The Dichotomy of Leadership

5 minute read


As always, I don’t agree with or use everything I read, but I will still try and summarize it here. If you are new here, read why I put my semi-personal book notes online.

I’m surprised none of my startup friends have read this book given how insanely well rated it is. That may be because it’s relatively new having been published in 2018. One small mistake I made was not reading their previous book, Extreme Ownership which does get referenced in this book. I’ll have to add that to my to-read and come back to review my notes at a later date. Overall it’s a great book. One thing to keep in mind when reading this book is the dichotomy of leadership might also be renamed balance. A couple of other books I’ve read talk about this “dichotomy” as well.


For every positive behaviour a leader should have, it is possible to take that behaviour to the extreme, where it becomes negative


The authors talk about strategies for balancing:

  • humbleness vs passivity
  • aggressiveness vs recklessness
  • discipline vs flexibility


Deeply care about your people while still being willing to put them in risky situations. Resolute but not overbearing; know when to mentor and know when to fire.

One fundamental principle is to take ownership of every mistake, never placing the blame on others in the team. Finding the balance between micromanagement and laissez-faire. Empower your team to lead and take ownership by allowing them to own.

Find the balance between leniency and domineering. Know when it is important to hold the line and when it’s important to build some “leadership capital” by allowing slack in your decision. Spend that capital when it matters and you need to pull rank in making a decision.

Don’t be too quick to fire, but don’t spend too long mentoring a lost cause. When you find the balance hold the line. I think this sounds very familiar to the section Good to Great where I also refer to a commonly known startup saying regarding this necessity.


Training should be hard but also smart, only aggressive and disciplined can attain this balance. I would add empathy is important here since as a leader you need a feedback look to understand what aggressive means from person to person.

Hold people accountable for mistakes while allowing them the freedom to make them.

Train members past easy tasks into limits that will allow them to grow and prepare them for future challenges. The sense of accomplishment and growth will be valuable. Focus on fundamentals (like pointing stories in lean product development). Know that only repetition builds habits.

An aggressive mindset should be the default setting. An aggressive mind is a proactive thinking computing, contemplating mind. Aggressive doesn’t mean angry or irresponsible. Aggression needs to be targeted at the problem, not at the people.

Discipline but not rigid. The author gives an example I relate to. Start by learning the rules of a dance style. Eventually, you’ll feel it’s as easy as walking. Rules shouldn’t stifle, and with discipline, they can give freedom. From personal experience, even before reading this book, I can relate to how I learned to salsa dance. I made sure to learn the rules to the point where they were second nature. Only then, when I knew the rules so well, did I know when it was good to break them. It seems the author suggests something similar here.

Hold people accountable, but don’t micromanage. The individual needs to have ownership and the ability to make the decisions to successfully fulfill their task to the specifications. Accountability is important, but the person should also understand the consequences to their team so they are accountable to the team and not just the leader.


As a leader, one must also acquire balance. Humbleness and passiveness aren’t the same thing. Humble leaders can switch into being a follower as well. Being a follower at times causes your team to feel like subordinates preventing them from having ownership. A leader will follow when a teammate has a great idea of specific knowledge that puts them in a position to lead for a particular feature or user story. This also solidified the feedback look of the team wanting to actively participate and contribute giving them both autonomy and agency. Good leaders create leaders.

Don’t over plan. And if others in your team are concerned about a negative outcome which is stifling their ability, check out the section that deals with that in The Five Dysfunctions of a Team because I think that book does a great job addressing it. Also, in general, I think lead product development methodology to planning is ideal and applicable here. I see a lot of individuals who plan the future when it’s impossible, which the author also mentions. In many of those cases, it’s better to have a process that allows you to predict the future that is constantly changing as new data becomes available. I like lean product development for this as well. Just like the author, I realize that big technological breakthroughs or market shifts due to external circumstances are difficult to impossible to predict. It’s better to have a system in place to rapidly adjust than to plan every single step.

Leaders must be humble enough to listen to new ideas, willing to learn strategic insights, and open to implementing new and better tactics and strategies

Willink and Babin

Focused but detached means you must find a way to understand the minutiae of a situation while still seeing the forest. I like to think of this as putting in all the work necessary when a path is decided, but don’t let your ego get the best of you if you are wrong and the outcome is incorrect. Be detached when wrong so that you don’t have the incentive to convince yourself you were right. In this situation, you won’t care who was right or wrong, just that the team accomplished the goals.


I’m torn on this book. On one hand, I think life is complex, so seeing an entire book written from the standpoint of focusing on balance makes sense. However, I want something definitive which many other books have. This may just be another cognitive bias where we want a definitive answer even if it is wrong because it makes us feel that there is an answer.

I think this type of false-confidence is very dangerous when it comes to the long term and have to constantly remind myself and my peers of it even though it is so enticing at times. This author mentions it in terms of arrogance and another author mentions it in terms of a type of overconfidence from thinking a current situation is the same as a past situation.

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