Would You Trade Tomorrow for $1M?*

*Question borrowed from Brad Lea, entrepreneur, CEO, and host of the Dropping Bombs podcast.

If you’re here looking for my next book recommendation and lessons in leadership, fear not–I’ll be back next week with a discussion about learning. In the meantime, it’s Thanksgiving … depending on when you read this, you might be somewhere in the course of your holiday weekend. Perhaps you partook in some festivities or a lavish dinner. Or maybe your plans dissolved into the tumult that has been (and is) 2020. In any case, allow me a chance to express my own gratitude–for you, my reader, and for those parts of my life that mean the most. We all have them, those things that matter above all else. In good years we tend to lose sight of them in favor of work, money, travel, personal and professional goals, external stressors. In bad years, the same thing happens … we lose sight of what matters and what we have and concentrate on how bad the year’s been. But it’s absolutely vital that we don’t. That we don’t lose sight of what matters the most and what we have to be thankful for.

Maybe I’m just another person online expressing gratitude who doesn’t deserve it. I’ve thought that plenty of times since March, since COVID-19 made proverbial landfall in the U.S. ‘They’ said the virus may have been here as early as January; some believe earlier. It doesn’t much matter any more, not after a quarter-million dead and millions more sick, disabled, affected by this novel coronavirus. I’m compelled at this point to acknowledge each and every one of those who lost their lives, either due to COVID-19 or as a result of complications that arose as a combination of pre-existing ailments and exposure to the coronavirus. Any loss of life is tragic, no less so for the family members left behind. We should embrace those around us, even if only virtually, who have lost a family member or friend to this pandemic. To the many more who serve in healthcare, emergency response, and public safety–we are grateful for you and embrace you, for the time you’ve sacrificed with your own families and friends to remain ready for the next shift.

I’ve experienced pain in my life. And loss. And amazing blessing. More than once, I’ve caught myself waking up in the morning ‘dreading’ the day ahead. Because of work often times, but also the litany of personal and household tasks we all face. Calling the bank, trying to fix an insurance bill, scheduling a doctor’s, defending a decision to the boss. The lists never seem to end and often justify feeling terrible all day. Not to mention waking up! Just the alarm sound can send shivers down my spine. Then I caught a podcast episode from entrepreneur Brad Lea. He’s a controversial figure to some and isn’t shy with his opinions. But it was his Thanksgiving episode that got my attention. He focused on how we feel getting up in the morning and asks a simple, provocative question: “Would you take $1M and forgo waking up [tomorrow]?”

Well? If you answer ‘yes,’ then are you saying your life is only worth a million? And what would you do with it? What would be the point? Assuming you answer is ‘no,’ or perhaps HELL NO! … then think about what that means. Your life is worth waaaaaaaay more than a million dollars. That much is obvious, to your family at least if not yourself. Once you believe that, you realize waking every morning is akin to receiving at least a million bucks in cash. Every day. This is Lea’s point … approaching your life this way exposes how minor every other disturbance or nuisance is that you’ve been dreading. To be alive with open eyes is a terrific gift. We only have so much time in this life to make a difference in the lives of others, so why waste any sliver of it feeling shitty about the day ahead. That doesn’t mean we want to do all the things we have to do. But it does mean “we get to,” as Lea reminds listeners, and that we have the opportunity to move our own lives forward. If you’re unhappy or unfulfilled with some portion of your life, the gift you receive the next morning is a chance to change it. And change it now, since we don’t know how many more wakeups we’ll get.

I am immeasurably grateful–yes, for you dear reader–but for my family first. For my wife and children who stand beside and behind me every day. I am grateful for the small cadre of truly close friends with whom I’ve stayed in contact for years. I am grateful for the roof over my family’s head, the food on our table, and the scaled-down Thanksgiving dinner we enjoyed last night. And I am grateful to be alive, to have an opportunity to make a difference where possible and serve where I may do the most good.

I hope you are grateful for the live you’ve had, not to mention the life left to live. Today, tell someone you love them. Tell someone else you appreciate them. And tell yet someone else you’re there for them. We’re in this together seems trite now, we hear it all the time. Doesn’t mean it isn’t true. More binds us together than would tear us apart. Remember what’s important and keep your priorities straight. Stay safe this holiday weekend and strive to lead better. The world’s counting on it.

“Vision” Isn’t License to Dismiss Reality (Part II)

We left off in Part I with a once-in-a-career opportunity. The chance to prove how awesome the missile operations community could be. My generation’s golden opportunity the make a better world for the crewmembers to come after us. Like my peers in similar units across the ICBM force, I was charged with assembling a new team, building a training program, and keeping the squadron ready to fight. Oh and make everyone smarter. Dream come true, right?

Of course. And I had no idea how we’d do it. We had a generational problem. Our young crewmembers were motivated and intellectually curious. Meanwhile our commanders who’d succeeded in the old system held on for dear life, openly resisting changes universally supported by their own Airmen. In remaking any organization there is risk. To trust junior officers with so much was antithetical to our mindset. You had to serve at least 15 years before receiving a fraction of the autonomy my peers and I now wielded. The Secretary of the Air Force and four-star officers advocated for delegation and the devolution of responsibility. Many of the commanders caught in the middle drug their feet. And me? I brought my first five instructors into a conference room and told them the truth.

“I have no idea how this is going to go. Everything’s new. The only two things I ask for are your flexibility and patience.” I asked them to be patient, mainly with me; I knew I’d make many decisions in succession with little to no information or guidance–only to overturn half of them in another day’s time. We needed to be flexible given the inevitable scheduling nightmare. The central scheduling office lost most of the authority to schedule training for more than 300 people, leaving individual units to do it for themselves–setting up monthly simulator and classroom sessions. Guess who started out as the training scheduler for our squadron? Yep. Me. More on that in a future post.

I did know what our squadron’s training emphasis should be, on a mode of thinking and operating that hedged against the unknown. Our crews were always smarter than we gave them credit for, yet we admonished them to stick to the checklist and “don’t think” (a genuine quote from too many sources to count). So my vision for our instructors was simple: our crewmembers should be “Ready for Anything.” How do you enable something like that? I’d argue it’s actually quite simple. You describe the problem, that our training is too restrictive and unimaginative. You give up as much decision-making responsibility as possible. And finally, you let go and watch magic happen. And our first five instructors, plus the dozens who came after, did not disappoint.

As the unit evolved and we adapted, the instructors quickly took ownership of their own opportunity to reinvent the missileer-as-stunted technician into an adaptive operational expert and creative leader. The instructors embodied this image themselves, devising some of the most challenging training scenarios anyone had ever seen. Each one developed a signature problem set, augmented by our own crews’ inputs for stimuli. Even as our instructors turned over and the initial cadre gave way to a set of leaders ‘home-grown’ in the new system, we eschewed the limits of pre-built scripts in favor of manipulating simulator inputs in real-time, based on the individual crew’s decisions and actions. If the event was going well, we could ‘up the ante’ and make it tougher. If not–if the crew faltered and found themselves overwhelmed–we turned down the heat or ‘paused’ the whole thing to talk through the problem. I didn’t direct them to do this. Though I may have helped refine their skills in knowing when and how to adapt their teaching methods, they figured it out on their own, through months of trial-and-error, and pushed our squadron to incredible levels of performance. Many resisted and didn’t appreciate being trained “so hard.” They were afraid of making mistakes and “looking bad.” If this sounds strange, that’s because it is. But it’s how we grew up. Training wasn’t for learning, it was for proving yourself worthy of promotion. Training was a proving ground and operations, where the mission actually happens, was where we bided our time hoping nothing happened to get us into trouble. Such a world doesn’t build leaders, it only fosters fear and stagnation.

Okay, it all sounds great then right? Our instructors performed well, our crews slowly came around as their skills improved. My bosses appeared content with our new direction and I felt personally fulfilled after work every day, despite the 14-16 hours spent away from home six days a week. So what’s missing throughout this self-promoting narrative? Who’s missing? My peers. Our sister squadrons. A full 75% (probably more) of the 300-person operations group who weren’t subject to my sheer force of will. Herein lies my biggest lesson, and among my career’s biggest failures. I was so married to my vision, I neglected most of the team and a reality that hid in plain sight.

An ICBM operations group includes four squadrons–three devoted to combat, one devoted to advanced training, facilities, and intelligence planning–and a quality assurance (QA) division (“standardization and evaluation”) tasked to assess warfighting readiness and provide technical advice. These five units, plus group leadership and its staff, add up to more than 300 people. In my role as an instructor supervisor, I was responsible for five individuals who trained 65-80 crewmembers and worked alongside 15-20 facility managers. At its peak, a “healthy” squadron numbers about 100 personnel. This means there were two other instructor supervisors doing the exact same thing in two other squadrons and another instructor supervisor in the support squadron who worked to keep us all on the same page. In the weeks I spent crafting my vision and pushing into uncharted territory, I conferred with my counterparts zero times.

Don’t get me wrong, we talked every day. We saw each other in the hall. We joked, complained about work and life, compared notes on the small potatoes. But as I pushed my squadron hard, I didn’t share what we were going through or the philosophy behind it. I didn’t ask for feedback or input. I didn’t ask what I was missing, or even if they’d like to share methods. As our five instructors evolved into brilliant experts, we noticed our squadrons growing distant from each other. Someone with a competitive edge might relish this moment. And I did, at first. Until I saw the toll it was taking on our relationships. Young lieutenants got into arguments because our crewmember thought the other wasn’t trying hard enough. At the same time, our commanders clashed as their junior supervisors executed their own visions of success in a vacuum. The extent of my failures as a leader came to a head when my own boss was scolded harshly by his boss (the commander of the whole 300-person organization) for not working out an issue at a lower level. The trigger? I’d called out the QA team for what I perceived as a rules violation in how they debriefed scripted assessments. I didn’t talk to anyone on that team before submitting the comment. I chalked up my previous failures at reconciliation to QA’s ‘poor attitude’ and resistance to change. The damage was done and fissures opened everywhere that had been bubbling under the surface for months, if not years.

Some of our crewmembers, now having trained in the ‘new’ system for two years or more, were coming back from 36-hour deployments fuming about the other squadrons. They don’t know what they’re doing. They aren’t willing to look up the answer, they just ask! I can’t believe they missed that step. I can’t believe someone that senior asks such dumb questions. These aren’t a leader’s thoughts or words. They are lamentations of people conditioned to think their way is the best and only way. No amount of equivocation conceals the fact that I’d conditioned them that way. I’d pressed so hard toward my vision that I’d been willing to sacrifice every opportunity to train alongside our sister squadrons. I didn’t have any direct control or authority over those units, and so I dismissed them. I’m honest when I say I didn’t mean to. But it also doesn’t matter whether I meant to; what matters is what came of my actions. A breakdown in our most important personal connections.

Back to Elizabeth Holmes and Theranos. Remember them? Breakthrough disease detection with a drop of blood. Device no bigger than a toaster oven. It never worked. The technology wasn’t there. But Holmes’ vision ruled in spite of true constraints and her own team’s skepticism. She was so invested in her vision of the future, so driven to achieve it, she shut out the input most vital to long-term success. And it costs hundreds their jobs, billions of dollars, and many good people’s reputations. I was deeply invested in demonstrating to the world how strong a community we could build in missile operations. For so long we’d failed to lead and develop our people, we all knew we could do better. With an opportunity and the “keys to kingdom,” I hit the ground the running. Literally at times, with a reputation for running up and down the halls “fighting world hunger.” But I never stopped to talk to my peers about what we should do or how we should proceed together. I thought I had the solution and took off without regard for how many others, all invested in the same thing, would be damaged. I ignored reality–the multiple commanders and senior leaders, four different sets of crewmembers at different stages of organizational evolution. And did I mention most of those 300 were aged 25 or less? Not only did I break vital connections, I perhaps tainted the outlook of dozens of young officers who would go on to lead the “new missiles.”

I’ve learned the hard way, living through and attempting to lead organizational change, that the only thing you can count on during a change initiative is how much your change will change. “Organizational change management” (OCM) is really “organizational change initiation and response.” We take an idea and start down a path, only to take several turns along the way as you listen to feedback and tweak your methods. What matters most, I think, is deciding when and with whom to initiate. It’s a lot like a first impression. The ideas may be good, your vision may be appropriate, but how you initiate that change and execute your plan must be well-conceived with all of the stakeholders in mind. And you’ve got one shot. I should have leveraged my instructors to connect with their peers across the hall, as I should have done with mine. I should have cultivated relationships in parallel–updating my commander so he could confer with his peers–and sought criticism across units through my peers, and pushed to exchange personnel so we could all learn from each other. It’s easy with hindsight to see what I did wrong and how I’d do it better. But none of us get that luxury. The best we can do is pass it on to pay it forward. Learn from my mistakes, don’t neglect the very team upon whom you will rely. Don’t be so married to a vision that you dismiss reality around you: the people for whom the vision was built in the first place.

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