For CEO of Stack Overflow Prashanth Chandrasekar, leadership is all about flexibility in the face of change.
Since Chandrasekar took the helm in 2019, he has led much of this change, moving the business away from advertising-based revenue to a more holistic model. But there’s little more emblematic of his philosophy than the developer hub’s approach to the AI giants.
Last year, the Stack Overflow butted heads with Google and Open AI for training Large Language Models with its wealth of community-driven developer data. Now both Google and Open AI have signed major deals with Stack Overflow – paving the way for a new licensing model that compensates businesses for fuelling generative AI platforms.
As Stack Overflow revives its developer job board with a co-branded Indeed partnership, Chandrasekar reflects on the importance of meeting change head-on.
Did you always want to be a CEO?
Not exactly. I never thought specifically about the CEO role, although I did naturally gravitate towards leading teams. My first experience of this was when I was captain of my cricket team. I think that initially sparked it: athletics and sports. As time went on, I discovered that you can lead companies, you can lead countries, you can do all these things and I gravitated towards that sort of role. It’s fun, challenging and rewarding to bring people along.
What do you think makes a good leader?
Inspiring and empowering people to deliver a common mission. For me it’s all about inspiring folks to operate as more than just individuals? Can they operate as a team to deliver on their North Star?
There’s lots of things a leader needs to do to get there. You need to deliver a culture of trust, where you’ve got integrity and intent going into this common mission. You need to be highly capable and results- and performance-oriented. And my own personal philosophy is I want to be as non-dualistic as I can. It’s easy for people to take hard positions on one side of the equation, but the reality is all very context-dependent. There is no right or wrong answer, generally speaking. You need to be empathetic and open-minded to bring the best out of your team.
What do you think your staff think of you?
They’d probably think of me as somebody who drives pretty hard. But I aspire to be highly approachable and empathetic towards people too. I’d probably say I’m like a velvet hammer. I’m going to drive towards progress. I’m not going to be brash about it, but I am going to be direct.
I compare it to being in the gym. Your trainer isn’t there to coddle you. It’s all difficult if you want to build muscle or endurance. Ultimately people will be grateful the trainer said ‘let’s push harder’, because they were able to produce something they never imagined that they could. So that is how I view the world. Especially in high-growth companies, in companies that are trying to transform and do something completely new in a highly competitive technology ecosystem.
What do you look for when you’re hiring for your leadership team?
There’s two axes: character and competence. Your character could be a lot of different things. Is this person well intentioned? Will they be a cultural addition? Will they operate as a great team member?
The second axis is all about competence: are they good at what they do? Are they skilled? What is their track record or history? Have they shown they can demonstrably produce results? And are they the best at what they do in this space?
What’s the best business advice you’ve ever received?
It’s actually advice I received from my brother. He’s in private equity and a very competent guy.
His advice is just to add value. That’s what we’re here to do. If you don’t add value, then there’s really no point. Why even organise as a company or as a team if you’re not adding value, adding components and making things better than before? So add value in whatever you’re doing. If a company is in an ecosystem, it better add value to that ecosystem. If you’re a member of a team, you better add value for the team to get better.
What do you consider to be the biggest challenge in business right now?
The rate of change is accelerating almost logarithmically. The number of compounding effects you have to deal with, over which you have no direct control, can be overwhelming for a lot of people. The rate of change is dramatic and a lot of companies can’t keep up.
In terms of technology, the thing that’s in the news is the most is AI. The AI transformation is very exciting in the context of driving productivity and efficiency, as well as its ability to bring the world closer to operating with intelligence at its fingertips. But the rate of change within AI is extremely high.
It is fascinating to see the chess moves from the folks trying to compete. That’s the beauty of capitalism – ultimately the consumer will benefit, because everybody’s trying to outdo each other. But there’s a lot changing on a weekly basis. And these are very, very big bets being made. There are tens of billions of dollars being invested. There’s a lot of economic value at stake.
What’s the main driver of change in your business?
AI provides an opportunity for developer workflow to change. Previously, the workflow was a certain set of steps in the software development process. That has changed over the past 18 months and will continue to change.
That’s the biggest driver. Previously, people would go to Google then come to Stack Overflow. Now people go to their AI tools. They may want to engage with the community because humans are very important in the loop. [But] that’s why we are partnering with all the AI companies. We are wherever the developers are. The user interface has splintered into all these AI tools and that’s okay. We just need to show up in those places.
What’s been your proudest achievement in your current role?
I joined the company as CEO in 2019. I was hired after 11 years of the founder running the company. He created this great foundation for the community but the primary two business models were advertising and talent job listings.
That was a great first set of moves to get it to where it was. What I’m proudest of is transforming the company into something that’s beyond that public platform supported by ads and job listings. We made the hard decision a while back to move out of the job listings business and we are now reintroducing the job board in a slightly different context, that works for us now.
We’re still keeping ads but now 70% of our company’s revenues are recurring, non-advertising revenues. I think it was about 10% when I joined the company.
Which book do you think every business leader should read at least once?
One that’s worth mentioning is Five Dysfunctions of a Team by Patrick Lencioni. I was introduced to it many years ago. It portrays the various elements of really making sure your team is aligned and operating as one, as well as the common dysfunctions teams encounter as you work together. So it’s not personal to anybody in the team, it’s just humans coming together.
To my earlier point, if you’re not working together to add value and do something better than it was before, then why are you together? How do you make sure that the team is operating at 100%? One of the primary responsibilities of a leader is to make sure the team you’re responsible for is operating in a highly aligned fashion. This book does a good job and helping with that.
What is one piece of advice you would give to your successor?
Around that compounding, logarithmic situation going on – it’s very important for people to continue to stay hyper focused on the mission of the company. There’s a lot of stuff that happens that may be out of your control, and things will change. Change is inevitable. It’s important for my successor to keep in perspective always that the mission is what should drive daily behaviour, irrespective of what’s happening. Because there’s a lot that is going to look like chaos. It’s going to be hard to plan a lot of long-term thinking.
The way to really plan long term is to stay true to the mission. For everything else – keep a very open mind about changing course to be able to get to where you want to get to.
