What is an Executive?

As we continue to grow as a business, I’ve been reflecting on what it truly means to be an executive—especially in a company that’s transitioning from transactional management to transformational leadership. It's an exciting phase, but it requires a different level of leadership, decision-making, and patience, both from me and my executive team.

My executive team is measured across several key levels:

Revenue, profit, and cash – The core financial metrics that drive sustainability.

Projects – Are we executing the right initiatives, and are they getting done?

Team results – How is each executive's team performing within their specific vertical?

Behavioral review – How are executives aligning with our pillars of leadership?

Of these, the first two metrics are relatively straightforward and measurable. But it's the third and fourth - evaluating behavior and leadership — that’s much more subjective, and frankly, the hardest to measure. As we scale, it’s becoming clear that this subjective element is not just important—it’s critical to the long-term success of the business.

One of my processes for evaluating executives at year-end involves asking them to write two letters:

1. A letter to the shareholders, outlining the company’s performance for the year.
2. A letter to me, detailing their personal performance over the year.

As I work through this year's reviews, I’m seeing incredible results in terms of growth—revenue, profit, new projects (like moving). But I also see that we’ve become more focused on transactional management: get things done, check the boxes, move on. While there’s a place for that, I believe we need to shift more toward transformational leadership—where vision, strategy, and people development take center stage. So, let's talk about what an executive truly is, particularly in a transformational company.

Defining the Role of an Executive?

As the business evolves, I need to grow alongside it, as do my executives, and our processes. And for that, I need an executive team and processes that are capable of making thoughtful decisions more deliberately. It’s a challenge for me—I built this company by moving fast, making gut decisions, and "shooting from the hip." But now, I need patience, and more importantly, a well-defined decision-making process at the executive level.

Transformational leadership is where my focus lies now. This means:

1. Communicating vision and expected outcomes clearly.
2. Measuring performance in real-time.
3. Coaching and teaching team members toward growth and success.
4. Making changes when necessary, whether in people or processes.

In contrast, transactional management looks like this:

1. Tell people what to do.
2. Check if it’s done.
3. Move on to the next task.

While transactional management can be effective in the short term, it doesn’t scale. It’s exhausting, and it doesn’t build the kind of leadership necessary to sustain a business that will grow to $100 million and serve the community for the next 100 years.

The Difference Between Workers, Managers, and Executives

Firstly, Workers, Managers, Executives all carry the exact same value to the organization, society, and humanity, without each other we have nothing.

Here’s how I see the various roles in an organization:

A worker executes tasks as directed. A solid worker is reliable, efficient, and consistent. At the end of the day, they go home free of the burden of higher-level thinking and decision-making.

A manager oversees goals given to them by a VP, using people, budgets, and some decision-making autonomy to meet those objectives.  A good manager is decisive and marshalls the needed resources to be effecive.

A vice president takes strategic direction from an executive and turns that into action while regulating the day to day activities. A good VP makes thousands of decisions to keep things moving.

Executives, however, operate on a different level. They are responsible for building and executing strategy based on the company's vision. They need to balance sales, profit, cash flow, and resources while managing relationships up, down, and across the organization, while taking care of customers. Being an executive requires an intuitive understanding of when to act quickly and when to ask the right questions. It’s about having a bias for action but also knowing when to pause, reflect, and gather more information.

Communication and Cohesion

One of the most important parts of being an executive is communication:

Communicate with employees to keep them aligned and motivated.

Communicate with peers to ensure consistency and collaboration.

Communicate with customers to manage expectations and build relationships.

Communicate with the CEO and the board to ensure everyone is on the same page regarding strategy, execution, results, and trajectory.

A high-functioning executive team delivers a cohesive message across all levels, creating momentum that can drive the business forward. Right now, my personal focus is on fostering that momentum through patience, discipline, and timing.

The Murkier Side of Executive Leadership: Discernment

One of the more subjective aspects of being an executive is discernment. It’s not just about making quick decisions—it’s about knowing when to act fast and when to pause for reflection. Executives must contemplate what’s important, what isn’t, and how to seek feedback to improve decision-making. Right now, our executive tools for controlling budgets and making material decisions need refinement, which makes communication all the more crucial, more questions of depth need to be asked more regularly to speed things up.

Measuring Executive Effectiveness

I’ve been reading *The Effective Executive* by Peter Drucker, which offers solid insights into time management, prioritization, and decision-making. However, I feel like there’s another dimension to explore—one that includes managing upward, evaluating risks, and considering how actions mitigate those risks and finally how to communicate that to the final decision makers.  (For a Ben curated summary of Drucker via  ChaptGPT 4ptO see below).

Ultimately, executive effectiveness, in my view, is about contributing in a meaningful way to core business metrics (sales, profit, cash) while building a team that can succeed without you. Over time, executives should cultivate successors who are capable of taking their place, which is a true measure of leadership success.

The Challenge I’m Facing

Right now, my staff meetings feel more like brutal, transactional updates—a rundown of all the to-dos that I can keep in my head. This is exactly what I’m working to change. I want us to evolve beyond that, into a leadership culture that is focused on strategy, long-term vision, and transformational growth.  The key elements to this to be transformational:

1. A better process for decision making.
2. My commitment to being more patient, actively listening, and allowing room for thoughtful dialog.
3. The executive team self regulates and follow through cohesively.

In closing, what I’m learning is that the role of an executive is to strike the delicate balance between fast action and thoughtful decision-making, between the operational and the visionary. It’s not an easy shift, but it’s one that I’m committed to making—and I believe it will make all the difference as we move toward the next stage of our business.

• Ben

ChatGPT4ptO Summary Currated by Ben:

Peter Drucker’s *The Effective Executive* is a timeless guide to improving executive performance and leadership by focusing on key habits and decision-making processes. Drucker argues that effectiveness is a skill that can be learned, regardless of personality traits or natural talents. The book outlines practical strategies for cultivating effectiveness in order to maximize personal and organizational success. 

1. Time Management

Drucker emphasizes that time is a critical resource for executives. The first step toward effectiveness is understanding how time is spent. He encourages leaders to track their time meticulously and identify activities that waste time. Once identified, these inefficiencies can be reduced or eliminated.

2. Focus on Contribution

Effective executives focus on the results they contribute to the organization, rather than on effort or activity. This involves asking the right questions: "What can I contribute that will significantly affect the performance and results of the institution I serve?"

3. Building on Strengths

 Drucker advocates for leveraging strengths—both personal and within the organization—rather than focusing on weaknesses. This means placing people in roles where they can excel and developing personal talents instead of trying to improve on areas of weakness.

4. Setting Priorities

Effective executives know how to set priorities and concentrate their efforts on the most important tasks. Drucker encourages leaders to resist the temptation to do many things at once, emphasizing the need to work on one task until it is completed, rather than scattering focus.

5. Decision-Making:

Decision-making is a key function of an executive. Drucker explains that effective decisions are the result of a rational process that includes defining the problem, exploring alternatives, and considering the consequences. He also underscores the importance of knowing when a decision is necessary and when inaction is the better choice.

6. Delegation and Empowerment

   Effective executives delegate tasks that can be handled by others, allowing them to focus on the most impactful work. Drucker also emphasizes the importance of empowering employees to make decisions within their areas of expertise.

Core Takeaways:

- Effectiveness is not innate; it’s a learned discipline.

- Time is the most limited resource, and managing it effectively is key.

- Focus on results and contributions, rather than tasks and processes.

- Use strengths to your advantage and avoid focusing on weaknesses.

- Prioritize rigorously and work on the most important issues.

- Decisions should be well-considered, based on facts and alternative solutions.