Hustle, Planning & Strategy

Get off the sales hamster wheel, and start getting strategic

Do you love podcasts? For me, they have become a great way to learn on the go, whether in my car or while out hiking. One pro tip however, I speed up the playback by 1.5x so I can get through episodes faster.

I have a bunch of regular podcasts that I always tune into. One of those is NPR’s Planet Money, which hit my sweet spot for entertaining and informative. What makes the podcast so compelling is it is not just about bland economics, for example this one episode I listened to recently talked about baseball, food vendors, and sales.

Food vendors do not get much attention. You go to a game, the vendors hawk their wares up and down the stands, and you grab a hot dog or beer or some peanuts. Beyond the game time theatrics of slinging food and drinks though is an interesting case study in what it takes to be an effective salesperson.

In the episode, they feature one of the stars of the food hawking world, Jose. He typifies what makes an effective salesperson. Many would call it his hustle and stop right there, but hustle only gets you so far. As my friend Keenan says,

“I don’t care how hard you hustle or grind. If you’re working on the wrong shit, it doesn’t matter.”

Hustle does matter. Jose is owning the stands, moving quickly, spotting opportunities, and is the last person working each day. When most people would call it an early night because of weather or lack of sales, he is willing to put in the work. That partly explains how he has been the top salesperson for the past several years, even though he does not get the premium goods to sell (namely beer).

Before the hustle though comes two critical elements for success: strategy and planning. As I mentioned in the previous post on trying easier instead of harder, grit and hustle are incredibly important life traits. But sales is a profession that can chew you up if do not focus your efforts and switch from low-impact to high-impact activities.

Let’s start with planning. All the hustle in the world does little good if you got no game. And by game, I mean the simple act of planning your effort so you can reduce the amount of work you do. It about doing the right stuff, not just doing any stuff that comes to mind.

Planning is not that hard. But instead of planning, we procrastinate and refuse to spend the time upfront to figure out exactly what we are going to do. We just plow ahead without so much as a thought. Thinking is the critical ingredient when it comes to complex sales and executive relationship building. It is also what is often missing because many reps rarely  take the time to plan anything.

Jose had a plan, based on the weather, the game, and data from previous sales. He knew exactly what to expect because he walked into work with a plan in mind. He also made sure to record his past sales efforts so he can understand what worked and what did not work.

How often do we find ourselves doing the same dumb things over and over again just because “that’s how we’ve always done it.” A well-known quote often misattributed to Albert Einstein, but is still relevant is:

“Insanity is doing the same thing over and over again and expecting different results.”

When we do not plan, expected insanity to ensue.

Along with planning, you need a strategy. This is often not a strong suit for salespeople, many of whom are more oriented to action and tactics. Again though, strategy is a critical thinking exercise that helps us to reduce wasted effort and focus on things that work. Applying strategy is also how we overcome the potential pitfalls in our plan.

Sales is often an “in the moment” activity. That means we are reacting to and proactively positioning in the context of engaging with customers and prospects to introduce our solution. As a once great boxer said, all the planning in the world does not matter once you get punched in the face. So think of your plan as what you think will happen, but consider your strategy as what helps you navigate when the plan goes sideways.

You may object and call that execution. However, what is guiding the action and tactics you are using? Strategy is what drives execution, and it is the foundation for our actions. If execution is our "what", and planning is our "how", strategy is our "why". From the "why" derives all of the tactics and methods and tools we need to accomplish our goals.


Jose had a strategy. In the moment of “The Pick” where all the vendors choose the items that will be sold in the park that evening, he knows who picked what and where they will be selling. He uses his experience to adjust his plan so that he chooses the optimal product and location for the game based on the competitive situation and the market conditions.

Many would look at food vendor sales as something not all that complex. While it may not rise to the level of complexity of enterprise software sales, you can see what planning, strategy, and hustle can produce. Particularly with a commodity item and many options in the stadium, a little planning and strategy goes a long way towards winning.

Just think of what a little bit of planning and a strategy can do for your sales. My guess is adding these core elements to your selling efforts will make your life a whole lot easier. Whatever can make your hustle more manageable and leads to better sales results is something worth considering.

What will you change up today in your sales planning and strategy setting?

Mark Birch, Founder of Enterprise Sales Forum

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