A panel of early-career product managers got refreshingly honest about breaking into the role, debunking the myths, and surviving the first 90 days.
There’s a version of product management that lives in LinkedIn posts and job descriptions — the PM as visionary, strategist, and “CEO of the product.” Then there’s the version that actually exists: messy, rewarding, full of questions you don’t know how to ask yet, and occasionally including a LinkedIn photo of your dog.
At a recent Product Anon event, a panel of practitioners at the beginning of their product careers sat down to talk through what it really looks like to get into PM — and what nobody tells you once you’re there. The conversation ranged from career pivots and 65-job-application marathons to the moment you realise you are absolutely not, in fact, the CEO of anything.
Here’s what they had to say.
The Winding Road In
None of the three panellists arrived at product management via a straight line. That, it turns out, is very much the norm.
Hugh Osbourne, who has been a product manager for around two years at a startup — where he also wears the hat of UI/UX designer — came from four years in design. His entry was less a deliberate pivot than an act of self-preservation. “I was sick of being told what to do,” he said, “which is a terrible place to be in a small startup working directly with a founder.” His solution was to push until the founder gave him the product manager title while he kept the design responsibilities too. The upside: “I got to tell myself what to do.”
Jane (Ryan) Card, an Associate Product Manager who spent a year at Delphi before moving on, came from a people and culture background — change management, learning and development, organisational transformation. What drove her towards product was a creeping sense of distance from the end user. “I felt really far removed from the customer,” she said. “I can say that my customers were employees, but I felt like something was missing.” Seeing colleagues do CX and innovation work was the tipping point. “That’s the shit that I want to be doing. That type of work is cool and fun and interesting.”
Heike Radlanski, now a product manager at Expert360, a talent-matching platform, came through digital marketing. She had stumbled into a product owner role within her marketing position and enjoyed it — but it was a career break that crystalised the decision. “After that, I was like, I need a job. I don’t want to go back to marketing. I think I want to go into product management.” What appealed was the cross-functional nature of the work, the focus on uncovering real user needs, and the shift from promoting a solution to actually being part of building one. “In digital marketing, you’re promoting a solution — you’re not necessarily part of the solution,” she said. “I wanted to be part of finding problems and defining solutions.”
Getting the First Role: More Grunt Than Glory
If there’s a theme running through the “how did you actually land it?” conversation, it’s this: persistence, networking, and a willingness to play a long game.
Jane took a strategic approach from the start. She joined a government-funded Digital Jobs Program that offered career coaching, tuition, and an internship. But the real breakthrough came from showing up — genuinely and consistently. She built her network, had coffee chats, and eventually posted on LinkedIn with a photo of her and her dog. “Everyone loves a good dog,” she said, “but through that I was introduced to 20 or 30 different people.” One of those connections was a VP of Product who, a month later, reached out about an open role. It had been listed as Senior Product Manager — too senior — but was reclassified as an Associate PM role to make it work. “About 90% of the jobs I’ve had have been in the hidden job market,” Jane said. “So keep being curious.”
Carrie’s path was more grinding. She wrote approximately 65 applications. She did a product management course. She had coffee chats. “I don’t necessarily think the course really helped, but it was interesting,” she said. “I didn’t get the impression that whoever interviewed me cared about the fact that I got this course.” Towards the end, hope was fading — she was about to walk into a digital marketing interview when a contract PM role came through. “Don’t give up. Keep going. You’ll eventually get to land the role.”
Both emphasised the value of translating previous experience deliberately. Carrie highlighted product communications as something her marketing background gave her real fluency in — something she noted that many PMs deprioritise. “Product comms is, quite surprisingly, not something that’s well done in a lot of products. It’s like the last thing product managers really get to.” Jane pointed to the transferable power of collaboration, stakeholder management, and navigating organisational complexity. Her advice: ask people in product roles what they actually look for when hiring. “It’s a pretty good chance you’ve probably got some of those skills already.”
The Biggest Misconceptions
This was where the panel got most candid.
Hugh arrived thinking product management meant making decisions — that he’d finally get to be the one calling the shots, in contrast to his years as a designer being handed requirements. The reality was a recalibration. “Thinking that I was the person slamming my fist and saying ‘this is what we’re going to do’ was wildly incorrect,” he said. “It is a discussion in which you are one person.” Product, he found, is far more democratic than autocratic — and the further he got from a founder-led context, the more that became apparent.
Carrie had absorbed the familiar line that “the PM is the CEO of the product.” She now considers that one of the more damaging myths in the discipline. “There’s some stuff that’s really fun, and there’s also some really shit stuff too,” she said. The grunt work is real. Time is always short. “You’ve never going to have enough time to put stuff in the backlog” — something her people manager delivered not as bad news, but as a matter-of-fact welcome to the job.
Jane had done the reading, taken the courses, loaded up on frameworks. She expected that preparation to translate into clear, applicable answers. It didn’t, quite. “There are frameworks out there — some of them are great — but you won’t likely be in a situation where you can apply something that’s written in a book to a situation and have that work.” Product management can feel circular, iterative, and messy in ways that no framework fully anticipates. Learning something new often means going back to the drawing board. “I just didn’t expect that as much to be the case.”
Advice for the First 90 Days
The closing question — what would you do differently in your first 90 days? — produced some of the sharpest advice of the night.
Carrie would start asking hard questions earlier. “Not easy questions, but maybe some challenging questions — or you have to ask the same question over and over because you don’t get the answer and you might need to reframe it.” Sitting with that discomfort is part of the job, and the sooner you practice it, the better. She’d also lean harder on the cross-functional team. “You don’t need to figure it all out on your own. If you’re working with engineers or designers who have worked with product managers before — ask them what worked and what didn’t.”
Jane would spend the onboarding period talking to customers as aggressively as possible. “Spend that time getting to know your customers.” She’d also invest deliberately in meeting people across the organisation — not just to be sociable, but to understand what’s keeping people up at night and where the real points of friction are. “Getting genuinely to know people across the business, but also what are some of the things that are really important to them and their challenges.”
Hugh offered the contrarian take: get outside the organisation entirely. The risk of spending your onboarding learning “how to do product the X-company way” is that you absorb one approach as if it were the only approach. “There are so many different ways to do product,” he said. “Experience how other people approach it, and see very different ways of solving those problems.” Events like Product Camp, he suggested (with a self-aware shameless plug), are one way to do exactly that.
The Thread Running Through All of It
What ties these three stories together isn’t a common background or a tidy career arc — it’s a pattern of deliberate curiosity. Each of them noticed something that wasn’t working, started asking questions, found people willing to talk, and kept going longer than felt comfortable.
Product management, it turns out, selects for exactly that. Not the person with the best instinct for decisions, or the one who’s read the most books, or the one who can apply the most frameworks. The person who asks the awkward question, reframes it when the first answer doesn’t land, and builds a picture from the ground up.
That, at least, is something you can start practising before you even have the job title.
