The Strategic PM Learning Guide: When to Learn on the Job vs. Take a Course

I once spent $2,000 on a product management course only to realize I could have learned the same skills by volunteering to lead a new initiative at work. But then I tried learning technical product management purely on the job and created a spectacular disaster that could have been avoided with some structured learning first. Both approaches to learning have their place – the trick is knowing when to use which.

Let's cut through the noise and get strategic about your PM learning journey. No more throwing spaghetti at the wall or following generic "PM learning roadmaps" that don't account for your unique context.

The PM Learning Matrix: A New Framework for Skill Development

Before we dive into specific recommendations, let's introduce a framework I've developed after observing hundreds of PM career trajectories.

🎖️ War Story: As Head of Product, I once had a talented PM who was excellent at execution but struggled with strategy. She took several strategy courses but still couldn't translate theory into practice. The breakthrough came when we paired the courses with a mentor and real project to apply the learning. The lesson? Learning method matters as much as the content.

The PM Learning Matrix categorizes skills based on two factors:

• Risk of Learning Through Failure
• Depth of Theory Required

This creates four quadrants:

1. Learn by Doing (Low Risk, Low Theory)

• Daily standups
• Basic user interviews
• Feature specification writing
• Sprint planning

2. Structured Practice (Low Risk, High Theory)

• Product strategy
• Prioritization frameworks
• Stakeholder management
• Roadmap creation

3. Formal Training First (High Risk, High Theory)

• Technical architecture understanding
• Data analysis and experimentation
• Machine learning product management
• Enterprise pricing strategies

4. Guided Experience (High Risk, Low Theory)

• Crisis management
• Major product launches
• Team restructuring
• Executive communication

When to Trust Experience (And When Not To)

🚨 Reality Check: Most PMs default to "learning by doing" because it's free and immediately applicable. But this can be like learning to swim by being thrown in the deep end – sometimes it works, but often it's unnecessarily risky and inefficient.

Trust Experience When:

• The cost of failure is low (like improving your daily standups)
• You have a strong support system to provide feedback
• The skill is highly context-dependent
• You have time to iterate and improve

Invest in Courses When:

• You need to understand fundamental theories and frameworks
• The cost of failure is high (like managing a major product launch)
• You want to learn from others' mistakes
• You need structured practice in a safe environment

The Learning Journey by PM Type

Different types of PMs need different learning approaches. Here's how to optimize your learning based on your role:

B2C Product Managers

Learn on the Job:

• Consumer behavior understanding
• A/B testing execution
• Feature prioritization

Take Courses For:

• Advanced analytics
• Behavioral psychology
• Consumer research methodologies

B2B Product Managers

Learn on the Job:

• Client relationship management
• Feature request handling
• Sales enablement

Take Courses For:

• Enterprise pricing strategies
• B2B metrics and KPIs
• Technical architecture

Technical Product Managers

Learn on the Job:

• Agile ceremonies
• Sprint planning
• Developer collaboration

Take Courses For:

• System design principles
• API product management
• Technical architecture patterns

Creating Your Personal Learning Stack

💡 Quick Win

Start by auditing your current skills against your target role. For each skill gap, place it in the PM Learning Matrix to determine the best learning approach.

Here's a step-by-step process:

1. Identify Your Gaps

• Map your current skills
• Define your target role
• List the missing capabilities

2. Categorize Each Skill

• Use the PM Learning Matrix
• Consider your context and resources
• Assess the risk of learning through failure

3. Create Your Learning Plan

• Balance formal and informal learning
• Set specific timelines and goals
• Find opportunities to apply learning immediately

4. Measure and Adjust

• Track your progress
• Gather feedback
• Adjust your approach based on results

Common Learning Pitfalls to Avoid

The Course Collector Syndrome

Taking courses without applying the learning immediately. Always pair courses with real projects.

The Pure Experience Trap

Relying solely on experience, even for high-risk areas. Some mistakes are too costly to learn from firsthand.

The Framework Fanatic

Focusing too much on theories without enough practical application. Frameworks are tools, not solutions.

Next Steps

1. Map your current skills and gaps using the PM Learning Matrix
2. Identify one high-risk area where you need formal training
3. Find one low-risk area where you can start learning through experience
4. Create a 90-day learning plan that combines both approaches

Remember: The best PMs are perpetual learners, but strategic ones know when to learn through experience and when to invest in formal education. Your learning journey should be as carefully product-managed as any feature in your backlog.

What's one skill you've been trying to learn purely through experience that might benefit from some structured learning? Share your thoughts in the comments below.

Ready to level up your PM skills? Check out our curated directory of product management courses, filtered by your specific needs and learning style.