How Stack Overflow Harnesses the Power of Flexible Leadership

January 12, 2022

The world is full of polarized views. People seem obsessed with being right (and with proving others wrong). In the data-driven technology space, this simple binary makes some sense. After all, data is usually clear cut: yes or no, this or that, zeros or ones.

Take Stack Overflow, the world’s largest software developer network, community, and platform, serving close to 100 million monthly visitors. It might be a little surprising to learn that the leadership style at Stack Overflow is decidedly not binary. In fact, the team intentionally takes a non-dualistic approach that relies more on empathy, flexibility, and context than on the concept of right versus wrong. 

Stack Overflow CEO, Prashanth Chandrasekar, joined Blake Bartlett on The BUILD Podcast to talk about how his company’s non-traditional approach to leadership and decision making have helped them become such a successful and respected force in the developer world. 

“Based on my experience, it would be shortsighted if we didn’t take an empathetic view,” Prashanth says. “There are likely multiple answers to any particular challenge. A balanced, non-dualistic approach to problem solving ensures you are considering the context of the situation, which is always highly relevant.”

Step 1: Let go of the myth that there’s one right way to do things

It can be really tempting to try to apply someone else’s wildly successful playbook to your own organization, but Prashanth says this is a dangerous trap. “Blindly adopting someone else’s playbook is a massive mistake. Every company is different—the people are different, the stakeholders are different, the customers are different. You can’t just rinse-and-repeat what worked for someone else. You have to think for yourself.” 

This doesn’t mean that playbooks and frameworks are always a bad idea. They are often an expedient way to educate yourself about the tools of the trade and the different ways to approach a particular challenge. It’s just important to maintain your perspective and consider the context of your own unique situation. 

“We each deal with different kinds of problems as a result of the journey we’re on,” says Prashanth. “But, we’re all in the problem-solving business, right? It’s just a matter of being deliberate and thoughtful and operating with your unique strengths in mind.” 

Bottom line: Don’t assume the solution that worked for someone else will work for you. Learn what you can from what others do, but know that it’s ultimately up to you to find the best solution for your specific situation, strengths, and desired outcome.

Step 2: Adopt a flexible, non-dual approach to leadership

Traditional business schools teach students that they have to choose one position and stick to it. And even though—in real life—there usually isn’t one right or wrong answer, people continue to feel like they have to pick A or B and ignore all the gray areas that lie between the two ends of any spectrum. 

Prashanth takes a different approach for himself and the leadership style at Stack Overflow. Non-dual leadership uses the power of empathy and flexibility to adapt successfully to a world that is always changing by replacing dogmatic thinking with dynamic, ego-free thinking. 

“As a leader, you have to come into any situation with a point of view. That’s what you’re being paid for,” Prashanth says. “The challenge is that you only have one lens through which to assess the situation and form that opinion. So, you need to live by the idea of strong opinions loosely held.” 

In other words, do the work to develop your initial opinion based on the information you have at your disposal, but then be open to looking at the situation from other points of view. And then, as you learn more and gain empathy by looking at the world through other people’s eyes, be flexible enough to adjust your opinion. 

>> Learn what 4 leadership qualities every CEO must have at high-growth companies.

Step 3: See what happens when you forge your own path

One of the key benefits of flexible, non-dual leadership is gaining the ability to assess situations and opportunities with a much higher degree of objective accuracy. Another is gaining the ability to make choices that might go against the advice of the mainstream playbooks, but which are perfectly suited for your organization and situation. 

Stack Overflow has built their business in a very non-traditional way that bucks the commonly accepted “best practices” in two critical areas:

Product → Brand → Community versus Community → Brand → Product

Most software companies start with a product obsession. The early years are spent going deep on the product, the customer, and finding product market fit. From there, the most well-traveled path takes an organization into the realm of brand development, and finally to the third pillar of community. 

“For Stack, we did things completely the opposite,” says Prashanth. “We created our community first, and focused on growing that, eventually reaching the 100 million monthly users we have today. Along the way, we established a massive brand, because every developer and technologist now knows Stack Overflow because they use it every day to get unstuck when they are up against a technical issue. And it’s only now that we have begun our product-led journey, creating SaaS products, specifically a private Stack Overflow for Teams product.”

Instead of following the universal path of starting with a product and building up to a community, Stack Overflow created a different journey based on their specific circumstances, their purpose for being, and the problem they were trying to solve for their audience. In their case, their audience didn’t need a product, they needed answers. So, a community was the obvious starting point. 

SMB → Mid-market → Enterprise versus Enterprise → Mid-market → SMB

Another example of how Stack Overflow took a completely opposite approach to most other companies is how they entered the market with their SaaS product. Most companies test the waters with a SMB and/or freemium offering, and then work their way up to staking out territory in the mid-market and enterprise arenas. Once again, Stack Overflow flipped that traditional playbook on its head. 

“It made sense for us to start in the enterprise, because we already had a community and a platform that was operating at the scale of 100 million monthly visitors, so—why not?” says Prashanth. “We were already equipped to help large companies knock down silos, facilitate asynchronous collaboration, and share knowledge all across their organizations.”

Having achieved success with enterprise, it’s only now—approximately three-and-a-half years after the initial product launch—that Stack Overflow is launching mid-market and then SMB and even freemium offers. 

Prashanth acknowledges that no strategy is perfect, but emphasizes that the most important thing is to develop your plan based on your unique situation, “Everything comes with positives and negatives, but the point is that your strategy has to be very specific to your circumstances and your company.”

Another example of a big strategic decision that can benefit from a non-dual leadership approach is the question of whether to go product-led or sales-led.“Instead of blindly choosing a sales-led or product-led approach, the right answer for a company might be a combination of the two or switching back and forth,” says Prashanth. “In addition, you have to remember that what is appropriate now might be very different from what’s appropriate in the medium- or long-term.”

Again, not every question boils down to an either/or choice. And not every decision needs to stand forever.

>> Read why Atlassian increased their average sales headcount by 45% and how they are doubling down on sales while maintaining a product-led model.

5 Tips for Getting Started with Non-dual, Flexible Leadership

In closing, Prashanth offered a few starter tips for leaders and organizations who want to embrace a flexible, non-dual approach to the way they engage with the world and its challenges:

1. Be Different. “If you want to win, you have to be different,” says Prashanth. And while taking the road less traveled comes with its own challenges, those aren’t impossible to overcome. “Not following the herd can take you in a counterintuitive direction that may bring an element of negativity for a while, or keep you from optimizing certain elements of the business. But, if you can keep moving forward and build yourself a solid foundation, you’ll be in a stronger position from which to optimize in a more agile and efficient way.”

2. Always listen to the people closest to your customers. This will give you a sense of appreciation for what you’re building, keep you close to your “why,” and help you develop greater empathy.

3. Own your decisions as a leader. Right or wrong, you need to be responsible for the calls you make. Never point the finger or pass the buck. Go ahead and think big. Inspire your team. And then provide leadership that ensures everyone is rowing in the same direction.

4. Stay flexible. On the flip side of owning your decisions, you need to stay open to change. “Always be open to changing your opinion,” says Prashanth. “There will always be new dynamics as you scale, and different strategies will be appropriate at different stages.”

5. Be contrarian and be right. Train yourself to see the opportunities that others overlook. Avoid being dogmatic in your beliefs or your decisions. “Don’t let the herd influence you to become more generic and less specific to your own path and to your own company,” says Prashanth.

To hear more from Prashanth and Blake, tune in to hear the full episode on The Build Podcast.


OpenView, the expansion stage venture firm, helps build software companies into market leaders. Through our Expansion Platform, we help companies hire the best talent, acquire and retain the right customers and partner with industry leaders so they can dominate their markets. Our focus on the expansion stage makes us uniquely suited to provide truly tailored operational support to our portfolio companies. Learn more about OpenView at openviewpartners.com.