Good lessons learned from bad leaders

As we go through life we will encounter a few bad leaders. One option is to complain about them & another is to learn from these bad leaders.  For the past few years I have focused on the latter point. I separate these leadership lessons into a good trait to incorporate & be mindful to not replicate.

Good Trait to Incorporate:

Think of leadership almost as a surgeon would... Even if the body as a whole is dying of cancer - there still might be several good organs that others could use... Focus on what a bad leader does well & incorporate it into your own leadership style.

Expectation Setting - A previous boss of mine was a remarkable expectation setter... As a whole an uninspiring leader... However could teach a whole class on how & why expectation setting is important. Make sure employees understand what success looks like, how to act, how not to act, when to ask for help, and any other relevant information. Every good leader should aspire to this level of expectation setting.

Before assigning any task or project - think about how you would like it done. Customize this to employees & their unique skill-sets if possible. Expectation setting is the map that you are having people follow, but a map is useless if it is not able to be read.

Being inspirational - While not an essential component to leadership, inspiration can prove pivotal at key moments. Inspiration can be used to grow a company or motivate employees towards deadlines they might not otherwise meet. There is a dark side of inspiration though, being enticed by someone who is inspirational but not a leader. In the past I have been seduced by a leaders charisma & was let down by their leadership abilities at a later time. In the long run inspiration can have an immense value in leading.

Words can fail us - I believe that this is a vital concept not only in leadership but in communication in general. There are a few people in the world who are excellent with their words - able to express exactly what they mean in a quick & concise manner. There will be times when showing something will prove better than saying it out loud. There will be times when someone's first language is not your own - be compassionate about this.

If something is unclear ask again what someone means rather than guessing. It may take an extra moment or two but that can save a lot of time vs. doing something totally wrong. Be aware of your employees communication strengths. Perhaps with one employee you can communicate what you want from gestures & eye-contact. With others though it could be needed to write out specific instructions or spend extra time explaining. The spoken word is an imperfect means of communication, good leaders know this & find creative alternatives.

Be mindful not to replicate:

Another key role of the surgeon other than taking out bad organs is that of performing transplants. It is essential to not adopt(transplant) specific traits or practices of our bad leaders. This section ranges from what a leader should already do before hiring employees - to micro/macro interactions that compromise their leadership.

Where you are going & identity - If expectation setting is about the micro interactions between boss & employee. Then knowing where you are going & identity are the macro relationship between employee & company. Goals of where the company is going should be set in place before any employee is hired. Being intentional with a what the long term vision, narrative, values, people, and practices are is key.

If someone knows where they are expected to go it is just a matter of how //  getting there. The road itself may prove to be difficult, but the individual knows where they were going... It does not whether an employee is motivated or not, they cannot achieve a vision if they do not know what that vision is.

What does identity really mean?. The most powerful brands in the world make it very easy for consumers to know who they are & their values. An example I have been thinking about recently is Harley Davidson. While this brand is not something I personally identity with - I easily understand the companies viewpoint.

Here is Harley Davidson's internal positioning statement:

“The only motorcycle manufacturer

That makes big, loud motorcycles
For macho guys (and “macho wannabes”)
Mostly in the United States
Who want to join a gang of cowboys
In an era of decreasing personal freedom.”

Even though this internal positioning statement might be polarizing Harley-Davidson is clearly stating what their values & identity are. Every employee & customer is able to understand with ease what this company is all about. If you are ever in a leadership position be sure to be intentional about internal position before any employee is hired. Is essence with a clear position you will hire better employees as they will be authentically attracted to what your brand is all about.

Build camaraderie but not too much comfort - The best leaders create an environment of camaraderie, but never allow comfort that would compromise their leadership position. In professional sports this occurs when a coach takes feedback from players during practice. However when the game is on the line they make the final decisions that are best for the team.

To put it another way never be the boss who tries to be best friends with every employee. A healthy distance will do a world of difference for how you are perceived by everyone.  I do not believe it was a coincidence that when a previous boss of mine tried to be buddy buddy with everyone, no one in the company respected him. Being a leader is a conscious differentiation - it is about being better than anyone. It is about when times are tough someone will lead & others will follow.

Not being present as a leader - You are trying to have a conversation about your future with the company in the bosses office - then... before you are able to build up the courage to say what you want to... The bosses cell phone on the table pings. Then a few moments later it starts ringing. Your boss looks at you sheepishly... "I am going to have to take that..." & for you that is all you need to know... Your boss is not going to give you their full presence & probably never will. When 10 minutes later your boss asks what you wanted to talk about, now you are the sheepish one... "Nothing of importance" you reply... Value your employees time with your full undivided presence as a leader. Never allow a situation like the one I just described happen if you care about your employees.

Likewise when managing a team that is remote or not all in the same place a leaders presence is even more important. In this way be consistent with your presence, set up a weekly video meeting. Make sure that employees know that you see them as real rather than robots. Having had many leaders who were not present with me, I always try my hardest to be mindful of giving my full presence to the people under my care.

The best leaders learn from the bad leaders of their past:

As I was writing this,  I realized how grateful I am for the bad leaders of my past. It is these bad leaders that have forced me to grow in ways the good leaders never would. It is easier for me to put myself in the shoes of the bad leaders & think what I would have done differently. I am a student of leadership, and in being one I take every opportunity available to learn & improve myself. Life is all about the climb, not being bogged down by the weather of the moment & aspiring to always higher peaks. I would be curious to hear what others have learned from the bad leaders of their lives... How did they change you? What do you do to not become like them when you are in a leadership position yourself?

-Tim O'Sullivan

A New Chapter.

Photo by John-Mark-Kuznietsov

I knew it would feel different... That first step on Indian soil compared to when I had first come to India 6 months before.. When I was younger I did not imagine dedicating a chapter of my life to living in India. I am happy that I remained open-minded // patient enough to embrace all that has been India.

I arrived to India without having a job - the company that I had planned to work for decided not to hire me the night before my flight. I have always believed in myself - so I figured worst case... an expensive vacation. Within a week I had found a job in a travel company as a content writer // social media manager.

This would be a type of work I had never done before. While my work life has not always been ideal, I am a part of a team of people from over 6 different countries. This has been one of my families while living in India. As someone who is constantly looking to understand the globalized world in a deeper way my fellow co-workers have been a boon.

Another family for me while living in India has been the expat community. People from Egypt, Russia, Brazil, Sweden, England, Nepal, & various other areas of India. This has been the backbone of my social life. However instead of running bar crawls I participate in them, ever asking questions about different peoples culture & lives.

While I am grateful for this past period of my life - I am keenly aware it has ended. I will search for more meaningful work living in the United states within the next few months.

A little about me to future employers - 

I am someone who is constantly looking to optimize my life. I am unwilling to live in a world where good enough is an acceptable standard operating procedure. I want to be a part of a team. Working with others - picking their brains about different strategies or tactics is how the best ideas come out I believe.

I believe that analysis used for games such as chess can be valuable in a business setting. Surely nothing will ever be as black & white as running a chess board state through a computer simulator, but we can review business decisions as such. A commitment to growth through feedback is the reason to me that that analysis is done. I was advised recently that feedback is fundamental to our own development.

Photo by Hiedi Sandstorm

Where Will I go Next?

I've always had the notion of owning my own business. Leveraging my abilities as a passionate generalist to bring in new ideas & perspectives that will achieve long term growth. I guess that is a sexier way to say be a consultant. I prefer accomplice though. When I think about the word accomplice - I think mischief, disrupting something. What I hope to disrupt more than anything is the cancer that is bad leadership that exists in the world.

I am a leadership nerd. I love reading histories of ancient rulers innovative strategies to create a better life for their people. With the current world configuration ancient kingdoms have given way to companies. In particular CEO's are symbolic of regional kings & queens throughout the ages. My allegiance is to good leadership first & foremost but my highest priority when I come back to the United States is learning good leadership in a hands-on setting. I still have more theoretical knowledge of leadership vs. practical experience so I am committing to being a follower right now.

How can you help?

I will for sure need some mentorship... What are some lessons in leadership that I can learn from you? What do you define as good // bad leadership? I want to collaborate with people to have conversations about different leadership perspectives in different industries.  

As a passionate generalist I am able to bring in a lot of different perspectives that might not be known by a someone who is a specialist. In this way I bring a valuable perspective to the table. I will be grounding myself in a bit more of the fundamentals of business such as finance & basic business planning. Creating a network // consistent content that I am thinking about will be a big part of my future as well.

I am ecstatic about what my future holds. Thank you everyone for all of the support via social media, whatsapp, & in person. Without the support of all the people I love I would not be able to be following my dreams like I am right now.

With love,

-Tim O'Sullivan

Photo by Mantas-Hesthaven