The Advisor

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Why "Why" Is the Most Important Question We Should Ask Ourselves in Business & Life

Updated: Sep 10, 2018

By Mica McCurdy, FreeForm Events


Strategic thinking is applying a process to achieve an outcome. You do it all the time! You’re probably doing it right now, as you read this magazine seeking to build your skills and improve your business. The challenge is to get into a routine of applying strategic thinking skills when day-to-day life takes over and our critical thinking time takes a back-seat role. When we don’t practise this routine, there’s no critical thought to ensure we’re still moving on the right path to reach a goal—or maybe there isn’t a path or a defined goal at all!


Simon Sinek’s “Golden Circle” is a simple, effective process that we at FreeForm have adapted and now live by. It’s just three steps, each a straightforward question, to apply strategy to nearly anything.


First: ask “Why?” Why do I do this work? Why did I start this business? Why did I take this contract, buy this Costco membership, or get Tinder? “Why?” is the powerhouse question that centres everything we do. The goal is to get to the heart of the matter. I like to channel my inner three-year-old when working through this process, first asking “Why?” and then asking it three more times. In strategic thinking, answering “Why?” doesn’t need to be a big, future-thinking endeavour; it just needs to be honest and specific.


For example:

Why a Costco membership? Why do I pay money to shop at an industrial grocery store? Well, I want fresh, affordable produce. Why? I like food, and I like saving money when shopping for food. Why? I want to eat healthily on a budget.


Second: ask “How?” How are you going to make it happen? This question is all about methodology and operationalizing your “Why?” It also helps to reveal the challenges you might experience by highlighting the difference between what you could be doing and what you are doing. This question is process-oriented and helps guide the intention of your decision, question, or challenge.


For example:

So how do I do that? I define what healthy means and what my budget is. Right now, I grocery shop weekly and eat vegetarian (with some occasional fish), though I find I spend more money on groceries than I’d like to and end up buying things I don’t use or eat right away. Instead, I could shop biweekly and budget for groceries on a monthly basis, rather than weekly. To better manage how much food I buy and how healthy it is, I can use a vegetarian meal planning guide.


Last: ask “What?” What is it that you need to do now? What are your options? What are the next steps? This question is concrete and definitive. It’s a good opportunity to make a list of to do’s or capture pros and cons. As the final step, it helps hone your original question to something concrete and actionable.


For example:

What now? I revise my budget and write a grocery list. I research which store has the best prices for the majority of the things on my list, and plan to shop there for this two-week cycle.


Here’s the thing—when you routinely ask “Why?”, you are more aligned with your purpose and you improve your ability to navigate change deftly. Strategic thinking is necessary when you make budget cuts or hiring decisions, when you’re deciding to take a contract with a new client, or when you’re going back to start work with an old one. You do this when you’re grocery shopping after a long day at work and when your child asks if they can sign up for a new sport. In a time when the answers to self/business improvement are so heavily commercialized, it’s easy to forget that we have the skills within ourselves to navigate ruts, confusion, and difficult situations, or just to make a darn decision.


So stop, evaluate, and listen. Take a moment to run through the why, how, and what (always in that order!), and give yourself an opportunity to evaluate the situation and listen to your intuition. Strategic thinking is really just taking the time to stop and think.



Mica McCurdy, FreeForm Events

Mica is co-founder of FreeForm Events, and has worked with non-profit and for-profit teams. FreeForm Events is a full-service event and facilitation company based in St. John’s, Newfoundland. With clients from across Canada, we work in leadership development, workshop creation and facilitation, youth engagement program design, environmental justice conference management, and numerous strategic planning processes. In everything we do, we strive for fun, engaging, and participatory work that is grounded in social justice and builds the community’s capacity.