One day as a kid, I went to my school in the civil dress on my birthday. It was a beautiful jacket that my parents had purchased from Chandigarh, with a small horizontal zipper at around my navel. I was ten and I felt like a hero’s kid in school, just showing up myself here and there.
While moving around, one of our seniors hated it and he pulled me towards a corner by holding the zipper. The jacket was torn. I was sad and I told her the story to my grandma at home. She advised me that I could have slapped or kicked that senior even if he was two years elder to me. “When they are at fault, and on purpose, you should stand up and pay back. Why not?” (Related post: When a grandmother raises a tomato, opens in a new tab in Medium)
Sometimes I struggled to put her advice in practice but the “why not” gradually became a part of my approach to work, early in my career. In my second job in a digital agency, I was doing technical writing and I would often ask the managers why they are not doing certain things in a certain way? Why the sales pitch is not shared with the project managers? Why the marketing campaigns were planned by marketers without any role by the technical writer? There were many why nots?
When I started my independent consultancy, sometimes I would mistime my questions. I learnt it slowly that early does not always means the right time—we need to anticipate the likelihood of the positive result of such a discussion and so the important of the timing of the questions.
One time I was working on a CRM’s Help Center strategy and the team had purchased a WordPress theme. When I came to know that they have two customer support engineers too to respond to the support tickets, I asked them—”Why not Zendesk?” Why WordPress (Intercom was not around those days). And it worked in their favor. I designed their entire support center in Zendesk and they saw a huge ROI.
While doing a Help Center project for a B2B real estate in the US in 2011, their themes in the templates were ordinary in the experience. Although it was not part of scope of my contract, I proposed them to redo the themes for better responsiveness on smaller devices. My “Why not?” was not taken well, and I lost the contract midway.
Now after working with many global product teams, I feel that *Why not?* is my way of working. It is not about questioning the why or how something has been working in an organization. It is more about knowing the system and how the system components are mapped or are interconnected so far and where we can do better.
Every team needs the right leaders and not all the leaders work with the same thought process. People have their own approach to their work, how they get started, use their judgement and experience, and apply their skills to the work. For me, making the organization think of what they have been doing and why and for how long, is very important, and my “Why not?” is one of the ways to build those conversations. Asking the right questions at the right time is one of the most important skills that I build in my teams.