When It's Time To Experiment

This is the Unbreakable Business newsletter - created just for COOs and Operations Teams who want to build a company that won’t fall apart.

Today’s issue is a bit different - I’m going to give you a candid look into something I’m testing with my team around our OKRs and planning process.

It might work, it might suck, and I won’t know for about a quarter or so.

But I’m gonna lay it all out for you here:

• How we were doing OKRs prior and the friction it causes

• What we’re trying instead and why

• Some additional reading, if you’re interested ;)

Enjoy!!

🤝 My love affair with calendar quarters

I’ve always been a big proponent of Quarterly Planning.

I’ve written articles about it, shot videos about how I do it, and spent a TON of time refining the process inside my company.

So you can imagine how I might have felt when I got the feedback from my team that it wasn’t working that well for them.

We’ve had a pretty big quarter of change - rebuilt how our sales funnel is tracked internally, a huge shift and improvement in data, and a lot of work around our product stack and how it fits into the market.

In other words, we’re moving fast, and…well, I don’t think we’re breaking things, but we’re definitely changing things.

Here’s the rub:

The team was feeling like setting OKRs that were 13 weeks long didn’t leave enough room to adapt to the changes we were making.

They wanted a tighter feedback loop. They wanted to adjust without feeling like they were “abandoning their goals”. They wanted to RUN.

And if I’m being honest, I’ve felt it too. I ran my first company on 6-week cycles (right out of the Basecamp philosophy on product management) and it was awesome.

🧩 Making it all fit?

But here’s the thing - my company today is a lot more mature and complex than that first one.

We track financial results very closely, which are always tied to the calendar. We do financial forecasting quarterly, which I don’t see us changing - actuals are held against the forecast, which comes from the books getting closed on a calendar month.

Bottom line: the OKR system needed to fit INSIDE of a calendar quarter.

There was one other item that needed some attention: the number of OKRs we were tackling.

We’ve long held ourselves to this mantra: “no more than three OKRs in a quarter - one net new initiative, and two improvements.”

But what I’m finding is that as we increased the scope of what we expected (quantifiably measuring attainment with compensation tied to it), it became clear that having one person drive three initiatives per quarter in addition to running their business function was…too much.

Not that it can’t be done - it’s just that it comes at the cost of quality. At the cost of critical thinking. And most importantly, at the cost of recency (trying to remember why we selected the metrics we selected, what the context around it was, etc).

🔨 Building products vs. building companies

NOTE: This is straight from the Basecamp book I linked above - and it’s driven my product management decisions for YEARS.

When you’re scoping a piece of work, there are really only three variables:

1. Quality

2. Time

3. Scope

Assuming that we always want to do top-quality work, that leaves time and scope as the two that can flex.

Basecamp talks about their philosophy as “fixed time, variable scope” - in other words, setting the goal of what they’re going to create in the world, understanding the value that it should drive, and then making it fit by doing less, asking tough questions, and prioritizing shipping over perfection.

I’ll say that last part again: prioritizing SHIPPING over PERFECTION.

Yes, this discussion is right at home if we’re talking about building software products.

But your company is a product too. It needs to be built, improved, and refined. So can this same approach of fixed time and variable scope apply to ALL of the goals and projects in a company?

We’re gonna go find out.

🛬 Here’s where we landed this quarter

A calendar quarter is 13 weeks long. Inside of those 13 weeks, this is the cadence we’re piloting:

Two key principles that we’re encouraging for this test:

1. Unless they fight for it, each leader will have only one OKR for each cycle. They’ve gotta have a really good reason to pull two, and it’s gotta be based on capacity - in other words, there are two things that need to move forward and they’re down to put 50% effort into each.

2. We’re documenting our progress weekly in Notion, and sharing with the leadership team and the company as a whole. Working in a shared space will make us all smarter.

This first one has already yielded some interesting conversations - but they’ve all ended up productive in the end. I do believe that multitasking is generally a “productivity myth”, and am curious to gauge whether or not our overall throughput as a team goes up…by doing less.

How’s it all gonna go? I don’t know, but I know that most of the team is stoked about it (including me). But I’ll definitely circle back up in a quarter or so and let you guys know how it shakes down.

If nothing else, I’m having some fun “building in public” with you guys 😎 

‘Til next time,

✌️ MV

📽️ Check Out The Podcast

This past week on the SaaS Academy podcast, we brought on Mark Hopwood, who runs a killer platform in the non-profit space. We had an awesome chat about what the work is like in the non-profit world and the lessons learned from growing his company.

📗 Tumble Down The Rabbit Hole

I mentioned it above, but if this type of stuff interests you, ya GOTTA read Basecamp’s book on product management called Shape Up. It’s free, it’s great, and it’s really…um, shaped my thinking over the past few years.