Why approachable beats intimidating every time
Samir Pradhan’s leadership philosophy: be authentic, give people agency, and never be afraid to look like a clown.
Samir Pradhan started his career as a software engineer before discovering the challenge of product-market fit. It piqued his curiosity. “It made me realize that it’s not just about technology. You have to find users who want it,” he says. That’s when his career shifted focus. He worked at Microsoft, Google, and Pinterest before landing at Shopify as VP product.
But that’s just his resume. It doesn’t tell you anything about why Samir’s team loves working for him. Beyond the Linkedin bullet points, Samir has developed a unique leadership style that builds trust with teams, creates a safe space for hard conversations, and most importantly makes work fun.
It’s not that complicated, he says: Leaders simply need to show up as their authentic selves. For Samir, that means sending daily Slack voice notes about everything from spilling coffee on his pants before a big presentation to why he sits alone in his car sometimes.
And according to the people who work with him, this approach has completely transformed how their team operates. In a recent conversation, Samir explained how he creates the kind of environment where people actually want to show up and do their best work.
Dayna: One of your team members was hyping up your management style, which is why we’re talking today. How would you describe your leadership approach and why do you think it works?
Samir: I believe in three things. The first is authenticity. This is part of what makes me the leader I am: when I say something, you can tell that I’m telling you my truth. I’m not reading off a script. I’m not speaking the corporate line.
The other thing is agency. We hire smart people. You don’t want to micromanage them. You want to give them the tools and the space to build the right things.
Third is accountability. Everyone has a different style of getting things done and I appreciate the diversity of styles. But in the end, I look for the accountability that it actually got done.
I just realized they all start with “A”! Authenticity, agency, and accountability—that’s the core of my leadership style.
Dayna: Anything else that you do as a leader to motivate your team?
Samir: I push people to get better at their craft. For me, that means being a coach versus a micromanager. I’m helping them hone product skills by thinking about the user, the product, and the business from a first principles perspective. I believe that a large part of what makes people happy and productive is the learning they get from their work. Not just the earning! My approach here is to give people space and freedom, then the feedback I give them is rooted in, “What moves the needle to make things better?”
Dayna: I love that. I understand you also send silly voice notes to your team on Slack. What’s that about?
Samir: I believe that when someone speaks, it’s way more than the words they say. It’s the tone of their voice. It’s the volume of the excitement. And so I can communicate so much more richly by speaking versus just typing. I want people to not just hear what I’m saying, but also feel how I’m feeling.
I talk about everything from spilling coffee on my pants to updates about important projects we’re doing. There’s always something different that I’m talking about, but the underlying theme is that it’s authentically me.
Dayna: I hear you also shared with your team that you often just sit alone in your car.
Samir: Yeah! I drop my kids off at school, and then I sit in my car for like 10 minutes. And I just breathe and I think about my day and I think about what I’m grateful for and the things that I’m excited about. I’m a very positive person. I wake up every morning excited.
🎧 One of Samir’s infamous Slack voice notes:
Dayna: One thing that struck me about those voice notes is how vulnerable you are in them. Why do you think it’s important for leaders to show vulnerability?
Samir: I think a lot of people look at senior leadership and think, “scary,” and I want people to look at me and think, “approachable.” You can’t manufacture approachability. I am the same way with everyone every time, as in I’m a goofball one-on-one as well as in a large group. They know what to expect.
Dayna: So do you take the same approach when you’re speaking with more senior leaders than yourself?
Samir: I’m the same way. I make jokes and try to lighten the mood wherever I am.
Dayna: You mentioned you’re in the middle of turning around a team’s culture right now. How do you approach that?
Samir: This is where I lean on authenticity the most. One way to approach this exercise is to say, “Here’s what’s working well, here’s who’s doing well, here’s what’s not working well.” I really try to tell people, “Here’s why we’re doing this.” And then acknowledging that despite all the changes that can be made, it won’t always be perfect. Because certain hard truths just exist about the space or the work. Can people find happiness in doing what they’re doing or do they just need better places to be? And can I be on their team helping them to do that?
Dayna: How has your team reacted to this approach?
Samir: It’s still a work in progress, but every one of my leads has come and told me that they feel more heard and more involved. They feel more positive about their work. That it’s easier to get alignment cross-functionally and that they are just happier. The biggest thing they’ve told me is that they can have hard conversations now versus just kind of keeping it in. People have also told me the cross-functional team culture is better because of this too.
Dayna: Shopify seems like the perfect place for this style of leadership. Was that part of what attracted you to the company?
Samir: Huge part. Also, I had so much respect for how mission-driven Shopify was. Everything traces back to this very high purpose idea of making commerce easier. I was very attracted to the fact that AI is used so much internally to help bolster execution, to run faster. And I think in general, the level of craft that people have here is just extraordinary.
Dayna: What would you say to other leaders who want to build this kind of environment but don’t know where to start?
Samir: Start with being yourself. Just tell the truth, even when it’s messy or you don’t have all the answers. Give your team real agency by trusting that the smart people you hired can figure things out. And then hold everyone accountable, including yourself.