I started working as a PM around 9 months ago at a very large multinational company. Think over 50k employees worldwide. We work with a lot of different products and industries but my product is a legacy HRM/HCM product that has been an afterthought and actively failing for years.

Of course I had no idea about this when I started. But we’ve lost 75-80% of our customers in the last decade, and in the last 7 years we have only gained a single new customers, which isn’t even technically new, they are coming back to our product.

I was hired to lead a modernization effort for this product. To summarize to those who are technical PMs, I was hired to bring the product into the 21st century by building new integration methods like APIs and leading an automation effort. Our existing integrations are almost all file-based and most of our product requires specialists to sit and manually do stuff in the user interface.

We have a huge amount of major challenges with my product, which is making my job very difficult as a PM:

• Tech stack is ancient, so hiring new developers is difficult. It’s mainly PowerBuilder, SQL Stored Procedures, and COBOL.
• Most people on the team have worked here for decades and are used to old ways of work, so leading a modernization effort is extremely difficult. For example, we are trying to build modern APIs with literally 0 API developers and without a software architect on the team.
• Since most of the team is close to retirement, they couldn’t care less about the future of the product. They know this is their last job and they’re riding it out until they retire.
• Product is built on decades of legacy and customer specific business logic almost everywhere. There are so many identical ways of doing pretty much the same thing which were built years or decades ago and we need to live with now.
• Doing almost anything takes at least an order of magnitude longer than what I’m used to at any other company I’ve worked at.
• Hiring just isn’t possible since we can’t sell the product. Leadership doesn’t want to hire people to modernize the product, but they still want the product modernized with the existing staff.
• Leadership couldn’t care less when I bring up these challenges. I get the usual “let’s do the best we can with the resources we have” or “just use AI”. They are somehow okay with things that should take a junior developer a week at most taking 6-7 months for 2 senior developers to ship.

To be completely honest, I’ve never in my 10 year career seen anything like this, nor have I received any kind of training in how to lead a modernization effort given these kinds of major challenges. I honestly feel like I’ve been set up to fail from the start.

I’m trying my best to get the hell out of here if I can, but it’s extremely difficult to find work in Sweden right now given how high unemployment is here currently, and the fact that Sweden is in a recession isn’t helping either. Finding any job is extremely competitive. So I might need to try and survive and manage this situation for a year or two before I can find something else. I just hope the stress and anxiety don’t kill me before I find something else.

To those who have been in such a situation where you need to work as a PM on a product that has been actively failing for years, do you have some tips for how to survive and manage the situation?

Hi all!

Mid career PM here with 12 years experience. Starting to feel like i’m hitting a ceiling at current job and don’t love management so starting to look outside. Doing few applications and optimizing my LinkedIn for more recruiter outreaches.

Last time I did this was in 2021-2022 (how i landed my current job) where I got about same amount of recruiter outreaches, but i got way further in the funnel. These days, the recruiter outreaches either get ghosted over scheduling back and forth, or after I talk to the recruiter I don’t even make it to the hiring manager screen.

Is this what they have been talking about with people cutting their resume to make themselves seem younger and less experienced to move forward in processes??

I’m a PM for Machine Learning and Data Analytics in a technical software app that has been around for a while so we are well established. I am one of the few at my company trying to stay ahead of the latest developments and news in AI which makes it harder to convince others that there are risks and issues

A couple weeks ago ArtCraft launched vibe coded “replicas” of Adobe Products and MS Office Apps. I have also noticed the rise in people vibe coding on LinkedIn which replicates some of our workflows but they are no where near the level of polish and depth of an established product. However, i feel it’s just a matter of time until a capable and credible clone comes out.

I want to ask how are other software PMs dealing with the fact that their area/software could be replicated in the next several months. Are there ways to pivot your product or change the moat that makes it more difficult?

The last product manager was really hands on and there are really high expectations here. How do I place myself for success? It has been 4 days after joining and the expectation is that I will start leading the roadmap and the execution but my confidence shatters everyday

So, I am currently working in a startup but my degree is not related. I do not have a business or computer science background. I just kind of fell into this, I didn’t even know it existed if I’m being honest 😅.

That being said, I am working on a social media app and I would like to become more technical so that I can understand better and work more profoundly with the engineers. I have some basic understanding of what APIs are, I have some basic knowledge of what GitHub is, being aware of how adding code and changing code works inside GitHub, I’m also learning basic SQL commands on the side (trying to master window functions and CTEs) but I honestly don’t know what else should I learn. I would appreciate any recommendations.

Hi! I’m a Sr. PM in the SF Bay Area with about 8 years of experience in Product, mostly at smaller companies that ended up getting acquired.

I’m currently looking for a new role, and I’m realizing that interviewing is my biggest weakness. I get really nervous and have a hard time translating what I do into the language/frameworks people expect from PMs - strategy, product sense, metrics, “craft,” etc.

I have impostor syndrome because I haven’t worked in big tech, and I know PM can look really different from company to company. At the end of the day, I care about doing good work, being dependable, and getting things done. My manager and team consistently tell me I do a great job, but for whatever reason, I have a hard time internalizing that.

And if I’m being real, work is not my identity. My job is just a means to an end that lets me have a life I really care about outside of it.

A lot of my free time goes toward volunteering with animal shelters, spending time with my own animals, traveling, and just enjoying my life. I want to do “well” in my career and be financially stable, but I care much more about my personal life than being obsessed with Product. As a result, I don’t think I “speak” in the way that SF Bay Area PMs speak.

Looking at roles right now, I sometimes feel like every Senior PM job is looking for someone who lives and breathes the “craft,” and that’s just not me. Interviewing in corporate feels like learning a secret language. There’s such a specific way you’re supposed to talk about your work, and it feels so far removed from how people actually talk and work day to day. It just feels really far from human - it makes me sad. I’m getting a lot of interviews, but I’m not landing them.

I’d really love to connect with anyone who might feel the same way! People who like to do a good job at work, but don’t make work their whole identity. And if anyone would be open to mentoring me, especially around interviewing and helping me communicate my experience better, I’d be really grateful.

If any of this resonates, I’d love to connect!

EDIT Thanks to everyone who reached out! I feel less alone knowing I’m not the only one who feels this way. I’ll send DMs to those who are interested in connecting soon! 🙂

I've been thinking about this and kinda frustrated it's not clearly stated.. but product management is naturally a role built on coordination, not just shipping. A huge chunk of the job is unblocking people, chasing alignment, catching things that fall between teams and roles. None of this shows up at performance review time, and should it?

Curious how other PMs see this:

• When you’re rated or reviewed, does that kind of work actually get credited, or does it just get absorbed as “part of the job”?
• Has anyone had a manager who actually noticed or valued this, rather than just judging you on output/roadmap delivery?
• If it doesn’t get measured, do you think that’s a problem, or just the nature of the role?

Not sure that's the right flair, there wasn't one for existential dread.

I recently joined a company that's all in on AI. I didn't know this when interviewing, the impression I got was that they were working with it but it was still very much the human doing the work. I'm 3 months in now and that's absolutely not the case. Every single person in the company is expected to leverage Claude heavily and our usage is monitored. During onboarding I've been trying to read docs and guides, manually writing PRDs and requirements, documenting workflows and similar activities all so I can just learn. But if I ask a question I'm told to ask Claude. If I'm not sure how something works I have to ask Claude for a demo. Need to know how a certain metric was tracking? Claude. I got pulled up by my manager last week because I was too slow getting a document out and she just went and got Claude to generate it. I can't deal with it.

It's no different in engineering then. The engineers aren't even allowed to write code other than to make small adjustments to Claude output. We have senior people here with 15-20 years of experience and they're just babysitting Claude.

But you know what's the worst part of it all? It's working, and that terrifies me. In my last company we were using a little bit of LLM support but not much and management there didn't allow it access to any of our systems and documentation and as a result I didn't think much of it. It was a helpful aid but I didn't get the hype about it taking over jobs. Now I am genuinely fearful. This week I was doing some discovery work and in less than a day I had extracted user feedback and metrics from our gathering tools, cross referenced it with assumptions driving a new idea, generated some forecasted outcomes and validated the commercials, fully specified an MVP and had the PRD published in Confluence. And all I did was babysit Claude through the whole thing.

I see comments here regularly saying that the PM that just moves tickets is in trouble or the person who is just a project manager and go-between but I think it's far worse. I think we're all in trouble and sooner than we think. I'm a senior PM, I'm very involved and do everything from discovery through to post release monitoring so definitely not just a ticket mover.

There's a project ongoing now in our company where we are putting together a full schedule of customer surveys, feedback sessions, screen recording etc. and it's all going to go into Claude to assess them and produce a prioritised list of things to do and roadmap it. If it succeeds then I expect the PM function here will be made redundant.

How is everyone dealing with this in other LLM-forward companies? Are you seeing the same?

If you were able to choose a domain to specialise in, what would it be and why?

There are a lot of people here working on projects of some sort - side projects, startups, podcasts, blogs, etc. If you've got something you'd like to show off or get feedback, this is the place to do it. Standards still need to remain high, so there are a few guidelines:

• Don't just drop a link in here. Give some context
• This should be some sort of creative product that would be of interest to a community that is focused on product management
• There should be some sort of free version of whatever it is for people to check out
• This is a tricky one, but I don't want it to be filled with a bunch of spam. If you have a blog or podcast, and also happen to do some coaching for a fee, you're probably okay. If all you want to do is drop a link to your coaching services, that's not alright

I wanted a realistic problem to practise with, ideally something relevant to my current role in healthcare technology.

I used AI to help frame a hypothetical product outcome for an EHR:

Reduce the time physicians spend identifying relevant patient history in the EHR, while maintaining clinical accuracy.

Based on :

• Why Doctors Hate Their Computers, The New Yorker
  • https://www.newyorker.com/magazine/2018/11/12/why-doctors-hate-their-computers
• The Provider Perspective
  • https://pmc.ncbi.nlm.nih.gov/articles/PMC6452954/

The goal is to use this outcome as an input to my prototyping exercises, exploring possible solutions and testing assumptions. Does this seem like a reasonable approach? Is there anything I should consider before moving into prototyping?

Context: a small student team, 2 weeks left on a competition deadline, and a working AI speaking-practice app for one niche: people who understand English but freeze when they speak (starting with Algerian students preparing for visa or job interviews).

The debate in our team is whether to add more languages now (bigger addressable market) or stay with one language and one audience until we have evidence of impact.

Here is how I see it, and I would like you to challenge it:

- Narrow: clearer problem, faster to test quality, easier to talk to 10 real users and measure a before/after change in confidence.

- Broad: bigger market story, but each language multiplies QA, content and voice work, and we have no demand data for any of them yet.

Questions:

1. What evidence would you require before expanding to a second segment?

2. How do you present a bigger vision to evaluators without building it?

3. Any examples where going broad too early hurt a product like this?

No link here to respect the rules, but I can share the product if someone is curious.

If you're adding embedded payroll to an existing platform, making it optional seems like the safer choice but then you're maintaining two different experiences for customers who use payroll and those who don't

I want to see whether anyone has dealt with this when expanding a SaaS product into a new service

1. Everyone in the company wants to be a product manager except the product manager.
2. The product manager probably would want to be the product manager without everyone wanting to be the product manager.
3. Being a yes person is the easiest path to keep a career even as you watch your product turn into a lump of mouldy cheese.
4. New tech companies wants a PM with X years experience when the industry / sector is only 0.5 of X years old.
5. Old tech companies want a PM with domain experience + sub domain experience literally down to have you worked in an office that is southward facing if not we don't want you your not experienced enough.

Moan over prayers for product.

EDIT: I can't believe this got so many responses thanks for being a highlight in my 10 month "career break"

A PM in my company recently left, and I got moved to take over their portfolio. Part of the projects handed over included this major feature that they’re already well into the development cycle.

Here’s the problem: it is a customer facing feature which solves a lot of internal problems, but there’s virtually zero actual benefit to the customer. In fact, it even makes life harder for some of them.

I’m now due to present to the whole company about this supposedly new fancy feature the team spent months working on as the new PM. I genuinely have no idea how to defend this feature.

This sub can get pretty negative and pessimistic. I know that people mostly post their negative experiences online, so i'm hoping to see some positive experiences.

Maybe share your #1 tip for job enjoyment as well.

I worked as a BA for 10+ years and still feel it's not my cup of tea. Jumping from meeting to meeting just to discuss the same requirements again and again, try convince different stakeholders and then explain it to Dev and QA. Firefighting almost everyday. Maybe I worked with the wrong teams or I really didn't learn / grow up in the role. Though I work as a fractional PM for very early stage Saas startups, i want to understand from veterans what your day looks like? Is all the theory we learn about PM is actually applied while doing the job? How do you manage work between meetings? How you manage playbooks and other documentation and maintain it over time, If I have to prepare for full time roles for higher package or get freelance work with higher pay, what is your suggestion? Kindly guide me to become a PM

I have found conversations here to be useful because, unlike LinkedIn, the anonymity of Reddit allows a community to discuss topics without the back-drop of self-promotion. In recent weeks I’ve seen more and more screenshots of this sub in my linked in feed.

I don’t think there’s anything we can do about it but it does somewhat sour the feeling of this thread. Maybe that’s just Reddit in general now. Anyone else feel the same, or feel that it isn’t a big deal?

Within our org, there’s very little product leadership. It’s created a culture of product management being essentially project management and not really ever giving proper requirements. It’s closer to ‘let’s build this’, then we all have to figure it out.

We don’t want to throw the person under the bus but we want to call out to management that product as a function is very weak.

How would you go about it?

Anyone here work at a B2B data business that has introduced AI summarisation and/or MCP?

How would you say it has changed user behaviour? Are you noticing a change in the way users navigate to your data on website/dashboards?

Hey,

I’ve started in a small shop with two devs. My tasks include the product and project management. Unfortunately our devs aren’t really capable of implementing stuff to spec, so I thought okay let’s give them leeway but then they don’t think about UX or implications. I’m also told that they’re architecturally weak. Now my solution was to jump in as I’ve worked as a dev for multiple years, but that takes away from time engaging with customers and moving the business further.

How should i handle this situation since ultimately a buggy not functioning mess delivered to late falls on me. I’ve proposed to hire a engineering manager or at least very senior dev but that looks like very slim chances.

Thanks in advance, this situation puts a lot of stress and pressure on me

I am subscriber of both Lenny's newsletter and Stratechery (by Ben Thompson). I have been thinking about both products and their businesses.

The value of lenny's newsletter (including the podcast) is primarily helping mid and mid+ product managers to land a promotion or a better job. The product is the opinions of lenny's guests. If you think about it, you listen to his pods because of his guests. It's a lot of best practices and a lot of takeaways from his guests.

Stratechery is a different product. I subscribe to read and listen to Ben Thompson's opinion and reasoning. That's what I pay for. It's to think better and honestly, it's also intellectual entertainment.

Lenny's business is, by revenue mix, an ads business from the podcast under sponsorship. Lenny has one of the best audience for tech ads - tech managers and executives. They have the corporate budget to spend for tech solutions. You can see the product is more and more skewed for this audience.

Stratechery is 100% subscription. The audience has a certain overlap with Stratechery but not by much I bet. Stratechery is very useful also for tech investment. There are a lot of tech investors. Ben would have helped these folks made a lot of money if they followed his take on Facebook. That's for sure.

I found lenny's podcast is getting more and more skewed towards AI for product managers. It's no longer for me anymore. It used to be much richer in terms of content, like product marketing (April Dunford), Strategy, JTBD, etc. Now it's just like SF AI echo chamber.

What's your take at this moment for Lenny's newsletter and podcast?

I've seen people posting about Winter Arc challenges for other professions. And, I wonder how about PMs having Winter Arc Challenges. It's better late than never. If someone has something, I would like to try it out.

Let's learn, complete challenges, and build together :)