Why Leaders Need to Embrace Blue Sky Thinking

Charlie @ Worksoul
6 min readNov 3, 2023

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Pie in the Sky Ideas Drive Long-Term Business Success

When you stop dreaming, you stop growing.

Innovative companies like Airbnb, Uber, Netflix — why were they successful? Because their disruption completely changed how we view their industries.

But as that innovation has subsided, what are we left with? Often times, we are left with products that aren’t that much better than the predecessor companies they disrupted in the first place.

The dream of cutting cable for streaming content has just led to the need to buy cable all over again, but our channels are just being called something else. Fees, poor hospitality, and safety fears are driving customers back to hotels in droves.

The kicker? As companies go from innovative startups to board-managed, publicly traded companies, innovation almost always dies with it. We are so focused on maintaining our grasp on current customers, that we lost sight of what got our business there in the first place — pie in the sky ideas that are laser focused on solving consumer challenges!

Innovation and creativity are essential for business success. When you stop investing in new ideas, you open up the door for the disrupters of the future to take your spot and push you out.

Yet many leaders dismiss ideas that seem unrealistic or far-fetched, sticking only to safe, incremental improvements. While pragmatism is important, the most transformative innovations often start as pie in the sky visions.

That is why, when working with organizations, I start with a simple question: “If everything goes your way, what does your perfect future look like?”

If you can’t describe your vision for the future in a perfect world, you are already behind, operating in a world of constraints that upstart companies won’t hold themselves to.

Get rid of the constraints, and build your vision for the future with a blue sky mentality.

What is Blue Sky Thinking?

Blue sky thinking refers to the open, creative process of generating visionary, imaginative ideas without concern for current constraints. It’s about thinking big and outside the box. Blue sky thinking allows people to detach from limiting views and expand their perspectives. The term evokes images of cloudless blue horizons, symbolizing the freedom to imagine and reimagine without boundaries.

What I believe is that, by proper effort, we make the future almost anything we want to make it.” -Charles Kettering

People sometimes use the phrase ‘pie in the sky’ dismissively, to criticize ideas as fanciful or unrealistic. But ironically, many innovations that once seemed like pie in the sky became reality through determined work and creative problem solving. Blue sky thinking supplies the vision, while pragmatic planning turns vision into action.

Will we always be able to realize the vision we come up with in this scenario? Of course not! But when you set that vision, you can better understand the constraints, both current and future, that are blocking your path instead of having those constraints limit your ability to think like a visionary all together.

Why Do I Make My Executives Practice Blue Sky Thinking?

At the end of the day, if my executives can’t dream of their perfect-world future, their people are also falling behind in knowing how their day-to-day execution not only impacts current strategy, but long-term goals and objectives!

When we ask, “wouldn’t it be great if…..” questions, we then get to ask, “Well, why can’t we?”

Overall, this type of thinking:

  • Stimulates creativity and big picture thinking. Removing constraints encourages people to expand their perspectives, leading to innovative insights.
  • Allows free exploration of possibilities. When you temporarily suspend judgement in the blue sky phase, people feel comfortable sharing unconventional ideas that could spark breakthroughs.
  • Creates space for vision. Blue sky thinking lets you envision an aspirational future, energizing people around audacious goals. Vivid visions will then guide strategy and decision-making.
  • Reveals new growth opportunities. Exploring ideas without limits can uncover hidden opportunities for creating value and expanding capabilities.
  • Inspires passion and optimism. Possibilities that once seemed remote can ignite people’s imaginations and hopes, fueling enthusiasm.

While too much blue sky thinking without connection to reality can be counterproductive, as a starting point it offers valuable creative freedom.

Going from Pie in the Sky to Action

We’ve removed the constraints on our thinking and have some new innovative ideas and a stronger vision for our future. Now what?

Blue sky thinking is just the start. The businesses and leaders that can take those ideas and action them are the ones that will win and build incredible solutions in the process.

Processing your vision is what sets people apart. How can you do this?

1. Articulate the Vision

Begin with a clear and compelling articulation of the idea. This means taking the time to fully describe the vision, no matter how bold or far-reaching it may be. Make sure it is documented in a way that is understandable and inspiring to all stakeholders involved.

2. Break Down Your Vision

Deconstruct the vision into its core components. What are the essential elements that make up this idea? By breaking it down, you can start to see which parts of the vision are the most crucial and which are supportive or supplementary.

3. Quantify and Qualify Constraints

Conduct a feasibility review to evaluate the practical aspects of the idea. This includes resource allocation, market analysis, technical requirements, and potential roadblocks. A thorough understanding of these factors is essential for turning an idea into reality. While we want to remove constraints through ideation, now is the time to really say, “what stops this idea from being possible right now?”

4. Establish Actionable Milestones

Once the vision is broken down and understood in parts, establish key milestones. These milestones should represent significant progress points on the journey to achieving the overall goal. They should be measurable, attainable, and tied to a timeline. For each milestone, determine the specific steps needed to reach it. This translates high-level objectives into more manageable, operational tasks that can be assigned and tracked.

5. Pick Your First Step

Time for action. Start small, but start moving and testing your vision. The sooner we start building, the better we can refine the idea and can help to demonstrate the concept’s viability.

6. Feedback Loops

Deliver early and often and gather and integrate feedback as you go. You probably won’t end up where you thought you would, but integrating feedback can mean ending up somewhere better.

7. Review and Revise

Your vision isn’t a set and forget activity. As we build, we can’t lose sight of it and as we learn new things, we can reflect and adjust. Remember, this is an exercise in dreaming, so as you get closer to your vision, never stop dreaming bigger.

Guiding Blue Sky Thinking in Your Organization

To master blue sky thinking, leaders should guide ideation and development processes. Useful approaches include:

  • Set regular blue sky sessions. Schedule time for unconstrained ideation, removing organizational barriers. Make it fun and stimulating.
  • Create safe spaces. Establish trust and psychological safety so people feel comfortable sharing unconventional ideas freely.
  • Offer thought catalysts. Introduce diverse stimuli like new technology demonstrations, customer trend reports, and perspectives from other industries to trigger fresh thinking.
  • Foster diversity. Enable groups with diverse thinking styles, backgrounds and expertise to ideate together. Cross-pollinate ideas across silos.
  • Reward experimentation. Flip the typical penalty for failure mindset. Reward small experiments and celebrate lessons learned.

Leadership will show the organization what appetite they have for innovation. If you lead the charge and show the benefits, your people will buy-in and follow.

Conclusion

The real power of blue sky thinking is its ability to make us reconsider our limitations. It encourages a form of leadership that’s both visionary and grounded, capable of dreaming big while also meticulously planning for those dreams to take flight. As leaders, the sky isn’t our limit; our willingness to dream and adapt defines our boundaries. So go ahead, start dreaming!

Recommended Further Reading:

  1. “Thinking, Fast and Slow” by Daniel Kahneman — For insights into the psychology of decision-making.
  2. “The Lean Startup” by Eric Ries — To understand how to convert blue-sky ideas into practical business models.

Reflection Questions:

  1. How often do you engage in blue-sky thinking in your organization?
  2. What systems do you have in place to evaluate and implement blue-sky ideas?
  3. How can you cultivate a culture that encourages creative thinking without losing sight of practical limitations?
  4. Can you recall an instance where a pie-in-the-sky idea led to a successful innovation? What can you learn from that experience?

About Worksoul

At Worksoul, our mission is to revolutionize the workplace experience by fostering compassionate and effective leadership, nurturing personal and professional growth, and cultivating a harmonious balance between work and happiness. Follow and check out our newsletter for more!

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Charlie @ Worksoul

Exploring ways of empowering professionals to thrive and find better ways to work @Worksoulco . Bridging the gap between achievement and happiness!