Documentation for the Long Term

Ensuring that processes are followed correctly and consistently

Before we get into this week’s newsletter, it would be incredibly helpful for you to fill out this Think Like an Owner Audience Survey. It takes less than 2 minutes and any feedback is incredibly appreciated!

In any business, documentation is key to ensuring that processes are followed correctly and consistently over the long term. However, creating documentation that stands the test of time can be a challenge, especially when individuals come and go within the organization. Documents and videos are often the first thing a new employee has to go through. In this more idealistic thread of mine, I explored what the potential solution to clearly outdated documents could be (while keeping them personalized): building a system of reminders to update pages and trying to have dynamic info where possible. But, thats the ideal.

There are more practical ways to build documents for the long term. We will explore some best practices for structuring documentation that will ensure it remains relevant and useful over time.

Use Position Titles Instead of Individual Names

One of the biggest challenges of maintaining documentation over the long term is ensuring that it remains relevant even as individuals and duties change. To address this challenge, it is best to use position titles rather than individual names in your documentation. This makes it easy to update the documentation as individuals move on and new people take over their roles.

For example, instead of referring to “see Samantha for onboarding new employees,” refer to “See the HR Manager for onboarding new employees.” This way, even if Samantha moves up the organization, the documentation remains relevant and can be easily updated with the new HR Manager’s process.

Use Centralized Systems

Another challenge with maintaining documentation over the long term is ensuring that it remains accessible and up-to-date. One way to address this challenge is to use centralized systems for storing and sharing documentation. This could be Notion, Confluence, your ERP, or physical papers in the office.

For example, instead of taking a screenshot of the annual holiday calendar each year and including it in your documentation, refer people to the HR system where the calendar is stored. This way, if the holiday calendar changes, you don’t have to update your documentation – people can simply refer to the HR system to find the current calendar.

Organize Documentation with the Future in Mind

When creating documentation, it is important to think about how it will be used in the future. This means organizing it in a way that makes it easy to find and use over time. I tend to find legal documents incredibly annoying in that they say “refer to Section A”. Documents should have hyperlinks to other documents, but ideally the process is in one document.

You could organize your documentation by department or by process. If you choose to organize it by process, make sure to include a clear and detailed table of contents that makes it easy to find the specific process you’re looking for.

Update Documentation Regularly

It is important to update your documentation regularly to ensure that it remains relevant and useful over time. Anytime a new hire notes something that is inaccurate, I note in my Reminders app to fix later that day. Set a schedule for reviewing and updating your documentation on a regular basis – this could be monthly, quarterly, or annually, depending on the type of documentation and how frequently it is used. As Josh Tweeted, “There are classes of documentation with different review cadences and ‘standards of correctness'”.

By following these best practices for structuring documentation for the long term, you can ensure that your documentation remains relevant and useful even as your organization evolves over time.

Thanks to Everest Brady for his help, writing, and research in assembling this week’s newsletter.

I wanted to take a moment to recommend an exciting opportunity for those in the small business community – the first annual HoldCo Survey.

As someone who understands the importance of staying informed and up-to-date in the business world, I have found that industry reports such as the McGuireWoods Independent Sponsor Survey or the Stanford Search Fund Survey can provide valuable insights. Data is key.

That’s why I believe the HoldCo Survey is a fantastic resource that can help answer some of the common questions around best practices for SMB HoldCos. These include shared services utilized across the HoldCo, minimum EBITDA for a Bolt-On or Tuck-In acquisition, and how to fund equity on PortCos.

By participating in the survey, you’ll be contributing to the SMB HoldCo community and helping others on their journey. Your submission is 100% confidential, and the survey takes only five minutes to complete. The goal is to publish a full report on the findings, which will provide valuable insights and help inform business decisions.

I encourage you to take the time to fill out the HoldCo Survey and contribute to this important initiative.

HoldCo Survey
The first annual HoldCoSurvey, brought to you by HoldCoConf, is a first-of-its-kind effort to gather and publish information about small business holding companies.


Buffett’s Lectures at the University of Notre Dame (1991)
“I read annual reports, but I don’t read anybody’s opinion about what’s going to happen next week, or next month or next year.”
Meeting the Seller (Updated) – by Guesswork Investing
March 21, 2023 | Issue #81


‎Founders: #295 I had dinner with Charlie Munger on Apple Podcasts
What I learned from having dinner with Charlie Munger and rereading The Tao of Charlie Munger.

This Week on Think Like an Owner

‎Think Like an Owner: Chenmark Series 1: Founding Ideals – Ep.163 on Apple Podcasts
Please take 2 minutes to complete this audience poll and give feedback on the podcast This episode is the first in a three-part series we are running on Chenmark, one of the most well-known and studied holding companies in the entrepreneurship through acquisition world. And for good reason! Since it…

This episode is the first in a three-part series we are running on Chenmark, one of the most well-known and studied holding companies in the entrepreneurship through acquisition world. And for good reason! Since its founding in 2015 they have acquired 11 operating companies, completed 30+ acquisitions when including add-ons, and has over 600 employees today.

This series is not meant to be a one-stop-shop for everything Chenmark. The Higgins’ have appeared on Invest Like the Best, there is a fantastic case study by A.J. Wasserstein about them, and they share their thoughts every week through their Weekly Thoughts newsletter, which is one of my favorites. Instead, this series is meant to dive into topic gaps, where I am most personally curious, and areas of change for Chenmark.

For this first episode, we cover the risk/reward of their path early on, founding ideals, and various pivots and challenges in starting Chenmark. The second episode focuses on their operating ethos, culture, and incentive structures. The third and final episode takes a deep dive on their CEO recruiting function and what has to happen to keep Chenmark on their growth trajectory. We hope you enjoy the series, please enjoy this first episode with Trish Higgins and Palmer Higgins.

This episode Q&A features CEO August Felker of Oberle Risk Strategies, answering the question, “Can I just roll the insurance from the company I just acquired into the ownership of my business?”

Every CEO and entrepreneur needs support from a team of expert professionals like attorneys, bankers, and accountants like Hood & Strong. Less often mentioned, and just as important, is insurance. And August Felker at Oberle Risk Strategies are the experts that you need on your team to navigate the insurance needs of your company as dozens of past podcast guests have partnered with them to do. Oberle helps you evaluate where your current and soon to be acquired company needs for insurance today and what it might need tomorrow. please reach out to learn more about how Oberle can help with insurance due diligence at Or reach out to the CEO, August Felker, directly at [email protected].

This Week in SMB Twitter

Think Like an Owner is sponsored by:

Ravix Group – Ravix Group is a fraction CFO, outsourced accounting, and HR consulting firm serving small and large businesses alike. Whether you or someone you know is getting started, searching to buy a business, or building out an organization, Ravix will help on the journey. To learn more about Ravix Group, head to their website and tell them Think Like An Owner sent you.

Hood & Strong, LLP – Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected]

Oberle Risk Strategies– Oberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and Employee benefits programs. If you are under LOI, please reach out to learn more about how Oberle can help with insurance due diligence at Or reach out to the CEO, August Felker, directly at [email protected].

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