Good Strategy Starts With Good Questions

Good Strategy Starts With Good Questions

Recently, I’ve been listening to several new podcasts and audio books. It’s amazing how much excellent content is out there, covering pretty much anything from business to meditation or even murder serials (if you’re into that).


One of my favorites right now is the Knowledge Project with Shane Parrish, who also writes the terrific Farnam Street blog. The Knowledge Project “explores how to better understand yourself, others, and the world around you, covering mental models, stories, and lessons that help you master the best of what other people already know.”


Another favorite podcast of mine is Masters of Scale hosted by Reid Hoffman, where Hoffman (co-founder of LinkedIn and partner at the venture capital firm Greylock Partners) and other hosts interview business leaders to craft very engaging stories that recount how successful companies have scaled from startup to multi-billion industry transformers.


Both podcasts share very insightful nuggets of wisdom on how people think — as business leaders and as consumers. In listening to both, I’ve come to realize how important it is to understand my own approach to thinking through problems and process. Putting these insights into practice has helped me to be more mindful of how everyone else processes and acts on new information — and how to adjust my approach accordingly.


I believe good strategy starts with good questions.

From this, I’ve developed a new point of view on strategy. I believe that good strategy starts with good questions. I have also learned that asking “why” and “what if” style questions can be great methods to paint crystal clear visions and motivate teams to step out of their comfort zone.


This is why one of my principles is to ask the right questions, and the hard questions.


The Power of Asking Better Questions

Simply asking better questions is one of the most efficient ways of generating better insights, upon which great ideas, products, experiences and strategies are built.

Think about it — getting better at critical inquiry really doesn’t cost you any more, nor does it take a great deal more time to practice. In fact, I would argue that when done effectively, asking good questions as part of a healthy business planning exercise can save any organization a lot of costly misfires down the road.

The art of socratic questioning is one of the essential tools in the toolbox of the strategic, first principles based, design-minded thinker. It helps us form more well rounded ideas informed by a wider diversity of thought. It brings us closer to the ‘truth’, while having to rely less upon faulty assumptions.

It inspires the exchange of ideas and furthers innovation. When done tactfully and with empathy, it can improve trust and morale.

Start With Why

One of my favorite questions to ask is why (or why not). Asking why is a great starting point for developing a strategy because the right answers help you clarify your vision and plan, which in turn helps the team get on the same page for smoother execution.

Products and projects tend to just drift along without a clear understanding of the bigger purpose of ‘why’ we’re doing what we intend to do.

By the way, the right answer usually isn’t to make more money – that’s more of an outcome of the real purpose.

In one of my favorite examples of how to do marketing right, Simon Sinek brilliantly explains the importance of starting with why in his Ted talk, “How Great Leaders Inspire Action,”which has since gotten over 45 millions views.


Ask why in the right way. Some people may get defensive about being asked why, and see it as questioning their credibility or approach. This is fair. In order to avoid this kind of response, it is important to ask “why” in the right way.


First, don’t make it personal. Keep it objective. It’s about the goal, not about the person or team.


Second, ask why in a positive, reinforcing way, vs. a criticizing way. This means not literally asking “why” all the time. For instance, you could challenge a prevailing point of view by asking, “have you considered another approach, such as..” , or “did you ever consider…”

Finally, be cognizant of your tone, in how you ask, or question others by asking why. Asking why should be meant to move people forward and bring them together onto the right path, rather than be perceived as pulling them back, or stopping them in their tracks.

Ask: What If?

Another of my favorite questions is “what if?” Asking what if is a great way to stimulate creative solutions to problems, or to break a team out of a cognitive logjam.

Use what-if style questions to help the team mentally simulate a desired future or scenario in vision setting. It’s also a great way to run a simulation before execution. This exercise basically follows the same rules of brainstorming – generate ideas while deferring judgement. The only limit is the team’s imagination.

Here are some example what-if questions:

  • What if we had ‘x’ vs. ‘y’
  • What if we did not have ‘x’
  • What if that had gone this way
  • What would be the doomsday scenario- what could go wrong?


How to Practice Asking Better Questions

In the HBR article, The Surprising Power of Questions, the authors assert that “questioning is a uniquely powerful tool for unlocking value in organizations.” Yet, it is all too common that executives aren’t provided much training in the art and science of good questioning.

I definitely agree that questioning is a learnable skill that can be improved through practice.

Ask why, what if, and how — in that order

In this article, innovation expert and questionologist Warren Berger explains how a sequential approach of asking 1.) Why, 2.) What if, then 3.) How has been central to the problem-solving process for many innovative companies including Netflix, Pandora, Square, Nest, and Airbnb. The article also presents actual examples of how these companies used this method to overcome challenges.

Ask Why Five Times

The 5 whys method originated in Japanese auto manufacturing and is now widely popular in design thinking. For instance, IDEO, is a big practitioner of the 5 whys methodology.

I have used the 5 whys method in much of my experience design and product strategy work. It’s actually quite simple, and can be an incredibly effective and versatile method to uncover root causes of problems, to dig deeper into underlying motivations in consumer behavior, or even to build collaboration or bring about creative solutions within teams. The 5 whys method doesn’t really require any sophisticated tools or documentation. It just requires an open-minded approach to problem solving, and benefits from the same rules as brainstorming.

Ask Better Questions to Set Better Goals

In the book, The Personal MBA, Josh Kaufman makes a great point about the motivational power of a clear vision and goal setting. Well formed goals excite and motivate people. It helps ‘paint’ a picture in their minds of what is to come, and helps them gain a better appreciation of why we are striving to get there.

The more specific and precise (non fuzzy) the goal, the easier it is to visualize and be excited about it. Fuzzy goals like “improve our online customer experience” don’t give your brain enough material to work with. Instead, a more specific, concrete goal such as “product description to purchase in 5 clicks or less,” or “purchase to shipment in 12 hours” is more easily simulated and planned into steps and sub goals. Once your mind makes a conscious decision to complete the goal, it starts to automatically simulate how to get it done.


Ask Proactive Questions (Pre-Mortem)

Proactive methods of inquiry such as the pre-mortem can help mitigate risk through imagining the potential hazards of failure. Too often, we look back on failed projects and ask ourselves, “what happened?” Many teams will do a post-mortem retrospective to piece together how things went wrong.

Post-mortems are certainly valuable to dissect what causes failures. But, why not do it proactively, before failures happen? A pre-mortem allows you to work backwards, and look at the individual factors that could lead to failure as well as the actions to take in order to pre-empt failure. Once you’ve identified these factors, you can start thinking about how to best avoid or mitigate these risks from occurring.

For instance, you could think upfront about what could go wrong with your product’s go-to-market strategy and the marketing channels that you’re looking to use. Or, you could begin to imagine what might happen if customers don’t respond to your product as expected.

Or, you could market test a new product with a small segment, then use those learnings to inform future pre-mortems before scaling.

Here are some good questions to ask during a pre-mortem.

  1. What would be the impact be if product messaging fails to resonate with your target audience?
  2. What if customers don’t want to pay for our product? What if we’re addressing the wrong customer segment? What if we’ve got customer needs wrong?
  3. What would happen if our technology program wasn’t adopted? Or, what would be the downstream risks of a data breach?
  4. What if our costs exceed budget halfway through the project?


Want Better Answers? Ask Better Questions.

It has been said, “If you want a dramatically better answer, the key is to ask a better question.” I couldn’t agree more. Look for opportunities to build your skill of inquiry into a habit. When someone comes to you with a problem, don’t immediately respond with an solution; instead reflect on the situation using questions to dive deeper.

Try this next time someone responds to your idea with a reason why it cannot work: first pause, and reflect on the situation. Then respond with a thoughtful question or two that moves you both to a reasonable solution. Ask the kinds of questions that will spark more creativity among the team, and that will unlock new insights.

The best questions can help you reframe problems in unexpected ways. They also encourage fresh viewpoints and diversity of thought which leads to better solutions. Finally, well crafted questions have the power to inspire the exchange of ideas and fuel innovation.

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