Change Management Product Management Product Portfolio

Challenges and Change Provide a Bonanza for Product Managers

Product Managers Challenges

Part 2: Building entrepreneurial skills

©2011 by Karl Hellman and Robert S. Siegel
Part 2 of a 4 part series

In part 1 of this series, we discussed where product managers find entrepreneurial opportunities.   Part 2 focuses on how product managers acquire entrepreneurial skills. 

Product managers learn how to do entrepreneurial work the same way people learn most complex tasks.  The Air Force asked Herbert L Dreyfus of the University of California, Berkeley and his brother, Stuart, “How should jet pilots be trained?”

So the brothers Dreyfus developed a model of how people learn skills like driving a car (since neither flew airplanes) or playing chess-or becoming entrepreneurial.

They identified 5 stages of development:

Stage 1: Novices use rules.  And they take a long time diagnosing problems and deciding on an action in response.

Stage 2: Advanced Beginners begin to note perspicuous (very clear) situations.  They still use rules when they don’t recognize the situation.

Stage 3: Competence brings more recognition of situations.  At this stage the driver, the chess player, or the entrepreneurial product manager has to sort out the few important things they recognize from the many presented.  The learner uses judgment and feels elated when he or she is correct, and guilty if they are not.   If guilt pushes them to fall back on rules, they won’t grow.  Only accepting the responsibility for using judgment pushes them on to the next level.

In Stage 4: Proficient, situational discrimination, or the ability to spot situations and associate responses.  Action becomes easier as the product manager sees and understands what needs to be achieved.

And finally Stage 5: Expertise, The expert product manager has developed a vast set of patterns and solutions based on their experience and knowledge.  Therefore the expert is able to see what he or she needs to do without having to consult the rules or calculations used in earlier stages.

We can apply this model of learning to product managers learning to perform entrepreneurial work, namely, to find anomalies in their business and then turn those anomalies into opportunities-into products that meet customer needs, processes
that are more efficient and effective, strategies that look at the world differently, and programs that have never been tried before.

Rules for Novices

Novices makes use of a wide range of rules: 

Fact-based approaches

Novices begin by learning fact based approaches to analyze the market, customers, competition, business core competencies, financial picture—i.e., the current business situation.

Tools and skills of innovation

Ron Dunn, CEO of Cengage Learning says, “Foremost among the skills the [novice] needs to develop is the ability to listen to customers and translate their unsolved problems into the technologies and capabilities of their firm.  I’d label this skill, the ability to translate.”

 The process

Novices are supported by a formal stage gate process.  They need to understand the steps of the process and the business-thinking required at each step.


Novices need financial skills to value their ideas and to assess the idea’s potential.

Market forecasts

The novice needs the ability to understand market research, challenge research conclusions, and develop forecasts.

Reduce risk.

Novices need rules to apply to their fact-base to eliminate risks.

Access to customers, markets, the world at large

Novices needs direct contact with customers, access to industry experts, tradeshows, etc. as input to spot anomalies.

The principles and best practices of creativity

Creativity is a skill that can be learned and improved upon with training.

 A learning philosophy

The genius of product management is learning. Don’t get upset by failures.  Don’t obsess on success.  Focus on learning.

Opportunities for Advanced Beginners and the Competent to practice seeing the patterns

The Advanced Beginner and the Competent build skills through practice.  Here are some ways to support  them:

Serving as apprentices to an expert entrepreneur

By working with an expert, the apprentice learns to apply the entrepreneurial skills in real situations.

Managing training products

Training products—smaller brands that would never make the portfolio on business criteria alone—are the perfect places to give the advanced beginner the opportunity to practice finding the anomaly, creating the business case, receiving limited funding, acting, measuring, learning.

Conducting product debriefs

Set aside time to examine your product experiences. It’s the only way to gain the full benefit of the time and resources you’ve invested. Remember to examine to learn—not to punish.  If you examine to punish—punishing failure—pretty soon everything will begin to look like success.  If you examine to learn—the whole world will open up before you and lay at your feet.

Supporting your Proficient and Expert

The world is completely different for the proficient and the expert.  You support these most prolific entrepreneurial product managers differently.

Give them freedom

The proficient and the expert need the very opposite of the novice’s rules.  They need the freedom to improvise, the time to explore, the support to learn from the unexpected.

Streamline and adapt your process

The proficient and expert are most adept at understanding anomalies. They need to state their hypotheses—spell out what they think the anomaly is, what opportunity it implies, and the strategies that might take advantage of the opportunity.

Hypotheses need to be validated and refined through technical and market research.  The refined hypotheses need to be converted into technical and market trials.

Finally, the trial results need to be turned into learnings and the business strategies and programs they imply.  At this point entrepreneurial work becomes strategic marketing: Identification of target markets, competitive and technical positioning, and the executional disciplines of product roll-out.  Actions are measured, and learnings documented and course corrections made.

Give them special access to resources

The proficient and expert need access to people—cross functional teams. They need the unrestricted (but, of course, audited) budget. They need to access to the larger world—the trade association, the industry think tank,  TED (, to burning man, (, to MOMA, to the symphony, to Orbiting the Giant Hairball (Gordon MacKenzie’s wonderful book).

Give them special access to decisions

Streamline the access the proficient and expert entrepreneurs have to top management.  Give them an express lane to decisions.

Make your proficient and expert people your mentors

Your proficient and expert are the mentors your novice, advanced beginner, and competent entrepreneurs need.    As little as three hours of mentoring a month significantly increases the productivity of the less experienced people.  And it’s also well established that the more experienced people benefit just as much.  They get a fresh look at their own expertise through the eyes of the people they mentor.

Your company’s entrepreneurial work shifts as your people develop entrepreneurial expertise:

Product Manager

Next: Part 3: Building an entrepreneurial culture

How entrepreneurial is your company? Go to to take a 10 question quiz, and get an immediate assessment–and ideas on how to make your company more entrepreneurial.

Karl Hellman
is President of Resultrek (, an international marketing consulting and training firm.

Robert S. Siegel
is an experienced Product Management Executive, Content Creator and Web Developer.  Mr. Siegel authors three popular blogs:,, and (closed).

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