From Bunny Slopes to Big Hopes: Knowing When to Stop, Reflect, and Redirect
I was going fast.
Too fast.
Way too fast.
Especially for my 6-year-old reflexes.
So what did I do?
I sat down.
It was my first time skiing with my parents, after only a day of ski school lessons. We had just gotten off the lift, and I was excited to show off what I had learned.
But as I got going, I realized that I was going too fast, and I didn’t know what to do.
Thankfully, I had the wherewithal to just stop.
So often in life, we start heading in a direction and just keep going, even when we don’t know what we’re doing, where we’re going, or realize we’re headed towards possible disaster (or maybe just results we don’t really want). We just keep going, doing what we’ve always done, or what we planned to do, regardless of the results.
So how do we avoid disaster?
Not actually the author
That’s where having a roadmap and a backlog come in. We don’t need to have every detail planned (in fact, we often don’t want to have too much detail too far out), but enough that allows us to know where we’re headed and periodically affirm that we are, in fact, headed towards the results we’re looking for (like safely getting down the mountain on our 6-year-old little legs).
In a previous post, I shared an overview of the Iteration Next framework, which includes being crystal clear on the outcomes you’re looking to achieve, understanding who you’re serving and why (including yourself), breaking big problems down into a manageable roadmap and backlog, and running and learning from experiments as you iterate.
Once you know the overall outcomes you’re looking to drive, you need a high level roadmap that outlines the key milestones you need to hit along the way in order to get to your defined destination. Not meant to mark out every step in detail, think of this more as the key milestones you’d like to hit along the way towards achieving your outcome.
Once you have a few milestones outlined on your roadmap, you can start creating your backlog, or “to do” list, for the first milestone. Ideally, you want these to be independent, small enough in size that you can check them off with a small-ish amount of effort, and directly correlated to the milestone and outcome.
So in the example of my skiing as a child, a few of the things that my parents might have put on the roadmap for me becoming a confident skier would include getting gear that fit me, my successful completion of the beginner ski school program, and completing 5 green runs with no falls. Then the backlog for the first milestone might have included asking friends if any of their kids have outgrown their ski coats, researching rent vs buy options for skis and boots, and purchasing a new helmet.
While it seems straight forward, figuring out how to shape our roadmap, and what goes on the backlog, can be tricky business. Here are a few things you can keep in mind as you’re developing (or re-assessing yours):
Be real about your points A & B
When creating your roadmap, you need to be honest with yourself about where you’re starting from and where you want to go. You wouldn’t want driving directions taking you from Chicago to New York when you’re actually starting in Colorado and headed to Florida.
When you’re building out your roadmap for that project at work, you’ll need to honestly assess whether your team actually has the skills you need and be real about what your leadership team will expect for a successful outcome. When building out a roadmap for your fitness goals, you’ll have different milestones if you’re already running 15 miles a week vs it’s been 15 years since you ran 3 miles.
When doing this step, it’s important to make this assessment without judgment - in the end, it doesn’t really matter where you’re starting from, or what you believe you “should” be starting from - what matters is that you know your starting place so that you can set appropriate milestones for your situation.
Prioritize
When we start mapping out those key milestones in our roadmap, it’s easy to get overwhelmed by all the things we could be doing, or work on things farther out than we need to. To help with this, consider prioritizing those milestones (and perhaps even breaking them down). A few criteria you could consider might be derisking (what do you need to do now to eliminate risk later), dependencies (what do you need to do now so you can do the other things later), or value (some things are more valuable than others).
When my parents were thinking about the gear I would need as a skier, they started with what worked for my 6 year-old body before worrying about what I’d wear as a teenager, assuming I’d even still be skiing at that age (I was). They also put me in ski school first to ensure I’d learn the basics of pizzas and train tracks before hitting the advanced terrain.
Start with only a few “to dos” and build from there
The best backlogs have high detail for the next few things to be done, and then a decreasing amount of detail from there, with just placeholders for the things that are further out. This is in part because you know a whole lot more about the tasks immediately in front of you, and in part because if you plan too much detail for the things farther out you end up re-doing your plans when things inevitably change.
When planning your backlog for that big presentation you’ll be giving, you’ll want to start with figuring out the outline of your talk and confirming that it aligns with your audience’s needs and expectations before stressing about the placement of the chairs in the room or what you’re going to wear. If you're working on a milestone for building a fitness routine you can live with, you may want backlog items like carving out time in your calendar on a regular basis, buying proper running shoes or other equipment, or purchasing a gym membership before worrying about things like signing up for a triathlon or building out an expensive home gym.
It’s easy to fall into the status quo, continuing to do what we’ve been doing, or planned to do, just because that’s been the plan all along. By stopping periodically to regroup, realign, and replan, we can ensure we’re headed to successfully achieving our goals, iterating towards the people we want to become.
Do you have a roadmap and a backlog? Or are you headed towards disaster?
As you think about where you’re headed and how you’re going to get there, you probably realize there's an opportunity to explore this further. Want some help? Book your free strategy session and let’s dig in.
How will you iterate towards the person you’re becoming?
August 8, 2024
About the author:
Christina Von Stroh is a leadership coach who helps her clients become wildly successful by applying iterative software development practices to achieve their dreams. Want to work with Christina to help you iterate towards the person you’re becoming?
Book your free strategy session.
