January 15, 2024

3 Ways to Engage and Retain Cultural Cowboys

In earlier blog posts, I introduced you to a special brand of business leaders and internal entrepreneurs known as Cultural Cowboys. Their special value comes in generating new value for their companies, and for the internal and external people involved, by the way they create new businesses, and new ways of doing business, in established systems, and improving the systems in the process.

So far I have shared how to find them and develop them. Now it is time to talk about how to keep them engaged by the way we utilize and reward them.

1) Tough Nut Challenges

To keep Cultural Cowboys engaged, don’t ask them to maintain or operate the status quo. Ask them to take on something new and challenging.

In their role as intrapreneur, they thrive on being asked to assess and solve complex challenges that often span functions, organizations, even companies and bridge the internal company with its external environment. 

Cultural Cowboys are silo busters, in the best sense of the phrase. They know that most challenges and most creative solutions do not come about from pitting my way against your way. They don’t compromise and debate as much as they synthesize and create – create holistic solutions that sees the “truth” from multiple angles and uses that break through barriers (including mindsets) and enroll others to join them in coming up with great, new ways of seeing and new solutions.

2) New Venture Investments & Cultural Cowboy Ideas

Sometimes the situation is not a vexing problem to solve as much as it is the potential opportunity for growth. Cultural Cowboys have the mindset and skill set to take on something new and turn ideas into realities. The ideas can come from the Cultural Cowboy or from other places in the business. The important thing is to unleash their passion and power for internal entrepreneurship.

Cultural Cowboys stay engaged by being asked to help shape the future. They see around corners and work around boundaries so they connect the dots of what can be and what it will take. To stay with the metaphor, these Cowboys shepherd the best ideas to market and create value with those who share the ride.

3) Freedom & Reward Portfolios

As you may imagine, people who are practical and yet creative are not motivated by being tightly managed. This is not to say that they don’t respect leadership and business systems and structures in place. It’s more that they don’t want to be defined or limited by them. Freedom to go outside the usual boundaries to learn, network, get new ideas, create new things is important to them.

They love to have a stake in the game and be rewarded (financially) for that stake, as any entrepreneur would.  But many companies do not have that sort of leeway in their compensation structures. So, look to other sources of measurements and rewards from what I call the 5 T’s of Measurement™: Time, Talent, Treasure (money), Trust, and Talk.

Freedom to use their time and develop their talent (and the talent of others) in creative ways is important. For instance, I know a Cultural Cowboy who sent her direct report in the food business off to see what he could learn analogically from presenters in other industries.  Turns out that engineers who inform concrete mixing, sparked a multi-million dollar product breakthrough idea of what to do with cookie crumbs.

Trust and Talk are less tangible but valuable rewards for Cultural Cowboys. They love to be entrusted with challenges, opportunities, and confidential information that require new ways of thinking. Talk can mean a well-earned reputation as go-to people to call when you want to do something new or are stuck and want to move. It can also mean calling on the Cultural Cowboy’s voice to advise, speak, teach, and inform a situation with a fresh perspective.

Company Treasures

Cultural Cowboys used wisely are one of your company’s most valuable and rarest assets. One cautionary piece of advice is not to let them fall through the cracks reorganizations, mergers, or other transitions happen that shuffle the structure. They may have a “day job” that fits neatly in an organizational chart box, but their exponential value comes in the ability to weave between functions and between internal and external boundaries. Those who do not know them or appreciate them may find them expendable and let them fall through the cracks. At times where there is a lot of disruption and goals for doing new things or for doing business in new ways, Cultural Cowboys are best used leading initiatives rather than falling as collateral damage.

At the same time, it is wise to appreciate that Cultural Cowboys are often in demand in multiple places and may need to move onto other pastures to stay fresh and grow. If you cannot keep them in your company, keep them in your friendship network. They can be of help from the outside, serving in an advisor role.


Cultural Cowboys are known by their interests and talents that exceed usual boundaries. The best way to use them and keep them engaged is in doing new things and solving complex challenges in new ways. If your goal is status quo, they are not for you. If your goal is to thrive, go in search of Cultural Cowboys now!  Some of them may well be under your own roof as Hidden Treasures.