I got up early this morning and had a nice hike. I didn’t plan, I happened to wake up a little after 4:00 (wtf is wrong with me?), and thought an early morning hike to Mailbox Peak would be fun. Along the way, I started thinking about leading teams, and now this post happened.
I better explain Mailbox Peak. It’s a massively popular hike in the Seattle area that climbs (steeply) through the forest before coming out of the woods into a summit push that gains almost a thousand feet in the last half a mile. It sounds worse than it is, but it’s worth it, because at the top you have a 360 degree view of the surrounding mountains. It also has a mailbox, and I’ve been meaning to put an AB Testing sticker on it for years.
Planning?
I did not plan in advance. If I’m going on a multi-day backpacking trip, I plan extensively. I need to make sure that I have food, water, first aid, clothing, and everything I need to survive. Often, when I’m doing a 9-10 mile hike like today, I will still pack the night before and throw the pack in the car just to make it easier. It’s light planning.
Today, I woke up and had to find a pack (Thanks to folks at Jeli who gave me a nice Cotopaxi day pack that worked perfectly). I had to pack some food, water, throw a bit of first-aid materials in the bag (just-in-case), feed the dog, and get on the road. Short story is that it took me a while. I mentioned earlier that Mailbox is hugely popular. Usually when I hike it, I do it early morning on a weekday. Today, I got there at 5:30 am, and pulled into the next to last parking spot. I knew the trail would be crowded, so I made a quick decision to take the “old” trail up. The old trail is a grind. It’s steep and rooty, but it’s not that bad, and I only saw a few people on it before the trails merged near the summit. I improvised, and it worked.
Now - I suppose I also got away with no planning because I’ve done some hiking before. I know (generally) what to bring and what I’m getting myself into, so heading out without a plan works (and worked well).
Start With Why
As my mind was wandering on the descent, I thought about the three different levels of planning I will do for a hike. The purpose is the same. I want to get some exercise and enjoy the beautiful nature in the pacific northwest. I want time alone for my thoughts, and I want to be safe.
And then, of course, I went in search of a metaphor.
When I lead teams, there are some things I plan a lot, some things I plan a little, and some things that I don’t plan at all. The why is the same. I want to help teams achieve results through accountability, transparency, and psychological safety. None of that happens on its own, and a lot of it takes time, so I think and plan on how we’re going to get there a lot. At the same time, there are pieces of that why where I don’t need to plan, and because I’ve done this before, sometimes I don’t need to plan at all.
In Start With Why, Simon Sinek talks about the importance of starting with purpose and belief, rather than focusing on reacting to external factors. If you keep a strong center on why you do what you do, how you do it can vary, and you will still reach results. I think there’s also a tie-in to Thinking, Fast and Slow by Daniel Kahneman. Today’s hike was all fast thinking. I didn’t deliberate on what I needed to do to get my butt to the trail and up the hill, I just did it.
In Practice
I have a new team. I don’t know them, and they don’t know me, but I know what I want to accomplish together with them, and I know how I’d like them to work. I have an Obsidian folder filled with things for me to think about, notes on what has worked or not worked for me before, things I want to remember to emphasize, references to books, and more. As I said before, I think a lot about this, and knowing that team results cannot happen without a plan, I make sure I have one.
Some plans are shorter. For years, I’ve held a weekly leadership meeting (not necessarily just direct reports), and a bi-weekly full team meeting. Every Monday morning, I create the agendas for these meetings to make sure the time is well spent and valuable. It takes five minutes, and it makes a difference.
And, as you’d expect, a lot of what I do is “in the moment”. I try to make sure I can jump on spotting a teachable moment, offering a course correction, or finding ways to walk the talk. For example, one of the best ways to build trust and psychological safety is to be vulnerable yourself. So when I screw stuff up, I admit it, and we talk about it - without a plan (because who plans to screw stuff up?).
Mission Accomplished
I made it to the top of mailbox, had some food and water, and completed one small plan I’ve been thinking about for a while.
The view was fantastic, and worth every bit of leg soreness I have. Yes, it was crowded, but who wouldn’t want to go see this.
-A