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Business Insights from Andrea Hill

Use your list-making skills for strategic thinking, to create new things to think about.

Use a List to Jumpstart Strategic Thinking

Originally Published: 05 June 2015
Last Updated: 26 October 2020

Software & Service Links

The links below are for services offered by Andrea Hill's companies (StrategyWerx, Werx.Marketing, MentorWerx, ProsperWerx), or for affiliate offers for which we may receive a commission or goods for referrals. We only offer recommendations for programs and services we truly believe in at the Werx Brands. If we're recommending it, we're using it.

You find yourself with an extra half hour at your desk and you know you should spend some quality time getting the view from above the forest, thinking about your business. But you don’t know where to start. You sit there, thinking about thinking, and a feeling of dread hits you.

Don’t despair, you're quite capable of strategic thinking. You just don't know how to get started. That’s when it’s time to make a list.

Oh, now you’re excited! You know how to make a list. But before you start, listen up. This is not a to-do list. If you write a to-do list, you’ll be back among the trees. Use your list-making skills to create new things to think about.

Start with Big Questions

This type of list starts with a question. Here are some really good ones (there are dozens more):

  1. Why do my customers buy from me?
  2. Where else do my customers spend their money?
  3. If I could do anything at all with my business, what would I do?
  4. What questions do I have about running a business (that are still unanswered)?
  5. What mistakes have we made in the past six months?
  6. What questions do our customers regularly ask us?
  7. What would I like our website to do that it isn’t doing yet?
  8. What do I wish my employees knew or could do better?
  9. Why do my customers buy from my competitors?

When you ask yourself a question, you immediately engage your brain. It will leap at the opportunity to go into solution mode. Instant strategic thinking! In this brainstorming phase, just write answers to your question as fast as they come to you. Don’t question or challenge any of the things you think of – just go with the flow until you find yourself slowing down.

Next, review each item on your list and think about whether or not it suggests an additional item or two. This takes you to a deeper level of thinking and will yield a few more items to put on your list.

Examine Each Item Closely

Now concentrate on each item on the list. Think carefully about what you could do to better understand, solve, improve, address, or build upon each of the items. This type of thinking is also strategic, taking you out of brainstorming and into problem solving. You don’t have to have all the answers to each item yet; you just need to identify what you can do to get answers, or what steps you must take to better understand something.


Last, prioritize your list. Some of the answers from your initial brainstorming will be much more important than others, so they should go at the top of your priority list. You may even find a few that have little or no value, so feel free to erase them entirely.

What do you have now? A to-do list. But it’s a strategic to-do list, designed to help you focus on things that have real impact on your business success. Spend the next several days, weeks, or even months working through the items on your strategic list.

And next time, don’t wait for a surprise opening in your schedule. Schedule time in your calendar to think strategically about your business at least once each month (I prefer weekly). Now that you know what to do with that time, you’re bound to come up with some exciting plans and changes that will take your business to the next level.