I had the pleasure of changing things up this week and had Andrew Capland join me and 600 professionals for a candid conversation about promotion readiness. Instead of my usual framework-forward-snackable lesson, we got to have a conversation. It took me back to when I joined Andrew’s podcast, Delivering Value, to share some uncomfortable but career-shaping learnings. Check it out here if you want to get a behind the venear of awesomeness look The Career-Altering Feedback No Leader Wants to Hear.
To prepare for our conversation, I asked those joining us:
“What’s the single biggest thing holding you back from that next step right now?”
Across Senior PMs, Group PMs, and Directors, the answers clustered hard (71%!!!) around three themes:
“I don’t have clarity on what great looks like at the next level.”
“I struggle to communicate my impact so leadership hears it.”
“My manager doesn’t see me as next-level ready yet.”
People wrote in saying
“I’ve tried asking what the next level looks like, but I never get a clear answer.”
“I’m spread too thin to show up as the next level.”
“How can I convince my line managers that I’m ready to take on leadership responsibility?”
“How do I represent my value to a hiring team so they see me as senior-level?”
If you’re a promotion-ready Director or Group PM, you can probably see yourself in at least one of these.
To help you turn this into something concrete, I pulled everything into a Promotion Readiness Checklist and worksheet so you can assess yourself across five areas: clarity, scope, impact story, sponsorship, and capacity.
You can grab it here:
Promotion Readiness Checklist & Worksheet
The rest of this substack is Q&A from the live conversation with Andrew, plus questions that came in from the audience and the survey that we got to noodle on after our conversation, and now share our thoughts with you.
Q&A with Andrew Capland
What trends are you seeing in product and growth leadership right now?
I asked Andrew what he’s noticing across his portfolio of work and in conversations with the leaders he is coaching right now.
Andrew:
“I see a lot of hype around AI. There’s this promise that it’s going to automate things, make life easier, and reduce the need for certain roles. But what I’m seeing on the ground is the opposite.
People are busier than ever. There’s more input, more expectations, more ‘can you also do this with AI’ on top of everything else.
The vibe I get is that folks are more burned out than I’ve ever seen. There’s this firehose of new tools, new features, new expectations, and the rate of new things is just relentless.”
He also shared something that surprised a lot of people:
“There are companies that, in the last year, have quietly lost product-market fit. They weren’t bad companies. They had a great run. But the market moved, competitors changed the game, or in some cases, AI reshaped the category.
You can feel it on the inside. Demand shifts. Features that used to be premium show up for free somewhere else. It forces the company to rethink the whole portfolio.”
I have noticed the same trend, even before the AI wave. In my career and the companies I worked at have been impacted by the financial crisis and Covid, leaving me either jobless or needing to scramble and have to shift the entire business approach. I talk about how to think about product as a system within the market and what to do when these shifts inevitably happen in When the Growth Playbook Breaks.
Andrew’ encouragement:
“One thing I’m trying to get everyone to realize is: there is no safe company, no safe role, no safe path. Waiting for the ‘stable environment’ before you work on your skills or your career is a trap.
If you’ve been waiting to get ready, now is a great time for that. The uncertainty isn’t going away, so building your own operating system matters more than picking the perfect company.”
That got me thinking about my own role change at the beginning of 2025. I’ve had 4 VP, GM and CPO roles and have decided to go solo and invest in my brand and portfolio rather than investing in another company’s. Stay tuned for the “how it’s going post” coming at the end of this year.
What changes between Director and VP? How do you think about that jump?
Then we moved into promotions. I asked: “When you think about those different levels, what does good look like at the different levels? Specifically, what changes between Director and VP?”
Andrew’s framing:
“The way I think about it for a lot of folks I work with is that you go through an identity shift.
As a Director, you’re still pretty close to the work. You might be the one running the plays, maybe a player-coach. You’re still the person who can jump in and fix the funnel, change the onboarding flow, and write the growth experiment.
To get to VP, if you’re still the best doer on your team, that’s a red flag. The shift is going from player-coach to coach-first.”
He broke it down into three tangible skills he sees in the people he supports at VP and above:
“Number one is focus, paired with a longer time horizon.
The senior leaders I work with are constantly asking, ‘What matters most for the business right now?’ and then they protect that at the expense of everything else.
They’re not chasing every opportunity. They’re narrowing in on the few bets that matter and thinking about them over quarters and years, not just this sprint.”
This advice really resonates with me. At the VP level, you are thinking about horizons and bets and having the hard tradeoff conversations at the executive level. The decisions are made before you enter the room to “make a decision”. In Break the Build Everything Revenue Flat-Line Cycle I talk about the frameworks you can use to start doing this well.
Then:
“Number two is communication.
“More specifically, it’s the skill of translating your ideas for very different audiences: non-native English speakers, cross-functional partners, your exec team, your board.
You see it when something big is happening at a company. There’s usually one person everyone turns to and says, ‘You tell this story.’
They’re the person who can take a messy strategy, clean it up, and say, ‘Here’s the version I’m going to share at all-hands, here’s the version for the board, here’s the version for the sales team.”
When I think about the point of communication, it is the single most important skill I see everyone needing to get great at. When I launched AI-Powered Executive Communication, I thought PMs would sign up. Instead, my cohort was comprised of builders, founders, a surgeon, and communication leaders in the office of the CEO. According to Yoodli’s co-founder, two-thirds of professionals struggle with public speaking. Now, this does not mean on stage, it also means advocating for yourself and explaining your work clearly. A really poignant reminder that your greatness is locked behind your ability to communicate and relate to your audience.
And finally, Andrew’s third point:
“Number three is creating systems for other people to thrive.
You get to a point where you can’t win by doing more yourself. You have to scale your influence and your impact without scaling your units of work.
For me, that often means making artifacts: documents, frameworks, templates. Things that capture how you think and make decisions in a way that other people can take and run with when you’re not in the room.”
You can hear how different that sounds from “run more projects” or “ship more roadmap items.” I teach the AI Executive Stack to the leaders I work with because, in practice and in every conversation I have, the same pattern shows up: around 60% of executive time is spent re-hashing information. The only way to accelerate is to let AI handle that churn so you can spend your energy on higher-impact strategy. Dec 18th, Subha and I will go through how to add agents to the product update flow.
Why do strong Directors stall out?
I asked him something I see all the time in my own work, wondering if his observation would be different. “Why do people who are good at the job stall around Director?”
Andrew:
“The most common pattern I see is that the context changes, but the leader doesn’t.
What made them successful at one stage of the company stops working. Maybe they were the scrappy operator who could do everything. Maybe they were the best IC on the team. That was valuable for a while.
Then the company grows up, the problems change, and the stakes are higher. The job needs someone who operates differently, but they’re still trying to win the old game.”
I love Andrew’s ability to distill the learnings. He pointed to three specific traps:
“First, doing too much yourself. Your calendar is full of execution. You’re in every meeting, touching every decision, fixing everything personally. That worked when you were a Senior PM or a new Director. It doesn’t scale.
Second, talking about your work as tasks instead of bets. When you’re still framing everything as, ‘We shipped X, we launched Y,’ leaders don’t see you as a portfolio owner. They see you as a very productive project manager.
Third, hoping the organization will discover you’re ready. They wait for their manager or their VP to notice them, instead of designing for visibility and sponsorship.”
His litmus test:
“If you look at your week and you’re still the person doing the most individual work in your area, that’s feedback. It doesn’t mean you’re bad at your job. It means you haven’t made that identity shift yet.”
How should product leaders think about impact if they aren’t in a classic growth role?
Several people asked some version of:
“How do I think about impact and promotion if my work isn’t as easy to quantify as B2C growth metrics?”
Andrew’s answer:
“Every product leader has a business model. Even if you’re not doing traditional growth work, your work supports some financial outcome: revenue, margin, cost reduction, risk reduction, retention, expansion, or capacity. Your job is to define what success means in your model and measure it in a way your executives recognize.
“You don’t need perfect data. You do need a clear story: ‘Here’s the business problem. Here’s what we tried. Here’s what changed.’”
He emphasized that the story matters as much as the spreadsheet:
“The people who move up aren’t the ones with the perfect dashboards. They’re the ones who can sit down with their VP of Finance or their CEO and explain, in simple terms, why this work matters to the business.”
To get really good at this, I recommend Andrew’s Growth OS, it combines the hard growth skills and reframes your ability to approach the work at your company and also think about your own positioning.
When someone tells you they want the next level, what are you looking for?
Near the end, I asked: “If a Director comes to you and says, ‘I want to be VP,’ what are you looking for?”
Andrew:
“First, I want to see that they understand what VP-level work is in their context. If they can’t describe what great looks like at that level in their company, then we’re at the beginning of the journey, not the end.
Second, I want to see that they’ve already started doing pieces of that work. Are they taking on portfolio-level problems? Are they shaping strategy? Are they coaching other leaders?
“Third, I want to know who is going to vouch for them when they’re not in the room. Promotions at that level are team sports. Your manager can’t do it alone. You need a sponsor who will say, ‘Yes, this person is ready.’”
The throughline in all of this: people are not getting blocked because they aren’t smart or hard-working. They’re getting blocked because they don’t yet have a clear picture of the next job and the skill set that is valued at this next job, they haven’t shifted into that identity, and they don’t have a repeatable way to communicate their impact. What stuck with me from our conversation was the words “It’s a different ladder.” To me, this meant you have to reframe and put value into learning a new set of skills.
Audience questions that we didn’t get to live
On top of the live Q&A, there were some powerful questions from chat and the survey that we didn’t get to answer in real time, so here is our attempt after the fact. If you have others, leave them in the comments, and we’ll aim to get to them shortly.
“What AI tools do you recommend for creating systems?”
When people ask me this, usually they are expecting a shopping list or a magic wand, but they really need the system.
I think in three layers: capture, think, and output. For example, my own system is built around a single “brain” where everything lands (docs, notes, meeting summaries), an AI layer that helps me synthesize and see patterns, and a set of repeatable outputs like my Executive 90 updates and decision memos.
That’s what I call the Executive AI Stack for researching, decision support and communication every week, and most importantly capturing the learnings and delta and feeding it back into the system. Subha and I will walk through how to add agents to your product update flows on Dec 18th, so you can save time and focus on what matters.
If you’re specifically interested in competitive intel and market signals, I broke down how I use AI to build a living system for learning what your competitors are up to in AI-Powered Competitive Intelligence.
“How do I increase visibility without feeling like I’m bragging?”
and I think a similar flavor of the same
“I like promoting my team and our accomplishments, and struggle with self-promotion. Any advice?”
I’m not a natural self-promoter either, so I had to reframe visibility as “being useful at scale.”
Early in my career, I would walk into exec reviews and talk about what we shipped. Nobody cared about the engagement numbers or the A/B test. The shift for me was moving from “we launched X” to “here’s the business bet we made, what changed, and what we learned.” That’s what I wrote about in “From Feature Factory to Finance Fluency.” The career story I spoke through is taking a maps feature that was about to die, and turning it into a financial, strategic story that the executive team could say yes to.
A simple pattern I use now is: we → I → we.
We: “We’re working on this company-level goal.”
I: “Here’s how I’m steering the portfolio, the trade-offs I’m making, the risks I’m watching.”
We: “Here’s what changed for the business and what the team is doing next.”
That way, the team is still the hero, but your judgment is visible in the story and that is a core VP skill. If you want a concrete structure for these updates, Stop Losing in the First 90 Seconds walks through how I frame executive updates as Context → Meaning → Direction so it feels like service, not bragging.
For another lens on this, Andrew has a great section on visibility in “Why Hard Workers Don’t Get Promoted (and what to do instead)”. In it, he contrasts “press-release updates” with teaching the company why your work matters.
“Engineering is stretched thin, leadership keeps adding priorities, and I’m stuck in the middle. How do I push back without hurting my future?”
I’ve been in that sandwich: executives adding priorities, teams underwater, and you in the middle trying not to be “the bottleneck.”
The move that changed this for me was to stop debating at the feature level and start showing the portfolio. At Nextdoor, instead of saying “we can’t take that on,” I started walking in with a simple picture:
Here are the 2–3 big bets engineering is already carrying
Here’s how they map to our horizons (protect core, grow, future bets)
Here’s where your new idea would fit, and what would need to move or shrink to make room
Make the work, the trade-offs, risks, and upside visible in business language, not backlog eye-roll language.
“How do I make my work visible when the impact cannot be quantified well?”
Most of the important work I’ve led hasn’t had a neat dollar sign attached to it. Reliability, platform investments, enablement, quality, internal tooling, they’re famous for being invisible. The other question to ask yourself is why? Is it hard to quantify because it is not important to the business? Is it hard to quantify because you do not have the tools to translate “quality” to a revenue outcome?
Depending on the answer there is a different approach. One that I teach in Develop CPO Level Skills to translate product metrics into financial ones, another is to get yourself on a project that does matter to the business, and fast. If you are not on one of those projects bottom line is you are not getting promoted.
“I’m a one-person marketing show. How do I free up time from executing so I can think about the future?”
This is where I see a lot of solo leaders burn out. They’re running every campaign, every asset, every launch, and there is literally no oxygen left for strategy.
The first step is not more hustle, it’s clarity. Andrew calls this “Clarify and verify” in his promotion piece: if you and your CEO can’t articulate “marketing wins this quarter when…,” you will stay in reactive mode forever and the CEO will continue to wonder why everything is so slow. Once that’s clear, I like to do a brutally honest calendar and task audit. For two weeks, write down everything you do. Then run a three-bucket exercise:
Stop: things that don’t move your core metric
Systematize: things you can templatize or hand to AI
Stay: the high-leverage activities you keep and protect
On my side, “Simple: Product Lessons from Nextdoor & OpenTable” is one long argument for stripping away the non-essential so you can get the bike up the mountain. The same mindset applies to your calendar.
Then I block “CPO time” on the calendar: 1–2 hours a week where your only job is to think about the funnel, the next quarter’s bets, and the story you want leadership to hear. If that block gets bumped every week, that’s not a time problem; that’s a role-design problem worth surfacing.
Where to go from here
If you saw yourself in the survey buckets, here are a few places to go for clarity, immediate next steps, and results.
If your gap is understanding what great looks like at the CPO level:
That is the heart of Develop CPO Level Skills. We translate vague “be more strategic” feedback into a concrete picture of VP/CPO-level product leadership and build the operating system to get you there. The next cohort starts Jan 15th.
If your gap is understanding what great looks like at the growth leadership level:
Andrew’s Growth Operating System is a deep dive into how high-performing growth leaders think, prioritize, and build systems. It’s a strong compliment if your world revolves around acquisition, activation, and revenue.
If your gap is communicating in a way leadership can understand your impact
AI Powered Executive Communication is where we take your real work and turn it into a repeatable system for status updates, promotion narratives, and executive storytelling, so your impact is heard and remembered inside the company and on the street.
And if what you want most is a sounding board:
This is the kind of work I do one-on-one with Directors and VPs and Andrew does with Growth leaders who are “almost there” and want 2026 to be the year they stop guessing and start operating like the next-level leader now. If that’s you, reply or reach out, and we can talk about coaching.
Here is to a great 2026!
