The Key to Strategic Success

August 5, 2021

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?”

The Dear Strategy Podcast Episode 128 was released on March 15th of this year. It is now almost 5 months later, and I’m just getting around to writing the post that goes along with it. So what gives?

Well, as I explained on the podcast, we’re going to be doing things a bit differently going forward – and that just happens to be intertwined with the Dear Strategy question that I am going to address in this post.

I’ve been involved in developing product and business strategies since 1992. I’ve been a practitioner, a consultant, a teacher, and a coach – and I estimate that I’ve either developed or helped other people develop well over one hundred different strategies. No I haven’t seen it all, but I’ve certainly seen a lot – a lot of good strategies, a lot of not so good strategies, and a whole lot of strategies that fall somewhere in between. And if I were to identify the one common thread that ran through all the best strategies that I’ve ever been a part of, it would be that not one of those strategies started out quite the same as they ultimately ended up.

When I started this podcast and blog, I did so with the intention of making the subject of strategic planning more accessible. My background, believe it or not, is in electrical engineering. Sure, I had taken a few MBA-level courses on strategy and strategic planning; and they were informative enough. But school is, by no means, where I learned how to be a strategist. I learned that by just doing it – over and over again. I learned through failure; I learned through success; and, in quite a few instances, I learned by re-writing the rules that everyone else was trying to teach me.

With each strategy I developed, I was earning the right to call myself a strategist. Yet, I was never completely comfortable saying it out loud. Why? Because I didn’t go to school for it. I hadn’t read all the right books, I didn’t study with all the right professors – heck, I didn’t even have an MBA! And I was far from alone in my feelings of insecurity. As I started to look deeper, I found that many people in the corporate world felt exactly the way I did. They intuitively knew what to do, but they somehow felt they hadn’t earned the right to do it; mostly because they felt they didn’t have the right credentials, the right backgrounds, or the right level of command over the requisite strategic “lingo.” And that exact feeling is something that I wanted to help people (and, quite honestly, myself) overcome.

So I set out on a journey. I read all the “right” books, I took at least some of the “right” courses, and I dedicated a good amount of time and energy to learning all the “right” language. That journey led me to become a strategy facilitator, coach, speaker, and even published author. I had earned the credentials – and my sole reason for doing so was to help inspire others around the fact that you really don’t need any of those credentials to be good at developing strategies. And that’s exactly how the Dear Strategy podcast came into existence.

The idea behind this podcast and blog was to take the knowledge that I had gathered over the years and make it less intimidating to others. I wanted everyone to know that they had the ability (and the right) to be a strategist; and that this wasn’t a label that should be exclusively reserved for people who learned it in school. Strategy is fluid, it’s inspired, and it doesn’t have to follow anyone’s pre-determined set of rules. So if the only thing standing in the way of someone creating the next game-changing strategy was the feeling that he or she somehow wasn’t qualified to do so, that’s a problem that I really wanted to help solve.

The original format was simple – allow people to ask any question that was on their minds about the subjects of strategy and strategic planning, and then answer those questions in a safe and unintimidating forum. The idea was also to provide a resource that could be easily referenced and bookmarked for continued and ongoing use, which is where the blog portion of the podcast came into play. As the format evolved, I also started bringing in some “strategy stories” – which were meant to illustrate how some of the concepts covered in the questions are (or aren’t) being applied in real life situations. Those episodes have been really well received, and are going to provide something of a springboard for where I’d like to go next.

And that brings us to a bit of an announcement, which also happens to be the answer to this week’s question:

“What is the single most important common element that you see in successful strategy executions?”

My answer: The willingness to pivot. Which is exactly what I am going to be doing with the strategy for this show.

Contrary to the way some businesses may behave, a strategy should never be seen as an absolute promise. Rather, a strategy is simply a plan – and plans are expected to change. To be more precise, in Episode 126, I provided a more complete definition of strategy that I think helps to drive this point home. In that post, I defined strategy as being “a plan to achieve a goal under a set of anticipated conditions.” Even though I wrote it, this has become my new favorite way to describe what having a strategy is really all about!


“A strategy should never be seen as an absolute promise. Rather, a strategy is simply a plan – and plans are expected to change.”


Every strategy has three basic parts: a plan, a goal, and a set of anticipated conditions. And all of those parts need to work together. Conditions change, goals change, and plans change. And any change to one will have an inevitable effect on the other. Which also means that it should not only be acceptable, but it should also be expected that your strategy will evolve. And it’s a good thing, too. Because if you couldn’t change your strategy, you’d have a much lower chance of ever being able to achieve your goals.

So where does all of that leave us with respect to this podcast and blog? Well, as you may have guessed, it’s time for us to pivot…

It’s been just over 4 years since I started Dear Strategy, and I think, over that time period, I’ve been able to realize the original goal that I set out to accomplish. And, with that in mind, my intention is to keep these episodes and posts online so that people can continue using them as a reference for all of their otherwise unanswered strategy questions. I might even compile these posts into a book someday just to provide another medium for those who might be interested. But, at least for now, I have no intention of taking any of this content offline as a result.

But now I want to go in a slightly different direction. In addition to reaching our original audience of would-be strategy creators, this show has also found a nice little niche of providing a supplemental resource for clients of my training business, Strategy Generation Company. One of the challenges of attending any corporate training class is that it is extremely difficult to retain even a fraction of the material that is actually being conveyed. Learners need time to think about, digest, and apply what they’ve learned if they want to have any chance of retaining the most salient points from any given workshop or course.  Well, as it turns out, in addition to the workbooks and toolkits that we normally provide with our training classes, this podcast and blog has come to serve as an additional resource that our learners can use to reinforce the material that we teach in our classes. And so, going forward, my plan is to double down on that approach.

Some of the most impactful elements of any class are the examples that accompany the learning. I can teach the theory behind a concept, but once I give an example of that theory actually being applied, everything seems to come to life for the learner. The good news is that I have amassed literally hundreds of examples over the years. And, so, my goal will be to share some of those examples through this forum so that existing and future clients can refer back to them any time they want to.

So what will these examples look like? Of course, many of the stories that I use to support concepts inside the classroom are about what well-known Company X or Company Y did. And although those examples can certainly be useful (and entertaining), they’re not exactly the types of examples that I want to share here. Why? Well, for one thing, in order to maintain that safe environment that I talked about earlier, I’ve always adhered to a policy of never (or at least very rarely) sharing actual company names within the context of this blog. And I plan to continue that policy for the foreseeable future. Plus, I’m not sure how useful it would be for you to know my opinions about why Amazon or Apple or Tesla may or may not have done something, when, in reality, I have no actual inside information about any of those companies; or, for that matter, any of the other popular companies that consultants like me seem to reference all the time. And if I actually did have any of that inside knowledge, I most certainly wouldn’t be able to share it with you anyway!

Instead, the examples that I intend to share here will be real-life examples of strategic problems that I commonly see, and how those problems were solved using the tools and methodologies that we’ve been referring to in this blog. Names will still be hidden, and situations will be genericized. But my hope is to take the concepts that we’ve been talking about over the past 128 episodes, and show how those concepts can actually be applied in real-life scenarios.

Regarding the frequency of the episodes, that remains a bit up in the air. Obviously, I’ve taken some time off to re-energize, re-focus, and re-strategize. And I won’t lie, keeping up with even a bi-weekly schedule of podcasts and posts has been challenging to say the least. So, at this point, I’m going to try to commit to monthly episodes, and I plan on starting that beginning in September of this year.

So that’s pretty much the plan – and also the answer to this week’s question. Strategy is dynamic. And that includes the strategy for this show. So I’m going to pivot. And, in so doing, I’m going to do my best to accomplish my latest strategic goals.

Oh – and one more thing. You know that MBA that I referred to earlier? Well I never did commit to getting it. Not because I don’t respect the degree, but because, for me, it was just never something that I felt I needed (or wanted) to pursue. I used to be afraid to talk about that – but now it is a decision that I have become quite proud of. Because I firmly believe that when we accomplish things as a result of our backgrounds, they tend not to have near as much of an impact as when we accomplish things in spite of our backgrounds. I only mention that because, for those of you who, like me, don’t happen to hold that extra piece of paper – it doesn’t make you any more or less credible as a leader, a businessperson, or a strategist. There are many ways to learn, and college is just one of them. So feel good about yourself, obtain as much experience as you can, and stay tuned for more tidbits of knowledge here on Dear Strategy!

Listen to the podcast episode
Dear Strategy: Episode 128

Are you interested in strategy workshops for your product managers or business leaders? If so, please be sure to visit Strategy Generation Company by clicking the link below:

Strategy Generation Company - Strategy Training and Inspiration

Bob Caporale - Host and Author of Dear Strategy Podcast and BlogBob Caporale is the founder of Strategy Generation Company, the author of Creative Strategy Generation and the host of the Dear Strategy podcast. You can learn more about his work by visiting

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