HRTech Interview with Yen Tan, Head of Expansion and Manager Products at 15Five
Yen Tan, Head of Expansion and Manager Products at 15Five chats about manager effectiveness coaching and why it’s a necessity in business in this HRTech interview:
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Hi Yen, tell us about your time in HRTech and your latest observations from the market?
Supporting HR with technology has been the obsession of my career. My co-founder, Sid, and I were two students at UCLA when we started asking the questions that would lead us to build Kona. Before we wrote even a single line of code, we set a goal to talk to a hundred managers and HR practitioners about their pain points, their most stressful days, the things they wished they had learned before stepping into a leadership role. We surpassed that goal, and I think that instinct — to listen deeply to the market — has stuck with me ever since.
Since 2020, we’ve spoken to more than 2,000 managers, HR leaders, and L&D experts across various industries and team sizes. Our key takeaway? Managers and HR leaders are overwhelmed and getting very few systems of support.
People teams today are asked to do the impossible: drive engagement, improve retention, deliver belonging, support DEI, reinforce company values, and coach entire populations of managers — all while being told to do more with less budget and headcount and resources. On the other side, managers are asked to juggle business outcomes and OKRs, team morale, psychological safety, career growth, collaboration, and innovation — all of it, with almost no formal training. We expect managers to “figure it out” on the fly and drive performance. We tell HR to swoop in and fix the results of that trial-and-error approach. It’s a vicious cycle. It’s no wonder HR is exhausted.
That’s where technology, especially AI, is playing a powerful role. AI has gone from niche to mainstream at breakneck speed, opening up more than “productivity gains”. Small HR teams can finally help managers lead with empathy and drive results. For years, those were framed as tradeoffs — either “hit numbers” or “invest in your people.” AI, when woven into a managers’ workflow, can help them scale the behaviors we know make teams thrive: trust, clarity, accountability, recognition without burning them out.
That feels like an incredible moment. We’re no longer asking managers to white-knuckle their way through the day-to-day. We’re giving them tools to actually drive greater impact without taking on more, and to do it in a human way.
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What about Kona makes it unique?
Kona meets managers exactly where they work and gives them the feedback they need to drive performance and support their teammates. We built Kona in Slack, Zoom, and Google Meet — the tools that power a manager’s work day. Very few managers have time to carve out for a separate workshop or e-learning module. Instead, we bring learning moments right into their 1:1 meetings, offering nudges and coaching the moment they interact with their teams. Plus, our AI-powered notes, action items, and review assist save managers hours on documentation.
For HR leaders, Kona is flexible and scalable. Great management looks different from company to company. There is no one-size-fits-all leadership style so we made Kona’s coaching style customizable — you can tailor it to reinforce your frameworks, your company’s values, and your success measures.
To top it all off, it’s the only manager enablement tool on the market that’s tied to your incredible people data in 15Five, the performance management platform Kona sits atop. Kona’s AI coaching tips reference dozens of data points from team performance reviews, engagement surveys, and team data to ensure that the manager gets extremely personalized and relevant coaching for their situation, learning opportunity, and direct report.
What is manager effectiveness coaching — break it down for our readers.
Great managers are made, not born. Great leadership is a skill set, and coaching is one of the most effective ways to build it.
Let me get specific here since coaching has quite a few definitions. Traditional executive coaching focuses on helping executives draw their own insights and building self-awareness. It’s about holding space for them to reflect, not giving them answers. It’s one of the best solutions for senior executives with complex people situations and business problems, and something 15Five also offers. However, this kind of coaching can be expensive and hard to scale, so it’s not often a practical resource for every manager in the org.
Manager effectiveness coaching is designed for tactical support to help everyday managers succeed. AI is great for this, allowing more managers to have access to “the answers” while still being precise and personalized. This kind of coaching combines tactical, people-first frameworks with business execution. It teaches managers how to run effective 1:1s, how to structure career conversations, how to balance empathy with accountability, and how to build psychological safety and trust. In other words, it’s about helping managers move from knowing what to do to actually doing it in the messiness of real work.
Investing in manager effectiveness coaching gives managers a foundation to support their teams, drive outcomes, and grow themselves as leaders — not just once, but sustainably over time.
Can you talk about some of the leading brands around the world that have relied on manager effectiveness coaching to drive better team protocols?
Pretty much every growth-oriented, performance-minded organization I know relies on manager coaching in some form. HR leaders are constantly coaching managers, even if there isn’t an explicit program or offering. They might brand “coaching” differently, but it’s there.
Let’s start with the classic example: Google’s Project Oxygen. That program identified and trained for eight behaviors that distinguish great managers, then reinforced them through coaching and feedback loops. Salesforce is another great case — their emphasis on people-first leadership principles, supported by structured coaching and enablement, has been key to scaling their culture. Atlassian is another company that invested in consistent manager frameworks, especially as they grew globally. And Meta, in the early days, doubled down on manager effectiveness to sustain a hypergrowth culture.
There’s a pattern across all these: they treat manager effectiveness as an always-on process. It’s not a one-off training or a once-a-year webinar. It’s an ongoing, layered system with coaching, data, feedback, and consistent reinforcement. Because managers are multipliers — they either multiply trust and engagement or they multiply confusion and turnover.
We’ve seen the same thing in smaller, more values-driven companies too — they may not call it “manager coaching,” but they invest in manager support, mentoring, peer cohorts, or embedded AI tools. If you zoom out, the trend is clear: you cannot leave manager performance to chance. The stakes are too high.
A few thoughts on AI and the future of HRTech as a segment?
AI is getting its well-deserved moment in the spotlight, and let’s be honest, it’ll be way more than a moment. Everyone is launching an “AI assistant,” adding generative summaries or weaving in chat-based coaching. But once the hype levels out, we’ll realize AI is just the baseline. In a few years, you’ll buy a tool expecting those capabilities the same way you expect tools to store data in the cloud.
The bigger hurdle is having AI literacy maintain pace with all the innovation in the space. Most of us are still learning what good AI usage looks like, what to trust, what to double-check. We’re basically writing the rules of engagement in real time. I think we’ll see something similar to how we teach students to verify Wikipedia citations — eventually there will be guardrails, best practices, and a shared sense of what “responsible AI” means.
Beyond productivity, I think there’s an incredible opportunity for AI to drive more fairness, equity, and inclusion in the workplace. Imagine an AI tool that flags biased patterns in promotion conversations, or one that helps managers standardize recognition practices across their teams. That’s where I see huge potential: not just helping HR move faster, but helping it move more humanely. This also happens to be where I think so many people overlook AI’s potential to add value.
If we get this right, HR can finally step out of the shadow of being “compliance police” and become what the function is meant to be — a strategic partner that shapes how people work, grow, and belong – and one that delivers meaningful business impact. That’s a future I’m rooting for.
Five HRTech innovators you’d like to shout out to before we wrap up?
This is tough because there are so many, but here’s my five — people who consistently push boundaries, advocate for better people practices, and challenge the status quo:
- Cara Brennan Allamano (PeopleTech Partners) — She’s one of the sharpest minds in people enablement, and her ability to build systems that scale is unmatched.
- Hebba Youssef (Workweek, I Hate It Here) — Hebba has made it her mission to bring real, honest conversations back to the people space. She says what many of us think but are too scared to say out loud.
- Julie Turney (HR@Heart) — Julie is a tireless advocate for making HR human again, and she shows up for the global HR community in ways that truly matter.
- Lauren Waldman (Learning Pirate) — Lauren is brilliant at explaining how learning actually happens, which is key if you want your manager programs to stick.
- Vanesa Cotlar (PolicyMe) — Vanesa reminds everyone that people strategy can be both rigorous and deeply personal. She’s proving it every day.
All five of them care deeply about making work more equitable, sustainable, and grounded in trust. And that’s what great HRTech should be about at the end of the day.
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[To share your insights with us, please write to psen@itechseries.com ]
Yen Tan is Head of Expansion and Manager Products at 15Five. Yen is a co-founder of Kona, acquired by 15Five in January. Their work on people-first leadership has been featured by Fortune, Yahoo, TechCrunch, Harvard Business School, Forbes, and more. Yen has spoken at conferences like SXSW and GitLab Commit and advised Fortune 10 companies on remote work strategy
15Five is a performance management platform focused on driving business results by improving employee performance, engagement, and retention.
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