How to Upskill as a Product Manager and Make Progress [Jason Knight]

How to Upskill as a Product Manager and Make Progress [Jason Knight] cover

Are you feeling stuck and not making any impact at your organization?

If so, you should definitely watch the talk that Jason Knight, a product consultant and advisor, gave at this year’s Product Drive hosted by Userpilot.

In his talk, Jason talked about how product managers can upskill to meet the challenges in their daily work and how to make sure that their organizations value their work.

Let’s dive in!

How to upskill as a product manager.


  • Product managers often don’t get the due recognition for their work and their role is often marginalized by frustrated leadership or other teams.
  • This happens because people don’t always understand what their role involves or see only a fraction of their work. Measuring the value of product management is difficult too.
  • The truth though is that product managers are to blame too because they are often unable to demonstrate their progress.
  • What’s worse, they actually often can’t make any meaningful progress because they can’t navigate the challenges of the role and the organizational landscape.
  • One way to change it is by prioritizing high-leverage work while delegating the rest to others.
  • Instead of staying in the zone of most competence, divide your attention across all aspects of the product, like the business, tech, and UX.
  • Without vision and looking ‘ahead’ it’s easy to get bogged down in ‘urgent’ low-impact tasks.
  • Allocating time for a specific research stage is often a no-go for leadership, so make the habit of interviewing customers continuously.
  • You can’t accommodate all customer requests, so build a robust decision tree to filter out irrelevant requests and learn to say ‘no’ instead of maybe.
  • To keep the development work going, work in small increments, ship them often, and resist the temptation to ‘just add this in’.
  • Tech debt will eventually catch up with you if you don’t take time to fix things as you go. Sell the business value of technical fixes to stakeholders and ship them in small batches, just like value.
  • To avoid wrong assumptions about your job, keep all the stakeholders engaged and informed.
  • Learn to speak in a way that resonates with them, and don’t just tell them but also show progress.
  • Want to learn how Userpilot helps product managers boost their impact and build successful products? Book the demo!

The dreaded eye roll

What’s the dreaded eye-roll?

That’s how Jason describes the reaction that you get when you tell someone they’re not getting what they want, like the special feature request or bug fix.

So even if you haven’t heard of it before but have been in product management for a while, you must be well familiar with it.

It gets even worse.

As the stakeholders feel like you’re not making progress, they often step in and start making decisions for you. You lose control.

Why people think product managers aren’t making progress

There could be a number of reasons why people question the effectiveness of product managers.

The ambiguity of product management

There’s a lot of ambiguity as to the role of product managers.

That’s because there are no 2 product organizations that would be exactly the same.

For example, B2B companies work differently from B2C businesses, and feature factories are very different from innovation factories. The way things are done also differs from market to market and vertical to vertical.

The consequence is that people’s expectations as to what product managers actually do vary dramatically.

The ambiguity of product management
The ambiguity of product management.

The iceberg effect

The iceberg effect is another reason why people don’t appreciate the work of product managers.

Basically, they see only a fraction of the work that you do for your organization and assume that’s all you do.

Without understanding all the things that happen behind the curtains, they can’t see the value that you bring to the business.

The iceberg effect.

The value of product management

‘Measure the value of work defined but not prioritized. Subtract from the work that is prioritized. The difference is the value of the product.’

‘1. Average ships per person in the team. 2. Conversion credit or attribution value of the team due to the ships.’

These were some of the responses that Jason got when he asked how to measure the value of a product team. Not exactly consistent or convincing.

Measuring the value of product management is not exactly straightforward, which is yet another reason why other teams or stakeholders may not give you credit for your contributions.

The value of product management
The value of product management.

Lack of alignment on success

Try this experiment.

Talk to people at different levels of your organization, starting from the top and going to the bottom, and ask them what their goals are. Do the same sideways, across departments.

You will be surprised to see how the definition of success differs across the organization. And you can’t demonstrate your success if everybody understands it differently and keeps pulling in their own directions.

Is giving up any easier?

When faced with a lack of understanding and the pressure to deliver features, some PMs give up. Instead of driving the product strategy, they simply fulfill requests.

Does it make things easier?

If you start saying ‘yes’ to every request, you may get a short respite but in the long run, things will get worse. That’s because trying to satisfy every stakeholder’s whim is unsustainable.

Giving up on product management
Giving up on product management.

Why do product managers need to upskill?

Let’s look at a few habits and practices that may be holding you back and stopping you from making a greater impact.

Problem 1: PMs are so darned helpful

Product managers have an incredibly high surface area which comes with tons of work to do.

It’s no surprise.

You truly care about your product and you’re ready to do everything to make it successful. The more you talk to others across the organization, the more problems emerge and you have to tackle them all.

The consequence is that you end up working on very low-leverage stuff while the high-leverage stuff doesn’t get done. Or worse, someone else steps in to do it for you and take away your autonomy.

What’s the solution?

First, don’t volunteer. As a product manager, you’re not meant to be the lender of the first resort but the last resort, so let others do the low-leverage stuff.

Instead, focus your energy and time on the high-leverage work. Allocate time for the important things and make it clear to others what you’re working on and why.

How to upskill as a product manager: don’t be so helpful
How to upskill as a product manager: don’t be so ‘helpful’.

Problem 2: The zone of most competence

When faced with challenging conversations or conflicts, people tend to gravitate to what they know best. So if you started as a developer, development is your zone of most competence.

However, the consequence of dwelling in this zone is that other critical aspects of product management get neglected.

How do you resist the pull of your zone?

By categorizing your time, recognizing where you’re spending it, and actively pushing yourself back into the center of the product management Venn diagram.

How to upskill as a product manager: leave the zone of most competence
How to upskill as a product manager: leave the zone of most competence.

Problem 3: Don’t know what to do next

It’s easy for a product manager to get stuck in the weeds.

The deluge of competing priorities and the relentless pressure to deliver mean that instead of focusing on long-term vision or strategy, you merely execute.

The catch is that without a clear vision, you have no way to effectively filter and prioritize opportunities. It also makes it more difficult to push back on random requests.

To break free from this cycle, take a “look ahead test”: envision where the product should be in the next three years.

Moreover, make sure to carve out time for deep thinking and don’t forget about building relationships with customers, users, and stakeholders.

How to upskill as a product manager: look ahead
How to upskill as a product manager: look ahead.

Problem 4: Research takes too long

Another aspect of product management work that often gets side-tracked is customer research.

That’s because there’s a lot of planning to do and the only access to the customer that you get is through the sales or customer success teams. There’s no time for actual conversations with users that would reveal new opportunities.

When you try to allocate time for research, you get intense pushback from stakeholders who don’t have the patience to wait for it and instead tell you what to build.

What can you do to address it?

First, make the habit of interviewing customers continuously, and not only at specific stages of the product lifecycle.

Instead of waiting to hear what users want from customer-facing teams, go for a ride with them. That’s how you get a first-hand account of customer needs and pain points.

Finally, get comfortable making bets. It’s not always possible to get sufficient evidence to justify decisions, so learn not to rely on it. Otherwise, you get nothing done.

How to upskill as a product manager: do customer research continuously
How to upskill as a product manager: do customer research continuously.

Problem 5: We’re not answering customers’ requests

Sometimes you may face the opposite problem – too much customer feedback and the pressure to accommodate it all in the limited time that you have.

As saying no is just too much work, you end up cramming the tiniest customer requests into your sprints and prioritizing them all religiously.

What’s the consequence?

Lack of progress on the big ticket items that bring you closer to your strategic goals. And whatever you ship is rushed and you have to constantly appease stakeholders waiting for their pet requests.

Here are a few tips on how to avoid it:

  • There’s no need to prioritize all requests – this takes too much time and effort.
  • Instead, develop a robust decision tree so that you can easily filter out insignificant requests.
  • Say ‘no’ instead of ‘maybe’. Creating false expectations doesn’t make anyone happy.
How to upskill as a product manager: find a way to filter customers’ requests
How to upskill as a product manager: find a way to filter customers’ requests.

Problem 6: Slow product development

As your product team matures, you develop more processes and procedures to increase your chances of success, like validation.

However, such processes make progress slow. You don’t get started soon enough and end up not delivering what you’re meant to, so keep delaying releases.

The result is that you struggle to turn your brilliant ideas into reality and deliver a working product to your customers. If the senior management sees that you’re not getting stuff done, they intervene.

How can you prevent it?

Work in short iterations and deliver products in small but frequent increments. Make it clear to everyone that you can’t build everything. As there are only so many marbles that you can put through the funnel at a time, prioritize flow.

How to upskill as a product manager: release small, release often
How to upskill as a product manager: release small, release often.

Problem 7: Tech debt

If you build lots of features for too long without taking the time to tidy up after yourself or going back to fix bad decisions you’ve made, you will sooner or later hit the wall of tech debt.

Delivery will slow down due to more frequent downtimes, and you’ll spend more and more time firefighting.

This often results in customer and leadership dissatisfaction, and you lose the trust of the engineers and developers who have to resolve to shadow roadmaps to tackle technical issues.

To avoid falling into the trap, collaborate closely with the technical teams so that you’re aware of their issues and allocate enough resources to deal with necessary fixes.

To secure the buy-in of senior leadership, show them the business value of fixing technical debt.

Finally, the release fixes incremental alongside the functionality that delivers value.

How to upskill as a product manager: prevent tech debt
How to upskill as a product manager: prevent tech debt.

Demonstrating progress

How do you actually demonstrate progress to the key internal and external stakeholders?

Don’t keep stakeholders at arms’ length

Keep your stakeholders in the loop. If you don’t talk to them about what you’re doing, they will make assumptions and that’s how you lose control.

It doesn’t mean constant engagement as neither you nor they have the time for it. Keep them engaged just enough.

To get your message across, learn to speak their language. Avoid technical jargon or theory and speak about your work in business terms.

What if they’re not listening?

Keep repeating the message.

Again. And again.

Until they get it.

Show and tell

Whenever you talk to stakeholders, use the roadmap to illustrate progress. It’s not a sprint retro, so show them not only what you’ve achieved since last time but also what’s coming up next.

To make your narrative more compelling, use customer feedback as evidence and speak in terms of business goals.

Mix things up by inviting guest speakers. For example, invite a CS colleague you’ve collaborated with on a feature to share their perspective on the work you’re doing and its impact on the organization.

Finally, don’t forget to praise your partners from across the organization. You can’t build a great product without their help, so recognize it.


As there are a lot of misconceptions about what PMs do, they often struggle to get their progress recognized. And sometimes there’s no progress because they buckle under external pressure and compromise on good product management practices.

To avoid this, PMs need to prioritize the tasks that make a true difference and find ways to demonstrate the effects of their work.

If you want to see how Userpilot’s analytics and feedback features can help you make better-informed decisions, help you get stakeholder buy-in, and better communicate your results, book the demo!

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