Employee 1 and Beyond: A System Set-up Checklist

Tuesday, September 18, 2018 - 08:38
A person setting up multiple laptops.

This is version 1.0 of this document. Updates will be made if/as necessary.

Knowledge sharing in a company of one (YOU) is trivial. All the information can live in YOUR head, in YOUR inbox, and on YOUR laptop. In the spirit of getting shit done, this strategy will work for a while until it doesn’t. Eventually, you become a bottleneck or a single point of failure when you add the first contractor or employee into the mix. Worse, once you cross a team size of about five to ten, a lack of consistent communication tools, workflows, and team norms can cause work gridlocks, communication breakdowns, duplicate work efforts, passwords to get leaked, and so on.

In the past decade, I’ve worked within (as an employee) and alongside (as a contractor/consultant) at least a half a dozen company founders or small teams going through this exact pain point as they attempted to grow. I’ve had the benefit of being able to research, implement, and evolve these systems and processes to find the best fit at each stage of their growth while they continued to strive for peak performance. I also had the great fortune of working in the capacity of a COO as new departments formed and these systems now had to adapt as the new interfaces between these departments had to be bridged while the company evolved in size and shape.

What follows is a recommended set of tools and implementation details that I would put in place starting with employee #1 or contractor #1 at any company. This recommendation (current as of Q3 2018) is the culmination of all of my past experiences, all the shared knowledge, and input from an exceptional group of peers along the way. While this recommendation may not be appropriate forever if your business takes off and becomes wildly successful, they should reasonably grow with you from a team size of one to 50 (or at least through your first few phases of growth).

A Few Caveats

  1. Do not get hung up on one specific tool over another. Asana and JIRA are perfectly good substitutes for Trello on the project management side, and there are many alternatives to Pipedrive on the CRM side. Instead, mix and match the tools to your liking and focus on achieving the goals highlighted by the implementation details. Ultimately, the goal is to support your overall business workflow, team communication, and performance.
  2. Some of these tools may not be relevant to your business in your industry. I’ve mostly been in the web development and software product industries and therefore will recommend some tools that touch on that genre. Please skip over any unnecessary items while taking what’s useful or relevant to your situation.
  3. Some of these recommendations may seem obvious if you’ve been in this industry long enough. However, I’ve seen relatively mature companies with intelligent team members lacking in one or more of the areas discussed below.

The Summarized List

Please note that while you may already be using these tools, there are specific implementation details in the subsequent sections that I found to be critical to maximizing the gains from each individually and as a collection.

  • G Suite (Email, Calendar, Team Drives, Groups)
  • 1Password Team
  • Trello
  • Slack
  • DocuSign
  • Pipedrive
  • GitHub
  • OKR Scoreboard
  • Project Reference Guides
  • Communication Norms Document

Specific Implementation Details and Justifications

G Suite

While there are alternatives, I can’t imagine running a business without G Suite (or an equivalent service) to provide all its off the shelf tools (email, calendaring, and online docs). Opening an account should be step one the minute that you have secured your business domain. Create your [email protected] email and use that to complete the rest of the details in this checklist.

Sidenote: G Suite has many configurations that you can explore, but below are the critical pieces to get operational.

Email

This one is standard practice, but every employee in your organization should have an account because this becomes the entry point for systems that you can integrate with a G Suite (e.g., Slack, Trello).

From day one, ensure that two-factor authentication is available and required for all accounts. Help train individuals on how to use the Google Authenticator app before they are granted access to Groups or Team Drives that contain sensitive information.

Groups

This one is critical and often overlooked. The person setting up G Suite will tend to use their own email as the admin account for each external service the company uses (e.g. Amazon, Mailchimp) on each and start receiving all of the emails directly. This tactic is fine in the short term but problematic for two main reasons: 1) distributing the workload/knowledge/access and 2) easily adding or removing email history from an individual that may need access to this information now or in the future.

Instead, immediately create the following groups: * [email protected] (and assign yourself to it). * [email protected] (and assign yourself to it). * [email protected] (and assign yourself to it). * [email protected] (and assign to everyone in your G Suite account).

Later you can add [email protected] and other groups as you see fit ([email protected], [email protected], [email protected]). To get the most benefit out of this approach, I recommend the following policies:

  • Anytime you sign up for a new service that doesn’t allow for multiple people to be assigned as an admin (e.g., Amazon.com), use [email protected] This way, anyone within this group can reset the password to regain access to it if it is lost.
  • Anytime a service allows you to specify a billing address and email to send the invoice to, assign it to [email protected] This will allow you to open up this group to your accounting department with minimal effort. It will also help you track down purchased licenses and other details attached to the invoices.
  • Anytime a service allows you to specify where support or contact inquiries should go, use [email protected] (or whatever variation you prefer). This will give you an audit trail to determine lead volume, support volume, and SLA response times). It will also be critical when you can offload this to another individual or team. Often, a development team will want or need this access when asked to triage bug reports and other issues.
  • Anytime you want an email of long-term value to be stored so that future hires can see and access it, use [email protected] This allows you to avoid the hassle of finding and forwarding a bunch of previous communications. You can even reference them within the Google Group via a direct link, which can be incredibly handy during onboarding.

Team Drives

Google Docs and Sheets are incredibly powerful and feature-rich. They allow for real-time collaboration, complete version history, and fine-grained permission controls. However, it can quickly become a Wild West if there is no strategy put into how the documents will be shared and secured. Team Drives offer an ability for the company to take over ownership of the folders and files as well as provide top-level permission access so that every file dropped into each folder immediately gets the proper settings. These files are also more easy to find when searching. This approach is significantly better than allowing everyone to store all company files in their own individual drives because this information easily becomes lost in these individual silos and occasionally lost, particularly when people leave the company.

At a minimum, I’d recommend the following top-level team drives:

  • Admin
  • Contracts
  • Financials
  • Legal
  • HR
  • Sales
  • Team

If you do this correctly, you will be able to provide the appropriate access to all files and folders to a new hire within minutes.

Calendars

Use as you see fit. There are a lot of other great resources out there (e.g., Getting Things Done by David Allen) that can help create strategies for you and your organization.

1Password & 1Password Team

Visualize this typical scenario. A new person joins the team, and you now need to give them access to 10 to 100 different systems. The person granting them this access has to mentally determine which ones are worth passing along and also tracking down ones they might not have from other team members. This grantee then decides to get them over quickly via email, Slack, SMS, or some other method altogether. Using this haphazard approach, passwords are littered everywhere, and the new hire now needs to wrangle this together and potentially perform the same process if they help onboard the next person.

To me, there are few things as horrifying (given the severe pain of a data breach) as seeing people share passwords, API keys, and credit cards in such ways. Worse, when people leave an organization, how does one ensure their access can be turned off and while resetting and redistributing the passwords to the existing team members? It’s nearly impossible to do this securely without a strategy in place.

As a company of 1, you don’t need to splurge and pay the cost for a 1Password Team account right from the start. Ideally, you at least use tags or a naming conversion so that you can easily separate personal and business-related information. However, as soon as you find yourself needing to share a password with an individual or a team, creating a 1Password Team account will be essential. You can specify multiple vaults so that you can group passwords by severity (e.g., owner, admins, and team) in addition to each department (e.g., developers, designers, and support). Combined with the suggestion to use [email protected], you can easily share dozens (hundreds?) of passwords to admin accounts while still maintaining ownership and the ability to reset these passwords should there ever be an issue.

This password and secret sharing strategy is particularly powerful when you need to engage with outside vendors. You can create a vendor-specific vault and provide them copies of the limited accounts they need access to in a secure way with an audit trail of what they can access.

Trello (or a Project Management Equivalent)

While Slack (see below) can be powerful for real-time communications, I’ve found that outcomes of discussions and decisions are best tracked in a project management system. There are a lot of great resources on the web regarding how to best structure for your use case. However, I find that, at a minimum, each external project (e.g., client work) and internal project (e.g., company initiative) should be represented by a project with some individual issues/tickets used to track this. As more people join the company, this will be critical in surfacing what work is being done, when, and by whom.

Slack

While email and project management tools are great for some forms of communication, they can be terrible for issues that need to be hashed out in real time or face to face. This is where Slack is becoming an essential tool for most tech businesses, potentially more important than email and project management systems (although all three are needed).

Everyone will have different best practices here, but I’ve found that at a minimum creating a few organization level channels (e.g., #sales, #design) as well as a channel per project tends to work well and segment the information to the proper team or context. That way people can choose to enter/leave or mute/unmute as they see fit. However, be careful not to expand the number of channels too much because this leads to information sprawl, and that becomes unmanageable in its own right.

DocuSign

Even established companies can find themselves in a position of not being able to locate an NDA, contractor agreement, or customer contract. Often, it’s lost in an email archive of an individual that may or may not even work there anymore, which makes it a daunting task to hunt it down. Therefore, having a central audit location to track/manage that process is critical, particularly to avoid problems down the road if a legal dispute arises.

You may want/need to create two or more accounts if you decide to use this for your HR and sales departments. The reason being is that you don’t want a person on the sales team accessing employee files and contractor agreements that HR should be the only ones with access.

Pipedrive

At the beginning of your company, it will feel easier to track all sales and partnership conversations through email because it’s fast and frictionless. The problem occurs the when a project manager or team developer is receiving pushback from a client about a conversation that happened before the contract was signed and that only one person can access. This is where a CRM like Pipedrive can make it very easy to capture these conversations while not adding much overhead. Users will be granted a specific Pipedrive email they can put in the bcc field of all their emails, which Pipedrive can immediately ingest and associate with that lead or account.

I can’t stress how important this is, particularly when the number of leads, sales, and partnership conversation grows and spans multiple people. Digging through email becomes a hassle a best and a missed opportunity at worst.

GitHub

This recommendation may seem like a no-brainer if you work at a software company, and yet I’ve worked as a vendor for clients paying $100,000 to $1,000,000 for software they technically and contractually owned and yet had zero direct access of it. In my opinion, if your company builds or maintains a codebase that is separate from what is available in the public domain, a copy needs to live in a code repository that the company owns and maintains. GitHub is the defacto standard, although there are many great alternatives out there as well.

Depending on your specific desires or interests, you can integrate GitHub with Slack or other systems to receive notifications for particular activities (e.g., new ticket creation or comments added). You will need to find out what best works for your team or organization, but typically some level of visibility within a dedicated room in Slack is useful.

OKR Scoreboard

Ideally, you know your companies top 3-5 objectives in the next 90 days. Of course, not everyone has that level of clarity of focus and vision. If you fall into that category, I would highly recommend reviewing the Google OKR Guide for a quick introduction to the Objective Key Result (OKR) philosophy and methodology.

At this stage it is recommended to have a definition of and companywide access to these top 3-5 objectives along with additional detail regarding what each of them means, measurable key results to obtain them, and who is responsible for each.

Getting in the habit of doing this when the company is small will help keep focus as the company grows and new teams and departments form, opening up the door for misalignment.

Project Reference Guides

This is a tool within a tool, but in my opinion, it’s a practice that will serve you very well as your internal team size and external accounts continue to grow. The concept is the simple practice of creating a 1-2 page document for each project or account so that a new person can quickly locate key details (contracts, due dates, budgets, etc.). I wrote a more detailed article on this subject that features a template that you can copy and begin using immediately.

Communication Norms Document

You’ve spent all this time putting this all together, what could go wrong? Well, you may understand the strategy and nuance behind all of this, but not everyone will remember this expectation. By documenting where you expect certain forms of communication to happen and to get stored, you are reinforcing this expectation and setting yourself and the team up for more consistent and reliable communication.

This document may seem overkill. However, it is important to highlight this may not be practical to follow 100% of the time. Exceptions can and do happen. However, the more you can help define and follow the norms, the better. For the avoidance of doubt, as the company grows and the culture evolves, these norms should as well to reflect the best practices for that moment in time.

Final Thoughts & Feedback

I hope you found this helpful, particularly if this is the first time you are creating and growing a company. I’m certain that I can improve this checklist by including details or experiences from others like yourself. If you believe I missed something critical, please add a comment below or contact me so that I can consider it for inclusion!

Acknowledgements

I want to call out Kevin Bridges specifically (@cyberswat) for so much of the help and refinement of this process over the past six years. The work we did at (@drud) and previous companies shaped a significant portion of this recommendation.

Photo by freestocks.org on Unsplash

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About Rick Manelius

Quick Stats: Chief Product Officer of DRUD Tech. Author of Winning the Lottery Within. Graduated from MIT in '03 (BS) and '09 (PhD). Life hacker and peak performance enthusiast. This blog is my experiment in creative writing, self-expression, and sharing what I've learned along my journey. For more information, read my full bio here or contact me.