Answering uncomfortable questions and others lessons from mentors

“When are you going to sell your company?”

Photo Credit: Oberazzi via Compfight

Photo Credit: Oberazzi via Compfight

I was taken aback. My good friend and former boss, Sandeep Khanna had suggested that I talk to Pravin Madhani, kick-ass sales guy and serial entrepreneur who’d just sold his previous company for a sizeable chunk of change. My intention in meeting with him, was to learn about raising capital. This was in 2000, when the internet bubble had burst and we were still holding day jobs as we tried to bootstrap Impulsesoft, our Bluetooth startup.

I think my first response to Pravin’s question was a somewhat offended “We’re trying to build a business here – we’re not going to sell it.” To Pravin’s credit, he kept his laughter to mere chuckles and persisted.

This was the first of several meetings I had over nearly two years – usually months apart. Every time we met his first question would be about selling the company – a variant of “When are you..” or “Have you already..” Initially I felt very uncomfortable about this question and wasn’t sure if I really wanted to talk to him. To my we-are-trying-to-build-a-Sony-or-HP sensibility, his questions seemed far too commercial. Luckily good sense prevailed and I did continue to meet with him and he too met with me enthusiastically, despite my clear discomfort.

I came to not only value but look forward to my meetings with Pravin. Three critical lessons I learned from Pravin

The need for clarity Why are you in business or for that matter why are you doing whatever it is you are doing? Examine this closely. Each time you seek to answer this, go past the easy or evident answers. My meetings with him were always the exercises in asking Why five or more times. And clarity can only be achieved by asking uncomfortable questions

The power of diversity Of all the advisors I sought, Pravin was probably the one who was most unlike me. This I have to admit made me uncomfortable. I suspect I initially avoided or at least procrastinated meeting with him. The very fact that we were so different, thought very differently is what made my meetings however short and far apart, invaluable. To this date, I find myself asking “What would Pravin ask?”

Being yourself Pravin was the living embodiment of being yourself. What you saw is what you got – he made no apologies for the positions he held, which in hindsight all seem tame. Neither did he hesitate to say “I don’t know. I don’t understand it.” Several years after my first meeting, Pravin sought my marketing inputs for one of his startups. His engineering vp had persuaded him to have me come in. He told me “I thought marketing was all fluff and am never sure marketers really do anything.” I refrained from retorting that this was rich coming from a sales guy! The very next morning he called me and said how useful our meeting had been despite his initial skepticism. Despite his multiple successes (he did sell this second startup as well) Pravin’s been the same plain-spoken person with no airs about him. An example well worth emulating.

Thank you Pravin for being the person you are and challenging me on every occasion you’ve had. I’ve learned a great deal and in a small way passing them on to the next generation of entrepreneurs. I’m grateful that I got to know you and to work with you.


This is the third entry in my 30 days of Gratitude series.
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |

5 thoughts on “Answering uncomfortable questions and others lessons from mentors

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