Better Questions

Organizational culture emerges from the process of answering questions. The answers aren’t necessarily articulated explicitly, but they’re expressed in the decisions people make, the way people treat each other, and in so many other ways. Organizational leaders may be unconsciously undermining the very culture they’re trying to create, but they can’t change it until they start asking the right questions.

When things aren’t going well, we like to ask why?” Why is my boss always looking over my shoulder? Why do I have to babysit my employees? Why do we need this new policy? Why did so-and-so do that?

I think I have a set of better questions—kind of a health check for organizational culture—clustered around the core values of Clarity, Agency, Skills, Efficiency, Collaboration, and Loose-Coupling. These six pieces fit together like a jigsaw puzzle. My list may not be comprehensive or definitive, but I think it’s a good start.


Clarity affords focus.” –Thomas Leonard

  • What is our overall mission? Are we doing the right work, in a way that everyone can be proud of?
  • How does the overall mission map to strategic and tactical priorities?
  • Does everyone understand the constraints (budget, time, legal, regulatory, network security, corporate standards, etc.)?
  • When it’s necessary to adopt a restrictive or negative policy, do we clearly explain why?
  • Do we model positive thinking, open communication, and mutual respect at every level of the organization?


Men often oppose a thing merely because they have had no agency in planning it, or because it may have been planned by those whom they dislike.” –Alexander Hamilton

  • Do employees know what the mission is, what success looks like, and how their work contributes to it?
  • Do employees have the right amount of autonomy? Do they know how much autonomy they have? (The right” amount of autonomy varies by skill level, earned trust, etc.)
  • Do we recognize and reward success?
  • Are employees allowed to fail? Do they know what’s expected? How do we handle failure?

See also On Failing Successfully and Use Weird Rules” To Boost Your Creativity.


Happiness comes when we test our skills towards some meaningful purpose.” –John Stossel

  • Are we recognizing and supporting all skill levels?
  • Are we encouraging growth (i.e., skills development)? Discouraging it?
  • Are we trying to herd racehorses and/or race sheep?

See also Dreyfus Model of Skills Aquisition and From Novice To Expert.


The first rule of any technology used in a business is that automation applied to an efficient operation will magnify the efficiency. The second is that automation applied to an inefficient operation will magnify the inefficiency.” –Bill Gates

  • Is our organizational structure appropriate to our mission and culture?
  • Are responsibilities assigned to the right people/teams?
  • Do we have the right tools for the job?

See also Flow.


If everyone is moving forward together, then success takes care of itself.” –Henry Ford

  • Do we encourage collaboration across teams, departments, and divisions?
  • Are our IT systems set up to facilitate collaboration with minimal friction?
  • When an employee needs to find someone with certain expertise, how do they do that?
  • Are we actively seeking and removing barriers to collaboration?


There is some tension between individual efficiency and collaboration. The two need to be balanced. The real enemy of both, however, is unmanaged access or dependencies—that is, when individuals, groups, or business processes are too tightly-coupled. This is because the raw materials of both individual efficiency and group collaboration are time and attention. A balanced portfolio of collaboration and blocks of uninterrupted time for individual productivity is the best way to maximize your investment.

  • Do we manage dependencies across teams, departments, and divisions? What are the expectations about responsiveness (e.g., to email, IM, etc.)? Are we managing those expectations?
  • How much control do employees have over their time commitments? Is it OK to say no?
  • Do employees have the freedom and flexibility to meet outside responsibilities (work/life balance)?
  • Do we respect employees’ personal time?
  • Is everyone in the organization permitted (or better yet, expected) to point out unhealthy dependencies so they can be addressed?

Some level of interdependency within an organization is necessary and healthy, but any one individual or group should not be free to demand too much from any other. If one individual or group consistently leans too heavily on another, someone (read: management) needs to step in, figure out what they really need and why they’re not getting it, and allocate the necessary resources. Unmanaged dependencies drain both time and attention.

Note that some dependencies are deliberate. For example, some sensitive processes—like legal questions, press releases, or production web site changes—are deliberately bottlenecked to maintain control. There’s nothing wrong with that. I hold up loose-coupling as an ideal because mature organizations tend to err on the side of too-controlled, but it’s certainly possible to swing too far to either extreme.

See also Merlin Mann’s Revaluing Your Time and Attention talk.

Better Understanding, Better Culture

If you’re a manager or knowledge worker at any level of an organization, you should be routinely struggling with questions like these. Apply the scientific method: form a hypothesis, observe with an open mind, check your theory against reality, and revise it as necessary. When you’re asking better questions, Why?” will become clear.

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