Top 5 Challenges Product Managers Faced in 2024

2024 was a crazy year for product management; it got canceled more times than I can count…

From the continuation of Airbnb “getting rid” of Product Managers to my LinkedIn feed being filled with posts about how ‘product is dead’ and ‘all hail AI.’

It’s been a wild year!

But behind all the clickbait and polarising claims that always get mainstream attention (as I like to say, the only thing we like more than being told we’re right is telling someone else they’re wrong! 😆)

What were the real challenges that product managers faced in 2024?

Between the 150,000 people who read this newsletter and the most common challenges across my clients, here are the top 5 challenges that product people like yourself faced in 2024:

Product Strategy
Roadmaps vs Plans
Breaking down outcomes
Continuous product discovery
Stakeholders pushing solutions

Disclaimer: individual experiences may differ. Of course my data is biased to my audience and clients but I’m sure these will still resonate with you 👇.

1. Product Strategy

This made a lot of sense when you consider what Brian Chesky was trying to do at Airbnb with the product role.

What Airbnb actually did wasn’t to get rid of Product Managers altogether.

Instead, they made the role more end-to-end giving it Go-to-Market and commercial responsibilities.

This is a trend I’ve been seeing in product more recently.

There’s been a shift towards making the role more commercial (again).

I say again because that’s where product management started.

It started in marketing and was a very commercial role - remember the 4 P’s: Product, Price, Place, and Promotion?

The original product managers were responsible for their products end-to-end.

However, over the years, particularly with the rise of Silicon Valley product-tech companies, the pendulum swung the other way, favoring customer centricity and small independent teams.

The product role slowly morphed into one that looked heavily at the customer and in some cases entirely became devoid of any commercial responsibility.

This made a lot of sense at the time, as many companies (and their product managers) were too inward-focused, putting profits above their customers, and many startups exploited this gap.

The challenge, however, is that product management is about delighting our customers whilst making it work for the business.

Products must be sustainable.

Otherwise, we would scrape all fees and pay our customers instead of them paying us, right?

Now, whilst I’ve been observing this theme in the background, I believe it accelerated in 2024 because of the macro-economical conditions.

We went from a funding-rich, low interest rate, and all-round luxurious environment to a very constrained one.

We’ve all seen the layoffs and high inflation.

I felt this personally in the first half of the year, with zero new clients until April (that had me sweating!).

But as things picked up around mid-year, I’ve had more requests for workshops and coaching around product strategy than before!

Pretty much all my clients rebooted their strategy in some shape or form this year.

I also saw increased pressure on product leaders and product managers to own their strategy and commercial outcomes.

This also created an interesting trend where I saw product leaders and product managers from big product-tech companies struggle in some cases.

Coming from environments where they weren’t required to be commercial, they suddenly found themselves being asked to cut costs, optimize pricing, and own commercial outcomes.

I expect this to continue.

Skills such as business acumen, product pricing, and strategy, among others, will become more sought after.

Just as we’ve seen a rise in product discovery skills, I believe as these become more mainstream, strategy, and business acumen will become the new thing that will separate product managers apart.

If you want a place to start on product strategy, here are some of my top posts from this year:

I also recommend to start doing ‘product teardowns‘ like the one I did on MILKRUN when they went into admission here in Australia last year.

It’s a great way to get more reps and build your skills in this space!

2. Roadmaps vs Plans

This one surprised me, but Product Roadmaps was the second top theme for me this year.

Perhaps again, being influenced by the macro-economical shift.

Of course, if you reboot your strategy, then a new roadmap will follow!

But something I found myself spending a lot of time on was clarifying: what the hell is a roadmap!?

More specifically, the difference between a plan and a roadmap.

A framing I’ve been using for a while now to differentiatebetween roadmaps and plans is this:

Roadmaps:

Look at a long-time horizon.
They are flexible and iterative.
Describe the WHAT and the WHY (not the HOW or WHEN).
Customer-centric and outcome-focused.
A communication tool.

Plans, on the other hand, are:

More short-term. They look at the near horizon.
Are more static and sequential, as they need to deal with things like sequencing, dependencies, etc.
Describe the HOW and WHEN
Internally focused, a tool for internal use, not the customer.
Therefore, it is more output-focused.
A planning tool.

I wont recap the full webinar, you can watch it here.

*Screenshot from* *Product Roadmaps webinar: Roadmaps vs Plans*

FYI, this was also my top webinar, with over 400 registrations and 300+ people attending live.

The recording has also racked up over 1.4k views and counting!

Strategy vs Roadmaps

Of course, as part of all the work I did between strategy and roadmaps. I also found myself needing to clarity the difference between them too!

3. Breaking down outcomes

Let me share a real story to illustrate this one.

I’ve been coaching a founder for the last couple of months who has been trying hard to be the leader we all know and love—someone who empowers their teams with problems, not solutions.

But it wasn’t working.

The team (from his perspective) weren’t focusing on the most important problems.

They were going down rabbit holes, spinning wheels, and getting stuck in endless discovery.

Giving them problems hadn’t moved the dial at all.

My first point of call was to look at how he was framing the problems for the teams.

As most of you would be familiar with, he used the ‘team objectives’ model and framed the problems as OKRs.

An example of one of the objectives was this:

Objective: “Maximize user success when onboarding.”

Now, there’s a lot to unpack in that statement…

For example, what does he mean by ‘maximize’ and ‘success’?

However, the core issue was that this objective was too broad.

There are probably over a hundred things that the team could do to improve onboarding.

From minor flow changes to new features and cosmetic things like improving accessibility.

So, I wasn’t surprised that the team felt lost and equally frustrated with the process.

I asked him - based on what he knows (data, experience, context, etc) - what he believes is the most significant barrier to users completing onboarding?

He immediately replied, “import! …we have a high failure rate during onboarding when users go to import their data.”

Great!

What about if the team focused on reducing the number of failed imports?

This led him to revise the objective to:

Objective: “Reduce the number of imports that fail during onboarding.”

With specific key results on what kinds of reduction/success rate we would like to see.

This is a great example of why you can’t suddenly start “using” OKRs and expect amazing results.

There’s a real skill in setting objectives at the right level and creating focus for the team.

Shoutout to Vistaly who are trying to solve this problem. They have a neat product that helps you break down your outcomes, set goals at the right level and even map opportunities your backlog to it and more!
(Full disclosure I am an advisor but I joined because I believe in the product. This is such an underserved space I was even thinking of creating a product here too)

*Matt, co-founder of* *Vistaly* *talking through using Dropbox as an example*

But this is also a common mistake I see Product Managers make when they break work down and prioritize.

Here’s a common pattern I see:

Product Manager is given a big problem or outcome to achieve (say a revenue target).
Their first action is to immediately launch into a long discovery process with that outcome at the top of their Opportunity Solution Tree.
Given the scale of the problem space the solutions they come up with are large initiatives that will take several months to deliver.
They break the initiative down into ‘epics’ and user stories for delivery but nothing will be shipped to users until the full feature is done and our measures are all lagging business impact ones.

An alternative approach to this is to break down the outcome first.

Aim for “think big, work small” not “think big, work big”.

Rather than trying to dream up these big features that might drive revenue or [insert big goal] we should break the goal down first.

For example, revenue can be broken down to conversion or onboarding. Onboarding can be broken down into individual steps (like import for that founder).

What you’re doing when you do this is modeling your hypotheses.

e.g. We believe (based on data) that if we can decrease the number of errors during import, we will decrease the drop off rate at that step in onboarding and subsequently increase conversion.

*KPI trees are a great tool for breaking down outcomes*

When I think about it, it’s probably no surprise that this is number 3 as it strongly aligns to being more strategic.

We’re typically pretty good at breaking down the work, but breaking down the problem space is not something I see done enough!

You can read part one and part two of my newsletter posts on this topic. Part one was the second most read newsletter post of the year.

I was also invited to do a talk on this topic, which you can watch here.

And last helpful link, the good folk at Vistaly put together this comprehensive step-by-step guide on breaking down outcomes.

4. Continuous Discovery

Yes, that’s right, product managers are still trying to master continuous discovery.

However, many of my clients' challenges with this were aligned to number 3 and not breaking down their outcomes.

It’s hard to do continuous discovery and delivery when working with large and broad outcomes/problem spaces.

The bigger the problem space, the bigger the solutions and the longer your discovery cycles will be.

Or if you force your discovery to be shorter, the more uncomfortable you will be with proceeding, which is expected as there are still a lot of unknowns and the risk is high.

However, when we break down the outcome to be very small - say, a change in user behavior that we believe will lead to moving some product metric - the space for exploring is also small.

There’s also less risk, it encourages experimentation and facilitates continuous discovery and delivery better.

*It’s easier to do continuous discovery when you work more like the right than the left.*

In addition to that a decent chunk of my coaching this year was focused around continuous discovery and delivery.

The webinar I ran on this topic was also the 3rd most popular of 2024.

I also did 3 talks on the topic, so it seems to be a common challenge all around!

You watch the webinar and read my post on continuous discovery and delivery, but here are some tl;dr actionable tips for effective continuous discovery:

Break down the outcome/problem space first (see above)
Time box discovery (if you’re doing sprints, align discovery to them. E.g when you do sprint planning also plan your discovery activities for the sprint)
Leverage techniques like assumptions mapping to prioritize your assumptions and work from the riskiest assumptions down (do this along with time boxing by testing as many assumptions as possible within the time box.)
Re-frame Product Discovery to be about confidence, not coming up with final solution designs and specs. The idea is to have confidence in a direction and learn more as you go!

5. Stakeholders Pushing Solutions

You’d think that after decades of product content and numerous startup successes, we would have left feature factories behind by now.

But no.

Dealing with stakeholders bringing solutions, not problems was still a key challenge for my audience and clients in 2024.

One technique I used more times than ever this year to navigate this is what I call ‘working forwards not backwards’.

I shared this on LinkedIn and twitter (still can’t call it ‘X’) and it quickly became one of my top performing posts of the year.

Sure enough, writing a longer version newsletter post on it also had a similar reaction being picked up by several other newsletters like Mind the Product and Age of Product.

So, it is safe to say that this is still a widespread challenge many product people continue to face in 2024.

Here’s the technique:

When a stakeholder comes to you with a solution rather than a problem, don't try to work backwards, work forward.
Let me explain.
No doubt you’ve been in this situation before.
A stakeholder has read one of the latest Forbes article and they’re pumped to jump on the latest trend.
And you’re now being asked to implement it.
But it’s a solution looking for a problem.
The typical advice is to work backward and ask them, “What problem are you trying to solve?”
But working back to the problem can be a stretch for some stakeholders - especially those who aren’t used to working this way!
I can bet you’ve run into some resistance trying to do this before, right?
And it’s understandable.
Asking this question can be seen as challenging their idea.
It can also feel dismissive.
This is why I've found a more effective approach has been to go forward rather than backward.
Rather than trying to work backward to a problem, go with the idea.
Cast forward.
So rather than asking “what problem does this solve?”
Ask: "If we did deliver this solution, what does it mean? What does it mean for us, the org, our customers?”
What we're doing rather than trying to get them to articulate the problem - which sometimes can be hard - is facilitating their thinking around what they expect to be true if their idea was implemented.
We can then reverse engineer that end state back to what they think the original problem might be.
This is a great way to uncover the problem in a non-confronting way.
Here's a real example I did with a client recently:

*We started with the black post-it note and then work forwards to '“what we believe would be true for our customers (and then business) when we delivered this?”*

There's this new facial technology that can estimate your vitals, like blood pressure, etc - pretty cool stuff!
But in classic fashion it sounded a lot like a solution looking for a problem.
When we worked forwards - i.e. “what do we believe will be true/change for our customers when we deliver this?” - we uncovered several customers pain-points.
Namely that they currently need a nurse to visit them to take these vitals.
This is not only invasive but also takes time out of their day.
More interesting was when we looked at what does this mean for our business. A key problem is that rescheduling is common. Worse they have data that shows if it takes longer than 30 days their chances of converting drops by 50%!
The best part about this example is I don’t believe we would have unearthed that without following this process.
No way would they have said that if I asked them what problem it solves.
In fact, I bet they would have said the same first two things they did in this process which was “quicker” and “better customer experience”.

I shared 5 more techniques to navigate this challenge in the last webinar for 2024.

2024 in Numbers 🚀

And that’s a wrap for 2024.

This is my first one of these posts - yes I’ve dodged doing this for 5 years now!

Why?

Because I didn’t want to do one of those standard “year in review” posts.

They’re not actionable.

I started writing/sharing content because I genuinely want to help. So, I look at every piece of content through the lens of whether it’s helpful, or not.

And a recap didn’t make the cut.

But perhaps looking back at the key challenges you all faced this year and recapping the most helpful content might be.

At least, that was my thought process anyway - let me know if it doesn’t pass the test!

And if you are interested, here’s my 2024 in numbers:

Revenue up by 12.5%
Over 150k people read this newsletter 🤯
I trained 380 product managers/leaders
4x Senior PMs I coached landed a Product Leadership role (plus helped 2x more PMs landed a new role) 🥳
Coached twice as many founders
10x free monthly webinars (recordings here)
1,300 people joined those monthly webinars
5,000+ people watched the webinar recordings
160 people joined more than one webinar
And 1 person joined 5 (you rock! 🙏)
YouTube also doubled to over 2k subscribers and 55,057 views 👀
61x virtual and in-person coffees with amazing product people around the world ☕️🌍
And I tested a private coaching community (launching soon!)
- p.s. if you’re interested in getting support in 2025 to help achieve your goals - check out the landing page for more details and if you’re interested, register for a BIG launch discount!