November 29, 2023

5 Ways to Develop Cultural Cowboys into Intrapreneurs

In an earlier blog post, I introduced you to a special brand of business leaders and internal entrepreneurs known as Cultural Cowboys. These individuals come from various levels and functions within the company. They possess a unique blend of business acumen, wisdom, resilience, creative problem-solving skills, strong connections, and a proactive attitude. They have the special ability to generate new value for the company and the people involved, by creating new businesses, and new ways of doing business, that take hold and grow.

Serially Successful Intrapreneurs (SSI’s) Defined

Every business that wants to innovate, grow, and thrive needs to find, develop, and retain Cultural Cowboys while ensuring their success as serially successful intrapreneurs (SSI's). These individuals are invaluable assets, but it's essential to harness their distinctive expertise, skills, attitudes, and aspirations through effective utilization and leadership.

Last time we talked about how to find Cultural Cowboys, and now, in this post, we'll talk about how to develop them.

One SSI trait is the need to quench their thirst for learning and developing. In this respect, the proven strategies below can apply to any stage of a Cultural Cowboy career.  However, by nature, Cultural Cowboy’s have a bit of "free agent" spirit in them. They like to seek out opportunities, co-develop together, and they don’t find one-size-fits-all development programs motivating. If they find their development path patronizing, constraining, or thoughtless, you will lose them. You need to gauge the level of challenge and personalization given to each Cowboy, and negotiate what makes sense for them and for the business.  Once you do, they are open and easy to work with and grow with, and they will likely begin to introduce development ideas of their own!

Dolphin Tank Assignments: Nurturing Wisdom Through Supportive Challenges

“The Dolphin Tank™” is a technique that my team and I developed as a method of walking individuals and teams through tough-nut challenges.  It is a kinder, gentler “shark tank” experience. The Dolphin Tank™ gives SSI’s and others the benefit of friendly, systematic feedback from objective sources (even from companies and experts outside their own discipline).  Dolphin Tanks are useful at any stage of a project.

When developing Cultural Cowboys as SSI’s, it's wise to challenge them with increasingly difficult tasks while providing support in the Dolphin Tank™. This approach boosts their chances of success and confidence. They learn to consider various perspectives and incorporate previously overlooked context, fostering wisdom and prudence in facing present and future challenges. It also sets a good model for them to learn how to give and receive constructive feedback.

Life-Cycle Mentors: Fostering Growth Beyond Functional Silos

There are many ways that leaders can mentor Cultural Cowboy as SSI’s and ensure they mentor each other. One strategy is to assign the SSI a challenge from another’s functional area and then ask the functional lead to mentor, as needed, but not solve the problem.

Another strategy is to pair Cowboys and send them out to external markets and to external partners, with practical assignments so they learn while doing. Also, have them work with colleagues who interface with those markets and partners (e.g., sales, customer service, supply chain), and have a coach and sponsor. This way they learn the business from the outside-in and develop important relationships.  Cultural Cowboys love exploring the range, so these assignments are very interesting and useful to them. Also keep your SSI’s connected to the CEO and CFO who reinforce the big picture and the entire value chain the SSI’s are impacting.  

These things help SSI’s deeply learn the business of the business and the necessity of going beyond their silos. They also help Cultural Cowboys find new insights and respect for why things operate the way they do, so before they go challenging the status quo, they understand the context and develop ways to work with it and adapt it.

Going beyond silos can also occur by including budding SSI’s in cross-functional projects and problem-solving teams. Give them authentic roles and make sure their ideas are elicited and used in some way.  Debrief with them in between meetings, teaching them to be reflective practitioners.

As part of all these strategies, it is vital to get the SSI’s to reflect and think critically before, during, and after assignments.

Learn by Analogy & Analytics: Balancing Human Insight with Data

Big Data Analytics, AI, and other data tools seem to win notoriety as the go-to tools to use to learn and make good decisions. They are, in part, IF you ask the right questions and know how to use them wisely. Cultural Cowboy SSI’s need to become savvy at the human intelligence and wisdom required to work with and pair effectively with artificial intelligence and other smart tools.  Being immersed in real projects using these tools, learning how to tap their potential, and learning their limits and system effects is important. For instance, asking, “How will this dynamic statistical analysis play on the shop floor?” and then interacting with the people on the shop floor to find out if and how it can work, is part of what goes into being a master SSI. They learn to see and act on the big picture opportunities and the details of execution and uptake as one, seamless challenge.

One of the ways that smart leaders and SSI’s take complex data and insights and turn them into usable action is to learn and teach by analogy. People learn and change their minds, and consequent behavior, by tagging new things onto things they already know and believe. Sometimes these “familiar things” may be things already in the business.  Sometimes these “familiar things” may live outside the business. One example is showing how baseball uses data analytics and its effects, and then translating that to business plays.

SSI’s need to be taught how to become good teachers and translators to all kinds of people.

New Venture Investments: Empowering Leadership and Risk-Taking

I have been at the fountainhead and execution of many new ventures, and I know they are the quintessential task of an SSI.  Often a company has a vague notion of something they might want to do to create a new business or expand their reach, and they say “Go”.  Cultural Cowboys love this sort of freedom and challenge.

However, depending on the stage of development, they need specific responsibilities and roles. Make them part of the leadership team for three reasons. (1) Learn from, work with, and form friendships with other leaders. (2) Learn to acquire and use confidential information. (3) Collaborate and connect the information and ideas they have with the information and ideas others have, synthesizing it into a new model and execution plan that is high pressure, high stakes, and highly motivating for Cultural Cowboys. (4) Deliberately employ and shape their openness to risk and ambiguity with concrete intrapreneurial projects.

Harnessing Intrapreneurial Ideas: Valuing and Implementing SSI Innovations

Sometimes the new venture ideas originate within the SSI.  Taking them up on their ideas to build new businesses, or new ways of doing business, is a brilliant way to utilize the creative pragmatism found in Cultural Cowboys.

There is no shortage of ideas out there.  The trick is to find a good idea and one that will be developed, executed, and adopted seamlessly. When the SSI steps up, challenge them to stay in the hunt not just to come up with an idea or map the lay of the land. Challenge them (with support) to invest themselves in shepherding the idea all the way to reward, utilizing a Method of success that utilizes and creates value along the way.  This Method is the Third Angle Way of Thriving Method™ that we have developed from working with Serially Successful Intrapreneurs (SSI’s) for over thirty years.

The Method takes the tendency and gifts of Cultural Cowboys and makes them practical, useful, and welcomed in their current companies.


As we continue to explore the multifaceted journey of Cultural Cowboys, our next focus will be on keeping these vital innovators engaged and maximally productive. Stay tuned for insights on retaining and maximizing the unique value of your SSIs.