How Design Thinking Can Help You Ask the Right Questions (And Get the Right Answers) Addressing the right problems and coming up with the right solutions requires implementation of design-thinking practices.

By Dave Garrett

Opinions expressed by Entrepreneur contributors are their own.

Remember when Amazon was just the world's biggest bookseller? After broadening its products to include, well, everything and optimizing its fulfillment and delivery process in the late 1990s, Amazon became the world's biggest retailer.

And you may not be aware that the longtime children's plaything, Play-Doh, began its commercial life in the 1930s as an implement for removing coal residue from wallpaper. Another successful pivot, I'd say.

While some may say those evolutions were obvious, what is often overlooked is the detailed research, painstaking planning and nose-to-the-grindstone work behind the scenes that led to the decision and implementation of the pivot. In every case, these transformational changes could not be achieved without with asking all the right questions up front.

Asking the right questions requires building a diverse and highly competent team and employing one of the most vital techniques for managing any project: design thinking.

The power of the pivot

The design thinking concept has been a business staple for decades, but it has gained prominence in recent years as a powerful technique for organizations to deliver innovative solutions that please customers. It guides them to the truth quickly and hopefully faster than the competition.

Many successful entrepreneurs would say their most valuable resource is time. And it's true — in today's always-on, hyper-competitive business environment, time to market is critically important. The "new normal" of business is that "never normal" should be our guide; market conditions are constantly changing. Thus, business problems must be addressed right now, and design thinking provides a well-proven process for solving those conundrums, both pragmatically and creatively.

If you want to apply design thinking to your strategic planning process, here are a few key considerations to get you started:

Related: How Design Thinking Can Help Foster An Entrepreneurial Mindset

Does your value proposition match a 'must-have' customer need?

Are you producing the product or service you want or simply have offered in the past? Or the one that your targeted customer base demands? If it's the former, you're not on a pathway to sustainable (or growing) success.

Identify and understand your most important customer. If there are a bunch of them, focus most of your attention on one. Learn why they buy, what they're willing to pay, what value they see in the product and when they will see it (also known as the "buying trigger"). Keen analysis and design thinking will give you the insights to determine the leading (or lagging) indicators that drive purchase decisions.

Have you assembled a diverse team with the experiences and perspectives to identify all relevant challenges and opportunities?

Here, you are looking for diversity of thought and perspective — people who have applied wildly different "patterns" to similar problems. It's the only way you'll move from answering relatively simple questions ("Are we producing the right product for the customer?") to even more critical and potentially transformative questions ("Are we actually addressing the right customer?").

As new ideas emerge, design thinking will help you identify and refine your hypotheses so they can be tested and, ultimately, validated as the best answer for now. In today's never normal environment, it's not about the long-term solution; it's about a flexible stream of answers that, linked together, deliver long-term success.

Tap people for your team for their depth and breadth of demonstrated experience with experimentation, who have overcome barriers or stumbling blocks previously. Their experience and intuition will be valuable and hopefully complement your own on your journey to arriving at the best solution.

Related: How a Diverse Team Brings More Creativity and Engagement to Your Business

Can you embrace ambiguity?

Today's entrepreneurs need the resilience of yesterday's telemarketers. You need to know up-front that your life will be dominated by "structured learning through failure," ultimately leading to success. If you don't see failure as learning, you won't be around long enough to succeed.

Long gone are the days of planning schedules, be it annually or quarterly. In today's business environment, entrepreneurs must be constantly iterating. Fortunately, design thinking can help individuals who are taking on the risk of starting something from the ground up make decisions with incomplete facts and data at their disposal.

If you wait until you find the "perfect" solution, you'll never get the answer, and your business will never evolve. That's why it is so important to work with a diverse group of teammates collaboratively in order to unveil a broader set of pivot options. With a diverse team, you are better able to maximize the data you do have and then examine your options from every possible angle.

Related: Design Thinking Is Not A Process, It's A Mindset

Are you prepared to 'present and rebuild, present and rebuild again?'

It's important to have strong opinions, held loosely. Strong opinions help you drive forward. Holding them loosely allows you to pivot as the facts on the ground change. Design thinking isn't a one-and-done project. You're searching for the right answer for today's environment; it's unlikely it will be the right answer forever. So, you must exercise that agility muscle over and over; employ design thinking time after time by asking and answering the right questions through iterations and experiments. Times change, and your business must adapt. Design thinking is a sure-fire way to reduce the likelihood of being left in the dust.

Flexing your design thinking skills and embedding them into your strategic planning process gives you the tools to redefine how you work. Only by ensuring you ask the right questions can you tackle the right challenges and arrive at the right solutions to enhance the value you provide to your customers.

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Wavy Line
Dave Garrett

Project management expert and former entrepreneur

Dave Garrett is chief strategy and growth officer of Project Management Institute (PMI), the world’s leading association for project professionals. He was co-founder, president and CEO of, a community for project professionals established in 2000 and acquired by PMI in 2014.

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