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Wisdom is difficult to define in a narrow way.  It’s helpful to think about wisdom as the intersection of boldness and gentleness:

Boldness is being assured, confident, moving forward in the face of risks.  Bold people step out and stand out.  Boldness is not recklessness or rashness because it is thoughtful. Boldness requires deep situational awareness and tempered judgment.  When we think of boldness we think of words like brave, courageous, gutsy, dauntless, fearless, gallant, heroic, lionhearted, manful, stalwart, honor, and valiant. History shows time and again that bold actions often galvanize others into action and bring new resources into the situation.  The Romans said, “Fortuna favors the bold.”  Boldness is superior to timidity in every instance, but it is not necessarily immediate action.  Sometimes boldness is watchful waiting.

Gentleness is strength under control.  Gentleness is not softness.  Gentleness is not ambiguous or amorphous.  Gentleness is not weakness. The process of taming a wild horse is called gentling; the horse is every bit as strong as before, but now under control. The mother who sings softly for hours for a colicky infant is being gentle. The fireman who heaves the child safely through the window to another fireman on the ladder to escape the burning apartment building is being gentle.  The man who refuses to be bullied, responding in an even voice, is being gentle.  A great knight was a warrior who could resolve an issue while keeping his deadly sword sheathed.  

Every parent knows that children are not born with reservoirs of self-control.  Self-control is learned. Self-mastery is a lifetime adventure.

The process of a boy becoming a man is partially about learning to be gentle, to become strong and to use strength well.  Girls becoming women also learn to master their strengths for noble purposes.  Adult bullies and childish brats of any age use strength without control.  

Boldness and gentleness together are the vehicles of wisdom, expressing itself. Boldness and gentleness work together for good.  Nothing of lasting value happens without boldness.  Boldness apart from gentleness leads to tyranny.  Boldness and gentleness check each other’s worst tendencies and support one another. 

Managers miss opportunities to help their direct reports develop new skills and competencies if (1) they aren’t thinking about it, and (2) imagine development opportunities as really big things which take enormous effort.  Encourage people to come to you with developing and training ideas. There are certainly times when we should pursue high-commitment opportunities like mini-sabbaticals and working on an assignment in a new area.  Here are simpler, smaller ideas that can be done without a person doing less in their current role:

1. Meetings: Delegate running a significant meeting to them. Include them as an observer in a decision-meeting. Ask them to sub for you in a working meeting.
2. Ask them to explore a problem, new tech option, an industry situation, and then report their findings.
3. Recommend information and training materials to them – LinkedIn Learning courses, podcasts, books, good articles.
4. Send them to a conference or third-party meeting.  Ask them to report back.
5. Invite them to help you assemble a presentation, budget, or report for your boss.
6. Ask them to give a report/update to your boss.
7. Ask them to bring you a draft message or proposal as a starting point, then finish it together.
8. Introduce them to new people to improve their network.
9. As confidences permit, explain a situation you face to them, and ask them for their thoughts on how they would proceed if they were in your situation.  Review your thinking with them.
10. Encourage them to pick up a side project of their choice.
11. Ask what they’d like to do in the future.  Listen.  Help them think through what skills and experience would be required to do this.
12. Create a practice plan for an individual to sharpen a skill where you see they need improvement.
13. Read a book together and discuss your thoughts and reactions.
14. Ask “What are you learning?”  People respond when you establish a pattern of asking this question, because you are signaling how much you value learning.
15. Share stories about mistakes that you’ve made in past situations.

Two general aspects:

1. Evaluate the work you do, then delegate or include them in the work so they have the capability to do it in the future.  
2. Give them plenty of feedback, especially positive feedback. 

And if you’re not a manager … ask your manager to do one of these things!

Neel Doshi and Lindsay McGregor outline two types of performance in their book Primed to Perform:

• Tactical performance – ability to execute a plan effectively.
• Adaptive performance – ability to adjust your plan when circumstances change.

In “stable world” business situations, the fundamental question is “Are we executing a strategy which will enable us to reach our strategic goals over time?”  In the “stable world” companies win by executing their business model better than competitors in the same markets.

Execution is always going to be important, therefore tactical performance is always significant. 

The reality is that there are fewer and fewer “stable world” business situations going forward.  As the “stable world” business model evaporates, you can beautifully execute yourself into the ground. Therefore adaptive performance in the face of evolving business models is increasingly important, too. 

The authors identify 3 performance levers for adaptive performance:

1. Play (do people enjoy the work?)
2. Purpose (do people feel uniquely qualified to achieve outcomes?)
3. Potential (are we collectively creating meaning and value?)

There are 2 traps to avoid.  First, focusing so hard on execution that you miss the business model shifts.  Second, discounting the important of execution to the point where competitors eat your breakfast and lunch, and prevent you from pivoting to eating dinner in a different business model. 

I’m a really nice guy.  Polite. Courteous. Thoughtful. Kind.  Everyone who knows me knows this.  It’s a significant part of my self-identity.  I genuinely like being helpful and nice.

Being nice has been a limiting factor in my success at times.

I have learned that there is power of acting outside of your normal range. 

I rarely use swear words.  (I think them too often, and utter them rarely.)  My mother trained me to use a large vocabulary of non-swear words in order to make my points.  I had heard updates for three months about a critical-to-others project that was moving so slowly that “glacial speed” would have been a compliment.  I interrupted the umpteenth excuse-saturated update by saying “What the fu** are you going to differently so you can give me an account of actual progress next week?  If you don’t have an answer by tomorrow I will cancel this fu**ing work order!”  The project took a positive turn quickly.  My only regret was waiting so long to do it.  I also learned to bid some projects as a total bid, rather than per-hour.

One of the unexpected bonuses of my choice: that story spread.  A few people starting saying, “Oh yeah, Glenn is a really nice guy, but he has been known to call people out.” As another man put it –he knows much more about my complicated past – “Glenn is an Eagle Scout but he’s no boy scout.”

Another situation: I failed to get across my exasperation with a remote contractor. He did not pick up my frustrated “tone” in email.  I was weary of platitudes.  If we’d been together in person I could have raised my voice – or lowered it into a range he would have instantly interpreted as  dangerous.  I knew he had young children, and they had watched Toy Story, so I used this phrase to make my point:   “Mr. Glenn is unpacking his angry eyes.” Message received.

Reserve the “out of normal range” behaviors as special ammunition for specific situations.  Fifty F-bombs in a 10 minute tirade has none of the impact of a single F-bomb used judiciously.

Also, I’m still going to be nice.  It’s helpful for people to know I’m not cuddly teddy bear to the core, and can bring out a razor edge.  

A craft is a combination of learned skills and art that enables a person to create something useful and beautiful.  Crafts must be learned and practiced.  A craftsman is always working on his craft, even after other acknowledge his mastery. 

Leadership is a craft.  There are learned skills and some art.  A clever person once pointed out that art is just science with more than 7 variables.

The best way to achieve mastery in a craft is the apprentice model.  I studied how apprenticeships worked in the American colonial period, and much of the same is true today in certain crafts. 

There were three elements of an apprenticeship:

1. Study.  Someone has to teach you the basics of the craft.  No one is born knowing how to make horseshoes.
2. Practice.  Lots of practice.  Plenty of oversight and feedback.  Especially in the more artistic crafts much of the practice was imitating the work of the master (e.g., copying his paintings or sculptures). Interesting fact – the typical length of an apprenticeship in Western Europe and the American colonies in the 1700’s was about 7 years.  That’s about 10,000 hours. Craftsmen need significant practice and experience to develop a “feel” for their materials and how to work with clients and customers. Older apprentices would help teach the younger ones.

1. Association.  In every craft there are things which are more caught than taught.  It was very common for an apprentice to live with the master’s family.  Today we say things like “You’re the average of the five people you hang out with,” but this is ancient wisdom.

How was an apprentice “graduated” to being a master of the craft, able to set up his own shop and take on apprentices?  An apprentice had to meet three tests of readiness:

1. Mastery of the basics of the craft.  A master’s reputation was in part built on the quality of the work of his apprentices.
2. A demonstrated ability to learn on his own.  When you set up your new shop there is no master around to teach you anymore, yet you still have much to learn.
3. A demonstrated ability to teach others the craft.  This was needed to perpetuate the craft but also a recognition that there are some things you don’t learn until you teach others.

I encourage you to reflect on your own leadership work.  How are you doing with the three elements of study, practice, and association?

We are not nearly as rational as we think we are.  Our default behaviors are largely driven by emotion, passions, and self-interest.  It takes significant effort to pause and reflect.  It takes strong discipline to separate our actions enough from emotional responses that we can be thoughtful and decisive.  It takes courage to stand on principles and facts in the face of headwinds and tailwinds of trends and popular enthusiasm. 

“Men, it has been well said, think in herds; it will be seen they go mad in herds, while they only recover their senses slowly, and one by one.” (Charles Mackay, from “Memoirs of Extraordinarily Popular Delusions and the Madness of Crowds”)

Mackay published this book in… wait for it…1841.  We know many more examples of mad herds in the years since.

Part of your craft of leadership must be training yourself to “step up and out” of situations to better analyze what’s happening, and make decisions accordingly.  In the heat of events you revert back to your level of training and practice, not what you read about or heard once upon a time.  Therefore, build intentional practice and training into your self-care, so you an better lead others.

You see common patterns and practices in every biography of leaders worth emulating:

• Time invested regularly in solitude
• Journaling and conversations with trusted colleagues to explore complex ideas
• Study of historical examples
• Walking and other forms of exercise
• Surrounding themselves with disciplined people
• Delegating tasks to others, and abdicating from less important activity

These behaviors provide grounding, place you in the path of wisdom, and build your strength. 

One of the best reasons to study biographies is to observe how people acted in difficult circumstances.  They were imperfect people (like you), living in the context of their times (like you), facing uncertainties and risks (like you).  What worked for them?  How did they choose to relate with people (and enemies)?  How did they analyze opportunities and frame problems?  Where did they make strategic and tactical mistakes, and then what did they do next? What did they learn to do differently over time? 

Some have characterized this approach as having a pantheon of great people to emulate.  When you’re faced with something similar, you can ask yourself, “What would this person do and say?”  You combine what you know from their history with your current context and your imagination to make better decisions.  You can also explicitly avoid bad decisions made in the past.  It’s been well-said that the most underutilized assets in the modern world are history books.

Here are some members of my pantheon, in no particular order:

Teddy Roosevelt

Perry Marshall

Charlie Munger

Margaret Thatcher

Indira Gandhi

Dwight Eisenhower

Robert E. Lee

Barnabas the Apostle

Clara Barton

Dr. Martin Luther King, Jr.

Jocko Willink

Frederick Douglas

Barbara McClintock

Helen Keller

Winston Churchill

Golda Meir

Richard Feynman

My dad

I’m not listing a few living individuals whom I’m close to, who have mentored me.  You’ll have your own list of those people. 

We too often fall into a trap thinking that value delivered is proportional to project effort.  That’s quite rare. Projects tend to follow the patterns represented by the green and red lines in this graphic:

If you have a “green” type of project, it’s worth asking when you’re hitting a point of diminishing returns.  In software development, for example, the last 10% of the functionality often requires half the total project effort.  A classic bit of “big organization” political theatre is for an image-conscious leader to bask in the early value delivery, and then jump to another project before they hit the “slog plateau.” 

“Red” project patterns require significant commitment from sponsors because the results aren’t usually visible or useful until much later.  These projects are often the unsexy, unflashy necessary foundation work for long-term success.  Consider shaping a portion of this project to fit the “green” pattern to garner more project buy-in from leaders and stakeholders.  Explore parallelization of workstreams to improve delivery time (though you’ll probably pay a premium in overall effort).

Adapt your leadership and execution to the nature of the project.  Be mindful of how you coach the energy-needed-over-time equation with your team.  Use even a qualitative diagram like the one above to help set expectations.

It’s worth considering which skills will be consistently valuable, even as technology capabilities and business models continue to evolve quickly.  

There are three meta-skill domains, which underlie all other skill progress:

1. Self-leadership
2. Ability to learn new information and skills
3. Mental models for analysis and decision-making

These meta-skill capabilities enable everything else.

The four most valuable skill areas, both now and going forward:

1. Communication – the ability to share ideas, gaining perspectives, educating and engaging others
2. Sales & Marketing – we’re always selling and persuading, reaching new customers/partners, persuading people to buy or use or change
3. Finance & Markets – financial models and appreciation of interconnected markets and sub-markets are powerful toolsets with many applications
4. Coding – the 4^th generation digitalization of everything means that skills in coding concepts and thinking in algorithms are critical, even if you’re not a software developer per se

Note these are true for commercial ventures, non-profits, academic, and government institutions. 

If your strengths and desires align with these four, terrific!  Go deep, and apply broadly.

If your strengths lie elsewhere, work to combine a subset of these skills with your specific strengths to maximize your ability to deliver value over a long time. 

The one thing you cannot do is to rest content, deluding yourself that continued skills sharpening and acquiring better skills is unnecessary. 

Diversity of ideas creates richer imagination about a better future state, and more ways to potentially get there. 

Diversity of ideas – which come from diversity of people’s experiences, knowledge, and perception — is only powerful in a two-part framework:

1. Aligned objectives, which require shared values. We need shared values to align on the problem statement, and right and wrong ways to create solutions. 
2. The shared value of inclusion, which means we accept people as people with something to offer.

Diversity of ideas is an input into a process of making a decision.  High-performing teams solicit many ideas before making a decision.  Once the decision is made, the team pivots their energy into executing a plan to reach an objective.  Too often, we start debating the decision 22 seconds after people left the meeting – this is wasted energy and a poor use of diversity.