learning

The Founder’s Dilemma: When Humility Unlocks Growth

A few years ago, I was mentoring a promising founder—brilliant, driven, and relentless in his pursuit of success. He had built a solid product, assembled a strong team, and secured early traction. Yet, something was holding him back, and he didn’t even see it.

He felt the need to have all the answers.

One day, during a strategy session, I noticed his team hesitating to challenge a key decision. Their body language spoke volumes. When I probed, one of them finally admitted:

“He’s already decided. We know he won’t change his mind.”

The founder looked surprised. In his mind, he was leading decisively. To his team, he was shutting down discussion.

Later, in a one-on-one, I asked him, “What if the best idea in the room isn’t yours?” He paused. It was a question he had never considered.

That moment sparked a shift. He started making small but powerful changes—anonymous “Ask Me Anything”s to encourage open feedback, reverse mentoring to learn from his younger team members, and pre-mortems before big initiatives to uncover blind spots. He even began writing reflection notes after investor meetings, capturing key learnings instead of just defending his position.

The impact? His team became more engaged. Innovation flowed more freely. And when the company scaled, it wasn’t because of one person’s brilliance, but because he had created an environment where everyone could contribute their best thinking.

Humility isn’t about self-doubt. It’s about recognizing that the best ideas don’t always come from you—and that true leadership lies in empowering those around you.

Take a moment to reflect: Where in your journey can you step back, listen deeper, and create more space for growth? Often, the breakthroughs we seek don’t come from pushing harder, but from embracing the quiet power of humility.

1

Contradictions that count!

Summer of 2001, on a beautiful hillside in southern California, I went bungee jumping. It’s something I had always wanted to do. But this one was pushed on to me by my i-dont-like-to-close-the-deal customer.

Over previous ten months, we were discussing a product line take over deal with this telecom major in trying to help them with better manageable product portfolio and profitability. We had crossed several barriers internally, between companies and with stakeholders. We had also built several bridges to make it a smooth ride. More or less, all items on the checklists, to-do lists and contract terms were ticked off. But CEO was not yet ready to sign. Both teams had no clue on what was the issue. He finally agreed for a breakfast meeting with me to discuss the matter. That day, I saw a different person all-together. We talked about several things – technology, politics, personal hobbies, sports so on… surprisingly we found we had several common interests. I guess this would be true with any stranger we meet as well. Then, we came to the point. I asked him how do we move ahead with the deal. He said, he was very happy with every bit of preparation, but was afraid of contradictions in reality, that might lead to disintegration of trust and finally demise of the product line. This was really serious. I asked him how do we get over this. He said. He was not sure how. But asked me – have you ever done bungee jumping? I said, “No. But it’s in my list of to-do within next 3 yrs”. He said “Then, you will not understand my state. Let’s keep this deal in suspension for some more time. See you around.”

So there I was. My bungee-master and I, standing on a platform that was raised on a bridge at an elevation of over 140 feet above beautiful stream of water through the mountain cliff. Apt site. Master explained that he’d check everything to make sure I was safe. Then he’d count down from five. He explained that when he reached three, I should take a very deep breath. When he said tow, I should clear my mind completely. And on the count of one, I should dive. Not jump. Dive. “Go head on first”, he instructed.

My bungee master checked everything and declared that I was safe. Then he asked me if I was nervous. As I recall, I said something to myself – same thing I had told myself when I first climbed to base camp of Mount Everest, same thing as when I first jumped off the cliff in Nepal for Paragliding and every other time when took up something crazy…. : “what will happen, more than losing life? Let’s enjoy every minute”. But this was different. Master shouted – “are you ready?” He started, “Five”…. “Four”…”Three”… I took very deep breath. “TWO”… and I knew I was supposed to clear my mind completely, but I couldn’t because what popped into my mind was the “contradiction” that seemed a lot less menacing 140 feet earlier.

The bungee jumping brochure said, “It is absolutely, safe! We have performed over 75,000 bungee jumps and continue to proclaim our impeccable safety record without a single accident or injury of any kind.” Which sounded pretty good. So I signed up and paid. It was just before setting foot on mountain drive  at the camp office, that they gave me a release form to sign, which said, “I understand that bungee jumping is a potentially hazardous sport, which may result in….I freely accept and fully assume all such risks, dangers and hazards and the possibility of injury, death, property damage or loss resulting therefrom.”…What????

I was able to relate to the plight of my CEO friend. Preparations matter. But taking the step requires a lot more assurance than just – don’t worry, it’s safe. we have done it before, others have done it before! It is not a promise. It is just a hope. A few will jump, based on the hope. Especially when their desires for the adventure over powers the fear of unknown.

How many contradictions can you find in your own setup, conversations? How many times you see the guy preaching “open door” policy will always be unavailable, though at desk? and how often are yourself a perpetrator or willing accomplice?

One thing is certain. When people meet contradictions, they tend to latch on to the side of the contradiction that favors their pre-existing preferences. Which is why I decided bungee jumping was safe!

My bungee master said “one” and yes, I dove! Head first. And screamed, laughed, laughed, laughed. It was insane. I was, without contradictions myself!

And so I met my friend. Shared my experience. We closed the deal and went back to one more jump over the weekend. But the first one was the best!

its fun, to be a #dreamerdoer

Cracking the learning code!

Learning to play an instrument had been my childhood dream. I have tried several and failed in every one of them. Learning a subject is not that hard for me. Not even sports, adventure and business! But somehow, I’m not able to get through these musical instruments. Not anymore!

Somethings come natural to us. That’s where our heart and head synch-up seamlessly, and take us places. A slight skew in the match-up, will make it hard. As the skew gets more, difficulty is that much more! So, doing what comes naturally to us is the best way to enjoy this journey of life. But, it is not that easy as we want some more things to survive, in this journey! That’s when the story of “handwork” starts.

It’s one sunny February morning. I’m in the mood of writing our new corporate growth plan. Here comes our CMD. “We need to talk. It’s about the international symposium on next generation technology adaptation in the areas of healthcare, education and social well-being. I have accepted the keynote speech invite. Since, you work in Social Enterprises, can you please help me with the story?.” I respond, “Is that the Frankfurt one, in September?.” “Yes.”, comes the reply. I tell him that I’m on the same event and covering the social innovation as a subject of my talk. “Yes. I’m aware. But need your help with my talk”. What followed was an interesting experience of working with him for next 6 months for a 15 minute keynote! In the process, I had given him several notes, case studies, research papers and accompanied him to several primary healthcare centres, educational institutions and women self-help groups. I’m sure, he would have reached out to several others working in this area. We had a weekly synch-up meeting scheduled on Saturday mornings 10:30 am IST, irrespective of where we were! I had not worked on a project of this kind, with this intensity before! At times, I wondered what is this guy up to? Six month’s preparation for a 15 minute talk? I asked him… Why is he so paranoid about this? His reply made me change my perspective about learning things that does not come naturally to me. He said “I’m not as smart or as intelligent as many of you are. I have built this company and reputation in the industry through sheer handwork. I don’t like to leave things to chance or time, without doing my bit. Especially now that I’m an old man of 70 and respected in the industry, every word I speak should be valuable. I can’t just speak words without feeling them fully at heart and verified by my head. So, I prepare. Relentlessly, prepare to do justice to whatever I accept to do. It’s my way of learning, cultivated through several decades. Works for me.”

I think, it just works for me too! I never felt ashamed later, to sit in a class with toddlers to learn violin. Mess up with beats and rhythm, collect myself up and go for it again… Kept up with a goal to perform in front of my family of musicians in our annual get-together… Well, to my satisfaction!

What he weaved on that cold morning at Frankfurt, in front of several global leaders was magical. I could feel the weight of every word he spoke. Depth of every data he shared and actions he recommended and following through. It just worked very well. As a result, there was this new CMD with a freshly found mission for rest of his life. If, working for that 15 minutes can change him so dramatically and leave the audience inspired to take real action, imagine what it can do for anyone?

That evening, when I sat through the day and reflected on what I know of him, I think I got what made him effective in his craft – learning the tricks of the trade in a hard, but gentle way! The note that day, I wrote to myself as a reminder –

Be patient : Most often we notice progress only by looking back at how we were in the past – may be two/three years ago. Progress comes slowly and steadily. It is a phenomenon.

Be persistent: Don’t ever give up! Don’t get restless and look for a new trick or hack now and then. Learning is a process. Give it its time. Practice continuously, till you are happy with the effort and then do more of it till you get it!

Be humble : The arrogant will find it difficult to learn anything. Acknowledge inadequacies. Face it with courage. Find ways to overcome them than avoid. Good teachers help. Keep looking out for them.

Be inelegant : Give yourself permission to be inept. Ask dumb questions. Don’t fake it. Seek to learn.

Learning is a continuous process. Like breathing, learning is part of our life. But exactly like we do with breathing, we stop conscious learning when we get busy with life. But perfecting the art of learning will be handy, as ever.

be a #dreamerdoer