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Dear Strategy Blog

The official blog of STRATEGY GENERATION COMPANY.

  • Blog

The Business Of Roadmaps

  • July 23, 2019
Dear Strategy Episode 91
Dear Strategy: “How do I align my product strategy and product roadmap with our technology roadmap, in the face of a strong engineering organization?” Ahh, the product roadmap… such an overused yet somehow still elusive...

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Bob Caporale
  • Blog

Balancing The Old and The New

  • July 8, 2019
Dear Strategy Episode 90
Dear Strategy: “In a rapidly changing marketplace, how should teams balance the need to support the core business and the need to tackle innovation? What tactical steps can allow an organization to succeed at both...

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Bob Caporale
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Embracing The Future While Respecting The Past

  • June 24, 2019
Dear Strategy Episode 89
Dear Strategy: “How do I turn a disruptive threat into an opportunity – with a focus on turning the mindset of the company around from arrogance and defensiveness to embracing and taking action?” First, a...

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Bob Caporale
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Deciding Who Decides

  • June 10, 2019
Dear Strategy Episode 88
Dear Strategy: “Who decides the strategy, and should it be confidential? AND “Should strategy start at the ‘top’ or be a product management-level decision?” Although these were two separately submitted questions, I felt they were...

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Bob Caporale
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Strategy Training and Why You May Need It

  • May 29, 2019
Dear Strategy Episode 87
Dear Strategy: “Why do I need strategy training?”  If you think I made this question up so that I can spin the answer into a not-so-subtle plug for my own strategy training company, I have...

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Bob Caporale
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Getting The Word Out

  • May 13, 2019
Dear Strategy Episode 86
Dear Strategy: “I have a product that uniquely meets the needs of a large target market, but I can’t seem to reach them. What should I do?”  For regular followers of this blog (and podcast),...

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Bob Caporale
  • Blog

Understanding Your Target Market (Part 5 of 5) – Market Team Cards

  • April 29, 2019
Dear Strategy Episode 85
NOTE: This is the fifth 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

Understanding Your Target Market (Part 4 of 5) – Customer Personas

  • April 22, 2019
Dear Strategy Episode 84
NOTE: This is the fourth 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

Understanding Your Target Market (Part 3 of 5) – Customer Segmentation

  • April 15, 2019
Dear Strategy Episode 83
NOTE: This is the third 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

Understanding Your Target Market (Part 2 of 5) – TAM, SAM, and SOM

  • April 8, 2019
Dear Strategy Episode 82
NOTE: This is the second 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
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