How to Think Strategically, By Asking Yourself Questions

think strategically

As small business owners we’re great at many things, but strategy is usually not our strong suit.

Early on in my marketing career, I was struggling with a strategic issue and my supervisor told me I needed to “think more deeply.”  That didn’t help one bit.

In the small business world, we tend to operate in a “ready, fire, aim” way. And that’s ok, that’s what gets stuff done. That’s where a lot of innovation comes from. That’s why small businesses can be nimble and solve real-life problems faster than big businesses and that’s what moves our economy forward.

But, the transition from small business to sustainable company requires strategy.

As I’ve worked with many different small business owners, I’ve developed a few processes to make this “deep thinking” process a bit more tangible and more importantly, more doable.

First, An Analogy

Let’s say we were going to build a 10 story building. We first need an architect to draft the blueprint. Then we have a project plan. Prep the ground. Bring in utilities. Lay the foundation. Put up a frame and then plumbing and electricity. Lastly, we finish with sheetrock, paint, etc. That’s the rough idea (clearly, I’m not a builder).

But, what would happen if we tried to install the electricity before the frame was up?

We’d end up with a tangled pile of wires. That’s also what happens when entrepreneurs fly at 100 mph “getting stuff done.” It works. But only to a point.

So, how do we replicate that logical process in our business? How do we get from point A to point B?

That’s a little to vague for most people. So, a slight alteration of the question does the trick:

  • How do we turn a site visitor into a newsletter subscriber?
  • How do we turn a newsletter subscriber into a happy customer?
  • How do we turn a happy customer into a raving fan that refers us?
  • How do we get happy customers to buy more?

How to Think Strategically

Its all about moving a person from where they’re at to where they need to be. Particularly in the marketing world, this has a lot to do with what’s going on in your customers mind and emotions. What emotions does my prospect need to feel in order to justify purchasing my product? Once you’ve identified the pre-purchase state, you can work backwards to create it.

Let’s look at an example. Suppose we sell hiking boots. Here’s how we attack it.

How do we get an average person to purchase hiking boots? In order words, what is the mental state of someone who makes a purchase of hiking boots?

  • First: They must have a need (we need to get them to plan a hike or a camping trip).
  • Second: They must agree that their existing solutions are not adequate for their upcoming trip.
  • Third: They must be able to justify the cost of new boots.
  • Fourth: They must agree that our boots are better than the competition.

Ok, now that we’ve outlined the purchasing state, we must put a plan in place to create that state:

Depending on your business, you may use different media to do this. Some may use one video that walks prospects down this path. Others may use an email series. Others may use a webinar or hangout. That’s another strategic question for you. In order to get prospects from point A to point B, which medium will most easily get them there?

In this example we’ll use an email series:

  • Email 1: Tell about a local hike. Show pictures. Include testimonials from local people talking about how amazing the hike was, how refreshed they felt afterwards, and how much it helped them “clear their head.” Use whatever benefits your prospects need – the goal is to get them to desire and plan that hike.
  • Email 2: Write a review of “hiking shoes.” Include tennis shoes for neighborhood hikes on a sidewalk, cross-trainers for mild dirt roads and hiking boots for strenuous, yet rewarding hikes like the one mentioned in email 1.
  • Email 3: Write about the “cost” of using the wrong equipment. Tennis shoes will wear out 3 times as fast (costing you more) and they don’t support the ankles (therefore costing you more if you get a sprain). Show how a good pair of boots will last years and protect the wearer.
  • Email 4: Write a review of different hiking boots, highlighting the benefits of your boots. Include an offer.
  • Email 5: Stronger offer. Include an expiration date. Remind the prospects of how wonderful it is to go hiking (revive the feelings from email 1). Give a discount or offer bonuses to get people to act now. They just need to justify the purchase now.

Ask Yourself

This is a very simple example. But you can see how asking the right questions in the beginning helps us to frame out the email sequence in a logical way that is both educational and gets the sales job done. It sure beats writing a bunch of emails and hoping they work (just like wiring the building prematurely and then hoping the lights turn on).

In every situation, ask yourself how to get from point A to point B. Here are a few strategic questions every business owner should be asking:

  • How do I get my prospects to choose me over my competitors?
  • How do I turn purchasers into raving fans?
  • How do I turn raving fans into referral machines?

If you can answer those questions with well thought-out plans, you’ll be strategically moving your company from where you are to where you want to be.

Camping Photo via Shutterstock


Tyler Garns Tyler Garns, Business & Marketing Strategist at Tyler Garns Marketing LLC, has over 10 years of experience in the field and is a recognized expert in Internet marketing. Tyler specializes in building "done-for-you" campaigns. You can follow him on the Tyler Garns Blog.

8 Reactions
  1. Hi Tyler,

    I like what you’ve written about a pre-purchase state. So true. This especially resonated: “What emotions does my prospect need to feel in order to justify purchasing my product?”

    To me this is about a well-defined storyline told over time. It’s what great bloggers (and great companies) do and it’s what brings out emotion. If you deliver a consistent, engaging, honest, and helpful narrative with a specific message (a core mssg – your essence) and a key audience in mind, you’ll blast past the competition.

  2. Good articles, this reminds of a lesson from school that when looking for a solution don’t try to fine the right answers asks the right questions first.

  3. Nice analogy with the hiking boots and resonates well with how to think strategically. It is applicable not only for business but also for our daily lives as we go through challenges.

  4. Asking questions to yourself is pretty effective in terms of developing strategies because you can organize your thoughts more clearly. Breaking down your thoughts into a certain structure can bring the answers to you far quicker than you can imagine.

  5. While I like planning because it is simply indispensable to any business, I think trying things out and failing is better. At least that’s how I learned it. You’ll never really see how things will turn out unless you run it. From there, you’ll see how a customer becomes a subscriber and so on.