Hoodies & Operating Systems

It's Time for Joy

90 Seconds to Be Inspired

“I don’t want to get too corporate”... I hear some version of this quote from leaders as their companies grow. Being small and scrappy is a badge of honor for many of us, and thus it’s normal to resist the urge to document things, have a process, or god forbid, a communication cadence!

But growth and scale require you to operate in a different way, and this newsletter will dive deep into how to build more structure to preserve not ruin your culture. You don’t have to become suits, hoodies can remain.

One of those ways is to adopt an internal operating system - An Internal Operating System (OS) within an organization refers to the processes, structures, cultural norms, and decision-making frameworks that guide how the organization functions. Just like a computer’s OS enables hardware and software to work together efficiently, an organization’s internal OS determines how teams collaborate, make decisions, and execute strategy.

In the early stages, startups often operate with speed, flexibility, and informal decision-making. While this works initially, as the company scales, misalignment, inefficiencies, and culture drift can emerge. Implementing an Internal Operating System (OS)—a structured yet adaptable way of working—helps startups maintain clarity, speed, and alignment as they grow. Here are a few benefits:

  • Enables Faster & Better Decision-Making: A clear OS defines who makes decisions, how priorities are set, and how communication flows, preventing bottlenecks.

  • Prevents Scaling Chaos: What works at 10 employees often breaks at 50. An internal OS helps codify processes, team norms, and accountability structures so growth doesn’t lead to dysfunction.

  • Aligns Culture with Strategy: Without intention, culture can drift as new people join. An OS ensures cultural values are reinforced in hiring, onboarding, and daily operations.

  • Clarifies Roles & Expectations: Startups often have overlapping responsibilities. An OS brings structure to leadership, team collaboration, and performance expectations.

  • Increases Efficiency & Reduces Burnout: Without clear ways of working, teams experience decision fatigue, redundant work, and communication breakdowns. A defined OS streamlines workflows and keeps teams focused.

  • Supports Adaptability & Change: Startups pivot often. A strong OS helps teams navigate change smoothly by providing stability in how decisions, communication, and execution happen.

Below I outline my favorite (and most effective) tools to bring an OS into your company. Please let me know if you are using one that’s effective that I don’t mention!

90 Seconds to Learn a Little

There are about as many books on strategic planning or corporate operating systems as there are on leadership and management. It is CROWDED. Allow me to narrow down the list for y’all.

If you don’t want to read the entire newsletter, my TLDR comparative is here.

highlighted, dog-eared, post-it’d, and overall loved.

  1. Start with: The Advantage by Patrick Lencioni. You can read the book and hold a meeting or two on it with your team. The approach I’ve seen work the best is to start here and answer the Six Critical Questions as a leadership team. If you like the approach and feel it matches your philosophy, you can continue down the Lencioni path with The Five Dysfunctions of a Team and Team Genius. 

  2. Graduate to: Traction by Gino Wickman (a book about EOS). This one is more holistic and dives deep into the rhythms/rituals of planning which I love. You can pick and choose elements (i.e. the Level10 Meeting) but the most effective teams I’ve seen actually hire an EOS Implementer because to do it well, it’s a commitment and having an external partner who is an expert is very beneficial*** Before you do that, read the book and see if it resonates. ***Think of any partner you hire as an extension of your leadership team. Make sure they are values & principles aligned as I’ve seen several implementations fail not because of the system, but because of the partner. 

  3. Advance to: Scaling Up by Verne Harnish (a book about The Rockefeller Habits)

  4. Realize you need something more custom, call me and I can share some custom options based on your needs!

What these approaches have in common is a framework to take everything in your head and get it down. Writing is clarifying, and clarity is critical for the team to get on the same page.

Thank you Usman Ahsan for sharing this amazing visual!

90 Seconds to Connect

A friend was telling me about the dozens of coaches, consultants and advisors who are in her professional and personal world and the value they provide. As CEOs, CPOs, Leaders, we have more support available to us than our nuclear family or W2 team. 

Ask yourself:

What am I naturally gifted at that I wish I could spend more time on this year? 

What am I avoiding because it’s not interesting or not in my zone of strength?

If I could have support in getting something answered or accomplished that would be the greatest impact driver, what would it be?

Chances are the answer to the type of help you need lies in these questions.

If your goal is to create a successful business and life, don’t hesitate to surround yourself with the right experts to enable you to make this happen!

Inner circles are power, so let me know if you have a specific need but don’t know where to start in finding the right person. I got you.

One of my best performing experiments is telling ya’ll when I’ll be where all over the USA. The result? Amazing in person time with my peeps! Hit me up to meet for coffee if our travels overlap or if I’m coming to your town!

  • March: Greenville, SC / NYC / Las Vegas

  • April: Boston

  • May: Naples, FL / Atlanta / NYC

  • June: NYC

  • July: Spending a week at Atlantis in the Bahamas with family. Send tips (and sunscreen!)

Help expand my inner circle!

My company, ScaleJOY, has delivered quality experiences to hundreds of clients and has grown solely by word of mouth referrals. Spread the joy by sharing this newsletter, or connect them directly to me for leadership development, coaching, or offsite facilitation. Thank you for your continued support!