Stepping Back To Step Forward (#17–6/15/23)

John Hartley
4 min readJun 15, 2023

This week I’ve spent a lot of time thinking about the future. Roadmapping for the second half of the year, trying to determine where to make big bets, and thinking about where Curology will be in three years. It’s a very different mode than project management or performance management because it requires a very different brain space. The cone of uncertainty is the broadest it’s been for me in quite some time because there are so many paths to explore. It’s scary and exciting in equal amounts.

In his book “Leadership Strategy and Tactics,” Jocko Willink talks about needing to step back from a situation to properly assess and determine the best course of action. That initial step back is hard. Even if things aren’t on fire, the day-to-day tasks can drain you to the point where you can’t see past the end of your nose (or gun in Willink’s case). Stepping back is tough, but the further you progress as a leader or manager, the more important being able to step back becomes.

How do you get into that headspace?

I know for me I have to set a timer, put headphones on, crank some instrumental music (heavy metal, dubstep, or chiptunes generally), and push all notifications to the side. Even then the ability to step back comes in waves. I can usually push for 20–30 minutes to get the bulk of my ideas onto a page, but then need to let it sit and come back later to dissect further.

Our second-half roadmap breaks down into a few key categories:

  1. Broader business enablement
  2. Localized optimization within our internal customer bases
  3. Big, bulky initiatives that are too blurry to define other than the problem we’d love to solve

Starting broad, I had to look across the organization to understand where we are aiming and what our broad goals are, along with the business context and the microenvironment of what other teams are attempting to accomplish.

It’s easy to be selfish and say, “well, our team has x, y, z things we want to do, so we’re not worried about what other teams are up to,” but that’s a quick way to make your team irrelevant. Looking across the org requires a step back and requires communication with functions you may not normally talk to. Working with customers (easy when they’re internal) helps paint the picture of what each function cares about and gives you a lot of avenues to investigate. The investigation then refines the categories even further, helping you break them down into smaller chunks.

Those smaller chunks tend to become the projects that you and (hopefully) your Product Managers get to chase down. From there it’s either a prioritization exercise, dependency tree, or confidence exercise about how you order the projects for the remainder of the year.

Ultimately by taking a step back, reviewing the total landscape of your organization, and making some blurry decisions, you can more easily move forward. You can’t predict the future, but that doesn’t mean you shouldn’t try. Take your best stab at what the future holds and examine, measure, and course correct along the way.

What scares you about roadmapping or planning for the future? Let me know below!

What I’m Re-Watching: Fullmetal Alchemist: Brotherhood

Not everyone enjoys anime and I get that, but FMA Brotherhood is probably one of the best out there. With the right mix of humor, seriousness, fighting, and science, I’ve probably watched this series four times.

Mustang Unit

Something that stuck out to me this time around is Mustang Unit, the team hand-selected by Colonel Roy Mustang. Each has a unique set of specific abilities, each complimenting the other and forming an unrivaled squad. This is peak team building, so if you’re ever wondering how to add to your team or build a team from scratch, Mustang Unit is a great model to follow.



John Hartley

Engineering leader with a passion for building and growing teams. Writing about leadership and management in the tech industry. Director of Eng @ Curology