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Dear Strategy Blog

The official blog of STRATEGY GENERATION COMPANY.

  • Blog

Understanding Your Target Market (Part 1 of 5)

  • April 3, 2019
Dear Strategy Episode 81
NOTE: This is the first installment in a special 5-part series on Understanding the Target Market for Your Product or Business. This series was inspired by a talk that Bob gave at the Podfest Multimedia...

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Bob Caporale
  • Blog

Five-Year Strategies in Volatile Markets

  • March 25, 2019
Dear Strategy Episode 80
Dear Strategy: “Is 5 years a relevant time frame for your strategy when market trends and industries are uncertain in a volatile market?”  Here we have another question that is a derivative of something we’ve...

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Bob Caporale
  • Blog

Implementing Your Strategy Externally

  • March 18, 2019
Dear Strategy Episode 79
Dear Strategy: “You could have the best strategy, but what are some best practices to implement it effectively?” Last week, in Episode 78, I answered a question that had to do with implementing strategies internal...

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Bob Caporale
  • Blog

Implementing Your Strategy Internally

  • March 12, 2019
Dear Strategy Episode 78
Dear Strategy: “How do you build programs, projects, and, ultimately, products out of a strategy once it’s been established and accepted? How does it look from a complete, holistic lifecycle?  This is one of those...

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Bob Caporale
  • Blog

Determining a Product’s True Value Proposition

  • March 10, 2019
Dear Strategy Episode 77
Dear Strategy: “How do you figure out a portfolio investment strategy for a product that is a delighter but doesn’t bring in money on its own?”  Back in Episode 2 and again in Episode 38,...

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Bob Caporale
  • Blog

Communicating New Features To The Marketplace

  • February 25, 2019
Dear Strategy Episode 76
Dear Strategy: “How do you communicate new features to users in a fast, Agile release cadence?”  Here we have a question that could be interpreted as being somewhat more tactical than strategic. However, I am...

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Bob Caporale
  • Blog

Getting People Excited About Your Strategy

  • February 17, 2019
Dear Strategy Episode 75
Dear Strategy: “How do you communicate strategy to the rest of the organization with a small and newly formed team on a previously languishing product?”  There are a few key sentiments in this question that...

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Bob Caporale
  • Blog

Jobs To Be Done (and Other Frameworks)

  • January 28, 2019
Dear Strategy Episode 74 - Jobs To Be Done (and Other Frameworks)
Dear Strategy: “How do I best operationalize the ‘Jobs To Be Done’ framework in my everyday strategy work?” At least once a month, I get a question (sometimes officially and sometimes casually) about some framework...

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Bob Caporale
  • Blog

Strategy Career Questions (Part 3 of 3)

  • January 14, 2019
Dear Strategy Episode 73 - Strategy Career Questions (Part 3 of 3)
Dear Strategy: “How do I evaluate a Product Manager to Product Marketing Manager career transition?” As with the other career questions we’ve answered in this series, definitions are important. And there is perhaps no greater...

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Bob Caporale
  • Blog

Strategy Career Questions (Part 2 of 3)

  • January 4, 2019
Dear Strategy Episode 72 - Strategy Career Questions (Part 2 of 3)
Dear Strategy: “How do I evaluate a job opportunity that moves me from SaaS products to on-premises products but is one of the CEO’s initiatives?” The first thing we need to do before answering the...

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Bob Caporale
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