The Beauty of Educative Planning

This is part 3 of my 7-part series focusing on The New School Rules. If you missed previous parts, check them out here. Before we start, please take a moment and sign up for my newsletter.

We need to approach planning as a way of thinking, not a set product or plan that has value in and of itself.”

The New School Rules, pg. 11

Say what you will about Mike Tyson, but his response to a reporter prior to a fight about his opponent’s preparation nails the problem with our over-reliance on plans. “Everyone has a plan until they get hit,” he said, “then like a rat they stop in fear and freeze.” The origins of that quote float back through history tweaked by various prize fighters and military leaders. And it resonates as much in the workplace as it does in the ring.

In schools, we operate on an annual planning cycle. We set annual goals – often in the summer – and then often do our best to adhere to that plan and those goals. The main concern I have with this approach is that we are usually addressing last year’s deficits rather than today or tomorrow’s opportunity. Our system discounts current realities and values adherence to the plan over agility and front-line decision making.

The authors of The New School Rules propose a new way of planning in Chapter 1 that adopts the idea of, “plan for change, not perfection.” Here is another comparison of planning approaches from page 19:

Page 19 – The New School Rules

But how do you “plan for change” and still assure those around we are not just making stuff up as we go? Something I may or may not have been accused of in the past.

The authors suggest we build roadmaps instead of manuals. “In order to become more responsive and successful, organizations need to move away from plans that act as manuals and focus on building roadmaps and logic models. Rather than dictating specific actions, these approaches give people the tools they need to make quicker and better decisions on their own.”

A roadmap orients us to a common destination. It has suggested routes and highlights potential obstacles and points of interest along the way. A roadmap also paints a picture of a successful destination. But a roadmap gives flexibility in decision-making along the way and pushes that decision to the people closest to the action. Everyone has the option to follow the roadmap step-by-step, but those wanting to adjust and make the path work for them have that option. Essentially we are defaulting to a system that encourages differentiation and only falls back on rigidity as a last result.

Empowering our teams to make adjustments to a plan will help us as leaders focus on coaching our teams, painting a picture of success, and clearing obstacles along the path. This shift in focus from serving the plan to serving the people helps us use planning as an educative experience where we learn more about ourselves along the way. When reaching that destination then, rather than celebrating and giving credit to the plan, we honor our work and the thinking that took place among our team. The team is now stronger and ready for the next opportunity.

The authors paint a picture of successful planning as when…

  • There’s a greater sense of being alive
  • Teams and organizations have a clear and motivating purpose
  • Everyone is continuously evolving, improving, and aiming higher
Page 33 – The New School Rules

Where in your daily work has planning become a finite rather than infinite activity? Where has the plan itself become the focus rather than the people? Where can you give more agency to the performers of the plan and help guide them on a roadmap rather than script each move as in a manual?

As with most things, it’s about balance. At the end of the day, your teams need to arrive at the destination. Just remember that the arrival at the finish line or the completion of a plan is not the end of the work. It may be the end of that project or that school year, but we are playing an infinite game. And the goal of our infinite game is to keep playing and continuous improvement, not to win or lose.

Meeting a goal and sticking with a plan that destroys a team along the way is shortsighted. That approach may work when a singular outcome at a singular point in time is all that matters. That’s finite thinking. And finite thinking only serves us when we are ready to stop playing the game. I’m not ready to stop and I hope you are not either.

Thanks for joining me on this look at chapter 1 of The New School Rules. Next week we will think through chapter 2 together and examine a new way to look at teaming. Here is a quick quote as a teaser:

In the hierarchical model, good leaders aim to grant some degree of authority to their staff and teams, but this authority if typically contingent – it’s a grant and can be taken back at any moment. This dynamic erodes trust and doesn’t allow authority to spread.

Page 45 – The New School Rules

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Love the Work, One Routine at a Time

This is part 2 of an 8-part series focusing on Marc Lesser’s latest book, Seven Practices of a Mindful Leader. If you missed part 1, check it out here.

Practice 1: Love the Work

I initially discounted the value and importance of Love the Work. When Lesser asked us which of the practices we would make a priority for our thoughts throughout the day, it was not high on my list.

But then he asked us to identify three people we believe truly love their work and the values they held which make them stand out in our minds. This exercise was harder than it sounds, but pulling apart the values of love we see in others helped to identify our own. It’s much easier to talk about others than ourselves of course.

When Lesser is talking about Loving the Work he frames the discussion this way:

While there are many kinds and definitions of love, I’d like to focus on four qualities or practices that make up love. In Buddhism, these teachings are known as the four immeasurables, since it is said that, as you practice them, each of these elements and the four together will continue to grow beyond what can be measured.”

These four qualities are:

  • Loving kindness – The practice of caring for others
  • Compassion – Feeling another’s pain, understanding others, and desiring to help others
  • Joy – A deep sense of happiness that is not dependent on conditions
  • Equanimity – The practice of letting go of self-concern, of cultivating acceptance and composure

The values I shared about my three people revolved around the joy and equanimity I saw in their everyday work. They seemed to find find happiness in the growth of others and relished in even some of the most basic and repetitive tasks.

Those basic and repetitive tasks make up our lives. Whether those tasks take place at work or home, for the most part they are pretty predictable. And it is in these routine tasks where we find the space for what Lesser is referring to as “The Work” – cultivating mindfulness.

During the workday I routinely make decisions, coach my team, and attend meetings. Occasionally I get to speak in front of large audiences and create new systems, but those tasks are not the norm. At home I mow the lawn, walk the dog, and help my partner lead the day-to-day processes of a busy family of four (ie. get my sons to brush their teeth, take them to practice, and pay bills.) Occasionally we take a vacation or attend an awesome concert, but we can’t rely on those rare big ticket events to find the love.

If the work is cultivating mindfulness and that is the work we should love, then what are we doing when we are cultivating mindfulness. We are not speaking in front of a thousand people, going on vacation, or jumping in a mosh pit at a Green Day concert. It’s when we are at home or at our places of work doing the day-to-day, choosing to love the routine, choosing to love the reality because that is where we can grow into the leaders our families and teams deserve.

It’s not easy to embrace and fully engage with the routine. We think that other people’s lives are more exciting than our own because for the most part we only see their social media posts. Nobody posts pictures of the routine tasks. We may still be telling ourselves stories about some other life out there we might be living.

But, one does not cultivate mindfulness by posting a staged Instagram shot from one’s weekend in Sedona or reminiscing about our past. We become mindful leaders by leaning into and learning to love the routine because we trust it will bring more of the four immeasurables mentioned above to our lives and the lives of those around us. Mindfulness is the secret lining we find when we are fully present – no matter the activity.

I’ll end this post with Lesser’s definition of leadership as it will set us up nicely for next week’s post. But before we end, please take a moment to sign up for my email list so you get part 3 of this 8-part series in your inbox as soon as it’s published next week.

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Finally, Lesser breaks down leadership in this particular context into essentially three things:

  1. Think – leaders use intelligence to plan, envision, problem solve, focus, and see from a multitude of perspectives.
  2. Listen – they care about others and collaborate with others to execute a shared vision, which means being open, vulnerable, and curious.
  3. Hold Space – they try to be fully present, clear, emotionally open, and credible; they influence the culture by creating positive norms around storytelling, flexibility, and accountability.

Let’s spend some time thinking about these three actions over the next week as we move into the second practice of a mindful leader in part 3 of this series – Do the Work.

Thoughts to share? Jump into the comments below.

See you next week.

Book Recommendation – The Awakened Family

I’ve written before about transitions in parenting. And still, as my boys are turning a corner from kids to young adults, it’s been fascinating watching them develop their own interests and desires. All of a sudden they are making their own meals, decisions, and developing habits outside my direct control.

Their growth is so rapid that I worry sometimes that I’m not growing and adapting quickly enough to continue to meet their needs and give them space to contribute to the family as a whole.

As the boys grow and change, the entire family will turn a corner. All of a sudden we have four opinionated, confident, divergent, and independent people living together. It makes me wonder why we put labels on periods in our lives like “kid” and “young adult.” Will their ideas about our family carry less weight over the next ten years because their parents pay the bills? I’m not sure I want to live with two people for the next ten years who contribute to the family out of a sense of compliance. I don’t want to come home to “employees” either.

So that corner I mentioned will either be dangerously sharp with multiple switchbacks or intentionally smooth with a few bumps over the next decade. It’s coming either way.

I may be rambling, and that’s because I read an exceptional book recently that sparked much thought in how I want to be intentional and be sure I’m growing as a person as much as the boys are these next ten years. And even more important, that as a family we are growing into an ensemble rather than expecting the boys to conform to repeating our experiences and expectations.

I can’t recommend The Awakened Family by Dr. Shefali Tsabari enough for families with young people moving from single to double digits. It will make you think about the role you play in your children’s behavior. It’s humbling to read at times, but if you can remove your ego for a moment, it helps you realize the control you truly own. The punchline though is that the control lies only with your reactions. We can’t change our kids. We can change our own reactions to what they do or say, but that is the end of our locus of control. After reading this book, I believe understanding that limit will give the kids more space to evolve rather than spending their time trying to predict my reactions to their actions. It will be a work in practice.

Family life is beautiful and complex, and I would love to hear other ideas in the comments from folks on making that transition from living with truly dependent young children, to living with young people who need agency and partnership.

Thanks for reading.

Re-Reading on the Road

Wrote this several months ago, but forgot to post it. Hope you like it.


The first time I read Tim O’Brien’s Going After Cacciato I was sitting on the roof-top terrace of the Rex Hotel in downtown Ho Chi Minh City, Vietnam.

It was dark, I was 22, sipping a gin and tonic, and listening to the common night-time sounds of an incredible city in Southeast Asia.

This time I’m 40, on a business trip, sitting in a hotel bar in Houston, TX. I’m still sipping on a gin and tonic and this time listening to the common sounds of hotel bars across North America.

It’s amazing though how taste, words, and sounds tie a life together. I’ve re-read several books lately from my younger days and can’t recommend it enough. Rather than chasing the latest writer, revisit the favorites of your youth.

  • The same story means something different to your 40-year-old self than your 20-year-old self. That realization has hit me over and over. It’s a completely different experience.
  • The re-reading takes your mind back to that time and place. Midway through the first chapter of Going After Cacciato, I was back in Vietnam, back on Semester at Sea. I could smell Southeast Asia. I felt the night heat, the enthusiasm of my 20s. Careful…it’s a slippery slope. Trust me.
  • It makes me wonder where I will be, what I will remember, when I read it again as a 60-year-old. Which character in the story will I identify with then?

It’s also important to read when we travel because the stories serve as quick passages to our earlier selves. These time capsules allow us to continually check in with ourselves. They allow us to take a step back from our current self and realize how we have grown and changed.

I read several Paul Theroux novels while traveling through Europe on my honeymoon and now when I pick up Saint Jack, I can taste the bread and wine Kelley and I enjoyed on the Col Du Tourmalet watching Tour De France riders suffer up that mountain.

While living in Sosua, DR for several months I read much of John D. McDonald’s Travis McGee saga and recently rereading A Deadly Shade of a Gold, I not only checked in with Trav, and Meyer, but checked in with myself and remembered my thoughts during that point in life and how it felt to run on that sandy beach each morning.

Time is finite, and as many of us do, I often fall into chasing the latest title or gadget to make sure I don’t miss something exceptional. That affliction though often results in lukewarm and generic experiences.

By our 40s shouldn’t we know what quality means to us? I think so. The hard part is owning it and recognizing that now we go deeper into that quality. Not putting total blinders on to newness, but rather becoming better versions of our 20-year-old selves.

Whether reading Going After Cacciato on the roof of the Rex Hotel in Vietnam or at a cheesy hotel bar in Houston, our goal is the same as the protagonist in that story – self-acceptance. So maybe it’s not total blinders to newness, but the filter to get past our defenses must be strong. Stand watch, just like Private First Class Paul Berlin.

Let the Reading Path Circle Back

I rediscovered Zen and the Art of Motorcycle Maintenance recently due to a triangulation of events. I turned 40 which is the age of the father in the story, at work I had to pick a T-shirt with my favorite book on the front, and finally, in the last few years, I have spent a great deal of time thinking about Zen Buddhism.

Firstly though, I felt I better re-read the book because even though I read it in my early 20s, if I was going to wear it on a shirt to work I better refresh in case anyone asked questions or made any references.

Secondly, I was reminded that there are books we need to re-read during each decade of our lives. The titles are different for each of us, but there are 5-10 that resonate to a point in our early years that we need to revisit them as we move through the decades. I remembered a convoluted story about a father and son on a motorcycle trip, some other character called a Phaedrus, and the narrator going on and on about “Quality.” But revisiting the story, it became a powerful dive into values and personal freedom. This “re-read” provided much more meaning than trying to keep up with the most recent “must-read.”

We may start with a couple books from our 20s, a few from our 30s, and so it goes.

I’m continuing with these:

What am I missing? What’s on your list? Leave your thoughts in the comments.