Sanjay Mirchandani | Crain's Portland

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Sanjay Mirchandani


Puppet strives to drive the movement to a world of unconstrained software change. Its revolutionary platform is the industry standard for automating the delivery and operation of the software that powers everything around us. More than 37,000 companies use Puppet’s open source and commercial solutions to adopt DevOps practices, achieve situational awareness and drive software change with confidence. Puppet is a privately held company with more than 500 employees around the world. 

The Mistake:

I’ve been in the business now in excess of 30 years, and this particular mistake goes back to the early part of my career, where you could do no wrong in your head. I was fortunate to work at some wonderful companies at the peak of their growth, surrounded by brilliant people. Just landing the job was a big deal. Once you got in, it was all about calibrating yourself and proving you were good enough to be there.

I remember every time I was asked a question in a meeting, I felt like I had to know the answer. If I didn't know the answer, I felt like a failure. I was one of those people who would talk over everyone and impart my knowledge.

For the bulk of my career, I was a field executive or in field management, representing different companies. When you would come in for quarterly meetings, you were supposed to be the resident expert for your territory. If it was something that had to do with country X or geography Y, it was assumed you knew it. But in reality, you didn't know it. Would it work in the U.S.? Is it a cultural fit? Would it work in Japan or the Middle East? But oh my God, I thought I should know it.

At some point, I had a mentor who took me under his wing, and he told me it was perfectly OK not to have the answer. He said it’s perfectly OK to share my thinking, share my analytics. Share how you process the information. He suggested that maybe the meeting is getting a set point in the solution, not finding the solution.

Countless times before that conversation, I probably made an ass out of myself. That's a big thing to learn, that you don’t need to have the answer. You need to be prepared. You need to be able to talk through it. 

I like to make sure people feel like it's OK to be wrong, or it's OK not to have the answers.

The Lesson:

I've been surrounded by smart people at different points in their career. Young, more seasoned. And over time, I’ve learned that as someone who was leading the conversation. Sometimes it's better to frame the question as, “What are you thinking?” “What are your thoughts on this?”  Rather than, “What is the solution?” If you keep the conversation more open-ended, you can draw broader thinking across the room. Some people do better when they've had a chance to process. Others do better in real time.

I've worked in many major metropolitan areas, and some cultures do better when asked to participate, rather than when they are expected to just jump in. I've led a lot of meetings and like to ask people how they would approach something. I have a tendency to go around the room, getting them to give me more of their thoughts instead of just a conclusion.

I like to make sure people feel like it's OK to be wrong or it's OK not to have the answers. That's less intimidating and inviting to people of different cultures and personality types. If you were hesitant earlier in your career, you might worry that you have been perceived as wrong, which isn’t right. It’s perfectly acceptable for your answer to be that you haven’t thought about that, or here’s what I’m thinking might work.

I've seen both sides of it, and I know I work better, and most people work better, when they feel the right or wrong answer doesn't make or break their career. I’ve seen this play out again and again in numerous corporate situations, from crafting marketing campaigns to writing something as simple as job descriptions.

A job description for a systems engineer could read very differently for a candidate in the United States than it would in China. Years ago, it was unheard of for salespeople outside of the United States to cold-call customers. Someone needed to set up an appointment and come talk to you about it.

That’s a dated example, but it highlights how critical it is to ask questions and explore solutions rather than quickly create cookie-cutter, one-size fits all solutions in the moment. It’s important to think through these things and research and explore possible outcomes. The first thought that comes to mind isn’t necessarily the best, or even close.

Follow Sanjay Mirchandani on Twitter at: @mirchi111

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