy planning documents. However, they often encounter problems during this process.
Development Team: “This policy is too complex; I think it will take about 3 months to develop.”
Operations Team: “If we give different coupons and increased benefits per tier, it will create too much operational burden for us.”
User: (after launch) “The benefits aren’t enough, so I’m not feeling motivated to upgrade my tier.”
In the end, despite pouring in tremendous resources, there’s a high likelihood that a result will emerge that satisfies no one.
2) The good planner's approach
Senior Planner: (as soon as receiving the task) “CEO, that’s a good idea! May I ask what specific problem you want to solve with the ‘customer tier system’?”
CEO: “Hmm... there are many new users these days, but it seems that a lot of them never return after making a purchase. We need to create some regular customers.”
Senior Planner: “Ah, the key issue is the decline in the repurchase rate of first-time customers! Understood. I will think about the best way to solve that problem.”
The ‘why’ planner focuses on the ‘why (problem)’ of declining repurchase rates for first-time customers rather than the ‘how (method)’ of a customer tier system. Now their mind is filled with completely different thoughts.
Is the repurchase rate of first-time customers really low? Let’s check the data.
If it is low, why is it low? Is it possible that the first purchasing experience isn’t good? Or do they forget the reasons to buy our product again?
Is the only way to solve this problem the ‘customer tier system’?
How about giving special benefits only to first-time customers?
What about sending a message with product usage instructions two weeks after purchase?
Wouldn’t a simple point system be better than a complicated tier system?
Starting from ‘why’ broadens the range of solutions significantly. This planner can analyze data and might conduct short interviews with a few actual first-time customers. They will likely find a solution that has a much larger impact with significantly fewer resources than developing a complicated tier system over three months.
To become a capable planner, let’s find our ‘why’
In this way, the habit of probing into ‘why’ dramatically changes the quality of planning. It transforms you from merely ‘someone who handles assigned tasks’ to a ‘real planner who defines and solves problems independently.’
Then, how can we find this important ‘why’? It doesn’t require a grand method. There are things you can start doing right now from your seat.
Finding ‘why’ in data: What pages are users most often dropping off from? Why is that? What are the most loved features, and why? Data is full of traces of countless ‘whys’ left by users.
Finding ‘why’ from colleagues: Have a cup of coffee with colleagues from the development, design, or marketing teams, especially those closest to customers in the CS (customer service) team, and ask them, “What are customers currently finding most inconvenient?” You’ll likely gain insights into problems you were unaware of.
Finding ‘why’ from users: Ultimately, all answers lie with the users. If possible, meet actual users directly or at least grab friends or family to try out the service we created. Ask questions like, “Why aren’t you using this?” or “Why did you click here?”
Try to reduce the time you spend agonizing alone over planning documents. Instead, use that time to get up from your desk, view the data, talk to colleagues, and observe users. The answers to ‘how’ aren’t on your desk, but hints for ‘why’ must be found in the field.
For your next plan
If you read this and thought, ‘Ah, I need to start considering why!’ then you’re halfway there. For you, I offer two concrete measures that you can implement right away.
Apply ‘5 Whys’ to your current project: While glancing at the planning document for your ongoing project, ask yourself the question “Why do we need to do this?” five times for each item. You’ll likely reach a much deeper, fundamental goal than you thought.
Schedule a 30-minute coffee chat with a CS team colleague: Make time this week to talk with the colleague who receives the most customer inquiries. Start lightly by asking, “I’m interested in your insights for planning; how is the customer response to this feature lately?” You may discover unexpected treasures.
Asking ‘why’ can sometimes seem annoying and appear to require more effort. However, I am confident that this small habit will add an enormous turbo engine to your growth. I cheer for your future as you transform from merely ‘hardworking’ to truly ‘good’ planners.
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