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Leading with Why

improve your productivity legal operations legal process improvement Aug 16, 2021

I just got back from a four day horse trip into the Montana wilderness. It was a great experience—first time on horseback for both of my kiddos, and they got to catch 14” Yellowstone Cutthroat from crystal alpine lakes with their grandfather smiling by.

My dad and his best friend grew up stringing the friend’s horses and mules on multi-day trips in the Sierras, and my siblings and I did several trips into the upper Kern when we were kids. But that was different terrain and a different time, so we hired an outfitter for this adventure.

Terry has been cruising the mountains around West Yellowstone since he was a teen, and he’s been leading trips for nearly 40 years. He knows his craft, his country, his animals, and his gear. To say he’s an expert is an understatement. He’s so good at what he does that he can basically operate on instinct. Except for one thing: he can’t do all of the work alone.

So Terry has hired hands. Rail-thin Andy from Tennessee looks the part, with a showy feather in his Resistol and a couple of top snaps on his western shirt that never manage to meet. Baby-faced Eli from Minnesota has an easy smile to compliment the “yessir” work ethic he learned on his family farm. And garrulous Colby from the Northeast Kingdom of Vermont, who admitted she was more interested in ski-racing than high school and fell in love with the Northern Rockies at first sight.

These young people are earnest and hard working, but they are green. Fortunately Terry is a capable teacher, happy to share what he knows about adjusting a britchen, spotting wildlife, or the placement of coals on a dutch oven lid.

But I noticed something over the course of the four days: The young hands still had a lot of screw-ups. And while Terry was patient as he’d re-explain what the problem was and what the cowboys or cowgirl should have done different, his frustrations sometimes slipped out once his employees were out of earshot.

“I feel like I’ve gotta have my eyeballs on every little thing,” Terry admitted one afternoon. “These kids are eager and are good enough with the animals, but what they don’t know about the ins and outs of running an outfit could fill that lake over there.”

It came to a head in our preparation for the ride out.

Let me first back up. The ride up to camp had taken longer than advertised. Rather, the ride was fine, but we guests were sent ahead on horseback with Colby and Eli while Andy pulled the mules. Terry had some administrative work to attend to before he lost cell service and planned to catch up with Andy on the trail.

Apparently Terry found Andy stopped just a few miles in, re-loading the half-breeds a second time. They had to re-tie the canvas manties that cocooned our gear (and warm clothes!) on some animals, and re-sling coolers full of grub on another. We were expecting the mules about an hour after we reached camp. Over three hours later Andy crested the ridge above camp just as the sun dipped below it.

In retrospect, three spare hours in a beautiful place is a rare luxury these days. We certainly enjoyed the first bit of time as we stretched our legs and soaked up Montana’s glory. But the temperature drops fast at 9000 feet, especially when thunderheads boil up and drive the wind ahead of ‘em.

We weren’t without resources—the outfit had left up a three-sided cook tent and cached some basic gear behind an electrified bear fence. Still, the hands seemed lost as that first hour elapsed. Their instructions from Terry had run out and they—still learning the ropes themselves—weren’t sure what to do next.

After 90 minutes my dad made a comment about setting a kettle to boil, knowing from experience that anything warm would be an asset in declining weather (we were under a burn ban, so we were reliant on a Coleman stove and the one green cartridge leftover from a previous trip). Colby acknowledged his remark but took no action. Terry was the boss, and his instruction had been to wait on the mules.

After another hour my dad filled the kettle himself, and Eli hesitantly connected the propane and struck a match as the first hailstones thumped the tent. Fortunately we remained on the edge of the storm.

Still, once the mules arrived, everything was a scramble. In the early canyon twilight we had to sort gear, pitch tents (still fighting the wind), and cook dinner, finally eating an admittedly delicious meal under the glow of lanterns and headlamps. It worked out in the end, but we’d all been a bit puckered and moods were sourer than they ought to have been.

That experience colored my thinking for Wednesday’s trip out. Sadly, I needed to be in Portland for a Friday morning dose of reality, and I wanted to get at least as far as Pocatello that night so that Thursday’s drive wouldn’t be too much of a slog. I said as much to Terry on Tuesday evening, and he agreed to have our animals ready for a morning departure (the other family on the trip would stay behind to enjoy the mountains a few hours longer).

I didn’t hear the exact instruction Terry gave his crew regarding our early exit, but given what happened I can piece it together. Something to do with loading up early, so go catch the animals that were feeding in the next basin to protect the alpine lake near camp. And be sure to pick enough tart grouse whortleberries to deliver on the promised mountain pancakes for our final breakfast.

Clear directions on what they needed to do; at least as they resolved between Terry’s ears, knowing the context that he knew. But I’m pretty sure he made no mention of why we were packing early, or what the Grants were trying to accomplish with that accelerated schedule.

Turns out the animals were on the far side of the basin, 400 feet up and a good half mile from where the saddles rested on a downed tree. Eli and Andy dutifully trekked up to the stock, coaxing them near with soft words and trading bits of granola bar for their halters. Already the sun was higher than they’d hoped, and they still had berries to gather. So they hastily strapped the deckers to the mules and stuffed a quick red handful into their scarves on their way over the ridge.

Meanwhile we’d broken camp and packed our gear, holding out a rain jacket for unexpected weather and bear spray for unexpected encounters. By my third cup of coffee Colby had beaten the batter and warmed the griddle, but was stalling breakfast for the promised whortleberry mix-in. Terry made good time as he wrapped our belongings with deft diamond folds of the manties, and my boys used the finished packages as ottomans to steal a few extra winks of sleep.

We didn’t see the cowboys crest the ridge this time, catching only glimpses through the trees as they rounded the lake. Which is why we didn’t notice that they were leading the mules, but had left the horses behind. The hands knew we were supposed to pack up early, but nobody had said anything about riding.

So back they hiked to repeat their efforts. Colby tossed the meagre berries into her batter, enough to leave flecks of red but no discernible flavor. Terry grumbled his way through some busywork, not wanting his mules to bear their burden any longer than they needed to. And we waited. And waited some more. Again, not a bad place to be stuck idle, but the early departure we’d hoped for was slipping away.

We finally set off close to one o’clock with Terry at the lead, the rest of the crew staying back to finish breaking down the kitchen and load out the other family. Terry expressed confidence that we could make the return trip in just 3 1/2 hours. And we might’ve done it too, except he loaded the mules without realizing that his cowboys had assumed they’d have time to re-saddle the stock before setting off.

The first mule lost its load just beyond the ridge line, out of sight of the camp (and, fortunately for the cowboys, out of earshot too). Turned out the straps were twisted, the pad had slipped far south of where it needed to be, and I’m guessing a few other things were off that my untrained eye didn’t catch. I helped Terry unload the manties and watched as he re-worked the entire tack from nose to tail.

He kept remarkable patience—largely, I surmised, because he’d learned long ago that it does more harm than good to show a mule that you’re agitated. And it was a pleasure watching him work, able to provide a spare hand when he requested it. Again, the guy is a pro, but we both understood that he never should have needed to demonstrate his expertise at this particular moment.

The rest of the ride out was uneventful. Terry let on that his preferred punishment was a late-afternoon barn cleaning, “when it smells good and ripe.” My boys and I managed to grab takeout from the Olive Garden in Pocatello before it closed (my younger is a pastatarian, and he’d been without for four whole days). The late hotel shower felt awfully good, even as I debated between cleanliness and sleep.

Thursday’s drive was still a slog, not helped by smoky skies and triple-digit heat. But I made my Friday obligation: a meeting with a lawyer who, as it turned out, was frustrated with his need to spend so much time quality checking his team’s work.

Far be it for me to second-guess how a legitimate mountain man runs his pack trip operation, but if Terry were one of my lawyer clients, I’d give him this advice:

You’re trying to do too much. Whortleberry pancakes are a romantic idea and a nice touch, assuming everything else is going well. But when his team got behind the eight-ball, that little spiff became a distraction that led to haste, and mistakes, on the core mission. Ultimately it hurt the overall experience far more than it helped.

Don’t be afraid to slow down the entire operation to the speed of the slowest component. Our initial ride to camp was a story straight out of Eli Goldratt’s The Goal, where slowpoke Herbie and his too-heavy backpack causes his entire scout troop to make camp in the dark. Divide and conquer often feels like a good strategy, but if each division doesn’t have the tools to be self-sufficient then all you’re left with is divide. “Elevate the constraint” is what Goldratt teaches. In other words, try make sure that the overburdened resource (Terry) doesn’t suffer even more work when things go wrong along the way.

Finally, and most importantly, resist the urge to tell your team exactly what to do, and spend more time engaging them with why something needs to be done—what is it that we’re trying to accomplish for our customers? Hindsight is 20/20, but I have to think that if Eli and Andy had understood that I was trying to make time on the highway that evening, they would have pieced together the steps to help that happen. But once they got detailed instruction, they turned off their problem solvers and followed orders (not unlike Colby and the kettle that first night).

This is an especially tough thing for an expert to get good at. Counterintuitively, we feel like more explanation, perhaps a little redundancy, is the best way to stave off disaster. But as Sidney Dekker teaches in his classic book, The Field Guide to Understanding ‘Human Error’ the more complex you make a system the more likely it is to fail unexpectedly. (Check out Episode 3 of Tim Harford’s Cautionary Tales podcast for more on why).

It requires a culture where people feel safe asking questions, something that I could tell Terry had done. After all, the alternative is that your team members will make assumptions. Most people know what those will do to U and Me, but I learned it a little different when I worked farm jobs in my youth. “Assumption is the mother of all screwup,” the boss had told me (except he didn’t say “screw”). “I’ll never get as frustrated with you asking questions as I will if you mess something up because you didn’t.”

I wound’t be surprised if Terry’s patience got a little thin once all his guests had driven on down the road. Still, I think his experience with young hands, much like his understanding of mules, probably kept him from too much agitation. He’s running a complex operation to create good experiences for his customers. And at the end of the day my experience was a good one thanks to Terry’s quick clean-up skills.

But I can’t help but think that Terry’s getting a little long in the tooth to be carrying so much of the load on his own. He, of course, didn’t ask for my professional help and I didn’t offer it—I know enough about cowboy codes to step in that one. I’ve learned things over my years of working with experts, however, that I’m pretty sure could save him some headaches down the trail.

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