Search

Menu
Scroll to Explore
Drag

Asking the Right Questions for Meaningful Change

Article by Doug Von Feldt
April 29, 2025
Learn how to arrive at meaningful insights that will shape your organization for the better.

In Douglas Adams’ The Hitchhiker’s Guide to the Galaxy, the super-computer Deep Thought famously concludes that the answer to the “Ultimate Question of Life, the Universe, and Everything” is 42. This result, though mathematically correct by Deep Thought’s calculations, proves unhelpful and somewhat anticlimactic. Why? Because the pan-dimensional, hyper-intelligent beings who commissioned the question (the ones often masquerading as lab mice) never took the time to properly define what they were asking in the first place.

As a result, Deep Thought proposes the creation of an even more powerful computer—Earth itself—to determine the Ultimate Question. Tragically, the planet is obliterated by Vogons before it can finish this monumental computation. This ironic twist highlights a very real organizational challenge: the significance of having clarity around the questions we ask. If we haven’t fully fleshed out the exact query, even the most brilliant answer can land with an unceremonious thud.

When we embark on an organization design project, we risk falling into the same trap as the cosmic philosophers who built Deep Thought. We might form a project team, gather troves of data, conduct countless interviews, and draft well-intentioned plans—only to realize the initial question was ill-defined. If our “Ultimate Question” about how best to design or redesign the organization isn’t precise, the answers we gather may fail to address our real needs.

Below, we explore how to ask the right questions during an organization design project. By applying the metaphor of Deep Thought and 42, we can avoid the fate of receiving correct-yet-useless answers and instead get to meaningful insights that truly shape our organizations for the better.

1. Clarify the Purpose Behind the Question

Before gathering data, drafting process flows, or redrawing org charts, pause to understand why you’re seeking answers in the first place. Just like Deep Thought’s creators, you need to define the driving forces behind your inquiry.

  • Identify Desired Outcomes: Are you aiming to improve efficiency? Enhance employee engagement? Scale growth? Knowing the desired end-state shapes the context of your questions.
  • Align with Stakeholders: Communicate with the key sponsors, leadership, and team members. Make sure everyone understands what the project is trying to accomplish and why it matters.

If the bigger “why” remains murky, you may only arrive at partial truths or misaligned solutions—much like producing a singular, uncontextualized number: 42.

2. Ground Yourself in Organizational Realities

As Earth was meant to be a living, breathing super-computer gathering data from its inhabitants over millions of years, your organization design questions also need to be rooted in real-world observations. Organizational culture, market conditions, and existing processes all provide critical context.

  • Review Historical Data: Take stock of lessons learned from past reorganizations or structural changes. This historical perspective can keep you from repeating mistakes.
  • Conduct Interviews and Surveys: Engage employees at various levels to capture a full-spectrum view of what’s really going on. Often, frontline staff can spot inefficiencies or cultural pain points faster than leadership.

Without these grounded insights, your questions risk floating in the abstract—impressive yet disconnected from day-to-day realities.

3. Formulate Clear, Open-Ended Questions

Deep Thought’s creators fell short by not articulating their question beyond a nebulous pursuit of “the meaning of life.” In the realm of organization design, vagueness can similarly lead to broad, unproductive inquiries.

  • Use Open-Ended Formats: Instead of asking “Is our current structure good?” try “What do you see as the strengths and weaknesses of our current structure?” This invites reflection rather than a simple yes/no answer.
  • Focus on the ‘What’ and ‘How’: Questions like “How can we improve cross-team collaboration?” or “What changes would most help us deliver value to customers?” can reveal deeper insights.
  • Avoid Overcomplication: A well-defined, straightforward query that sparks meaningful dialogue is far more valuable than an overly complex or jargon-heavy one.

When questions are stated clearly, your team is much more likely to produce actionable answers rather than cryptic numbers or simplistic solutions.

4. Challenge Assumptions and Biases

Even the most carefully constructed questions can carry hidden assumptions. In many organization design projects, teams unintentionally assume certain structures, processes, or technologies must remain in place, limiting their creative thinking.

  • Play the ‘Devil’s Advocate’: Occasionally question your baseline assumptions. “What if we dismantled our traditional hierarchy?” can sometimes lead to more innovative designs.
  • Seek External Perspectives: Consultants, peer companies, or even new hires can provide fresh eyes. External vantage points can expose long-standing blind spots.
  • Use Data Thoughtfully: Data can anchor your team’s assumptions in evidence. But be cautious—over-reliance on certain metrics can skew your outlook if you aren’t considering all angles.

Much like the intergalactic travelers in Douglas Adams’ story, being open to unexpected questions can unearth surprising answers.

5. Involve the Right People

Vogons aside, any major organizational change must have buy-in from a wide range of stakeholders. If the “mice” in your organization (senior leadership) commission the project without properly involving middle managers, frontline employees, or cross-departmental teams, you’ll likely end up with incomplete data.

  • Create Collaborative Forums: Workshops, focus groups, or virtual roundtables foster inclusive dialogues about potential improvements.
  • Empower Diverse Voices: Be intentional about inviting people from varied departments, backgrounds, and seniority levels. Diversity of thought leads to richer questions.
  • Encourage Ongoing Communication: Keep feedback loops open. Your project team should remain agile, refining questions as new insights surface.

Just as Earth was designed to factor in the experiences of every being on the planet, a well-run organization design effort taps into the collective intelligence of its entire workforce.

6. Iterate and Refine

One of the most valuable lessons from Deep Thought’s saga is that complex problems can’t be solved in one sitting. The question “What is the meaning of life?” required millions of years of computation, and in our more mundane world of organization design, you’ll similarly need iteration.

  • Conduct Regular Check-Ins: Meet frequently with your project team to share progress, validate initial assumptions, and refine questions that might be too broad or too narrow.
  • Pilot Changes Where Possible: Before overhauling the whole organizational structure, test new ideas on a small scale and gather feedback.
  • Remain Flexible: Organizational dynamics shift as people, products, and markets evolve. Don’t lock yourself into a single line of questioning—allow your strategy to adapt as conditions change.

This iterative process helps ensure that when you finally arrive at the “Ultimate Answer” for your organization’s design, it’s both relevant and truly actionable.

Conclusion: Beyond 42—Asking the Right Questions for Meaningful Change

In the end, the most profound takeaway from the Hitchhiker’s Guide metaphor is that the right answer is only as good as the question you’re asking. Just as 42 lacked meaning without the Ultimate Question, a brilliantly crafted re-org plan will remain abstract if it doesn’t address the root challenges and aspirations of your organization.

By clarifying your purpose, grounding your questions in real data, challenging assumptions, involving diverse voices, and iterating thoughtfully, you move closer to the ultimate goal: an organizational design that enables your teams to thrive and deliver on your mission. In this sense, the “meaning of life” in organization design isn’t a single number or phrase—it’s the collective process of inquiry that brings everyone together to shape a better, more aligned future.

So the next time you hear someone exclaim “42!” in a meeting, you might smile. But remember: it’s not just about the answer. It’s about asking the right question so that your organization design—and everything that follows—truly makes sense.

Executive Guide: The Power & Potential of Shared Services: Streamlining & Scale

Fill out the form to access the guide.