Posts for Tag: organizational health

The Six Questions Every Leadership Team Needs to Answer

Photo by 愚木混株 Yumu on Unsplash

Layer 1: Clarity

Before a leadership team can align on execution, they must build shared answers to six fundamental questions. These answers are developed together, not handed down, so that every leader actually owns them.

These are Lencioni's six questions from his book "The Advantage":

  1. Why do we exist? (The core purpose beyond making money)
  2. How do we behave? (The values that define our culture)
  3. What do we do? (The business we're in, simply stated)
  4. How will we succeed? (The strategic anchors that differentiate us)
  5. What is most important right now? (The single thematic goal for this period)
  6. Who must do what? (Clear ownership and accountability)

How It’s Built

The leadership team works through these questions together in a facilitated session, typically offsite. The clarity and alignment sessions (Layers 1 & 2) work best with a dedicated facilitator so that the senior leader and every member of the leadership team can focus on content rather than process. The facilitator doesn’t need to be external, but they should not be the most senior person in the room.

What the facilitator does: surface assumptions that aren’t shared, push for more specificity when team drifts towards platitudes, ensure the quieter voices get heard, name disagreements the group is trying to skip past, and document outcomes in language the team recognizes as their own.

What the facilitator does not do: drive the team toward a predetermined answer, fill silence with their own ideas, or let the session become a presentation. The value is in the conversation, not slides.

You’ll know this is working when team members can articulate the answers in their own words, without reading them off a slide, and when the answers actually inform decisions rather than sitting in a shared drive untouched.

In the next post we'll look at what happens after the clarity session. Getting answers on paper is the easy part. The harder work is making sure everyone is actually acting on the same understanding. That's Layer 2: Alignment.

References: The Advantage and The Five Dysfunctions of a Team (Patrick Lencioni); The Effective Executive (Peter Drucker)

Why Your Culture Initiative Isn't Working

Photo by Shubham Rana on Unsplash

Organizational health initiatives fail because they’re deployed at the wrong level.

Leaders try to improve culture through values posters and all-hands speeches when they haven't even gotten their own leadership team aligned. They invest in manager training programs while the executive team models dysfunction. They roll out OKRs company-wide when the top team can't agree on what matters most.

The cascade must start with you, the leadership team you're part of, before it can spread. Get the top team healthy first. Then each member of that team does the same work with their team. Then their direct reports do it. Culture change is leadership behavior change that propagates.

The Leadership Operating System provides a repeatable framework for building organizational health. It integrates four proven methodologies into a system rather than a collection of tools. The sequence and connection points between them are what make it work.

The Four Layers

Each layer builds on the one before. Clarity asks: are we aligned on why we exist and what matters most? Alignment asks: does everyone know what they're doing and why? Cadence asks: how do we stay connected and course-correct? Development asks: are we growing the brilliance in our people?

Most leaders want to start with Cadence: the meeting rhythms and check-ins feel actionable. That's the wrong place to start. Before any of that can work, the leadership team needs shared answers to the questions most of them have never explicitly discussed together.

In the next post we'll work through the first layer: Clarity. It starts with six questions every leadership team needs to answer. Most teams never have. That's exactly the problem.

It's Not a People Problem

Photo by Bl∡ƙẹ Nyquist on Unsplash


Most organizational dysfunction is not a people problem. It is a clarity problem.

Smart, capable people underperform when they lack shared understanding of strategic intent, when alignment is assumed rather than built, and when the operating rhythm doesn’t create space for real conversation. Organizations respond with more communication or more process, but these address symptoms rather than root causes.

The core principle is simple: culture change is leadership behavior change that propagates. Get the top team healthy first. Then cascade. The goal is leaders who are aligned on what they need to achieve and why, with genuine freedom and accountability for how they get there.

Symptoms You Might Recognize

This framework is designed for leadership teams experiencing coordination failures despite having talented people. You might recognize these patterns:
  • Decisions get revisited repeatedly because people weren’t really aligned the first time
  • Status meetings consume hours without producing clarity or decisions
  • Teams duplicate effort or work at cross-purposes without realizing it
  • Strategic priorities shift quarterly without clear rationale
  • Talented people are frustrated because they “can’t get anything done”
If these sound familiar, the problem is almost certainly not your people. It's the operating system they're working within, and that operating system is a direct reflection of how healthy the leadership above them is. It's how and when leaders communicate, what they talk about, and how consistent their words are with their actions.

There's an excellent line from "Remember the Titans" that comes to mind. The team captain accuses another player of having a bad attitude. His response? "Attitude reflects leadership, Captain."

Leaders are frustrated that their organization doesn't run as expected, that people aren't energetic, that no one seems to be putting the organization first. The answer is the same as it was on that football field. Their attitude reflects what they're seeing from their leadership, from front-line supervisors to the C-suite.

If the problem flows from the top, so does the fix. That's where we'll start.

Generative AI is widening the leadership gap, and most leaders haven’t noticed yet

Photo by Katie Moum on Unsplash

Generative AI and all of its implications have been hard to wrap our heads around. We're producing more output than ever, and none of it tells people what actually matters. 

We're running faster on the treadmill, but aren't moving forward. In fact, we might be moving backwards as we create more systems no one fully understands and therefore can't diagnose or improve.  

AI models can now write entire software projects with minimal intervention from the user. I myself spent December "building" and iterating on a retirement planner tool. A related phenomenon is the use of OpenClaw, a free and open source tool that allows users to orchestrate multiple agentic AI instances using messaging platforms like Slack.  The podcast "How I AI" includes a number of interesting examples that seem to point to these agents being capable of autonomously doing economically valuable work. One person details how she uses 5 agents to run her homeschool, finances and coding projects, while a senior developer shares how these agents have allowed him get oriented more quickly when tackling unfamiliar codebases. 

That extrapolation might be a mistake though. As Cal Newport points out: code is different from most other knowledge work. There are millions and millions of lines of code online, including code snippets surrounded by explanations on Stack Overflow. So, yes, software developers can "write" code faster, but that was never the real bottleneck. For any company, the real bottleneck has always been and continues to be building products and offering services that enough people are willing to pay for. Figuring out what problems are worth solving, positioning effective solutions, and prioritizing iterative improvements continues to be the biggest challenge facing companies.  

Unique insights, judgement, and taste are still the enablers of successful businesses. A firehose of code with new features deployed daily has never driven market success: it's never positioned a product or built a sustainable business. We're creating more and more noise, and the signal is getting fainter and fainter.

Effective leaders who create clarity are needed more than ever to light a path through the cacophony. The leaders who figure this out will have a significant advantage. That's what the next post is about.