The 12 Dichotomies of Leadership for Development Managers
Finding the balance
Leadership is hard and it takes a long time to get good at it.
One reason is that you cant take any advice or principle to its extreme. If you do the benefit goes away. For example a leader should be detail oriented but if you pay attention to every detail you will end up a micro manager.
Another reason is because there is often contradicting advice on leadership. Its possible to see the exact opposite advice in back to back posts on social media. The common LinkedIn example I see is: “People are your best asset you need to treat them like family” vs “Stop saying your company is a family”
This two points are actually related. You see, leadership is a dichotomy. You have to hold two principles in tension and find the right balance in the middle. You cant go to either extreme.
You have to be detail oriented and not have to have every detail.
You need to develop good relationships with the people you lead but not so much that they forget who is in charge.
This all takes observation and discretion and through observation and discretion you can create the right balance.
Jocko Willink was the first person to make me excited about leadership. He wrote the book “Extreme Ownership” about taking ownership of everything in your work and in your life. Naturally many people took the lessons he was teaching to the extreme. They assumed that if a little bit was good, a lot was better.
He followed that book up with “The Dichotomy of Leadership”. In this book he was trying to show that leadership was actually a balancing act between two things, a dichotomy. You had to find the right balance. After his book came out, he posted these 12 dichotomies of leadership:
Confident but not cocky
Courageous but not foolhardy
Competitive but a gracious loser
Attentive to details but not obsessed by them
Strong but have endurance
A leader and a follower
Humble and not passive
Aggressive and not overbearing
Quiet not silent
Calm but not robotic, logical but not devoid of emotions
Close with the troops but not so close that one becomes more important than the other or than the good of the team, not so close that they forget who is in charge
Able to execute extreme ownership when exercising decentralized command
In this post Im going to give my commentary on each of the 12 as it pertains to being a development manager.
Confident but not cocky
In the tech world I see lots of people struggling to even be confident. I wrote about this in the Antidote to Imposter Syndrome. The core of that message was to build evidence not confidence.
Confidence comes from evidence that you have done this task before and have the receipts to prove it. You build a rock solid set of examples where you have what it takes to be in the game.
Mix that evidence with a little ego and you have a recipe for cockiness.
You see, the evidence is for you. You need to know you can do it. Once you feel like that evidence is for everyone else you have overcorrected. Flaunting your experience wont build you friendships and wont elicit new ideas. People wont give you their opinion if they think yours is already made up.
The dichotomy is to build the evidence and the confidence without feeling like you have arrived and that everyone can benefit from your experience.
Courageous but not foolhardy
Never give up! Never Surrender! - Galaxy Quest Crew
It takes a lot of courage to keep going when things get tough. You may be beat down and struggling to even see how you will pull it off. You may wake up every day and throw the white flag but you keep going. Those are the kinds of people we all want to work with.
But…
What if you are in the wrong fight? What if the battle cant be won?
This dichotomy is one of the most difficult because sometimes the right thing is to take a tactical retreat. If the work you are engaged in isnt going to move the needle on anything of substance why do it?
It takes discretion to know when you are being weak and need to be courageous and keep fighting or if you are in a losing battle and need to retreat back to conserve your effort for a fight you can win.
Dont be foolhardy and always complete what you start, because you may have started down the wrong path.
Competitive but a gracious loser
I love the tradition of shaking hands after a chess game. Even if the people don't feel it, it is symbolic of this principle. You need to play with all you've got, but when it is over, shake their hand.
They say in sales that "no" is a good thing. Not that you want to hear it that often, but it is information. If you can understand why you get a "no," you will learn a bit about your product.
Like getting to “no”, losing is information. What went wrong? What do you need to improve? How can you come back to the game more prepared?
Similar to the dichotomy: be confident but not cocky, your ego is what takes your competitiveness over the edge. Check your ego and accept the loss as good information for the next time.
Attentive to details but not obsessed by them
I am admittedly not a detail oriented person. I like the big picture and leaving the details up to other people. That means that I “tilt” in the direction of not being attentive to details. I am very good about not being obsessed by them.
I like being surrounded by detail oriented people. They look at the details and draw my attention to them. In this case I use other people to pull myself into the middle. A lot of my failures as a leader come down to missed details. Its a big area of improvement.
If you are a detail oriented person, you probably excel at your job as a individual contributor. Your work always has that polish that mine usually lacked 😁. However, once you are in leadership you will find that being deep in the weeds on the details will cause you to miss things. This is encapsulated in the colloquial phrase, “Cant see the forrest from the trees”.
If you dive in on the details and try to manage every detail you will lose sight of the big picture and fail to lead strategically. You will move from proactive to reactive since you are not looking up at the horizon but down at your feet.
Strong but have endurance
Strength and endurance immediately call to mind the physical. And indeed you have to have both in the physical world. If you are extremely strong but get winded climbing a flight of stairs, that is an issue.
In the software world I find I have more strength than endurance, but I am getting better at the endurance part. Strength is being able to jump in and solve an issue really quickly. Thinking on your feet and working late into the night. I love that stuff.
Endurance is working through a 6 month migration with customers and other parts of the company. That sounds miserable. However, most things cant be solved with a one night heroic endeavor. Most work is long and slow. The code might even be the easy part but coordinating with other departments and getting customers to move creates a marathon.
A leader and a follower
I would hazard a guess that we are all decent at following when it comes to the classical top down structure. We listen to our boss and work to do what they say. That is the core of how the business world works.
I recently heard a talk by a CEO and he said that his head of HR came to him and said, “We need to hire 12 people in the next 30 days. What should I do?”
His response surprised me.
“Figure it out, I didn’t hire you to tell you what to do. I hired you to tell ME what to do.”
We can follow if its our boss but what if its someone who reports to us? If you delegate something and expect the person to own it and they say, “Great! I need you to talk to so and so and get us this resource” Can you follow their lead?
Being a follower isnt just top down. Its being able to put your ego in check and let someone else call the shots, regardless of where they sit on the management chain.
Humble and not passive
I have a confession. I am a terrible dancer. I really want to be a better one, dancing looks fun and is a good social skill. I have also had plenty of opportunities to learn but I have been too prideful to display my two left feet to the world. Its not humility its passivity.
The hardest thing on your pride is trying new things. Embracing the beginner mindset. For people who are successful at life, becoming a beginners is tough. It hits the pride so hard that they often avoid it.
If you keep doing things that you are not good at and other people are better at you will constantly be reminded to keep your own pride in check at the things you are good at. You have a lot of things to be proud of but so what, switch the domain and you will be back to basics. There is a lot to learn in life.
Dont hold your accomplishes up over people and dont let your lack of skill keep you from trying.
Aggressive and not overbearing
“Default Aggressive” is another Jockoism. Your first instinct should be to go hard after a problem. However the saying isnt “always aggressive”. People who are always aggressive are not fun to be around. Everything is a competition, every word and action is trying to win a battle.
Everything is serious.
These kinds of people often get chided back from others with, “Boy, you must be fun at parties”. And rightfully so. They have no chill, there is no off switch.
Its a hard balance to be default aggressive and yet still be fun at parties. Likewise, if you are always chill, you may be losing because you need some aggressive action to get the ball moving.
Quiet not silent
As I have gotten more experienced as a leader I have found lots more value in the skill of listening. People assume that as you gain more leadership you have more answers. The truth is that the more that is under your leadership, the more you have to listen for answers.
I like what one CEO said to his head of HR who brought him a problem, “Figure it out, I didn’t hire you to tell you what to do. I hired you to tell ME what to do.”
A good CEO hires the right people and listens to them.
However there is a time to speak. You have to speak in order to lead. Your cant just listen. Finding that balance is hard. Im guessing most of us tilt towards the speaking side. We love the sound of our own voice.
However, I have managed people who I have to encourage to speak up. They are too willing to just listen and are not engaged in solving the problems facing the organization.
Listen intently but if you have something to say, you need to say it.
Calm but not robotic, logical but not devoid of emotions
I don't want to stereotype my industry too much, but if you are like me, part of the reason you got into computers is because you love logic, you love robots, and you have no problem being devoid of emotions.
That last part was from my wife 😁
Being calm and detaching from your emotions is a very important skill. Decision-making is always better when you are detached. Emotions cloud your thinking and can cause you to make an irrational decision that seems rational at the time. Being able to set them aside for a time to focus on the best decision for the current problem is something to aspire to.
On the flip side, emotions are how we connect with other humans. Shared emotions are some of the strongest bonds. People who are in touch with their emotions and the emotions of others are much better at empathy and building relationships. Detaching too far can cause you to become a robot devoid of things that make life meaningful.
Of all the dichotomies, this one is the most important to keep in balance and possibly the hardest.
Close with the troops but not so close that one becomes more important than the other or than the good of the team, not so close that they forget who is in charge
Its very important to have close relationships with the people you manage. This is synonymous with trust. You trust someone because you have a close relationship with them and you know they have your best interests at heart.
Its inevitable that those relationships will at some point come in conflict. If you have become too close you might have a temptation to choose the relationship over dealing with the conflict, even at the expense of the team.
Your friend might need to correct a behavior but you dont force it so that you can maintain the friendship. Even as you hold the expectation for others on your team. This will erode the trust you are building with others on the team.
Its such a hard balance to strike because in a way you are not in control of it. Relationships build themselves through shared hardship and mission. But its always important to check yourself and make sure you are still able lead the people you have a close relationship with.
Able to execute extreme ownership when exercising decentralized command
One of the hardest things is to release control. It is hard to give people complete autonomy. But that is what you need to strive for. We know that in computing decentralized systems are more resilient and yet when it comes to human structures we hold onto centralization. You need to find ways to allow your people autonomy.
The catch is that even though your teams are more autonomous, you are still the one who are accountable for their actions. When things go wrong it is your fault. And when things go wrong, the temptation is to give up on decentralization and pull everything back to centralized command and control. The balance is to let your teams operate while making sure they are following your commander’s intent.
This is an extremely difficult balance to achieve.
Conclusion
I wrote this post for myself as much as for others. Each essay on an individual dichotomy was a reminder to stay balanced. If you take leadership seriously, I highly recommend writing your own dichotomy series. Put your thoughts down on how to stay balanced. Reread your message to yourself regularly.
Finding the balance is not a single event. Its a constant set of micro-adjustments. There are times when you are in balance and some where you have fallen out of balance. Writing yourself a memo will help you to objectively view yourself and find the areas you are most likely to go off kilter.