How we work

It’s pretty daunting when your company grows from being just you (or a team of founders) to having its first employees. They are obviously not invested in the company the same way you are, so there are other expectations from both you to them and them to you.

Hiring is insanely expensive (especially if you end up hiring the wrong candidate or it doesn’t work out for whatever reason), so I’ve invested a lot of time in making the best prerequisites for both Sara and me (the first employee at Herodesk who started with us two weeks ago) to ensure this is going to be a success.

The whole people management space isn’t new to me. I’ve hired, fired, and managed teams for the last 10+ years. What is totally new to me, however, is doing it fully remotely. So, I guess this post is a brain dump of some of the preparation I’ve done and how I plan to structure it going forward…

I’ve already talked a lot about the hiring process, so I won’t discuss that. But once you’ve signed a candidate, there are a lot of things that need to get into place. Everything from the high-level stuff like “how do we work” to practical things like getting a workstation up and running and ensuring a smooth onboarding process.

My biggest fear is that Sara would start with us and sit at her desk after a few hours or days, looking out the window and thinking, “Uhm okay, what’s next then?”. You don’t want that, especially at a fully remote startup! So there’s gotta be a plan.

Phew, okay, so, where to start… The big stuff first: How do we work?

I believe you need to structure “how we work” so that we’re purposefully moving the business toward our strategic goals (it sounds like something out of a business book, but seriously).

There are three main tools that we use to structure our work daily:

1Password to store all passwords. This is the greatest productivity hack I’ve ever found. A password manager that seamlessly integrates across platforms and devices. If you haven’t got one, make this your priority.

Google Workspace as our “office”. Drive for shared files, Mail/Calendar for the obvious stuff, Google Chat/Meet for daily comms. (instead of Slack).

ClickUp is our “internal brain” for project management and internal documentation.

There are a few rules of thumb that I’ve implemented to ensure stuff doesn’t disappear and keep our work somewhat sane:

• Use SSO (single-sign-on) with your Google Workspace account whenever possible.
• Never re-use a password. Use random 32-char passwords for everything and store it in 1Password.
• Google Chat is our water cooler. Don’t talk about stuff here that you wouldn’t talk about at an actual water cooler.
• All persistent knowledge, project management, tasks, to-dos, SOPs, etc., are handled in ClickUp, so we know where to find things. (I can do another post on how I’ve set up ClickUp if you’re interested—let me know in the comments.)

That’s the tool stack. I also want to introduce some structure to how we work to ensure we’re moving in the right direction. Some of it is already implemented, but from 2025, I want to have this structure:

• OKRs (Objectives and Key Results) to set yearly goals (lightweight implementation).
• Quarterly follow-ups on OKRs to adjust and re-align short-term goals.
• 4-week Work Cycles (some call them Sprints, but that’s just silly; building a startup is a marathon, you can’t sprint all the time). In each cycle, we’ll plan what activities to execute that given month to move us toward achieving our quarterly goals.

For each Cycle, we plan what we want to accomplish for Product, Customers and Marketing. There’ll be an all-hands (Google Meet) at the beginning of each Cycle to present what’s planned and at the end to discuss what we did.

Every Monday morning will start with a Weekly Kick-off and end with a Friday Wrap-up.

Every morning, we start with a Daily Stand-up.

The purpose of this design is to ensure that every day, we’re moving a little closer to our overall yearly goals.

You never know what will happen, but I feel pretty confident that this structure to “how we work” will be great, at least for the next year or two.