Stop Fixing Symptoms: How the 5 Why’s Can Uncover the Real Problem.
Cracking Life’s Toughest Problems, One ‘Why’ at a Time
Hey Friend,
First, let me clear the air. Last week, I might have struck a nerve with some folks when I said leaders should stop spoon-feeding their teams with answers and start coaching instead. I saw the engagement (or lack thereof)—quiet streets out there! But hey, I trust you all took the learning even if you weren’t feeling my approach. I promise no one’s throwing side-eye here!
Now, onto something I’m sure will get you thinking: Critical thinking and how the “5 Whys” technique can help solve both work and life problems.
What’s the Deal with Critical Thinking?
We’ve all heard it a million times: “Think critically.” But what does that actually mean? For me, it’s about asking the right questions to get to the root of any problem, and a great tool for that is the “5 Why’s.” If you’ve ever found yourself chasing solutions that don’t stick, this method will have you peeling back the layers until you uncover the real issue. It’s like cracking open a box to find there’s another one inside, and another—until you get to the real prize.
My Fintech Adventure in Osogbo, Osun state.
Now, let’s rewind to my time as Business Operations Manager at a Fintech company. You know how much I loved my time there—except for the occasional fear of bumping into Eran Iya Osogbo. IYKYK. For those of you who didn’t grow up with Nigerian horror films, just know it was nightmare fuel back in the day.
This Fintech I worked for had just opened a branch in Osogbo, and it was basically a banking enabler with an app and a small mobile POS device. You know, the kind of tech that makes banking possible in unbanked areas. At the time, we had over 1,000 registered POS agents, but only about 35% were actively transacting. That meant 65% of them were sitting on these mobile POS devices, gathering dust and not making us (or themselves) any money. Worse, they held onto the devices even though they were free and could’ve been returned if they weren’t using them.
So, my manager—let’s call him Muyiwa—gave me my first task: reactivate at least 20% of these agents within the first quarter. No pressure, right?
But how do you solve a problem if you don’t even know what’s causing it? That’s where the “5 Whys” came in. Here’s how it played out:
The 5 Why’s: A Journey to the Truth
Why aren’t the agents transacting?
Agents said their mobile devices weren’t “working.” But wait, they were turning on!Why aren’t their devices working properly?
Apparently, they didn’t know how to use the devices correctly.Why didn’t they receive proper training?
Turns out, the sales agents (aka ambassadors) who signed them up got paid their commissions and ghosted like it was a bad Tinder date.Why did ambassadors skip training the agents?
Ambassadors were more focused on signing up as many agents as possible, because hey, more agents equals more money, right?Why was this the case?
There was no system in place to track or hold the ambassadors accountable for training. They were free to “close deal and chill” without doing the hard work of training.
By the end of it, we knew we had a training gap to close and a proper process for managing ambassadors. We went with our “Quick Win”, so, we launched a remote training series within the app and provided easy access to troubleshooting videos. Within a quarter, we successfully reactivated 20% of our inactive agents. A win!
How 5 Why’s Can Save Your Sanity—In Life Too
You can apply the 5 Whys to everyday life as well. Let’s say you’re consistently late to work:
Why am I always late?
I miss my morning alarm.Why do I miss my alarm?
I keep snoozing it.Why do I keep snoozing it?
I’m too tired in the mornings.Why am I too tired?
I stay up late scrolling through TikTok.Why do I stay up late?
I get into bed without any wind-down routine.
Boom! The real problem isn’t your snooze button—it’s your bedtime habits. Fix that, and your punctuality game levels up.
Takeaway
Critical thinking isn’t just a buzzword; it’s a necessary skill. And the 5 Why’s technique is one way to start getting to the bottom of problems - whether it’s at work or in life, asking the right questions is the key to unlocking solutions. The 5 Whys strips away the superficial layers and gets to the root of any problem. So, the next time you’re stuck, ask “Why?” and then keep going until you’ve peeled back the whole onion.
So, what’s the one problem in your life that could use a 5 Why’s deep dive?
Stay Sharp!
Tomiwa
Lean Process Improvement Enthusiast
(Still figuring out if Eran Iya Osogbo was ever real)





Yes. Eran oya oshogbo is real.
Why?
It felt real
Why did it feel real?
Because it could happen and you know people are wicked.
Why are people wicked?
Because humans are allowed a barrage of emotions
...to be continued