Tag: outcomes vs output OKRs

Unleash Employee Engagement: Proven OKR fixes and manager playbooks for startups

Engaging employees and developing high-quality managers is one of the most reliable ways I know to improve performance, retention, and product velocity. I recently revisited a set of lessons that crystallize what great leadership looks like in practice — especially for startups and product teams under pressure to do more with less.

Consider the arc of Russ Laraway’s career. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.

In 2018, he joined Qualtrics as the Chief People Officer, later focusing on helping the company’s customers think differently about employee experience. He also has a book on this topic coming out soon, which I’m eager to dig into because the playbook he’s refined is as practical as it is principled.

Here’s what stands out to me for startup leaders, product managers, and anyone navigating the IC to manager transition: you can systematically drive employee engagement while elevating manager effectiveness. Drawing across roles and company stages, Russ serves up usable wisdom whether you’re a first-time manager or a seasoned leader sharpening your product management leadership muscle.

He starts with the direction-coaching-career framework. In my experience, this trio clarifies why teams stall: unclear direction blurs prioritization, weak coaching slows skill growth, and neglected career conversations erode motivation and employee retention at startups. Pair this with a clean approach to OKRs — too many teams confuse outcomes vs output OKRs — and you get a durable operating system for focus and accountability.

What I appreciate most is how tactical he gets. He shares the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employee engagement surveys. I’ve used similar prompts to create safety in 1:1s, surface hidden risks in roadmaps, and ensure we’re solving the right customer problems — not just burning down a backlog.

Finally, he offers 13 recommendations for leadership reads for managers. I treat this as a compact curriculum: a way to level up how we set direction, coach for performance, and invest in long-term careers across the team. It’s the kind of list I hand to new managers and return to myself during planning cycles and performance reviews.

If you’re leading a product organization or building one inside a startup, the path forward is clear: anchor your rituals around direction-coaching-career, recalibrate OKRs to outcomes, ask the brave questions that reveal what your team really thinks, and keep sharpening your craft with proven leadership reads. Done consistently, these habits compound into higher engagement, stronger execution, and sustainable growth.

Inspired by this post on First Round.

October 22, 2025
Inside Tido Carriero’s Playbook: Build World-Class Engineering Orgs and Nail Product/Market Fit

I’m drawn to leaders who’ve built both high-performing engineering organizations and durable products. Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio, exemplifies that trajectory. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team — a pivotal IC to leadership transition that resonates with many of us in product and engineering.
What stands out in his journey are pragmatic lessons on building engineering orgs and launching new product lines at several top tech companies. His reflections on the pros and cons of single threaded leadership and the black box analogy for assessing a team’s performance offer concrete ways to interrogate how work actually gets done. In my own practice, I pair these lenses with outcomes vs output OKRs, tight product roadmapping and sprint planning, and a clean operating cadence that links QBRs vs OKRs. Together, these mechanisms create clarity in org design, planning, and execution — and make performance visible without micromanaging.
For new engineering managers and new managers-of-managers, I appreciated the practical “gems of advice.” That IC to manager transition is rarely linear; success hinges on shifting from personal velocity to organizational throughput. I coach first-time managers to build credible operating systems early: explicit decision rights, transparent prioritization, and lightweight feedback loops. One simple ritual I rely on is a weekly narrative update that forces crisp, outcome-focused thinking — a habit that complements any try do consider framework a team may use.
We also explored the path to product/market fit, especially for multi-product strategies — an area where many B2B teams struggle. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. My own playbook mirrors this: invest in fast product discovery, define a clear gate tied to must-have user behavior, and resist vanity launches until repeatable pull exists. Small, well-instrumented bets compound; “big bang launches” rarely do.
If you want to go deeper on finding product/market fit in the context of multi-product strategies, Tido shares more of his thinking here: https://segment.com/blog/finding-product-market-fit-again/. It’s a useful companion for leaders calibrating zero-to-one efforts alongside an at-scale core business.
The through line across these lessons is disciplined simplicity. Whether you’re architecting engineering orgs, coaching the IC to manager transition, or charting zero to one in a new product, choose mechanisms that surface reality quickly, reward learning, and keep teams focused on outcomes. That’s how world-class organizations build, ship, and iterate their way to enduring product/market fit.

Inspired by this post on First Round.

October 22, 2025
Build a People-First Org: Data-Driven Empathy, Skip-Levels, and Career Growth with Mark Frein

I recently had a deep-dive conversation with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor. As someone who scales product organizations, I was energized by how his people-first principles map directly to product management leadership.

Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In our discussion, he shared his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning. From my vantage point, that alignment looks like building clear hypotheses, instrumenting the employee journey, and iterating based on signals—exactly how we pursue product-market fit internally.

He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations. I translate these into playbooks my teams can use: structured, empathy-forward hiring; predictable skip-level rhythms; always-on feedback loops; and career frameworks that make growth expectations explicit.

On hiring with empathy, I lean on behavioral evidence, job simulations, and transparent expectations to reduce bias and improve candidate experience. When we model empathy from the first touchpoint, we accelerate trust, improve close rates, and lay the foundation for employee retention at startups.

For skip-levels, I approach them as discovery interviews—open, curious, and non-defensive. I triangulate themes across teams, synthesize the data, and close the loop publicly so people see action. That transparency compounds trust and gives me the earliest possible signal on risks and opportunities.

When it comes to gathering employee feedback, I blend lightweight pulse surveys with qualitative listening tours and manager office hours. The key is to turn insights into visible change, or we create survey fatigue. We anchor this work to outcomes vs output OKRs so we’re optimizing for impact, not activity.

Driving career conversations requires clarity. I publish ladders, competency matrices, and sample development plans, then coach on the IC to manager transition for those who want to lead. Empathy training for managers helps them ask better questions, calibrate feedback, and co-create growth paths that match both ambition and business needs.

If you’re a founder or early-stage people leader, this approach will help you scale the people function with intention. If you’re a current or aspiring manager, these tools sharpen your leadership and development chops. Most importantly, they weave empathy and data into a single operating system for your culture.

Inspired by this post on First Round.

October 22, 2025
From Zero Customers to IPO: Eric Berg’s Hard-Won Playbook for the Messy Middle

I’ve been revisiting the hard-won lessons behind durable product companies, and Eric Berg’s journey is a masterclass. Eric Berg is the CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.

From a product management leadership lens, the earliest chapters at Okta are a blueprint for zero to one B2B marketing and founder-led GTM. I break down his early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground, highlighting how tight product discovery, crisp problem statements, and ruthless prioritization turn ambiguity into product-market fit.

What stands out is the often-maligned “messy middle” — the stretch when traction exists but entropy expands. Eric’s moves on “moving upmarket” and evolving a “pricing and packaging model” are reminders that, when done well, takes a company to new heights. For SaaS pricing, I lean on value metrics tied to critical jobs-to-be-done, clear guardrails for discounting, and a win–loss feedback loop owned jointly by product and sales.

We then switch gears to team building and company building. The cultural patterns that stick with me: hire “folks up and down the org chart with the right ego to talent ratio” and operationalize a “disagree and commit” value so it’s not just a long-forgotten team motto. Practically, that means defining decision types (one-way vs. two-way doors), naming a DRI and approver for every call, time-boxing debate, and documenting the rationale so execution never stalls.

On execution mechanics, I’ve found that outcomes vs output OKRs paired with QBRs vs OKRs alignment creates a healthy cadence from strategy to delivery. When you layer in forward deployed engineers and structured customer advisory boards, feedback cycles compress without sacrificing focus — a powerful pattern in both product roadmapping and sprint planning.

Finally, the perspective shifts “as he approaches one year of sitting in the CEO seat” underscore the difference between building products and building a business. Capital strategy, talent density, and narrative become first-class product surfaces. As a product creator, I translate this into designing org APIs, setting explicit burn-to-learn budgets, and treating pricing, packaging, and GTM as core parts of the product.

If you’re navigating product-market fit lessons, wrestling with “moving upmarket,” or recalibrating SaaS pricing, this playbook maps the trade-offs from 0 customers through the “messy middle” and beyond. It’s a grounded field guide for product folks and operators who want to scale with clarity, strengthen culture, and accelerate learning without losing the thread.

Inspired by this post on First Round.

October 22, 2025
Inside the Engineering Cultures of Microsoft, Reddit, Looker & Twitter: Hard-Won Lessons

I’m endlessly fascinated by how engineering culture shapes product velocity, quality, and leadership outcomes. Drawing on lessons from Nick Caldwell’s journey, I’ve distilled the practices that consistently produce performance, clarity, and cohesion across teams. These are the ideas I reference when coaching product and engineering leaders, building org structures that scale, and aligning teams around outcomes.

Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.

Across Microsoft, Reddit, Looker, and Twitter, the cultural contrasts are stark—and incredibly instructive. I focus on how each environment sharpened a different leadership muscle: designing resilient organizations, navigating high-context communities, aligning product and engineering at scale, and translating mission into execution. The net effect is a practical playbook for product management leadership, manager development, and cross-functional collaboration.

From Microsoft, I take to heart what Nick believes is a massively underrated approach to organizational design. The company’s disciplined cadence of regular pruning and shaping the org chart keeps accountability crisp and prevents drift. Their management training and talent development systems create durable leadership pipelines, while what Nick calls the fairest performance review system he’s seen sets a predictable bar for growth. In my own practice, I mirror these principles with explicit role charters, outcomes vs output OKRs, and routine structure audits that keep teams mission-aligned.

Transitioning from a 15-year tour at Microsoft to Reddit came with a steep learning curve—and that resonates deeply with anyone making a big career move or an IC to manager transition. Nick’s advice maps closely to what I coach: re-anchor on the company’s narrative, over-communicate intent, and recalibrate decision speed to the culture. At Reddit, the mission-driven culture isn’t just branding; it informs how influence is earned and how leaders show up. That lens carries forward to leadership at Twitter, where connecting daily execution to mission keeps product and engineering grounded and resilient through change.

Looker offered a rare vantage point: leading both product and engineering. The result is a masterclass in reducing friction between two orgs that are often at odds. The insights I apply: define a single operating rhythm for product roadmapping and sprint planning, eliminate ambiguous ownership, and measure joint outcomes rather than siloed outputs. When product strategy, discovery, and delivery operate on one shared cadence, you unlock faster decisions, fewer handoffs, and cleaner accountability.

For managers looking to level up, these lessons are actionable: invest in management training, make performance systems transparent, prune org complexity before it compounds, and tie every roadmap bet to mission and measurable outcomes. For engineers eyeing leadership, study how culture sets the rules of engagement—then learn to translate that into decision frameworks, communication habits, and hiring signals that reinforce your product and engineering alignment.

This is a wide-reaching set of takeaways because the problems are universal: how to design organizations that scale, grow leaders systematically, and build cultures where product and engineering don’t just coexist—they compound each other’s strengths. If you’re rethinking your org chart, refining your OKRs, or preparing for your next leadership transition, these practices will give you a durable edge.

Inspired by this post on First Round.

October 21, 2025
From Developer to CMO: Archana Agrawal’s Airtable & Atlassian Playbook for Product‑Led Growth

I recently sat down with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. She joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. As someone who leads product teams and partners closely with go-to-market, her cross-functional vantage point immediately resonated with me.

We began by unpacking the messaging challenges of horizontal products like both Airtable and Atlassian. I’ve learned firsthand that breadth can blur the story if you don’t anchor it to a clear persona and set of jobs-to-be-done. Archana’s approach to narrowing in on the right persona while preserving platform flexibility mirrors how I guide positioning: focus on the core workflows that deliver immediate value, then layer in industry-specific outcomes and proof points. That balance keeps the narrative sharp without constraining the product’s surface area.

From there, we dove into the close interplay between product and marketing teams, particularly for product-led growth companies. We aligned on a principle I hold deeply: discovery signals, activation patterns, and in-product usage should directly shape go-to-market. When product and marketing share adoption, retention, and expansion metrics, it creates a single operating system for decision-making. The result is tighter feedback loops, smarter experimentation, and a more durable growth engine.

Organizational design was another major theme. We discussed how to set teams up to break down siloes and foster experimentation through shared roadmaps, clear decision ownership, and transparent operating cadences. As CMO, she oversees all the different marketing functions that report up to her and has established rituals for keeping a pulse on what most deserves attention. In my own practice, lightweight, recurring checkpoints across product and marketing create the psychological safety to test, learn, and rapidly scale what works.

While today’s conversation is of course a must-listen for marketers, I’d argue the insights are equally valuable for product, sales, and executive leaders navigating horizontal SaaS. As a former engineer-turned-marketer, Archana brings a unique, data-driven perspective to prioritization, experimentation, and storytelling—one that complements how I think about product management leadership and cross-functional alignment.

If you’re building in a product-led growth motion or stewarding a horizontal platform, you’ll find pragmatic ideas here: sharpen persona definition without losing breadth, align product and marketing on shared metrics, design rituals that surface the highest-leverage work, and cultivate a culture where experimentation is expected. These are the foundations that compound, regardless of company stage.

Inspired by this post on First Round.

October 21, 2025
Scale Smarter: Buy vs Build, Core Focus vs Innovation—Hard-Won Insights with Zendesk’s CTO

I recently sat down with Adrian McDermott, CTO of Zendesk, for a candid conversation on how to scale product and engineering without losing the essence of what makes the product great.

Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. I’ve long admired how that trajectory blends product management leadership with operational rigor, and I wanted to unpack the systems behind it.

We began with the classic scaling fork in the road: double down on what’s working or make a change. In my experience, this decision rarely fits a simple binary, and I asked how he navigates it in practice. He went much deeper than the “what got you here won’t get you there” advice you hear all the time in startups, outlining how to read momentum, market signals, and organizational readiness before flipping a switch.

Next, we explored the tension between venturing into new product areas and keeping the central product brilliant. He shared how they use the zone to win frameworks at Zendesk. I contrasted that with my own approach to product discovery and product roadmapping and sprint planning: protect core experience quality with clear guardrails while allocating explicit capacity for bets that expand the addressable problem space.

We then dug into the evergreen dilemma of whether to build or to buy. He walked through the origin stories of several Zendesk products, from the wins to the lessons learned. His take on the role of competition in product strategy and his definition of a truly great product resonated with me. For my teams, I evaluate buy vs build decisions through a simple lens: strategic differentiation, speed to validated learning, total cost of ownership, and ecosystem leverage; if the capability isn’t core to our unique advantage, I bias to buy and integrate, then instrument relentlessly.

In the back half of our conversation, he shared what he’s learned leading both product and engineering teams, along with practical go-to-market lessons that shape how features actually land with customers. We ended on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and I appreciated the way he adapts hiring profiles and loops to the phase of scale—tight generalists early, then rigor around outcomes vs output as the organization matures.

If you’re scaling a SaaS product, you’ll find actionable insights here: how to avoid false trade-offs, decide when to preserve the core versus explore, operationalize zone to win frameworks, and make smarter buy vs build calls that accelerate learning and customer impact.

As a product leader, these lessons reaffirm a simple truth: sustainable growth comes from deliberate portfolio choices, clear go-to-market alignment, and consistent, values-based hiring that raises the quality bar with every new teammate.

Inspired by this post on First Round.

October 21, 2025
My Proven Product Strategy Playbook: From Mission to NCTs That Align Teams and Drive Growth

I’ve spent years building and scaling products, and I continue to see one pattern derail even the most talented teams: a disconnect between product strategy and what product teams actually work on day-to-day. In this deep dive, I share how I bridge that gap with a practical, battle-tested playbook I’ve used to align teams, accelerate impact, and power growth at scale.

I start by getting brutally clear on the real work my teams are doing versus the outcomes we’re aiming for. Too often, teams are busy shipping features that don’t ladder up to strategy. The fix isn’t more process—it’s sharpening the connective tissue between strategy, planning, and execution so every sprint advances a clear, long-term narrative.

At the core of my approach is the product strategy stack: company mission, company strategy, product strategy, product roadmap, and product goals. When each layer is explicit and connected, prioritization becomes straightforward, trade-offs are defensible, and the team understands not only what we’re doing—but why it matters. I treat this stack as a system, not a document, and I revisit it frequently with my leads to ensure decisions remain aligned.

Here’s how I operationalize it. I anchor every planning cycle in the company mission and company strategy, then translate that into a crisp product strategy that defines where we will play and how we will win. From there, the product roadmap becomes a sequencing tool for outcomes, not a wishlist of features. Finally, I define product goals that are specific, measurable, and clearly tied back to the strategy—so everyone can see the throughline from mission to metrics.

When it comes to goal-setting, I prefer an alternative to traditional OKRs: NCTs. Outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs. The narrative clarifies the why, the commitments define the measurable outcomes we’re on the hook to achieve, and the tasks capture the critical work we believe will get us there. To implement NCTs, I pilot them with a single squad, ensure each narrative maps to the product strategy, pressure-test commitments against leading indicators, and keep tasks flexible as we learn.

Strategy is often misunderstood and has come to mean all sorts of different things. I’ve found that clarity around terms like “mission” and “vision” changes everything. Mission is enduring and customer-centered; vision is a vivid, time-bound picture of the future we’re building. When teams grasp the difference, alignment snaps into place. I’ve seen this playbook resonate across industries and company stages—from category leaders like Tinder and TripAdvisor to fast-growing startups—because it turns abstract strategy into concrete choices and accountable execution.

If you’re looking to uplevel product management leadership and bring more focus to product discovery and delivery, start by assessing your product strategy stack, then pilot NCTs in your next quarterly planning cycle. Tie every roadmap item to a narrative, stress-test commitments with real metrics, and empower teams to adapt tasks as insights emerge. The result is a more resilient roadmap, tighter alignment, and a team that consistently ships what moves the needle.

October 21, 2025
Mastering International Expansion: My Product Playbook Inspired by Faire’s CEO Max Rhodes

International expansion can be a powerful growth lever — or an expensive distraction. Through my product leadership lens, I’m always looking for patterns that separate the former from the latter. Recently, I reflected on insights from Max Rhodes to distill a practical, founder-friendly playbook for going global without losing focus.
Max Rhodes is the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. His vantage point is especially useful for product leaders scaling multi-sided marketplaces and navigating complex cross-border dynamics.
Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar.
In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.
After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. I found his decision framework refreshingly practical — a blend of timing, readiness, and strategic focus that maps well to the realities of product-market fit, capital efficiency, and operational maturity. I’ve used similar mental models to pressure-test when our roadmap should shift from depth in one market to breadth across many.
Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it. What resonated with me was the balance between a disciplined operating rhythm — clear goals, tight feedback loops, and cross-functional ownership — and a nuanced, market-by-market go-to-market strategy that respects local competitors and customer behaviors.
To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups I’ve leaned on this mindset during hypergrowth — encouraging PMs, GMs, and functional leaders to continually redesign their roles so we can scale scope without calcifying decision-making. The emotional lift is real, but the payoff is a more resilient organization that can execute across time zones and product surfaces.
Here’s how I translate these lessons into an actionable international expansion checklist for product leaders: validate pull (authentic customer demand and repeatable GTM motion), ensure supply and liquidity for marketplaces, map the competitive landscape by customer jobs (not features), stand up a clear operating cadence with measurable outcomes (not just output-based OKRs), hire for local context and cross-functional ownership, and define a fast, lightweight process for localizing product, pricing, and support. When those pieces click, international expansion compounds rather than distracts.
You can follow Max on Twitter at @MaxRhodesOK.

Inspired by this post on First Round.

October 21, 2025
Stop Promoting Your Top ICs: “When They Win, You Win.” Lessons for Modern Managers

I’m often asked what truly powers a high-performing product organization. My answer starts with managers. That’s why I was eager to revisit the work of Russ Laraway, a seasoned leader who’s been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital. His career arc mirrors the kind of product management leadership many of us strive to cultivate on our teams.
He’s written a new book, titled: “When They Win, You Win.” It’s a research-backed guide that resonated with me because it balances practical tools with the nuance required for the IC to manager transition inside fast-moving product teams.
One idea that immediately stood out is how broken the manager selection process often is. Too many companies default to promoting the highest performer, rather than looking for folks who explicitly demonstrate leadership chops. In my own teams, I’ve seen elite individual contributors struggle when asked to lead without preparation. We now assess for behaviors like an ability to set clear outcomes (not just outputs), coach consistently, give and receive actionable feedback, and create clarity during ambiguity—before offering the role.
Equally valuable are the raw ingredients Russ outlines to gauge whether someone’s truly ready for management—even if they weren’t the best individual contributor. I’ve learned to look for three signals in promotion and hiring loops: (1) a habit of elevating peers’ work, (2) structured thinking that translates strategy into weekly execution, and (3) a bias toward accountability paired with empathy. If you’re hiring managers from outside the company, build your interview plan to suss out the right hire. I like questions that probe how candidates set outcomes vs output OKRs, run 1:1s that compound performance, and handle underperformance without losing team trust.
The book synthesizes heaps of research into clear management frameworks I can put to work immediately. One takeaway is a practical list of the behaviors of highly-engaging managers. What’s worked for me: weekly 1:1s anchored on priorities and growth, explicit role clarity, lightweight career conversations every quarter, strengths-based recognition tied to outcomes, and crisp decision rights. When managers consistently do these basics well, engagement rises and product velocity follows.
There’s no shortage of management advice out there—often contradictory. What I appreciate here is the distillation into an essential, research-backed guide for the modern manager that cuts through the noise. The result is a repeatable playbook I can hand to new product leads and know they’ll have the foundations to build trust, set direction, and deliver business impact.
You can follow Russ on Twitter at @ral1.
His book, “When They Win, You Win.” comes out on June 7, 2022. For more details, see the Amazon listing: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666.

October 21, 2025
From PM to VP: Proven Tactics to Accelerate Your Product Career and Lead with Confidence

I’ve spent my career growing product teams and coaching product managers, and I’m continually drawn to leaders whose playbooks translate across company stages. One standout is Jiaona Zhang (she goes by JZ), whose journey offers an especially clear roadmap for moving from individual contributor to executive product leadership.
JZ is the VP of Product at Webflow. Before that, she was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems. She teaches product at Stanford and mentors rising product leaders. You may also know her for the widely shared article, “Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products).”
What resonates most with me is her framing of the product career path. Instead of a linear ladder, think of three distinct phases: contributing as a PM, managing PMs, and leading the function. I’ve used a similar model to guide my own teams, and I’ll walk through how I apply this framework in practice.
Phase 1 — The PM role: When you’re breaking into product, focus on environments that will compound your learning. I look for signs of strong product discovery, clear ownership of product roadmapping and sprint planning, and a culture that values outcomes vs output. In interviews, I ask how success is measured (OKRs, customer outcomes, adoption) and how PMs partner with engineering and design. Early mistakes are common: trying to own decisions without owning the problem, shipping features without a minimum lovable product mindset, and confusing velocity with value. To avoid these traps, anchor your work in customer problems, link every roadmap item to measurable outcomes, and practice crisp storytelling that connects strategy to execution.
Phase 2 — The managing phase: The IC to manager transition is a shift from doing the work to building the system that does the work. As you become more senior, zoom out from features to portfolios, from experiments to strategy. When hiring, I look for complementary archetypes across the team — the product creator who thrives in zero-to-one, the operator who scales repeatable playbooks, the analyst who brings rigor to prioritization, and the evangelist who aligns stakeholders. For first-time managers, my advice is to establish clear decision rights, define the bar for product quality, and coach toward autonomy. Balance mentoring with mechanisms: weekly product reviews, outcomes-driven OKRs, and lightweight rituals that reinforce clarity without micromanaging.
Phase 3 — The executive phase: At this stage, I treat the product organization itself as a product. Define a vision, clarify the customer (your CEO, exec peers, board, and of course end users), and build feedback loops. With the CEO, align on the narrative, business model bets, and the handful of company-level outcomes that matter most. With peers on the exec team, drive cross-functional planning so GTM, finance, and product are synchronized around impact, not just output. With the board, translate strategy into measurable progress and risk mitigation. The goal is to ship strategy: clear choices, intentional sequencing, and a portfolio that advances product-market fit and durable growth.
Whether you’re trying to break into product, grow into management, or step into the executive arena, this three-phase arc is a reliable compass. Invest in product discovery, tie work to outcomes, and develop the operating cadence that turns intent into impact. That’s how you accelerate from PM to VP — and lead with confidence at every step.

Inspired by this post on First Round.

October 21, 2025
Why the COO Role Is the C-Suite’s Most Fluid: Archetypes, No-Blame Culture, and CEO Guidance

I’ve long believed the COO seat is the most fluid role in the executive suite, and my perspective has been sharpened by learning from operating leaders who’ve scaled iconic companies. One conversation that stands out centers on Sara Clemens, most recently COO of Twitch and former COO of Pandora.

In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover:

The three main COO archetypes and which sorts of folks are best suited for those roles.

The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture.

Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.”

Guidance for CEOs considering bringing on a COO to the executive suite.

From my vantage point in product management leadership, the variability of the COO mandate is a feature, not a bug. Great COOs adapt to the business model, stage, and CEO superpowers. The best partnerships I’ve seen start with explicit clarity: What outcomes matter most in the next 12–18 months? Which constraints are real? Where will product, operations, and go-to-market intersect—and who owns what?

On archetypes, I map product’s needs to the operator’s strengths. If we’re pursuing step-function growth, I look for a COO who is comfortable orchestrating ambiguous, cross-functional bets. When the priority is scaling reliability and margins, I align with a process- and systems-oriented operator. When the goal is organizational transformation, I look for a builder who can reset norms while protecting momentum. Getting this fit right improves execution, reduces decision latency, and clarifies how we measure progress.

On the tactical elements of being a COO and what good strategy looks like, I anchor on a few principles that have never failed me: strategy is a coherent set of choices, not a list of initiatives; it prioritizes outcomes over output and forces trade-offs. We translate those choices into a focused operating cadence—clear goals, crisp leading indicators, and reviews that separate signal from noise. In practice, that means elevating outcomes vs output OKRs, pressure-testing assumptions early, and linking roadmaps to measurable value creation.

Creating a no-blame culture isn’t soft—it’s operationally essential. Blame keeps teams defensive; learning keeps them fast. I’ve had success institutionalizing blameless postmortems, pre-mortems for high-risk launches, and a norm of writing down hypotheses before we run experiments. We fix the process, not the person. Over time, this builds psychological safety and enables the honest retrospectives that high-velocity product and operations teams depend on.

As companies double in size, complexity compounds. This is where “decision rights” become a force multiplier. I recommend codifying who is the decision-maker, who must be consulted, and who needs to be informed before work begins. Whether you prefer RACI, DACI, or RAPID, choose one, teach it, and use it consistently. Pair decision rights with single-threaded ownership for critical initiatives and you’ll reduce escalation churn, speed handoffs, and preserve accountability as headcount grows.

Keeping pace during hypergrowth also demands an operating rhythm that scales. I align quarterly planning with a lightweight monthly business review, ensure product roadmapping and sprint planning tie directly to company-level outcomes, and maintain a disciplined change-management channel so emergent priorities don’t derail committed work. When the cadence is consistent and the artifacts are simple, leaders can move fast without breaking trust.

For CEOs considering bringing on a COO to the executive suite, my guidance is straightforward: define the mandate in terms of outcomes, not tasks; be explicit about the seams between CEO, COO, and product; and decide how you’ll make decisions together before the first decision. Align on metrics, communication rhythms, and escalation paths. Hiring a great COO is not about finding a clone—it’s about designing a complementary partnership that compounds your strengths and closes your gaps.

The through line across all of this is clarity—of strategy, of responsibilities, and of learning. Get those right, and the natural fluidity of the COO role becomes your organizational advantage.

October 21, 2025