Bootstrapped startups and the shit I learn in therapy

For a long time, we didn’t like the idea of corporate sounding “SOPs” (standard operating procedures) and felt we had better things to pay attention to — like deadlines and emails, thankyouverymuch.

Then all that changed.

Here’s what happened, why we wound up creating a playbook of SOPs, and what other company and agency leaders can learn from our experience.

In this article, you’ll find:

  • What a “playbook” is and why it matters
  • 4 key takeaways for other team leaders
  • Benefits our team has seen so far
  • How we chose a tool and put the playbook together

What do we mean when we say “playbook”?

There are playbooks and there are playbooks. It’s popular to call a marketable guide a “playbook” these days, and those are usually a series of business, marketing, or sales tactics you can run to see z, y, z


Heskin’s download is free and has some good stuff in it, btw!                                


And then there are the traditional playbooks athletic coaches rely on. You know, spiral bound with all the circles and loop-de-loop arrows saying you go this-a-way while that guy goes that-a-way.

But when we say “playbook” we’re not talking about a prescriptive PDF download or our favorite Panther’s plays here. When we say “playbook,” we mean a collection of standard operating procedures (SOPs) and thought processes — aka “how we do things ‘round here.” We mean a regularly updated guide that gives everyone on the team clarity, confidence, and more than a little of their sanity back.


What’s in our playbook?

If you’re anything like us, the first thing that came to mind when you heard “standard operating procedure” was a task checklist. Our playbook does include more than a few checklists, but it’s not all it has.

If you were to click around our playbook, you’d notice we currently have three different types of how we do things documents. Those are:

  • Processes: Step-by-step instructions for a specific task. E.g. Requesting time off or Submitting and reviewing pull requests
  • Processes for processes: Meta-level guidance. E.g. Creating a playbook page
  • How we think: Introduction to our thought process — the WHYs behind the HOWs. E.g. ValuesDiversity & inclusion, Content marketing strategy

How did we come up with those three? Well, we didn’t, exactly. These page types more-or-less arose naturally as we thought through the information (1) a new hire would need during their first week in various roles and (2) current employees need to excel in their jobs.

Note: If you’re curious about all that looked like, we’ll get into the weeds of “how we did it” a bit later.

For now, here are some of the biggest takeaways we’ve learned from putting this together and what the team thinks of it so far.

4 key takeaways for other founders and team leads

1. Creating SOPs positively impacts every level of your organization

A playbook (or collection of SOPs) positively impacts every level of your organization:

Founder-level perks

  • Quiet: Employees rely less on leadership to define and guide processes because they’re already recorded. This can mean fewer pings, emails, and approvals. Given you already make about 808439583 decisions per day, that’s good news.
  • Profitability: Maintaining profitability means (among other variables) maintaining efficiency. Because SOPs have a big impact on efficiency, they can have an impact on profitability.
  • Sanity: Well-documented procedures free you up to work on more complex and creative challenges where you (in all likelihood) excel as a founder. They help you work from your strengths.


Manager-level perks

  • Accountability: It’s easier to hold team members accountable for their work once you’ve clearly outlined what’s expected of them.
  • Onboarding: Integrating a new team member becomes faster, easier, and less frustrating thanks to checklists and references.
  • Better Processes: There’s no better way to find holes and weak spots in what you’re doing than to sit down and try to explain it.

Employee-level (and contractor-level) perks

  • Clarity: SOPs outline what to do and why, which gives employees a clear, repeatable process to follow.
  • Confidence: When you’re following a set checklist or procedure, there’s less room for nagging, “am I doing this right?” type of questions.
  • Efficiency: Less time thinking about “how do I do this?” and more time doing it.
  • Consistency: Individuals generate more consistent results because they’re following the same procedure.

Plus, as Asia Orangio pointed out on Twitter, all those employee benefits can mean employees enjoy their job more (they’re not roadblocked and frustrated) and you feel more satisfied as a manager (your people are happy!).

When we stepped back and thought about it, we’d rank all those improvements as urgent, important, or both for our team. And according to the Eisenhower Matrix, a simple and powerful decision-making tool, the playbook needed to happen.                                          



While your reasons for wanting a playbook may differ from ours, the benefits — and where they fall on your priority list — are worth considering.

2. Choose a documentation tool that works for YOUR needs

Many tools let you document procedures. Choosing the “right” tool to document, edit, and store them will depend on several variables. Here are a few you’ll want to consider:

  • What “job” are you hiring a playbook to do? What problems do you hope it’ll solve?
  • Who all needs to access/view it?
  • Who all needs to edit it?
  • Which text editor tools does your team already use?
  • Do you plan to keep it internal or release it to the public?
  • Do you need the tool that auto-generates fresh checklists for you?
  • Do you want to use a free tool or do you have a budget for a paid one?

Find a tool that meets almost all your criteria — remember, no tool will be perfect — and start using it.

3. Enlist help from your team, maybe VAs and writers as well

There’s how a process ought to work, how leadership thinks it does work, and how it actually works on a week-by-week basis.

To suss out those differences, spot improvements, and move the “actually” closer to the “ought,” you’ll need to talk with your team members and/or ask them to document how they’re doing what they’re doing.

If you’re particularly short on time, you may also need to pull in an admin, VA, or other forms of support to help you get processes down. Creating a comprehensive list of SOPs takes a good deal of time and effort. Distributing the effort helps ensure it doesn’t fall by the wayside.

4. Measure qualitative gains as well as quantitative ones

Yeah, it would be great to point to hard data around billable hours, tasks completed, or other metrics (“team satisfaction is up 15%” or “we’ve gained 12% efficiency every week!”). And who knows? Maybe you’ll be able to tie your playbook to hard numbers like that.

But so far, we’ve found the impact of our playbook is mostly qualitative — and no less critical. From the clarity it gives new hires during onboarding, to the teaching tool it’s become for our lead developers, to the sanity it’s helped the partners regain, team members cite plenty of benefits to having a playbook.

For example...

Qualitative results we’ve seen so far

Better onboarding

Our latest hire, talented UI/UX designer Nathan Nash, used it right away. He says, “I read it on my first day and reference it to learn about how to organize design files.” Bina, our project manager, also found it useful when she came onboard: "it was helpful when I started here because it covered a lot of admin details that get missed during meetings, as well as step-by-step guides on how to do certain things like track time."

On the flip side of the hiring process, partner Austin Price says, “Having a thorough playbook has also drastically improved the onboarding process. With each step of the onboarding process documented, hiring new Kritters has become a much smoother gives new Kritters a reference to help them get context and get up to speed more quickly.”    

“with each step of the onboarding process documented, hiring new Kritters has become a much smoother process..."

— Austin

Improved processes

The playbook also helps team members keep track of the many processes an agency requires. Garrett Vanglider told me, “Having a playbook allows our team to codify workflows and gives new (and old) team members a place to either learn or remind themselves of the processes we have put into place.” It also helps team members easily spot and make improvements. Garrett pointed out, “Since we're taking time to document our workflows, it also allows us to find new places to make tweaks and changes to existing processes for efficiency's sake.” Austin confirmed, “it’s helped us think through our processes more thoroughly, and see the holes where we need to create, document, and improve on missing pieces.”

Sanity and accountability

Finally, it helps with sanity and management. I could almost hear the sigh of relief when Austin said, “The playbook has been huge in a few ways for us. First, it got a lot of information and processes out of individual people’s heads and put it in one place where everyone can see it.” Garrett also mentioned the playbook has been an invaluable teaching and accountability tool. He noted, “I also personally love that when providing feedback to a team member I have something I can actually point to as an example.”

"I also personally love that when providing feedback to a team member I have something I can actually point to as an example.”

— Garrett                                       

But we didn’t get there overnight. Here’s how we decided to prioritize the playbook, choose a tool, pick a starting point, and get the team involved.

Choosing a tool, figuring out where to start, and getting the team involved

From the initial idea to what the team thinks of it, here’s an inside look at how we created our playbook.

We’ve tossed around the idea of playbook for some time

We’ve admired polished playbooks for quite a while. There’s the one Hanno used to have, the excellent one thoughbot put together, and the stupid-useful one by Human Made that gives us heart-eyes.

For years, we’ve dreamed of creating one ourselves, too.

Except we...didn’t get around to it. In the beginning, one of the reasons we pushed it off is because we were pretty small, and most of our procedures were common knowledge (or at least it felt that way). Then, as we grew, other tasks competed for our time and attention (client projects, payroll, generating sales, you get the idea). Those usually felt more urgent than documenting our thoughts.

Plus, whenever we did have some space, creating a playbook just didn’t seem, well, particularly fun.

Apparently, we’re not alone in this.

The tipping point (from “cool idea” to “let’s do this”)

But as the agency kept growing — and we kept not documenting — we started experiencing aches and pains.

The company wasn't falling apart, but we were all feeling stressed. Little details were slipping through the cracks: This task is a week overdue. This task wasn't part of the original scope at all. This feature is in the done column, but it's still buggy, what gives?

Andrew was trying to decide whether to hire a Project Manager (PM) and, if so, what a PM would need to do their job well. In the meantime, he brought on Brennan Dunn as a business coach, and Brennan suggested creating Standard Operating Procedures, also known as SOPs.

Let’s just say we weren’t immediately onboard...

At first, Andrew was resistant to SOPs. It sounded like a corporate acronym and reminded him of RFPs (Request for Proposals — Andrew says, “At one point in our early life as a company, we wasted a ton of time competing for big contracts through RFPs. It's not something I ever want to do again.”)

Thankfully, Brennan pushed through that resistance and explained SOPs aren’t jargon or suit-and-tie mumbo jumbo. In their most basic form, SOPs are checklists. They're step-by-step guides that explain how to accomplish repetitive tasks your team deals with. They’re checklists with benefits; well-written SOPs increase efficiency, provide consistency, and hold everyone accountable.

...but efficiency, sanity, and accountability were too good to turn down

Those benefits make sense. When you have to spend time remembering how to do a task, that's inefficient. When team members tackle tasks in different ways, results vary wildly. And when you don't tell people what you expect of them, it's hard (and unfair) to hold them accountable.

What’s more, SOPs aligned with one of Andrew’s long-term goals as a founder: “For the last year, I've become obsessed with the idea of firing myself repeatedly. I will consider my job at Krit successful when it can run at a high level without me.” From Brennan’s explanation, Andrew realized a well-documented playbook could be a huge step toward Andrew “firing himself.”

Choosing a tool, getting started, building momentum

Once we realized creating a playbook of SOPs was both a good idea and worth prioritizing, we turned our attention to making it happen. This involved choosing a tool, figuring out where to start, and involving the team.

One tool to organize it all

We knew, at minimum, the right documentation tool needed to have a text editor, permission settings (some people could view, others could edit), and linkable access.

Many options check those boxes. A non-exhaustive list includes:

  • Google docs
  • Dropbox paper
  • Notion
  • Custom website
  • Github
  • Tools like ProcessKit

While we’re big fans of Google Docs for visibility and collaboration, we’ve tried using Google Drive to organize similar past projects, and we always ended up with a mess of folders.

So, we decided to go with Notion.

At the time, this was because it didn’t require any development or design time, we’d heard good things about it and, frankly, had been itching to try it out. We’re on the Team Plan and are happy with it so far. It lets us share access with everyone who needs it (the founders have admin access and team members can create and edit pages) and allows us to organize the information coherently.


The only downside is it’s not our favorite text-editor experience (it can be a bit wonky at times), but no solution is perfect.

Which processes do we document first?

Once we picked a tool, the next decision point was, “well, what’s the first thing we should put in it?”

Building a complete collection of SOPs takes time and effort. We didn’t have the bandwidth to do it all right away, so we started small.

We chose a few procedures, including:

  • Inbound sales
  • Roadmapping sessions
  • Client on-boarding
  • Project management
  • Internal hiring
  • New employee onboarding
  • Bookkeeping
  • Invoicing
  • Content marketing

This list was a mix of easy wins, decently-defined processes, and critical procedures:

  • Easy wins: Processes like invoicing and roadmapping sessions Andrew had already begun documenting and would be quick to write down.
  • Decently-defined: Processes we understood well and just needed to tweak, such as Sales and Content marketing.
  • Critical: Processes that needed a lot of development but were also causing the most pain. These would take time to put together, but they’d address some of the biggest stressors in the agency.

Andrew started with easy wins (aka momentum builders), moved on to the decently-defined procedures, and then tackled the critical items.

Expanding the playbook and keeping it up to date

Once Andrew created a setup in Notion and documented those first few pages, expanding the playbook is largely a story of getting the team involved and keeping the pages up to date.

Getting others involved has included:

  • Team initiative: Tasking team members with creating and refining certain sections. For example, our wonderful PM, Bina, contributes to the Clients and Projects sections.
  • Admin support: We also brought in our incredible VA to help document processes like Bookkeeping, Expenses Reimbursement, and Sending Swag. Other founders have relied on their VAs to help, too.
  • Writer support: More recently, Andrew has brought me (a writer) in to fill out additional pages. This has looked like: me meeting with leadership to define the remaining key areas, interviewing appropriate team members, and then turning those conversations into an SOP.

From there, keeping the playbook up-to-date is largely an organic process. For example, we hire team members in new time zones and realize we need to clarify meeting times in the onboarding section. Or we implement a new process and replace the old approach.


At some point, we may need to set aside time to review the playbook on an annual basis. For now, this works well enough.

The current state of the playbook

Here’s what it looks like so far:                                 


We’ve documented key processes in almost every area of the business. Some are just quick notes, others are very detailed processes. And anything in gray is something we think we need but haven’t written down yet.

Our ideal structure of each page includes:

  • An overview: One to two sentences explaining the purpose of the page.
  • Table of contents: A summary of all sections on the page, if it’s lengthy.
  • A “why”: Why this process matters, or what the goals of it are.                                
  • Process details: How to do the thing.
  • Who to contact: Who to contact if you get stuck doing the thing or have any questions about the process.
  • Last updated: The date the page was last updated.

This list works for us, but keep in mind there are other items you may find helpful to include. For example, Asia Orangio adds a video to each SOP for extra guidance and clarity.                                                            

P.S. If you’d like to read some excerpts, you can find the whole playbook here.

Where do we go from here

It’s hard to predict exactly where we’ll go from here. But our best guess is this:

  • Adding to the playbook. There are still quite a few important pages and processes we need to get down, and those are next on our list.
  • Figuring out the “right” amount of process. There’s such a thing as too little and too much process. A year or so ago, we had too little. But it’d be just as easy to land on the opposite end of the spectrum as well, and stifle creativity and autonomy. Ideally, we want to find a happy medium. We’ll have to find the “right” level of process for our team.
  • Evolving. Our playbook will evolve as we do. Will it stay in Notion forever? Maybe. Will more of it go public? Probably. Will we have to figure out to keep it up to date every year? Definitely. We’ll face questions like these and more as we keep growing.

For now, we can confidently say documenting our SOPs in a coherent playbook is worth the effort and, if anything, we wish we had started sooner!

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