You Are The Product: How to Continuously Develop Yourself and Your Organization for Improved Performance
10 leadership lessons from elite coaches you can apply today to shift from high-performing contributor to a strategic leader with company-wide impact
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We’re thrilled to feature a guest post by Cassie Campbell, an executive and strategic advisor with 20 years building products and scaling businesses. She’s led product at both high-growth startups and large enterprises, taking products from zero to $250M in revenue. Along the way, she discovered that great product leaders aren’t the ones with all the answers—they’re the ones who ask better questions.
Today, Cassie helps founders and product leaders navigate strategic pivots and build world-class practices. She is also building an AI-native executive coaching platform, Arete.coach, designed to amplify human coaching rather than replace it.
Cassie interviewed the world’s top product coaches on the Women in Product’s Product Rising podcast—and in this article, you will learn 10 actionable leadership lessons you can apply today to level up yourself and your organization.
You Are The Product: How to Continuously Develop Yourself and Your Organization for Improved Performance
I just wrapped up 14 episodes for the Women in Product, Product Rising podcast, interviewing some of the most respected coaches in product management - Marty Cagan, Phyl Terry, and Teresa Torres, whose books likely sit on your shelf, and some new voices, like Rob Snyder, a sales-driven product-market-fit coach, and Tim Herbig, a product strategy and OKR coach. I expected to learn about product strategy and customer discovery, but what I didn’t expect was to uncover universal truths about leadership and transformation that apply whether you’re in engineering, sales, program management, or any function trying to create change.
I’ve had the privilege of being the Head of Product at 4 startups scaling from 0 to 1 and 1 to $250M ARR. Like many of you, I attribute some of those opportunities to being very good at my product craft. But there’s something unique that happens when you get to a certain level of leadership within an organization, which the Head of People at one startup shared with me — ”You shift from being on the product team to being on the leadership team.”
Fast forward and I’ve now had a few years coaching startup founders through uncertain times, macroeconomic shifts, pivots, and product strategy. But those words about shifting to leadership still rang true. So, when I produced a podcast on product leadership coaching, I also caught a glimpse into coachable moments that relate to a leadership team as a whole.
Here are 10 universal themes from product leadership coaches that probably ring true across many functions in tech and business.
1. The Excellence Paradox: Why the Best Get Better (With Help)
Meghna Shah, Partner at PwC put it simply: “Even Michael Jordan has a coach, right?”
Yet in business, we’ve created this backwards mythology. We think coaching is remedial—something HR assigns to underperformers. We believe that once we reach senior levels, we should have all the answers. That asking for help is weakness.
The opposite is true.
Phyl Terry, founder of Collaborative Gain, coach, and author of Never Search Alone, shared a story that shatters this myth. Jason Randall joined their peer coaching council in 2007 as a director of product. But here’s what’s interesting — he didn’t stop getting coached when he got promoted to VP. He asked for help again when he became CEO. Each new level required new skills, new perspectives, new coaching.
Coco Brown, CEO of Athena Alliance, is a talented and experienced public speaker. But when the opportunity came to address CEOs of some of the most well known companies of our era, in a relatively intimate environment, she strategically hired a coach to collaborate on how she could have the most impact in that moment. She got that opportunity through her track record and skills - and she leveraged that opportunity through strategic coaching.
The pattern is clear: The higher you rise, the MORE coaching you need, not less.
Tiger Woods worked with multiple specialized coaches and trainers throughout his career - including swing coaches, fitness trainers, and mental game coaches at various points. Serena Williams worked with coaches throughout her entire 23-year career. A race car team recently hired a coach friend of mine for performance and mindset coaching. Olympic athletes have specialty coaches for every aspect of their performance.
Why would leading a complex organization with thousands of people and hundreds of millions or billions in revenue require less support than hitting a golf ball?
You don’t need to be a professional athlete to recognize this truth. Ethan Evans has worked with four coaches simultaneously — two for health, one for peak work performance, one to clear mental baggage — plus a personal trainer. The total investment? About $1000 a month. Not forever, just long enough to level up. Many types of specialized coaching are surprisingly affordable, and the ROI compounds.
The cruel irony is that the more senior leaders become, the less feedback they receive naturally. Their teams are afraid to challenge them. Their peers are busy with their own domains. Their board meets quarterly. Right when the stakes are highest and their decisions affect the most people, they’re the most isolated.
This is why CEOs have coaches. Not because they’re struggling — because they’re smart enough to know they can’t see around every corner alone. They understand that at their level, a 5% improvement in decision-making quality could mean millions in value and hundreds of jobs.
Try this:
If you expect your team to have coaches or mentors, model it by getting your own.
Share openly that you work with a coach (normalize it for your organization).
Calculate the cost of your last bad decision—compare that to the cost of coaching. If you run a P&L, the cost of coaching is likely a fraction of a percent, and a course correction for your team gained through coaching can have massive upside.
But why do top performers need more guidance as they rise? The answer lies in a fundamental limitation we all share - and it gets worse the higher you climb.
2. You Can’t See the Problem From Inside
Jessica Nelson-Kohel, CEO and founder of The PMX Group, a niche product consultancy, introduced me to “immersive discovery” — the idea that outsiders see what insiders can’t.
“People don’t always self-identify the root cause of dysfunction accurately,” Jessica explained. Her niche consultancy is pulled into companies when the CEO or a CPO feels that there is something that can be optimized in the product development process — or if outcomes aren’t being achieved as expected. Clients always have a hypothesis about the root cause. “If someone’s just telling you what they think is going on, maybe 80% is accurate, but that other 20% could be everything.” It’s all a matter of perspective, and no one human should expect themselves to have a 360-degree perspective. Everyone has blind spots. You just need to stay curious about them and seek the perspective from others when you can.
But there’s another layer to this blindness that Tim Herbig, product strategy and OKR coach, revealed: Sometimes the problem isn’t that you can’t see the issue—it’s that your organization won’t listen to you even when you do. “Sometimes it’s the case that upper management doesn’t listen to internal voices about how something should be adopted,” Tim told me. “Maybe an external voice is just more heard, for better or worse.”
Tami Reiss, product leadership coach and former coach at Insight Partners, used a soccer analogy that perfectly captures this limitation: “When we’re kicking and running with the ball, it’s hard for us to see beyond our very immediate sphere.” The coach, she explained, can see the whole field—all the players, the opportunities for assists you’re missing, the defender coming up on your blind side.
I love a good surfing metaphor, so I use this one: You could be a star surfer, in the lineup, waiting for your killer wave. But, based on your vantage point, you might not be able to see it. You can just see what’s upon you. But someone from the shore can see beautiful lines on the horizon, and shout to you to hold, wave 3 in the set is looking like it will shape up nicer than the others.
Rob Snyder, founder, product-market-fit coach and Harvard Innovation Fellow, was even more direct about his own limitations: “I’m bootstrapping a startup. I can’t do this for myself. I need somebody else to look at my sales calls and untangle them.”
Try this:
Think about a challenge you face in your organization. What is your lens on the root cause? Then stretch to think if there are other forces at play that may not be obvious from your vantage point.
Triangulate multiple perspectives. Ask someone two levels below you: “What’s broken that I can’t see?”
Seek alternate perspectives deliberately - not to validate your thinking, but to sharpen it.
Once you accept that you need outside perspective, the question becomes: where should you focus that guidance first? For most leaders, the answer isn’t technical skills - it’s something far more fundamental.
3. Political Capital Is Your Real Currency
Phyl Terry’s words still ring in my ears: “If you opt out of politics, you get played.”
I learned this the hard way. Having grown so much in my career due to my killer instincts for execution and making big things happen on the development front, I didn’t know what I didn’t know when I entered some more highly political territory. Ally-ship and collusion were happening all around me, and I had not a clue. I started working with an executive coach who facilitated a 14-person in-depth 360 review. The 360 review revealed blind spots I didn’t know I had — stakeholders where I thought things were fine but the alignment and trust weren’t actually there. That political mapping showed me I’d been so focused on execution that I’d missed critical relationship gaps.
The coach helped me see that politics isn’t optional — it’s about understanding the landscape so you can actually get things done. In my next executive position, I vowed to have 1:1s with the L-team members on my calendar before those of my direct reports. Building rapport, earning trust, and knowing where my trust wasn’t quite warranted was crucial.
Phyl teaches a political mapping exercise that helped me see things through an elevated lens:
Map your allies, blockers, and neutrals
For every blocker, identify who THEY listen to
Build relationships with the influencers of your blockers
I once worked with a Chief Revenue Officer during a critical inflection point — we’d achieved product-market fit and were scaling fast, but we had to shift from “grow at all costs” to “grow while delivering consistent, high-quality experiences.” This created friction. Sales was selling features that didn’t exist, weren’t on the roadmap, and didn’t even have financial accounting models behind them. Finance didn’t know how to book the revenue. I was focused on building sustainable infrastructure. To the sales team, I looked like the person slowing them down.
The CRO had brought in a network of sellers who were extremely loyal to them. I realized: I didn’t need to convince the CRO directly. I needed to convince the people the CRO trusted most.
I started building intentional relationships with the most strategic sellers—including one particularly tenured rep who’d been instrumental in helping the company shift from founder-led sales to a scalable sales organization. We got regular 1:1s on the calendar. I listened to what he was seeing in market. I shared what we were working on and why—not to defend the roadmap, but to foster genuine empathy about the constraints and trade-offs we were navigating.
The breakthrough came during a 1:1 with the CRO. They shared frustration with the “finger in the air, make the target huge” approach to goal-setting. They wanted targets grounded in real sales capacity aligned with what product could actually deliver—ambition balanced with reality. Hearing the CRO acknowledge their own frustration with how decisions had been made was the opening I needed.
Those trusted sellers had been having similar conversations with the CRO. I hadn’t won by going through the blocker—I’d won by building relationships with the people the blocker listened to.
The proof came at our next executive offsite. During a retrospective, we listed things that made people mad. “Grow at all costs” made the list. As a group, we literally crossed it out together and agreed we would no longer operate that way.
When I eventually left the company, the CRO reached out privately while I was drafting the announcement email for the CEO to send to the entire company. They told me I should advocate more for the impact I’d had during my tenure—that I was shortchanging myself. That moment of trust and support, from someone who’d initially seen me as an obstacle to their goals, felt like the real validation.
Try this:
Direct ally-ship requires investment. Prioritize it early. Walks and coffee outings work wonders in RTO contexts. Regular video-chat meetings work great in remote contexts. Don’t reschedule these. Regular rescheduling sends a signal that this relationship is not a priority.
One People Ops exec I worked with would send any two leaders in conflict to a nice lunch, with the corporate card, and tell them they weren’t allowed to talk about work the entire time. Of course, work would come up, but typically after a period of time spent building rapport. Build rapport through talking about your non-work lives, which piques curiosity and fosters a sense of caring.
Don’t sit in conflict. Conflict can consume your emotional energy. Ironically, though, avoiding conflict is a subversive way to consume your emotional energy. The best way to deal with conflict is to acknowledge it directly with the individual and then move forward strategically.
Foster empathy while also carefully choosing who to trust. I remember walking with an individual who decided to leave their company - “I just can’t operate with integrity here.” Wow - powerful words. That’s an extreme end of the spectrum, but it’s a reminder that we’re not going to be able to get along with everyone, or please everyone, or help everyone follow the logical deductive reasoning we feel is so darn obvious! Some people aren’t ready. That’s ok. Let them be, and then do you.
Understanding that politics is your real currency is one thing. Actually building that currency is another. The key lies in reframing how you think about asking for help.
4. The Power of Shameless Asking
Just a few years ago, I didn’t think of asking for help as a strategic move. I’d built my career on being the one with the answers (of course, in concert with my team). But I didn’t like the idea of being vulnerable when in new territory, where I often forged ahead, independently, with grim determination. My first executive coach helped me unwind that.
Phyl Terry framed this so well: “Your superpower is asking for help, shamelessly.”
That being said, “There are two kinds of asking for help,” Phyl explained. “Independent or dependent.”
“Dependent is the kind of asking for help where you’re not learning anything, you’re not growing, you’re asking the person to answer it for you, do it for me, figure it out, I’m not going to learn anything. We all hate that. Nobody likes to be asked for help in that way.”
He gave an example: “I’ll get people like, ‘Phil, can you help me find a job?’ I’m like, what kind of question is that? I wrote a book and built a community with 30,000 people. You gotta go do that.”
But independent asking is different: “I’m working on this question. I’m pushing this forward. I’m really trying to understand how to work with this new boss from Amazon. I need to talk to somebody who can help me understand some specific things.”
When you ask for help this way, Phyl says, “there is an unlimited amount of help people are willing to give you. They love it. They feel honored. They feel treasured. And if you ask them for help and then you go use that and make something with it and then have a new question and come back, they really love that.”
The key insight: People don’t resist helping. They resist doing your work for you. When you show you’re actively working on a problem and need specific guidance to get unstuck, people line up to help.
Try this:
Frame your asks with what you’ve already tried: “I’ve attempted X and Y, but I’m stuck on Z.” Also, people are turning to ChatGPT, Claude, Perplexity with these kinds of asks. That’s great! But I encourage finding a human to listen and advise, who can bring lived experience to the conversation.
When you ask someone for help, follow up with what you did with their advice—people love seeing their impact. I recently had a call with a founder who gave me some GREAT advice that was actionable right then and there. I took that action (it was an email) and then in my follow-up thank you note to the founder, I let him know that I took the action. I hope it put a smile on his face!
Build a “personal board of advisors” who you can tap for independent asks. Former managers, peers, or co-workers can be great for this. If they’ve worked with you they likely want to support you in your career; in addition, they have a deeper understanding of your strengths and your blind spots. And that established relationship really helps. Plus it fortifies your network ties!
Once you’ve mastered the art of strategic asking, you might expect organizational change to happen quickly. That’s where most leaders get blindsided by an uncomfortable truth.
5. Transformation Groundhog Day
Heather Samarin and Vidya Dinamani, former Intuit product leaders and founders of Product Rebels, shared this when speaking about their work with Fortune 500 and Fortune 1000 companies: Real transformation takes 18 months minimum. Not a quarter. Not two quarters. Eighteen months.
But “transformation” you might say — what is that anyway? I work in a modern tech company and our processes are finely tuned, like a well oiled machine. *Chef’s kiss*. I don’t think there’s any way of working that needs to transform! (If this is you and you have 5 minutes to spare please do reach out to me as I’d love to bear witness.)
I’d like to gently point your attention towards the giant tidal wave that is already upon us. There is no escaping.
We are about to get “caught inside” the gnarliest set of AI innovation waves and will just be coming up for breath when the next wave clobbers us.
And each of those waves will require some change management or “transformation” within our teams. In fact, we may be in a consistent state of transformation for some time. Buckle up.
Might we be in for an era of Transformation Groundhog Day? Work-changing technologies and macro-shifts are likely going to be happening, consistently, on shorter and shorter time scales. Who will really have 18 months? Or if you take that long, what’s going to happen to your position in the market?
Here’s another complication: Most organizations try to shortcut it with training. They send everyone to a two-day workshop on “Agile Transformation” or “Customer-Centric Thinking” or “How to use Gen AI” and wonder why, three months later, nothing has actually changed.
“You can’t coach overnight. You can’t coach in a week,” Vidya told me. “You need to spend time understanding, working, and then there’s trust that’s built up.”
Try this:
Give enough resources and time. Quick fixes won’t work; authentic transformation requires time to grasp real issues and build confidence for change.
Foster a culture of experimentation and early wins. Early wins energize teams, reduce resistance, and show tangible benefits that help drive behavior change over time.
Embed behavior change to make new ways stick. This means sustained attention through coaching, reinforcement, and creating systems that support the new norms.
Training is great for shepherding teams into new contexts and ways of working — but integration is what counts.
6. When Training is Not Enough
Back in my “Big 5” days I had to do 120 hours of training per year. In more modern memory, L&D budgets are covering Maven courses. With advancements in technology, psychology, human behavior, and all of the things that go into people working in concert to build teams, technology, and business, training is essential.
Yet the fundamental misunderstanding about transformation is thinking that it’s an information problem. It’s not. It’s a behavior change problem.
Teresa Torres, author of “Continuous Discovery Habits,” gave me the key insight: “Training is for skills. Coaching is for behavior change.”
When you’re transforming an organization — whether it’s adopting AI, moving to a product operating model, or implementing any other fundamental shift — you’re not just asking people to learn new skills. You’re asking them to change how they think, how they make decisions, and how they interact with each other. Most importantly, you’re asking them to let go of what made them successful before.
Teresa provides concrete coaching guidance: When a product leader knows what their team should do but is scared to navigate stakeholder dynamics, Teresa explains: “That’s where a coach is amazing, right? Because a coach can help you work through that fear. A coach can help you understand where each stakeholder is coming from and how to position this. Whereas that’s not a hard skill... it’s messier. It’s a messy organizational tangle. I need a sounding board. I need a thought partner. I need someone to hold space and help me reflect on what’s the right way to do this.”
In the context of a product team shifting from a service mindset to an outcome-oriented customer-led one, Hope Gurion, product leadership coach and producer of “Fearless Product Leadership” podcast, observed: “Usually when teams want to become outcome oriented, the product skill that is least developed is customer discovery. They just haven’t had a need to do that before.” But teaching them discovery skills through training is just step one. The real transformation happens through coaching—helping them navigate the political reality of actually doing discovery when leadership is used to dictating features.
Try this:
Inventory your team’s skills and behaviors. Identify when training is needed and provided that whether through books, upskill programs, or pairing learners and mentors.
Also learn to spot when training is not enough. Bringing new ways of working into the real world can be difficult. Coach people through the application of their new-found skills in real-world situations.
If training isn’t enough for organizational transformation, what does work? The answer requires a complete reframe of what management actually means.
7. The Coaching Imperative: Your People ARE Your Product
Even in non-transformation contexts, coaching is an imperative. When Marty Cagan, founder of the Silicon Valley Product Group, said, “Once you’re a manager, your people are your product,” it wasn’t the statement itself that rewired my thinking — it was what came next.
“About 80 percent of your week is coaching and developing,” he said about first-level managers.
I literally laughed out loud. Eighty percent? I was maybe hitting 10% on a good week. Most of my time went to stakeholder management, fighting fires, and what I generously called “strategy” but was really just scrambling to keep up.
His ratio flips as you rise. If you manage senior leaders, “it’s about 20 percent of your time on coaching and developing and 80 percent on strategic context” — product vision, strategy, team topology.
The issue is being compounded with AI. I spoke to a CTO recently who said that he thinks the best engineers are those that have cultivated product sense — an engineer who knows how to refine the initial request by deeply understanding the business objectives and outcomes will be more effective than those that start coding right away. That requires experience — so he has a bias towards hiring senior engineers who bring that know-how and combine it with the powers of AI. He also sees the flaw in this approach.
If this trend continues, we will not be growing enough inexperienced builders into experienced ones. The unintended consequence is that there will be a shortage of talent.
Might the companies that win the long game be the ones that leverage AI while also coaching and growing early-career talent into the critical thinkers that can wield AI effectively? This will require an intentional investment in pairing, modeling, and coaching by our senior leadership.
While all your competitors focus on reducing headcount assuming AI will enable the remaining team to be more productive, perhaps taking a holistic long-term approach will involve a people strategy that trains on the critical thinking, collaboration, and growth mindset in tandem with AI fluency.
Try this:
Examine your people strategy — is it focused on optimization through cutting costs with the hope that AI will make them more productive, or on holistically building the team that will offer a competitive advantage?
If you want to invest in the latter, what will that take from a resourcing, expertise, and time perspective?
Consider bringing in coaching support — either for yourself to learn how, or to supplement what you can provide.
Understanding that your people are your product changes how you spend your time. But when you’re trying to influence change across the organization, time isn’t your only constraint — attention is.
8. The Urgency Test to Break Through the Noise
Rob Snyder’s insight about urgency versus importance shifted how I thought about influence. The insight: Importance doesn’t create action — urgency does. You can have the biggest, most important problem in the world, but if it’s not urgent to the people you need to move, you won’t get traction, budget, or alignment. Rob taught me to always ask: Is this in their top 5 urgent problems right now, or just important in theory?
Once, I was advising a founder. His fintech startup had stopped penciling when interest rates took a hike. They were looking for new opportunities. Their new solution involved solving a major problem for lending institutions like banks and credit unions.
“The size of this problem is this big!” The number was impressive on any scale. I knew they had been having multiple calls with banks with some signals of curiosity, but no urgent follow-ups.
I walked up to the whiteboard, and drew a circle in the middle. “OK - so it’s this big” and I drew the dollar figure within. Everyone seemed to feel good — that would be a good problem to solve. It’s a big number.
Then I proceeded to draw other circles on the board to the left and to the right. “If we think about the top 5 problems that are discussed in the boardroom of a target bank, is this problem #2, #5, or #10? Do we even know?”
The room went silent. They didn’t know. They’d identified a big gnarly problem to solve, but didn’t understand the relative urgency.
Whether you’re searching for product-market-fit for a product idea and a market; an idea and a collaborator; buy-in and a stakeholder — urgency matters.
“Everyone has an Asana board with stuff they have to get done,” Rob said. “Your solution has to fit into their board, not create a new one.”
Rob followed with another gem — when working with businesses, it’s not the business that is buying your product or your idea, it’s the person. You must offer something that brings that person to the table because it will make their life easier. You must appeal to the urgency that the person feels, not just the business or organization.
Try this:
For any idea you’re trying to sell, identify potential workarounds. People tolerate a lot of pain. If there’s a halfway decent workaround, that may be good enough for now.
When you’ve identified a truly urgent issue for the person you hope to influence, you’ll see them start to “sit on the same side of the table” with you. Lean into collaboration.
Become known for understanding the urgency of issues. You’ll find your support gets “pulled” more by your stakeholders - and you’ll need to do less “pushing.” Now that’s influence.
Getting on someone’s urgent priority list is just the first step. Actually changing hearts and minds requires a different kind of persistence - one that feels surprisingly uncomfortable.
9. Winning Hearts and Minds
I love simple ideas that have big power. Vidya shared this tip for leaders establishing a vision for a team shifting to a customer-driven strategy: “You’ve got to be sick of your own voice, but you have to express it with enthusiasm. Do it each time like it’s the first time. You are carrying that customer flag.”
When leaders become self-conscious about their repetition, she encourages further: “And so sometimes, you know, you just need a little boost because I think all of us, when we’re in the field and we’re like, am I, am I a broken record? Am I just talking to the void? And it’s like, no, people are listening, but it takes five, seven, nine times for something to register. So we say. You keep going and you’ve got to be sick of your own voice, but you have got to express it with enthusiasm.”
I was recently looking at a slide deck for a presentation and my co-presenter asked if we should remove a slide because it felt a bit redundant. I opted, intentionally, to keep the slide. “This is grounding for the entire talk - and some in the audience might not be fully attentive when we say it the first time. I think it’s ok to quickly touch on it again to keep hammering home the key takeaways of our talk.” Optimization of sharing a vision or communicating a point that must be internalized by your audience isn’t about getting it perfect the first time. It’s about repetition.
And sometimes it happens later than we hoped. Even years later. Even after the job is in the past.
I just received this very brave and introspective note from someone on LinkedIn — it had been years since we last connected. “I want to also apologize for all of the negativity that I was filled with. Thank you for putting up with that, and being the courageous leader that you are. It was an absolute pleasure to work with you (and I learn to respect what you did and your positivity even more so, in hindsight, as time passes).”
For context, I was working with a team that had been under-resourced, lacked focus (major shiny object syndrome), and was thrashing their way though a “grow-at-all-costs strategy.” I had a deep empathy for everyone involved. In every staff meeting I emphasized the vision for the team. I felt like a broken record. Honestly, sometimes I was giving myself the pep talk I needed in that context!
While it didn’t sink in to all hearts and minds in that moment, it eventually did. Our impact can span beyond the job to relationships that evolve over time.
Try this:
When you have a vision or a strategy, repeat it in every staff meeting. It may feel repetitive, but if some people start rowing in other directions because they either don’t know it or don’t understand it or don’t trust you to lead them there, you want to know asap.
When you’re not sure if your strategy is landing, try this question: “On a scale of 1-10, how much do you understand our strategy? On a separate scale of 1-10, how much do you believe in it?” It takes a brave leader to ask this question (I was privileged to witness this) and an even braver one to set a tone within the company that divergent perspectives are welcomed to the table.
All of these insights about leading others ultimately circle back to a meta-realization about leading yourself.
10. You are the Product
Perhaps the most profound reframe came from Tim Herbig: “I see my myself as the product.”
When I heard this, I reflected on if I’d been treating my leadership development as something that happened TO me - through experience, feedback, the occasional training. But what if I treated myself like a product I was actively developing?
Tim asks himself the same questions about his coaching practice that he’d ask about any product: Who’s my audience? What problem do I solve? How do I differentiate?
This shift changes everything. Instead of waiting for growth to happen, you become the product manager of your own development. You run experiments on your leadership style. You measure results through team performance and 360 feedback. You iterate based on what works. You don’t just hope to get better—you systematically build yourself into the leader your organization needs.
Turns out, I had been intentional - putting myself in uncomfortable situations to grow in new ways.
When I think of my own career, I think of it in growth arcs.
Arc 1 - strategic thinking, communication and influence, and analytical skill building during management consulting.
Arc 2 - product marketing and product management fundamentals.
Arc 3 - can’t hide behind a big team anymore... start-up product leadership going from 0 to 1 and charging forward with great execution.
Arc 4 - can’t hide behind a big CEO with a vision... strategic coaching and advising, helping founders navigate tricky situations.
Arc 5 - Summer of AI - jumping in the deep end to learn how to be hands-on and get how to use Gen AI to build Gen AI native products.
Now I’m on Arc 6 as a first time founder. Those arcs were intentionally chosen to give me a new platform to stand on each time.
Try this:
Option 1: The Product Management Approach. Define your “user personas” (who you serve as a leader with a 360 degree lens), determine what problems they face that are urgent and important to them, and test one leadership experiment this month. Check in before and after to see if that had a measurable impact.
Option 2: The Growth Arc Approach. Map your career in growth arcs like I did - what arc are you in now? Identify what capability you’re building in this current arc. Design your next arc: What uncomfortable situation will stretch you?
Option 3: The Feedback Loop Approach. Ask three people: “What’s one thing I could have done differently, since we last spoke, to help you most?” (I love asking this at the end of every 1:1 meeting) Document what you learn in a “Leadership Lab” journal. Pick one piece of feedback to act on for 30 days, then reassess
The Compound Effect
After 14 conversations with elite coaches, here’s what became crystal clear: These aren’t separate lessons. They’re each multipliers of one another.
When you start treating yourself as a product to be developed (Tim’s insight), you naturally seek outside perspective to see your blind spots (Jessica’s point). That outside perspective reveals you need to spend more time coaching your people (Marty’s bombshell). As you coach more, you realize you need coaching yourself (the Excellence Paradox). Getting coached teaches you to ask better questions (Phyl’s shameless asking). Better questions build political capital. Political capital creates space for the growth your organization actually needs.
It’s a virtuous cycle. Start anywhere-with any single insight from these coaches-and watch how it naturally leads to the others.
The coaches I interviewed have collectively influenced thousands of careers and hundreds of organizations. Their secret isn’t mysterious: They understand that growth isn’t linear, it’s exponential. Each improvement enables the next.
The question isn’t whether you need to change. The AI wave ensures that. The question is: Will you approach that change systematically, with help, patience, and the compound effect on your side?
Or will you keep trying to figure it out alone?
Thank you, Cassie, for transforming deep coaching insights into clear, actionable leadership tools. Your advice will help leaders grow with intention, particularly during times of big change.
Cassie would love to connect with leaders who currently work with executive coaches - she’s learning from their experiences as she builds Arete.
She also coaches non-traditional product leaders (CTOs, sales-led founders) who need strategic product guidance. Open to discovery calls and referrals.
Find her on LinkedIn or at CassieCamp.com.
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Level Up Community Spotlight
We are building more than a newsletter — we are building a community of ambitious high-performers. Every week, members of the Level Up Community are out there doing the work, sharing insights, and pushing themselves (and others) to grow.
In this spotlight, we are highlighting a few of the wins and insights.
This is proof that when you invest in yourself and your peers, everyone levels up:
Dipti Aswath (AI/ML Architect) shares lessons that separate sticky AI products from failures from her sold-out presentation.
Tatyana Arbouzova (Director of Quality Engineering) shares practical steps to turn your network into active allies and a link to the video recording.
Santhi Boppana (Associate Director) shares lessons on what makes her virtual accountability meetups successful.
Jordan Cutler (Engineering Leader) was promoted to Staff Software Engineer at Pinterest. Congrats Jordan!
Anand Vasudevan (Engineering Director) shares his new role as advisor to the University of San Francisco School of Management, Digital Marketing Program, and explains why he chose digital marketing. Congrats Anand!
Pawel Hajdan’s (Tech Founder) mentee won the People’s Choice Award at the Block Dojo Showcase. Congrats to you and your mentee, Pawel!
Consider joining us, we’d love to have you!
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