Leader Spotlight: Why delight still matters in product design, with Ken Frei
Ken Frei is a product leader and executive coach with more than a decade of experience building and scaling products across startups and public companies. Currently Head of Product at Hometown, he has previously led product teams at companies including Pura, Prenda, and Pluralsight, where he focused on human-centered product development, cross-functional execution, and building high-performing teams.
In our conversation, Ken shares lessons from leading product organizations and coaching emerging leaders. He discusses the shift from individual contributor to manager, how product leaders can develop meaningful influence, and why delight still matters in product design. Ken also reflects on the growing role of AI in product development and how teams can embrace new technology without losing the human perspective that makes products truly valuable.
From individual contributor to leader
What’s the most underestimated part of transitioning from an individual contributor to a manager?
As individual contributors, we tend to see things only through the lens of our world. A lot of times we’re just trying to get our work done as efficiently as possible. As leaders, you’re often in charge of multiple individual contributors and collaborating more cross-functionally, so you start to see how each person plays an important part in a larger whole.
When you’re an individual contributor, there’s so much work to do that it’s hard to get out of the weeds and see the bigger picture. Good leaders help people see that and ask the right questions to help them consider those things. Some individual contributors do this really well, and when I see someone doing their part but also seeing how it fits into the bigger picture, that’s when I start to recognize they’re a great candidate to step into a leadership role.
What people often underestimate is just how much everyone needs to work together to make something truly magical happen. Sometimes people also underestimate their own ability to influence and guide a project. I’ve had people come to me and ask me to solve a problem for them, and I’ve tried to get better at telling them they can have that conversation with the other person and solve the problem themselves.
Encouraging people to take a stab at it and use their influence and critical thinking helps things run smoother and helps them become more of a leader themselves.
How do you handle conversations with strong individual contributors who want to become managers?
I’ve had these conversations a lot, and I usually start by asking people why they want to be a manager. Sometimes it’s because managers get more recognition, people think they’re really smart, or they get paid more money. But they may not actually have a skill set suited for management or even enjoy that kind of work.
Being a manager is not always fun. You’re dealing with administrative tasks, and a lot of problems flow to you. Sometimes people get into those roles and realize they miss the days when they could just put their head down and do the work.
That’s why it’s important for companies to create incentive structures where great individual contributors can earn good money too. That way people who are strong ICs don’t feel like they have to move into management to accomplish their career goals.
When I talk with people about it, I ask questions like: Do you like leading people? Do you have a vision you’re trying to accomplish? Do you enjoy coaching and mentoring people? If the answer is yes to those things, management can be a good path. If the answer is more like, “I just like doing my work and being done when I’m finished,” then I usually steer them away from going down that route.
Learning to influence effectively
How do you help people develop meaningful influence without doing it just for optics?
When people try to insert themselves into situations just to appear influential, it’s usually pretty transparent. Everyone feels annoyed when that happens because it slows things down and often has the opposite effect, where people start to cut that person out of conversations.
If you really want to be influential, you have to be self-aware and know whether it’s a situation you should be involved in. If you’re passionate about the topic or you have unique insight or skills for it, that’s a good time to influence.
Storytelling and data are also important. If you can tell a clear story and use data or specific examples, people tend to be persuaded much more effectively than if you simply say you want something or think something should happen.
At the end of the day, most people just want to do a good job and ship good work. If you can explain why what you’re proposing will help accomplish that goal, people are much more likely to get on board.
Using AI without losing product judgment
How are you integrating AI into your workflows while acknowledging its limitations?
AI is awesome, and it’s also super new. At this stage, what I’m encouraging my team to do is experiment with it so we become more familiar with its capabilities. But you can’t rely on it completely without using your own judgment.
If you take whatever AI gives you and submit it as your work without editing or validating it, you can get yourself into trouble pretty quickly. Humans are still needed for that judgment.
AI can be a great partner for generating ideas, and it can also be a really good editor if you ask it to critique something. But if you’re just asking it to do the work and turning it in without reviewing it, it’s not quite there yet.
I encourage my team to use it as much as possible and share what’s working well and what isn’t. That helps everyone learn how to apply it more effectively. I also remind myself that this is the worst AI will ever be, and it’s only going to get better, so we can’t ignore it.
How do you treat AI as another stakeholder in the product process?
The job of a product manager is to define the outcome you’re trying to achieve and create a path to get there. You’re defining what success looks like and how you’re going to deliver something to customers.
AI is essentially another stakeholder in that process. If you give AI a bad prompt, you get bad output. Just like working with engineers or designers, you have to clearly explain what you’re trying to accomplish — what success looks like and what outcome you’re trying to create for the customer.
The better you articulate that, the better results you’ll get. If you can tell that story clearly to AI, it can be a really great partner.
Human-centered product experiences
What happens when AI-driven features don’t actually improve the customer experience?
Because we’re human, we still understand what resonates with people. I’m an endurance athlete and spend a lot of time on Strava, which is one of my favorite products. Recently they added an AI feature that analyzes workouts and gives feedback.
When I tried it, it basically repeated what I had already written. If I titled my workout “long run” and wrote that it felt hard but I got through it, the AI would say something like, “Good job on your long run. That was hard, but you got through it.” It didn’t add any value.
I remember thinking, what product manager let this get into the product? It’s cool to experiment with AI, but you still have to ask whether it improves the customer experience. If it just repeats what the user already said, it’s not helpful.
Why is delight still important in product design?
Sometimes my sense of humor can be childish or adolescent, but I think it’s important for products to have fun moments. Especially in B2B or enterprise software, products can feel really stale. Consumer products tend to feel more alive.
Even small things can make a difference. It might be a celebration animation, something surprising in the interface, or just a design that makes people smile. Those moments interrupt people’s thinking in a good way.
A good example is the dinosaur game in Google Chrome when the internet disconnects. Another example is the old version of Solitaire where the cards bounced across the screen when you won. They could have just shown a message that said “You won,” but instead they created something memorable.
Those small moments give products life.
Is it difficult to convince leadership teams to prioritize those moments?
It can be difficult. I’ve worked with leaders who were very buttoned-up and didn’t want anything that felt playful because they thought it wasn’t on brand. Those conversations often come down to trade-offs.
Personally, I enjoy working on products that have life in them. I like companies where leadership can laugh at itself a little.
If leadership is hesitant, one approach is to test the experience with customers. If the version with something fun performs better, the conversation becomes easier. You can present the data and ask whether you should choose the version customers liked less simply because it’s more serious.
Adapting to an AI-driven future
How do you stay optimistic about the future of product roles as AI evolves?
This is something I struggle with sometimes. I’m naturally optimistic, but I haven’t seen another technology in my career that creates this level of uncertainty. AI could potentially automate a lot of what product managers do.
The way I stay optimistic is reminding myself that I’m smart, capable, and adaptable. If I’m willing to keep learning and trying new things, I trust that I’ll find my place in whatever the new reality becomes.
The people who may struggle are the ones who cling to the past and assume the technology won’t affect them. If you’re willing to learn and figure out new ways to add value, I think people will adapt.
I also think there will be a growing premium on human experiences. The more technology automates, the more people will crave human connection and human perspective.
You can often tell when something online was written entirely by AI. It’s getting better, but there’s still something that doesn’t quite feel human, and people recognize that difference.
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