What The Word “Strategy” Really Means


For many companies today, the term strategy seems to have gotten watered down, or even worse, become a four-letter word. As if, somehow, strategy is a bad thing.

The Evolution Of The Word “Strategy”

We hear comments such as, “I don’t want to get too hung up on strategy–we need to get something done.” Or, “I can’t afford to slow down and take a step back. This plane’s already in the air.”

This is especially true in the technology space. No doubt, technology can be expensive. But it’s even more expensive when you take the ‘shoot, ready, aim’ approach to decision-making.

Strategy is not answering the how questions. That’s tactics. Strategy is asking the ‘what would it look like if?’ questions. The ‘why should we?’ questions, and the ‘what about this vs. that?’ questions. These are critical to competitive advantage, meeting customer expectations and relevancy in a constantly changing market, and they apply to any size business.

For a small or growing mid-market company, however, it’s even more important. Strategy is about having a plan and working the plan. As expensive as technology is for small businesses, it’s even more expensive when you have to do it twice, because you didn’t plan well the first time.

How Strategy Should Be Defined

A few years back, we made recommendations to a client, some of which they accepted and others they didn’t. They didn’t go with one of our software recommendations, and instead decided to go it alone in another direction. The client called me the other day to ask if we could reengage. They had purchased software that a vendor claimed was what they needed. The final price tag was well into six figures, but worse yet, it wasn’t working for them. They needed to start over.

They asked if we could help them get them back on the right track. Our approach, as always, is to begin with a modest strategic review to understand their situation, options and current state, and make a series of recommendations for moving forward. The CEO decided not to do a strategic review. He said his advisors were telling him that he shouldn’t have to spend money to tell him what he already knew, and that he didn’t have the budget to ‘take a step back’ at this point, given that he was already almost $200,000 in the hole.

Cash is sometimes tight for growing companies, so the dilemma is real. But for business owners and CEOs thinking they’re too small to be strategic, or can’t afford to take a step back — think again. Do it right the first time, and you won’t have to do it again.

Carpenters get it right with the adage, “Measure twice, cut once.” With the stakes (and dollars) as high as they are for many businesses today, it’s worth taking a step back to ensure you have a strategy and a plan for how technology, or any significant investment, is going to help your company. The alternative is often a never-ending cycle of spending and chasing magic bullet solutions.


What is strategy? Simply, it’s asking ‘what if’ or ‘why,’ before asking ‘how.’ It’s planning, then doing. It’s ready, aim, then fire.  And in the costly and complex world of technology, it can save a lot of money in the long run.


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