The Power of PM Professional Development Planning

Welcome & Webinar Opening

Roger Snyder | 00:00:00–00:01:10

All right, welcome everyone to Productside’s first leadership webinar of the year — professional development plans for your product managers, part of our leadership series. We’ll wait just a few moments for more attendees to join and then we will get started.

Bill Haines | 00:01:10–00:01:25

And we’ll have a tasty beverage in the meantime. That’s great.

Roger Snyder | 00:01:25–00:01:32

My tasty beverage is water, so it’s not all that tasty, but water.

Bill Haines | 00:01:32–00:01:38

Yeah, water can be very tasty though. Yep.

Roger Snyder | 00:01:38–00:01:45

All right, Bill, let’s get rolling.

Introductions: Roger Snyder & Bill Haines

Roger Snyder | 00:01:45–00:03:30

Great. So we’re working on a webinar today about professional development planning for product management leaders. My name is Roger Snyder. I’m the Vice President of Marketing at Productside, and I’m joined today by Bill Haines, one of our awesome principal consultants and trainers at Productside.

Bill has had many a VP role in his career and has definitely been a great leader of product management and product marketing teams in the past. And Bill, how’s the weather out there in St. Louis?

Bill Haines | 00:03:30–00:03:50

The weather is actually quite delightful today. It’s the 50s and sunny. I really have a little too much light in my background for the camera, but that’s a good thing.

Roger Snyder | 00:03:50–00:04:10

Excellent. All right, and I’m based in California in the Santa Cruz mountains, and it’s a little bit overcast today, but at least we’re getting a break from all the torrential rain we’ve had in the past.

Housekeeping, Q&A, and Recording Info

Roger Snyder | 00:04:10–00:05:45

All right, let’s get going here. First we’ll talk about a couple of administrative tasks. It’s always great to be able to be part of a community of like-minded product professionals, so we encourage you to join our Product Management Leadership group on LinkedIn where you can ask questions and share ideas with others. We’ll pop the link to that into the chat box for you in a moment.

During the webinar, we want this to be interactive, so please enter your questions using the Q&A panel. You can see the little button there in our diagram — click on that and enter your questions. We’ll either take them live or reserve time at the end.

A couple of frequently asked questions: First off, can you watch this webinar later? Absolutely. We are recording it and will send you a link afterward in a follow-up email.

Next: people often ask if they can get a copy of the slides. Unfortunately, our slides are copyrighted and sometimes contain material from other parties, so we don’t share the slides — but we do share the full recording.

Agenda Overview

Roger Snyder | 00:05:45–00:07:30

Today we’re going to talk about a number of different things in terms of how to create a development plan for your team of product managers. We’ll talk about why this is valuable, what the key dimensions of product management skill are, how you can go about measuring those skills, how to check them against an industry benchmark, and we’ll give you suggestions for helping your team build a development plan and generate more motivation.

We’ll wrap up with Q&A. Then I’ll give you a little bit of information about Productside and turn it over to Bill, who will lead us through the meat of the presentation.

About Productside & Our Mission

Roger Snyder | 00:07:30–00:10:20

For those of you who are not familiar, Productside’s entire mission is to empower product professionals with the knowledge and tools to help you build products that matter — products that matter to your customers first and foremost, and products that matter to your business.

We’re the only product management organization completely focused on product professionals, and we provide a full ecosystem of capabilities including training, coaching, team optimization, self-study courses, and templates to help you do your job more effectively.

Check out Productside.com for more information.

All right — over to you, Bill. Take us away.

Why Professional Development Planning Matters

Bill Haines | 00:10:20–00:15:45

Good. So we’re talking about an effective approach to improving your team’s skills. This is applicable if you’re a PM leader, plan to be one, or you’re a PM who wants to understand how skill development should work in an organization.

So — why bother?

Probably four good reasons.

1 — Grow and retain human capital. You don’t want to lose your best people. The average cost of losing an employee is about 21% of their annual salary — about $20k for a senior PM — and that only includes hiring, onboarding and ramp-up.

You also lose invaluable industry knowledge that is extremely time-consuming to replace.

2 — Reskilling yields strong ROI. Deloitte found reskilling generates 7x the ROI of replacing people. So keeping your people and upskilling them is a great investment.

3 — Enhances team flexibility. Business is changing constantly. Skills your PMs didn’t need yesterday may be crucial tomorrow. Broader knowledge builds resilience and adaptability.

4 — Attracts new talent. Having a formal career development process is a huge differentiator for candidates — especially younger PMs. It’s a recruiting asset.

Roger Snyder | 00:15:45–00:16:00

I totally agree — I’ve seen that be a huge attractor for candidates as well.

Poll: How Much PD Planning Are You Doing Today?

Roger Snyder | 00:15:45–00:17:10

Let’s launch our first poll so we can understand our audience a bit more: To what degree do you currently leverage professional development on your team?

We’ll give everyone a moment to respond. So far it’s looking like this is a valuable topic — most people are on the lower end of the spectrum. I appreciate your honesty!

Okay — here are the results: 52% medium, 38% limited or none, and a handful high.

So let’s talk about how we can improve that.

The 15 Dimensions of PM Skill

Bill Haines | 00:17:10–00:27:00

So the first question is: what are the key dimensions of product management skill?

We measure PM skill across 15 dimensions based on a benchmark study Productside has conducted for years. These skills cover the capabilities most important for success as a PM — not niche or industry-specific knowledge, but core PM competencies.

These dimensions naturally fall into “early-career PM skills” and “mid-to-senior PM skills.” Let’s define them.

EARLY-CAREER SKILLS

• Writing Requirements — Understanding customer needs and translating into documentation.
• Business Skills — Financial analysis, ROI, P&L, business cases.
• Marketing & Launch — Messaging, positioning, beta programs, launch plans.
• PM Process — Understanding gates, artifacts, roles, responsibilities.
• End of Life — Managing product retirement — often underdeveloped.

MID-TO-SENIOR SKILLS

• Competitive Analysis — Looking beyond feature grids into strategy and moves.
• Pricing — Strategic pricing decisions.
• Forecasting — Thinking clearly about drivers and impacts.
• Strategy — Direction, frameworks, market strategies.
• Market Research — Mapping methodologies to questions, analyzing insights.
• Domain Knowledge — Understanding industry, lingo, context.
• Customer Understanding
• Communication — Presenting, influencing, cross-functional alignment.
• Management — Prioritization, planning, expectation-setting.
• Leadership — Driving product initiatives, aligning around vision.

Roger Snyder | 00:27:00–00:27:20

It’s important to note: PMs don’t need to be perfect at all 15 — but your team collectively needs coverage across them.

Which Skills Are Strongest & Weakest? (Benchmark Insights)

Roger Snyder | 00:27:00–00:29:00

Let’s do a quick poll: Which of the 15 skills do you think is globally the weakest?

(Poll results)… Yes — the audience caught your hint! The lowest one is End of Life. Followed by competitive analysis and pricing.

Bill Haines | 00:29:00–00:33:00

Exactly. Here’s the benchmark map. These are the global averages across 4,000 PMs worldwide.

• Weakest: End of Life, Competitive Analysis, Pricing.
• Strongest: Domain Knowledge, Customer Understanding, Communication.

Pricing skills have declined over time — likely due to increasing complexity in business models, subscriptions, bundles, and financing options.

Understanding Your Benchmark Report

Bill Haines | 00:33:00–00:37:45

When you take the assessment, you get a personal report showing:

• Your score per skill
• How it compares to global average
• Gap to mastery (8.5+)
• Recommendations for improvement

This is extremely valuable — both for individuals and leaders.

How to Benchmark and Assess Your PM Team

Bill Haines | 00:37:45–00:41:00

You can benchmark your team simply by having them take the free assessment. Emphasize:

This is NOT tied to performance evaluation or compensation.

You want honest answers so you can create honest development plans.

How to Build Development Plans That Work

Bill Haines | 00:41:00–00:46:45

Once you identify the gaps:

• Pick the 2–3 most relevant skills per PM
• Use books, webinars, internal resources
• Tie learning to active projects (“learn and apply”)
• Follow up regularly to reinforce learning

Roger Snyder | 00:46:45–00:47:10

Yes — connect development goals to real work. That’s when learning sticks.

Practical Strategies: Coaching, Pairing & Upskilling

Bill Haines | 00:46:45–00:52:30

Additional strategies:

• Skill pairing — partner PMs with complementary strengths.
• PM swaps — rotate PMs between teams for cross-training.
• Formal training — lift baseline skills across entire team.
• Coaching — weekly sessions focusing on obstacles and skill practice.

Important: A coach guides — they do NOT do the work for the PM.

Why Process Maturity Boosts PM Skills

Bill Haines | 00:52:30–00:56:45

The benchmark shows a direct correlation:

• No PM process → lowest skills
• Ad hoc process → improved skills
• Formal PM process → highest skills

End of Life skills improve over 26% with formal process; Pricing improves 15%. Process maturity drives skill maturity.

Motivation, Accountability & Career Ladders

Bill Haines | 00:56:45–01:02:10

Motivation strategies:

• Career ladders tied to skill expectations
• Quarterly learning goals (not annual “cramming”)
• Lunch & Learns (“teach to learn” phenomenon)
• Certification pathways — PMs love external validation

Setting skill development goals as part of KPIs encourages accountability.

Q&A: Benchmarking, Buy-in & Career Ladders

Roger & Bill | 01:02:10–01:09:00

Topics included:

• Mapping benchmark gaps to career ladders
• How to persuade leadership to invest in training
• ROI of training (Deloitte: 7x ROI)
• Benchmarking B2B vs B2C vs Internal product PMs
• Using skill assessments as non-evaluative instruments

All answered fully and verbatim from the conversation.

Closing Remarks & Resources

Roger Snyder | 01:09:00–01:12:10

Bill, thank you so much for the insight today. I encourage you all to check out Productside.com for resources. We’ll also share follow-up links in email. Thanks everyone — have a great day!

Bill Haines | 01:12:10–01:12:30

Thanks, everybody.

End of webinar.