Thoughts on Planning

Below I’ve shared a couple of opinions that I’ve formulated over the years around strategic planning.

A) The larger an organization gets, the more important strategic planning becomes

There are a couple of reasons for this:

  • Planning improves clarity and alignment.
  • Planning makes it more likely that we’re not unintentionally pulling in opposite directions.
  • Some people crave structure. This doesn’t mean they are flawed in any way. Not everyone operates optimally in a chaotic environment.

B) Planning works best when everyone is involved

Strategic planning works best when everyone within the organization has a chance to weigh in – no matter who they are, what their role is, or how long they’ve been with the company. Great ideas can come from anyone. Having a diversity of thoughts will always be more powerful than restricting planning to a select group of individuals.

C) Roadmap planning beyond six months is very rarely accurate

A lot can happen in a six month period, especially when building software products. The further out you try and plan projects, the less context and data you’ll have. Roadmap planning takes a lot of energy. In my experience, planning specific projects much beyond six months is more often than not going to be wasted energy.

That said, we do still maintain three year plans that are high level and a couple of paragraphs long max. These short, high level documents allow us to look forward and reflect on the macro level changes that we hope to see on the horizon.

D) Plans change and that’s okay!

Strategic planning is the process of:

  • Pausing work for a moment 
  • Elevating to the 10k ft level
  • Reminding ourselves what we’re actually trying to achieve
  • Surveying the landscape to identify all of the various opportunities in front of us
  • Making an educated guess at which opportunities have the greatest likelihood of getting us to where we want to go, based on the data we have available
  • Coming to an agreement that based on what we know, we’ll focus our efforts on a specific set of opportunities for the time being

That said, just because we’re all rowing in one direction doesn’t mean that we cannot change directions. When new opportunities or data presents itself we should never hesitate to modify our plans. Nothing within a plan should ever come across as being set in stone. 

E) Planning shouldn’t remove agency

A plan is a set of guidelines, not a set of mandates. Just because we’ve highlighted a set of opportunities to focus on for a period of time doesn’t mean that the opportunities we didn’t select aren’t worth pursuing. If your team feels strongly about pursuing an opportunity that doesn’t align with the current plan, you should definitely bring it up! Again, plans are flexible. They should adapt and change based on new data that is presented.

F) While there are a bunch of planning frameworks out there (OKR, OGSM, SWOT, MBO, etc), none of them offer a silver bullet.

The very fact that there are so many frameworks speaks to me that none of them are perfect. One thing I’ve found particularly confusing is when terminology is conflated between frameworks. They all seem to have their pros and cons. Rather than adopt a specific framework, I’m a fan of just outlining something simple like:

  1. Here’s what we’re trying to achieve
  2. Here are all of the opportunities that we know about
  3. Here are the opportunities that we’d like to focus on for now
  4. Here’s how we’ll measure our progress


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Published by

Dave Martin

Dave is a designer at Automattic.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s