An Interview With Chad Silverstein
Ambitious efforts, properly done, deserve to be rewarded, encouraged and repeated even when they do not land.
Purpose has become the new currency of success in today’s workplace, and leaders who prioritize mission-driven cultures are standing out in the war for talent. To explore this important topic, we are interviewing Steve Woods.
As a part of this series, we had the pleasure to interview Steve Woods.
Steve Woods joined Inovia Capital as Partner and CTO in 2021 and has worked in software development, research and technical leadership for more than 30 years. As co-founder of three software and services companies based in the USA (Quack.com, Kinitos and NeoEdge Networks), he built strong, high-performing teams of product and technical experts based in both Silicon Valley and the Waterloo-Toronto tech corridor. Steve also led the growth and leadership development of the Google Canada product and engineering teams from 20 to over 1,300 people across a range of impactful products between 2008 and 2021.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
My career path is a bit of a winding road. I grew up in a small town in Northern Saskatchewan, which is about as far from a tech hub as you can get. Sports were not optional in our house, and neither was academic success. I played hockey competitively, was a nationally competitive golfer for a stretch and had a serious relationship with mathematics from an early age. In a small town you get lots of opportunities if you’re willing to show up, and I learned early how to be a teammate, a leader and a supportive cast member. I was always a curious builder and voracious reader. A family friend gave me a VIC-20 computer at 14 and I started writing software just to see what it could do. That pretty much set the stage.
A computer science degree and a stint in software showed me it wasn’t the path I wanted. Enterprise software leaves little room for real exploration. So after spending my savings backpacking, I headed back to Canada to learn more interesting things.
At the University of Waterloo, I earned a Masters of Mathematics with a focus on AI and the world opened up in new ways for me as an experimental researcher. I met some amazing people, learned about the cross-over between research and innovation in Waterloo. I could have continued in academia, but I wasn’t sure. Upon finishing my masters degree I was on track to return to Alberta for a great applied research role focused on important safety challenges in logistics, but a different opportunity came up. So I changed my mind and spent two years playing semi-professional hockey in Australia instead, writing software at night to have enough money to live, and honestly, thinking about the future.
I was recruited to DND in Canada to apply for my Masters work, and used this as a bridge back to extend my work with my supervisor and pursue my PhD in Computer Science with a renewed focus in Artificial Intelligence. I always encourage people to take different paths when the opportunity arises, and my own story speaks to that.
After a stopover in Hawaii for a while to do a postdoc with one of my favorite researchers in my field, and a stint in Pittsburgh at Carnegie Mellon in the late nineties, I co-founded Quack.com with a small team of amazing people whom I trusted completely. We pioneered the world’s first interactive voice assistant and within one year sold the company to Netscape/America Online for $200 million. That experience set the template for everything I have believed about teams and building things since.
After co-founding several technically ambitious startups, I joined Google in 2008. I started with 20 people on my team and in 13 years grew the Google Canada engineering and product organization to over 1,300. In August 2021, I joined Inovia Capital as Partner and CTO.
Can you share the most interesting story that happened to you since you began working in leadership, culture building, or purpose-driven organizations?
Never stop innovating. That was an invaluable lesson I learned leading a large engineering organization, and I learned it in a visceral way. One of my teams and I spent two full years building something I genuinely believed would matter to customers and partners and would add material returns to our company at scale. We got to the final stretch of the launch cycle, and then the project was shelved. I was frustrated and very unhappy about the turn of events; I had put 40 people’s time and my own credibility on the line for this project and felt the company was missing a huge opportunity. What happened next surprised me. At 10:45pm on the Friday night the project was cancelled, I received a call from a senior leader and he asked me two questions: did I agree with the decision, and did I understand it was his to make. I answered honestly on both counts, and what I anticipated to be a difficult conversation turned into something else entirely. The message was straightforward: keep thinking big because that is exactly what we need. That was reinforced in a meaningful way because going big and innovating had been worth rewarding even though the project never launched. It confirmed something I now tell every founder, CEO and CTO I work with. Ambitious efforts, properly done, deserve to be rewarded, encouraged and repeated even when they do not land. The best leaders I know are relentless about finding great people, empowering them to embrace the big picture and giving them the space to be as impactful as possible.
You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Curiosity with a destination: I have always built things: legos when I was young, software when a computer found me as a teen and companies when I discovered people I wanted to build with. My curiosity wasn’t always pointed in a specific direction. Sometimes learning needs to be open-ended to discover things you never would have found if you had been looking for them. But curiosity works best when it finds a destination. When I first came across AI in 1988, I couldn’t have predicted where it was headed. I just knew I’d never seen anything like it. That kind of directed curiosity, the kind that makes you go home on a weekend and rebuild code from your PhD just because you want to understand something better, is what I look for in the people I want to work with and invest in.
A preference for teams over solo achievement: I was a competitive athlete for many years, and the thing I found most satisfying was never the individual result, but winning with a group of people who had figured out how to function as a unit. That carried directly into how I think about building organizations. The best engineering cultures are those where the team’s success genuinely matters more to individuals than their own advancement. You can’t fake that. You have to hire for it and then build structures that reinforce it. That said, what constitutes a team is changing fast. Builders who were already exceptional are now operating at a scale that was not imaginable a few years ago. I’m spending a lot of time right now with AI-forward teams, understanding what is working and what is not, and it is one of the most exhilarating times I can remember to revisit long-held assumptions about what is possible and how quickly it can happen.
A high tolerance for being wrong: I’ve had startups go bankrupt, made investment decisions that looked obviously correct and turned out not to be, and I have held strong technical opinions and been proven wrong by a friend with a better argument. What I have never done is let any of that stop me from having opinions, making decisions and moving forward. If anything, I want to be accused of being too ambitious, of backing people with enormous goals and genuinely understanding why failure is a necessary possible outcome of real learning and real success. Failure is information. You collect it, you learn from it and you do not let failure prevent you from pushing forward.
Investing in people is something I love. I have known Nick Frosst at Cohere for many years, worked with him across many contexts and appreciate his insights, his experimental nature, his wild creativity and his dedication to get things done. It is a delight to see him and his co-founders achieve so much, and being associated with that journey is a pleasure. Tomi Poutanen is a brilliant multi-time founder I have known for a long time, and being alongside his ambitious and important journey at Signal 1 is a learning experience every day. The list goes on. Meeting gritty experimental founders like Scott Stevenson at Spellbook is a constant learning experience in customer-obsessed focus and the AI-accelerated pace of change he is driving in legal contracting.
Let’s now jump into the focus of our interview. What does a “purpose-driven culture” mean to you personally, and why do you think it’s critical for attracting top talent?
Purpose-driven culture means people have a reason to care that is bigger than the feature they are shipping this week. It does not have to be some grand statement about changing the world, but it has to be something real and something specific enough that people can feel it in their day-to-day decisions.
For attracting top engineering talent, purpose matters in a very particular way. Good engineers always have options. They choose where to work based on whether the problem is genuinely interesting, whether the people around them are worth learning from and whether the work will matter in the long run.
I am asked sometimes about how this affects builders — software, hardware, developers or engineers — and how our institutions should evolve in educating them. For me it’s obvious. We always encourage people who want to change the world to learn how (for example, how to cure a disease, build a better bridge or create a new material). The answer is that the tools are constantly getting better. Learn how to use them, learn how they work and what they can and cannot do, and apply that learning to your problem. Explore the possible and push the boundaries of each new advance to reach your goal. We are in the very early stages of new capabilities, and each clever application brings us closer to a material that allows us to build a space elevator, to a biological breakthrough that makes deadly cancers a thing of the past, and to insights into physics that will change the way we see and manipulate our world. There has never been a better time to be a builder, an inventor or an investor who backs curious builders with a purpose.
How did you identify and define the mission or purpose for your organization? Was it inspired by a particular event, challenge, or insight?
When I joined Google I arrived with one very clear goal: I wanted to build things that mattered and attract and empower the best product and engineering team in Canada. Not a good one. The best one. And I wanted to do it with a culture that felt like it genuinely belonged here, collaborative and fast-moving and unafraid, while also producing work that stood up against anything coming out of California or anywhere else.
That goal was not handed to me and it did not come out of a planning session. I arrived with it, and it became the organizing principle for every decision we made about who to hire, what projects to prioritize and how to handle the moments when things went wrong. That clarity did more work than any document or values exercise could have.
What role does leadership play in championing and modeling a purpose-driven culture? Can you share an example of how you or another leader helped reinforce your organization’s purpose?
Leadership models culture whether it wants to or not. The question is whether it is modeling the culture you intend or the one you are building by default.
Patrick Pichette, the former CFO of Google and now Partner at Inovia, was one of the best examples of this I have witnessed directly. When he first addressed a large group of engineers he said something along the lines of: “I know you think I am here to stop you from doing important things. That is not why I would come here. We are going to do the biggest things possible.” He meant it, and he backed it up in his decisions over time. People came to trust him because of this. That is how you model a purpose-driven culture from a leadership position. You state the culture, then you make decisions that match it consistently.
How do you handle skepticism or resistance from team members or stakeholders who may not immediately understand the value of focusing on purpose?
What I have found is that the most effective thing you can do with a skeptic is give them something concrete to evaluate. “Show me” is more persuasive than “trust me,” and if someone does not believe the team’s culture is what you say it is, invite them to spend time with the team. Let the evidence do the work, and if the evidence does not support what you are saying, the problem is not the skeptic but your purpose itself.
Ok, let’s talk strategy. Based on your experience, can you share “5 Steps to Build a Purpose-Driven Culture That Attracts Top Talent”? If possible, please include examples or stories for each.
1. Hire for curiosity first, credentials second, especially in the AI era
The best people I have ever worked with were the ones who needed to understand things, not because it was required, but because they could not help but understand. They asked questions when other people had stopped asking. They went home and kept thinking about the problem. Credentials do matter, but credentials only tell you what someone has done. Curiosity tells you what they are going to do next. In an environment where the tools and the problems are changing as fast as they are right now, the curious people are the ones who will still be valuable in two years and beyond.
Sometimes the pace of change feels overwhelming. Earlier this year I felt it was impossible to keep up so I made the choice to double down. I had some insightful disagreements with other technical leaders about how one could build great, reliable and powerful things with AI, and then I decided to stop debating and just do it. I went home and over the course of several weeks built a range of things, thinking carefully about how to build reliable and complex systems that could be expanded and managed over time. I was amazed. What I had seen and heard others doing had inspired me to experience it myself, and as an investor in such people I needed a sharper sense of what was possible and what the real challenges were. The result? I have never worked harder, learned more or felt more excited about finding the next great founders leveraging these technologies.
2. Build transitive trust: trust through layers, not just from the top
My colleague Kory Jeffrey, who worked with me at Google and is now a Partner at Inovia, and I call this transitive trust: the idea that you cannot personally maintain a direct trust relationship with every person in a large organization, but you can build a culture where trust travels. The way you do that is by being very deliberate about the people you promote into leadership. They have to model the same values you model, because the people reporting to them are watching them, not you. If the trust breaks at any layer in that chain, it does not stay contained.
3. Give people problems that are real
This is the step most organizations get wrong. They talk about purpose and then assign people to do work that does not feel meaningful. Engineers especially have a highly sensitive detector for whether the thing they are building is real or not. If the work is not consequential, no amount of culture investment will compensate for it. Give people hard problems, genuine constraints and real ownership of the outcome and then get out of the way.
4. Make career growth part of the culture, not a side process
Some of the moments I am most proud of from my years at Google were one-on-one conversations where I helped someone see a path they had not yet seen for themselves. I have always sought out people with ideas and given them room to pursue them. That means keeping an open door, being genuinely receptive to what people brought in and then doing the harder work of giving them the time and capability to explore it. An idea on its own is not enough. As a leader you have to actively create the conditions for people to explore their curiosity. When someone finds a way to pursue their passion inside your organization, you avoid losing them, you often advance your own mission and you build a culture of possibility rather than obligation or drudgery. Get the task done and done right, and then create the space for people to push beyond it. If you build a culture where growth is a priority for the organization and not just each person’s own problem to solve, the best people stay longer and also recruit other great people they want to work with.
5. Let the purpose live in the honest moments, not just the official ones
Every organization has official communication about its values and purpose, and almost none of that is what actually shapes culture. What shapes culture is what you do when something goes wrong: whether you learn from it and what you do when a hard decision has a politically easy answer and a harder right answer. If the purpose you describe in your all-hands meetings matches what you actually do in those moments, you have a real culture. If it does not, you have a branding exercise.
Can you share a specific example of how embracing a purpose-driven culture helped your company attract exceptional talent or achieve a significant business goal?
The clearest example I can point to is what happened at Google Canada over 13 years. What we offered was the chance to do serious engineering work in Canada, on a team with high standards, with people worth learning from and on problems that mattered. That was a genuine proposition and people responded to it.
The most meaningful measure of whether it worked or not was in the number of people who came back to the organization. For example, someone who needed a different project to get promoted, or someone who wanted a startup experience and needed to go explore it. And we encouraged those who did so; when someone on your team decides to leave to try their own thing, you need to support them and embrace it. That does not happen at places where the culture is simply a talking point.
What advice would you give to leaders of smaller companies or startups who want to build a purpose-driven culture but don’t know where to start?
My biggest piece of advice would be to start with the people you have, not the culture you want to announce. The mistake I see founders make time and time again is treating culture as something you build after you have the team. Culture is already there from the first day you hire someone. The question is whether you are creating a culture intentionally or by accident.
The most important decision a small company makes is the first 10 or 15 hires because those people will define every subsequent hiring decision by example. If the first 10 are curious, collaborative and honest about what is not working, the next 50 will probably be, too. If the first 10 are political, credit-seeking and conflict-avoidant, you will spend years trying to undo that.
One very practical thing to keep in mind: talk to your team about what is important to you and your organization, honestly and regularly. Go beyond doing this just in all-hands meetings, and do so in conversations and one-on-ones, where you’re actively listening to members of your team. The founders who build great cultures remain genuinely curious about what individuals on their team think.
What are some common mistakes leaders make when trying to create a purpose-driven culture, and how can they avoid them?
The most common mistake is confusing communication about culture with the culture itself. You can write the values on the wall, put them in the onboarding deck, repeat them in every all hands, but none of that is culture. Culture is the accumulated weight of the thousands of small decisions your team makes each day and making sure the people in your organization understand this even if they cannot articulate it themselves.
The second most common mistake is tolerating behavior that contradicts your stated values because the person producing that behavior is also producing results. This sends a message to everyone watching (and everyone is watching) that the values are negotiable. Once that message lands, it is very hard to undo.
The third is building a culture that works brilliantly at one scale and then being surprised when it does not work the same way at twice the size. What works for 20 people does not automatically work for 200. The trust structures, the communication patterns, the feedback loops all have to evolve deliberately or they will evolve in ways you did not choose.
How do you ensure that your organization’s purpose evolves and remains relevant as your company grows and the world changes?
Purpose does not evolve on a schedule; it is tested by circumstances and you either defend it or you do not. At Google Canada, the original mission we followed was to build something world-class and distinctly Canadian. As AI became the central challenge in the industry, the definition of world-class changed. We had to take that seriously and adapt what we were building without abandoning the underlying reason for building it.
In my experience, the organizations that manage this well never defined their purpose too narrowly in the first place. If you build a culture around a specific product or a specific technology, you are fragile, but if you build it around a way of working and a set of values about how to tackle hard problems together, you have something that can survive significant change in an external environment.
What trends or shifts are you seeing in the workplace regarding purpose, and how do you think these will shape the future of business?
The most significant change I am seeing is that AI is creating a visible divergence between organizations that invested in culture and ones that did not. When the tools change this fast, the only reliable advantage an organization has is the quality of the people and how well they function together. You cannot buy your way out of a culture problem with better software.
What I’m also seeing is that the best engineers, the ones everyone is competing for right now, are paying much closer attention to who they work for and why. They have watched what happened at companies that had strong cultures and ones that did not. The idea that top technical talent simply follows the money is wrong, and it has always been wrong. Top talent seeks the interesting work, the people worth learning from and the environment in which hard things can and are being accomplished.
In your opinion, how does having a purpose-driven culture impact not just employees, but customers, clients, and the broader community?
Engineering cultures that care about purpose produce better products. That sounds obvious but it is not trivial. When people are building something they believe in, when they feel ownership and a connection to why it matters, the output is different in ways that are hard to quantify but easy to feel as a customer or user.
The broader community benefits in ways that are not always visible. At Google Canada we took STEM education and startup support seriously because the people on our team cared about those things and it was an expression of the culture. The companies that build genuine, purpose-driven engineering cultures tend to reinvest in the broader ecosystem because the people inside them want to. That has a compounding effect over time that is hard to see in any single quarter but is very visible over the years.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people by building purpose-driven workplaces, what would that be? You never know what your idea can trigger. 🙂
Human ingenuity is a magical thing. I see companies that treat AI as a way to replace human insight with mechanical output as an enormous failure of imagination. Too often leadership at companies with enormous potential is convinced to downsize toward efficiency rather than the upside, toward enablement and empowerment and frankly toward more, not less. When it comes to teams, the default should not necessarily be smaller teams, but rather a focus on teams that are more agile with more people doing more ambitious things. By contrast having an excess of human capability and no new things to try, explore or attempt is a complete failure of leadership.
I would like to see a culture of “more” emerge, and with it an expansive mindset about what people can accomplish. I hope that starts taking flight inside companies, but more than anything I hope it starts with educators. Every time I’ve spoken to groups of students I find them excited, passionate and desperate to accomplish things, and so often underinformed about what is actually possible. Computer science is not mathematical drudgery. It is the skill set that lets you create everything. Software is the medium from which you build games, machines that reach the stars, tools that unravel the mysteries of the universe and breakthroughs that save countless lives. It is not an end. It is a beginning.
Too much education is focused on the task rather than the goal, and I would love to see that change. The internet changed the way information became universally accessible. Hopefully an organization out there, leveraging that foundation and AI, will find a way to make the world’s knowledge more useful to everyone who is curious, and in doing so unlock the ambitions and potential of a new generation of builders.
How can our readers further follow you online?
https://www.linkedin.com/in/stevenwoods/
This was great. Thank you so much for the time you spent sharing with us.
About The Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Steve Woods of Inovia Capital On How to Build a Purpose-Driven Culture That Attracts Top Talent was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.