Dear Strategy artwork

Dear Strategy

143 episodes - English - Latest episode: about 8 hours ago - ★★★★★ - 11 ratings

Are you a product manager or business leader who has questions about how to develop and implement successful product and business strategies? If so, then you’ve come to the right place! Dear Strategy is an award-winning blog and podcast dedicated to providing education and advice on the subjects of product strategy, business strategy, and business leadership. Brought to you by the experts at Strategy Generation Company, each episode features real-life questions and stories that are analyzed, explained, and turned into practical, real-world advice that you can take back and use directly on the job!

Be sure to visit us at dearstrategy.net for more great content, including our free educational blog featuring over 130 highly informative articles!

Management Business Careers strategicplanning businessstrategy productmanagement productstrategy strategy strategytraining
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Episodes

Dear Strategy 142: Practicing Diligent Follow-up

April 26, 2024 12:00 - 18 minutes - 16.9 MB

On this episode of Dear Strategy,  Bob expands upon his 2 golden rules of small business success, starting with Rule #1. Tune in to hear tips on when, how, and why diligent follow-up should be practiced within your business. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 141: The Two Golden Rules for Small Business Success

April 12, 2024 12:00 - 14 minutes - 12.9 MB

On this episode of Dear Strategy, Bob gives us his two golden rules for small business success: 1) Practicing diligent follow-up, and 2) Never treat your customers like they are a burden. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 140: All Bets Are NOT Off

March 29, 2024 12:00 - 13 minutes - 12.7 MB

On this episode of Dear Strategy, Bob responds to the idea that “all bets are off” when you begin executing your strategy. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 139: Exploring the Definition of Customer Value

March 08, 2024 15:00 - 11 minutes - 10.7 MB

On this episode of Dear Strategy, we discuss the definition of “value” in relation to developing strategic value propositions and implementing value-based pricing. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 138: Organizing VOC Methodologies

February 23, 2024 15:00 - 15 minutes - 14.4 MB

On this episode of Dear Strategy, we talk about the different methods that can be used for gathering the Voice of the Customer (VOC) and provide a structure for organizing those methods to optimize your customer insights. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 137: What’s With This AI Trend?

February 09, 2024 15:00 - 13 minutes - 12.8 MB

On this episode of Dear Strategy, we talk about how so many companies are embracing Artificial Intelligence (AI) and whether it’s really such a good strategy to have your system run your company! If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 136: A New Year and a New Venture

January 19, 2024 20:00 - 13 minutes - 12.7 MB

On this episode of Dear Strategy, we talk about how so many college graduates are ill-prepared by their educational institutions to enter the workforce – and how colleges should be paying more attention to this before somebody else does! If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 135: Business vs. Military Strategy

June 26, 2023 16:00 - 16 minutes - 11.2 MB

On this episode of Dear Strategy, we talk about some of the natural parallels between military strategy and business strategy and explore whether that analogy still works within a more modern business landscape. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 134: The Strategy of Politics (From a Neutral Point of View)

June 08, 2023 16:00 - 19 minutes - 13.3 MB

On this episode of Dear Strategy, we talk about how political strategy correlates with product and business strategy, and why that can create a dangerous environment under the wrong circumstances. But don’t worry – despite the topic, no sides were taken during the recording of this podcast! If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 133: How Strategic Planning Really Works

May 16, 2023 00:21 - 16 minutes - 11.6 MB

On this episode of Dear Strategy, we talk about our new strategy framework, the latest direction for our podcast, and how strategic planning really works – especially in the face of unexpected events. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 132: How to Approach Customer Segmentation

April 15, 2022 13:00 - 16 minutes - 11.6 MB

On this episode of Dear Strategy, we talk about the process of customer segmentation – discussing how it is defined, what it is used for, and how you can perform segmentation for your own strategic planning process. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 131: How Ego Eats Strategy For Breakfast

March 15, 2022 13:00 - 17 minutes - 12.3 MB

On this episode of Dear Strategy, we talk about the concept of “strategic arrogance” – describing what it is, why it can be so dangerous, and how you can keep it out of your own strategic process. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in strategy training or coaching for your business, please visit us at Strategy Generation Company.

Dear Strategy 130: How To Differentiate Between a Product Strategy and a Go-To-Market Plan

October 01, 2021 13:00 - 23 minutes - 16.5 MB

On this episode of Dear Strategy, we talk about the difference between a product strategy and a go-to-market plan, and why it’s important to have both of these key planning tools working together in harmony. Key Takeaways: A product strategy and a go-to-market plan are two distinctly different, yet very much coordinated planning tools. A go-to-market plan is a dynamic and continuous plan that exists throughout a product’s entire lifecycle and not just at product launch. Your product s...

Dear Strategy 129: How To Align Your Product Strategy to Your Corporate Messaging

September 01, 2021 13:00 - 29 minutes - 20.7 MB

On this episode of Dear Strategy, we talk about how you can align your product strategy to your corporate strategy, and why it’s so important to alert your company’s leaders when that alignment doesn’t quite exist. Key Takeaways: If you are a corporate leader, make sure that your corporate strategy exists and is clearly communicated. If you are a product manager or business unit leader, make sure that you have a firm understanding of what your corporate strategy really is. Be open to ...

Dear Strategy 128: The Key to Strategic Success

March 15, 2021 16:00 - 19 minutes - 13.4 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “What is the single most important common element that you see in successful strategy executions?” *** We also share a very special announcement, related to this question, about the future strategy of our show! *** Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strateg...

Dear Strategy 127: The True Value Proposition of College

December 23, 2020 17:00 - 14 minutes - 10.1 MB

On this episode of Dear Strategy, we talk about the true value proposition of college. Given the outrageous prices, coupled with the fact that many students aren’t coming out of college with all the tools they need to be successful in their chosen fields of study, it’s hard to see how there is any real value proposition left here at all. And, yet, people keep paying. So what’s really going on here? We’ll talk it all through, from a strategic standpoint of course! Visit our Blog to read the...

Dear Strategy 126: Testing Your Strategy

December 09, 2020 17:00 - 11 minutes - 8.3 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “Is there a way to test your strategy prior to implementation?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 125: Same Product, Different Brands

November 25, 2020 17:00 - 13 minutes - 9.52 MB

On this episode of Dear Strategy, we analyze the practice of offering the same basic product across several different brands – especially when some of those brands are positioned as premium and some are – well – not! Is this a good strategy for companies to take, or is it something that will eventually backfire on them? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re intereste...

Dear Strategy 124: Measuring Success and Learning From Failures

November 11, 2020 17:00 - 17 minutes - 12 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “How can we measure the success of our strategy using some KPI other than orders? How do we learn from our failures?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://stra...

Dear Strategy 123: Subscriptions, Subscriptions, Subscriptions

October 28, 2020 16:00 - 16 minutes - 11.2 MB

On this episode of Dear Strategy, we analyze the practice of turning almost everything into a subscription! We’ll talk about when this model works, when it doesn’t, and what the future looks like if companies keep trying to move their customers in this direction. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy...

Dear Strategy 122: Mature Products in Resistive Markets

October 14, 2020 16:00 - 13 minutes - 9.31 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “How do you manage the lifecycle of mature products in resistive markets?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 121: Ink Jet Cartridges and Other Captive Strategies

September 30, 2020 16:00 - 15 minutes - 10.5 MB

On this episode of Dear Strategy, we analyze the practice of charging as much for the ink jet cartridges as for the printer itself. It’s called “captive pricing” and, just as the name implies it’s a strategy that’s not exactly designed with the customer in mind! We’ll talk about why this model exists and whether it’s actually a good strategy for companies to take over the long-term. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to s...

Dear Strategy 120: Strategic Trapdoors

September 16, 2020 16:00 - 16 minutes - 11.1 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “What are the most important traps and/or disruptions to implementing a strategy?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 120: Four Strategic Trapdoors

September 16, 2020 16:00 - 16 minutes - 11.1 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “What are the most important traps and/or disruptions to implementing a strategy?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 119: When The Promotional Period Ends

September 02, 2020 16:00 - 14 minutes - 10.2 MB

On this episode of Dear Strategy, we analyze the practice of companies offering introductory pricing and we talk about what happens when those introductory pricing periods end. Companies have been doing this for ages, but there’s a right way to do it, and (at least from a customer’s perspective) a far less right way to do it. We’ll talk about some of the pros and cons of each. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up...

Dear Strategy 118: I Have A Strategy… Now What?

August 19, 2020 16:00 - 10 minutes - 7.15 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “What is the next step once you have a strategy?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 117: When Discounting Becomes Standard

August 05, 2020 16:00 - 12 minutes - 8.65 MB

On this episode of Dear Strategy, we analyze the practice of retailers offering so many coupons that their discounted prices pretty much become their standard prices. And we talk about how customers feel when everyone else has coupons but them! Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your ...

Dear Strategy 116: Finding The Resources To Execute

July 22, 2020 16:00 - 16 minutes - 11.2 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “We are a small company and have trouble finding the resources to execute on tactics. What should we do?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygenerati...

Dear Strategy 115: Out of Warranty

July 08, 2020 10:00 - 12 minutes - 8.98 MB

On this episode of Dear Strategy, we analyze how customers feel about products that fail outside of their standard warranty periods but long before their normal expected lives. Is it a smart strategy for companies to stick to those 1-year warranties, or should they be exploring a different approach that focuses on long-term customer loyalty over short-term cost avoidance? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to d...

Dear Strategy 114: Matching Your Resources to Your Aspiration

June 22, 2020 13:00 - 13 minutes - 9.69 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “How do you balance the creation of a long-term strategic plan with the resources needed to execute it?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneratio...

Dear Strategy 113: Built NOT To Last

June 10, 2020 16:09 - 18 minutes - 12.5 MB

On this episode of Dear Strategy, we analyze the story of a poorly designed refrigerator that lasted around 5 years before it finally bit the dust. And, of course, the warranty didn’t cover it. With more and more technologies being incorporated into just about every product we own, is this the new norm that we should be expecting from our previously long-life products? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date...

Dear Strategy 112: Strategies for Non-Core Products

May 26, 2020 13:00 - 12 minutes - 8.5 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “What are the key elements to have in a successful strategy for a non-core product? And what things should we avoid?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://stra...

Dear Strategy 111: Rethinking Airline Strategies

May 11, 2020 13:00 - 16 minutes - 11.3 MB

On this episode of Dear Strategy, we analyze an airline story involving a cancelled flight, a premium seat, and a not so premium re-booking experience. It’s fairly well known that flying isn't always the most customer-centric experience. But now, more than ever, airlines may need to start re-thinking their strategies – especially with respect to how they’ve been treating their customers. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List...

Dear Strategy 110: Products vs. Solutions

April 27, 2020 13:00 - 14 minutes - 9.67 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “I come from a business that sells products. How do we develop a strategy that moves us into being a more solutions-oriented business?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit ...

Dear Strategy 109: Balancing Dreams with Plans

April 13, 2020 16:00 - 15 minutes - 11.1 MB

On this episode of Dear Strategy, we analyze the stories of two failed ventures – Theranos and the Fyre Festival. Both of these stories started with big dreams and ended in scandal. So how can leaders tell when their own lofty goals are actually bordering on becoming lofty lies? And what should they do about it? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in hav...

Dear Strategy 108: Dealing With a Crisis Situation

March 30, 2020 20:37 - 27 minutes - 18.9 MB

On this special episode of Dear Strategy, we talk about why long-term planning becomes more important than ever during times of crisis. When unexpected events happen, many companies may actually be deterred from thinking about the future because everything in the present seems so uncertain. But companies that take the time to think past a crisis may just find themselves with a competitive advantage on the other side of the horizon. Visit our Blog to read the full post that goes along with ...

Dear Strategy 107: Dealing With Short-Attention Span Leaders

March 16, 2020 13:00 - 12 minutes - 9.09 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “How do I present my strategy to a leader who has a VERY short attention span?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 106: The Pros and Cons of Crowdfunding

March 02, 2020 14:00 - 15 minutes - 10.8 MB

On this episode of Dear Strategy, we analyze a story about a company that launched a product through a crowdfunding site but didn’t ultimately deliver the product that they originally promised. Find out when crowdfunding works and when it doesn’t, as we explore this growing trend in product marketing. Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strateg...

Dear Strategy 105: Prioritizing Target Markets

February 17, 2020 14:00 - 13 minutes - 9.39 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “Which one comes first – market size or product capabilities that match the market?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 104: Coupons and Exclusions

February 03, 2020 14:00 - 18 minutes - 13.1 MB

On this episode of Dear Strategy, we analyze a story about trying to use a coupon at a retail store, only to find out that certain brands have been excluded. What is this practice all about and why does it seem to be trending toward becoming the new norm? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy worksho...

Dear Strategy 103: Determining the Size of Your Target Markets

January 20, 2020 14:00 - 15 minutes - 10.8 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: “Thank you for the 5-part series that explained TAM/SAM/SOM back in April. Once I've decided what those are for my company, how do I then figure out how big any of those are in terms of revenue? What sources might I go to in order to figure out how big my market is?” Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest...

Dear Strategy 102: Staying Loyal to Your Loyal Customers

January 06, 2020 14:00 - 18 minutes - 12.7 MB

On this episode of Dear Strategy, we analyze a story about a retailer that decided to lift its standard price matching policies during the week of Black Friday. On the surface, it seems like this would be a good financial move. But is it worth upsetting some of your most loyal customers just to make a few extra bucks during this important time of year? Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the lates...

Dear Strategy 101: Our Strategy Beyond Episode 100

December 16, 2019 14:00 - 11 minutes - 8.28 MB

On this episode of Dear Strategy, we answer the following question… Dear Strategy: "What is your strategy beyond Episode 100?" Visit our Blog to read the full post that goes along with this episode. Subscribe to Our Mailing List to stay up to date on all the latest episodes. If you’re interested in having Strategy Generation Company deliver a strategy workshop for your business, please visit us at https://strategygeneration.com

Dear Strategy 100: What Is a Strategy?

November 18, 2019 14:00 - 15 minutes - 10.6 MB

This week's question is... Dear Strategy: “What is a strategy?” Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 099: When to Review and Update Your Strategy

November 04, 2019 14:00 - 10 minutes - 7.12 MB

This week's question is... Dear Strategy: “How do I better assess what should be the trigger level for reviewing and potentially updating my strategy?" Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 098: Product vs. Market Strategies

October 21, 2019 13:00 - 11 minutes - 7.82 MB

This week's question is... Dear Strategy: “What is the difference between a product-based organization and a market-based organization, and how does that translate into product and marketing strategies?” Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 097: Getting Buy-In For Your Strategy - Revisited

October 07, 2019 13:00 - 12 minutes - 8.34 MB

This week's questions are... Dear Strategy: “What is the best way to get continued buy-in for my strategy and ensure the organization remembers and ties their work back to the strategy?” AND “What are some methods to gain buy-in from the bottom-level up in an organization that is not structured as a product/service organization?” Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 096: Communicating Both The “Why” and The “What”

September 23, 2019 13:00 - 10 minutes - 7.17 MB

This week's question is... Dear Strategy: “How do you build a strategy that all levels of an organization can participate in and support – making sure to communicate the ‘why’ and not just the ‘what’?” Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 095: Long-Distance Strategy Management

September 09, 2019 13:00 - 10 minutes - 7.69 MB

This week's question is... Dear Strategy: “How do we best handle having the Engineering and Innovation groups working in different locations than the Manufacturing groups? (i.e. How do we manage the long-term strategy for Manufacturing and Engineering in two different locations?)” Read The Full Blog Post Subscribe to Our Mailing List

Dear Strategy 094: Measuring The True Value of Your Strategy

August 26, 2019 13:00 - 10 minutes - 7.38 MB

This week's question is... Dear Strategy: “What is the appropriate measure for the value of a project or product? Raw sales? Profit contribution? Something else?” Read The Full Blog Post Subscribe to Our Mailing List