Is Your Strategy Useful?

Mar 27, 2022

I get paid to deliver strategy. These requests come through telephone calls or casual lunches or formal whiteboard sessions with business owners, entrepreneurs, or senior leaders, but the assignment is always the same: come in, analyze a situation, and provide useful information that will either reverse downward trends or accelerate improvement.

It’s always helpful to get an outside perspective. You’re simply too close to your business or organization or project, and outside help in strategic thinking can help you recognize holes and blind spots.

But not all strategy is equal.

There is a massive difference in strategy and useful strategy. And that one little word—useful—makes all the difference.

It’s the difference between a wheelbarrow of information being dumped on your head and spreading out the same material on the ground to fertilize growth. In other words, it’s not about volume and force.

As the name suggests, useful strategy is advice you can actually use. It comes in a form you can comprehend and provides benefits that are real.

And in my experience, three traits make the difference. These three traits can transform strategy into useful strategy: trust, context, and subject matter depth.


A while back, I was having dinner with a high-level businessman from Florida. He wanted to engineer his business to the next level, and we were talking corporate strategy.

I could have listened for 30 minutes and started spouting off case studies, best practices, and Harvard Business Review articles.

Instead, I listened a bit longer, asked more questions, shared some stories from my own past, and actually cared for the man.

Gradually, he began to let his guard down and to share the depth and breadth of his world hidden behind the first layer of information. Mixed up in the question of growth is the complicated friendship/working relationship he has with a partner and investor. Oh, and he is exhausted from being the lead duck flying against the headwinds with no one to pass the head spot to.

With this information, my strategy morphed from quick judgment (Why are you moving so slow?) to a nuanced strategy that took into account both the bottom line and the personal relationships.

My strategy offering was better and he was more likely to accept it because we had started building the foundation of trust.

There was transparency and honesty going both ways, and because of it, the strategy we decided upon became far more useful.


In coaching, executives are often looking for a quick answer. How do I reverse downward sales figures? Who should I add to my board? When should I transition leadership? Should I upgrade my leadership team?

As a coach, however, the more I can understand the context, the better my answer will be.  So if I have an hour to spend, I’ll usually take 30-45 minutes trying to understand the context before we begin to work together to diagram a solution.

Michael Porter is one of the legends of strategy, and in this interview he talks about the factors that undermine strategy.

Interestingly, he is almost unable to draw conclusions because so many factors can trip up companies and strategies. It’s not simply about the competition or the organizational processes. You have to know the business, the market, the people, and much more. You have to understand the context.

Compare it to basketball. Tie game. 20 seconds left. You’ve got one possession. You call a timeout and the guys come over, looking for the play from you, the coach.

You’ve got a couple of tried-and-true plays you could call. They might work. But good coaching considers the context. Who’s got the hot hand? How many fouls does the other team have? Where do you have a size advantage?

As a coach, if you consider the context you will vastly improve your chances for success. As a client, look for coaches who give custom insights, not generic ones. And that takes a skilled and proven active listener.

Subject Matter Depth

If you’re looking for an executive coach, there is a huge difference between someone learning it on the fly and someone who has learned from experience. One spent an hour on Google; the other spent years making mistakes and tasting victory.

Either one is willing to share their learning with you. Which teacher would you rather learn from?

No one has subject matter depth on everything, but if I have layers of experience and scars and wounds, my strategy is far more likely to be useful than what the Wikipedia expert brings. There are three reasons for this advantage:

  • Agility—“I’ve seen it before, so I can adjust to a variety of different challenges.”
  • Confidence—“I’ve seen it before, so I know what works and what doesn’t.”
  • Understanding—“I’ve done it myself, so I know this isn’t a game. There’s blood, sweat, and tears here.”

Over the years, I’ve owned a variety of different companies. Sometimes I’ve done well and other times we haven’t. I’m pretty quick, however, to use examples from both categories so that my clients know that I’m not just guessing here.

My strategy isn’t just something I’m making up. It’s something I’ve used (and am using) myself. Or it’s things I have watched and learned from friends along the way.


Winston Churchill said, “However beautiful the strategy, you should occasionally look at the results.”

It’s easy to make strategy sound profound but much more difficult to make it actually useful.

If you’re in the strategy business, improving in these three areas—trust, context, and subject matter depth—will transform the advice you give. If you’re looking for strategy, finding help in these three areas makes all the difference.

And at the end of the day, in general, you’ll know whether the strategy you’re getting is good or not.  How can you tell? You won’t have to convince yourself that useful strategy is useful. You’re already using it.

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