Cowboys vs. Bureaucrats

Ever feel stuck between chaotic speed and suffocating process? This episode opens the conversation on finding the middle ground—what we call structured entrepreneurship.

We get into:

• Why cowboy chaos and heavy bureaucracy both stall growth.
• The tension between “move fast” and “follow the process.”
• How a bit of structure actually creates space for creativity and real opportunities.

If you’re trying to grow without losing momentum—or sanity—this one gives you language and perspective to rethink how your team works.

What’s one place where you feel the chaos/process tug-of-war right now?

Always growing.

Benno Duenkelsbuehler

CEO & Chief Sherpa of (re)ALIGN

reALIGNforResults.com

benno@realignforresults.com

Chapters

• 0:00 Cowboys Versus Bureaucrats Defined
• 0:39 Personal Background And Perspective
• 1:01 The Case For Planning
• 2:21 Gantt Charts For Smart Execution
• 3:04 Avoiding Too Much Detail Or Vagueness
• 3:48 Structured Entrepreneurship And Culture Balance

Transcript

SPEAKER_00: 0:00

Your team, or at least several of your team members, probably lean all cowboy or all bureaucrat. What I mean by that is cowboy uh leaning to cowboy, uh great drive, no process, a little chaotic, all bureaucrat, great process, but no entrepreneurial drive, innovation to speak of, right? Uh you need to balance the two, cowboy versus bureaucrat. Um, and you might have trouble finding creating that balance, right? A lot of our clients uh have trouble creating that balance. In fact, I have, you know, I struggled with that finding that balance. I'm a German immigrant who came to America uh in uh as a teenager, and Germany is the country that kind of freaking invented bureaucracy, the Prussians did, right? Uh a very engineering-driven culture. And then I came to America, the land of cowboys and um go west, young man, great entrepreneurial drive. Um, recently I asked a client of mine, um, would you rather die in the okay corral or suffocate to death by bureaucracy? You know, she laughed and she got it. But you know, the fact is, I love planning. And because I believe that sort of uh measure twice cut once, uh, that if you um you know you spend a couple hours planning something, it'll probably save you days or weeks um of doing it badly, um uh bad bad execution, right? Uh so uh planning is um you know it gives you in the end the time. Uh you know, I I I think of planning as, you know, it should drive maybe 60 or 80 percent of the activities so that you have 20% or more left over in the day to deal with the unexpected, the stuff that's gonna come out of left field where you have to fly, fly in and and react quickly to some uh crisis or some God-given opportunity that you're not gonna have time to take advantage of if if if you're stuck in the mud without any, you know, without proper planning. Um so uh I you know I'm a big believer in planning. Uh Gantt charts uh help us sort of force us to think 20 steps ahead, right? And it enables, they enable us to show visually to team members on our team or or in another department or in a client's team how we'll get from here to there. So we always strive, you want to strive to build that middle path, right? Enough process to scale, um, but enough freedom to create. Enough visibility so we can delegate and increase cross-functional collaboration, but not so much that it chokes entrepreneurial drive uh or stars creativity. In season three, episode six, I talked about how to use Gantt charts uh in product development, also in lots of different operational functions, uh, to use Gantt charts at the right level of altitude, right? You don't want to be down in the weeds uh where you have hundreds and hundreds of steps uh and mini steps and substeps to the substeps, and then you have hundreds of rows on a Gantt chart. I think that's that kills creativity and innovation, um, not necessary to do it at that level of detail. You don't want to fly so high that you had 40,000 feet and you have just you know two steps, beginning and end. That's not gonna work either. So you have to find that middle path. Uh build a cowboy versus bureaucrat framework that balances drive with discipline. Too much freedom is chaos, uh, too much process is death. Uh so the sweet spot is what I call structured entrepreneurship uh that allows and encourages and drives growth that um can encourage collaboration between different people inside and outside your sphere of influence. Um if your culture leans too cowboy or too cow uh bureaucrat, um let's find the balance that drives growth without killing momentum.