Enterprise vs Entrepreneurial: What Kind of Leader are You?

Oct 09, 2023

Let me ask you a few questions:

  1. Do you think most organizations need an enterprise leader or an entrepreneurial leader?
  2. Are you more wired as an enterprise leader or an entrepreneurial leader?
  3. What kind of organization needs what kind of leader?
  4. Do you think it is possible for the same person to be an enterprise leader and an entrepreneurial leader?

The Enterprise Leader  

The enterprise leader’s worth grows in proportion to the size of the organization. The bigger the organizational footprint, the more necessary the enterprise leader. Or the more mature an organization is, the more crucial it is to have an enterprise leader.

The enterprise leader is the man or woman who runs projects, who builds things out and stays with the tasks until completion. The enterprise leader doesn’t just jump from one idea to the next shiny idea. They’re the executers of the vision. As General Russell Honore said, “Giving the order might be the easiest part. Execution is the real game.”

Usually enterprise leaders are leading teams of teams, which means they are always thinking cross-department and in terms of organizational alignment. General, Stanley McChrystal wrote a book about the “teams of teams” concept and talks about the process here.

As far as personality, enterprise leaders are planners who think in terms of cause and effect. They keep a risk profile well within measure. They’re not boring, but they make slower decisions because they think about the context and the consequences of decisions. Ready, aim, aim again, fire.

An MIT article from early this century defined enterprise leaders this way, and it's still accurate: “[They] make decisions with the entire corporation in mind. In other words, ‘enterprise leader’ is not a job title—the term represents a way of thinking and behaving.” They focus organizational attention; they live in the tension between strategy and culture.

Larger, more complex organizations need enterprise leaders. I’ve said for years that it takes processes and systems to scale any organization. Enterprise leaders immediately get that and know instinctively what to do.

Entrepreneurial Leaders

But as important as enterprise leaders are, you can’t lose the entrepreneurial leader and culture. That is important for small start-ups and huge companies alike. Seth Godin says big businesses need to think like small businesses. This is tough to do without entrepreneurs around. 

Most of us have in mind what an entrepreneur is, and perhaps the stereotype isn’t that off. Entrepreneurs are agile, quick pivoters. They are resilient, and they start and stop easily. Passion is present for the enterprise leader, but it abounds for the entrepreneur and is a primary driver of action.

Innovation abounds as well. Entrepreneurial leaders are initiators, starters, and challengers, as this article from Entrepreneur (which ought to know) points out. Ready, fire, aim. Or sometimes just fire, fire, fire.

I’ve written elsewhere about three types of leaders. Entrepreneurs are the “launch the business” and “change the business” leaders. This is how entrepreneurs think, and they sometimes wonder why nobody else does.

Why You Need Both

Most successful organizations have both enterprise leaders and entrepreneur leaders. Google seems entrepreneurial, sure, but it has hundreds of enterprise leaders. Exxon Mobil may seem like a fixed behemoth of a company, but they have entrepreneurial leaders up and down the organizational ladder. Walmart is a beast. But in any department, you will find a particular concoction of enterprise leaders and entrepreneurial leaders.

Enterprise leaders organize the chaos in an organization. They take siloed departments and unify everyone around a common purpose. They see an exciting opportunity and question whether it’s a good pitch to swing at. They give customers a consistent experience. They streamline operations. Is your organization trending up? You need an enterprise leader to make sure you can keep up without burning out.

But enterprise leaders struggle to change the business. They don’t reinvent or anticipate future challenges very well. That’s where entrepreneurs lead. 

Entrepreneurial leaders disrupt, motivate, pivot, run fast and break things. These are things that every organization—large or small—never grows out of needing. Is your organization trending down? You need an entrepreneur. Is it not even trending? You need an entrepreneur.

Which way do you lean? Most executives lean one way or the other. There are exceptions (Sam Walton comes to mind), but it’s rare.

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