A Letter to Myself of 15 Years Ago

This week I am leading another Leadership Academy on Ending Homelessness. We sold out again. It is a great honour that so many people want to hone their leadership skills on this important social issue. As I was preparing and reflecting on the materials to be delivered this week, I wrote a letter to myself that I wish I had 15 years ago.

Dear Me from 15 Years Ago,

You struggle to listen to others at this stage of your professional development. Maybe you will listen to yourself from the future. Here are important lessons that you should learn sooner rather than later.

Leadership does not mean being superior. It means helping the people that follow you be super. You are smart. But no one likes to be bludgeoned by your intellect. The smartest person in the room is the first to be ignored if you NEED everyone in the room to know you are the smartest person.

If you inspire people, that is leadership. If you feel it necessary to order people, that is a dictatorship. Know how things turn out for dictators? They are obsessed with losing power to the point that they bully others. Don’t do that.

Think first in and last out each workday is the way to go? Working multiple weekends a month? It isn’t. To work your best you must take time to rest. You may think you are impressing others with your commitment to 12 hour days and coming in on weekends. Soon your friendships will fall apart and your marriage will change – and not for the better.

Others need you to demonstrate humility and confidence. You don’t understand what that really means yet. So instead you demonstrate humiliation and arrogance at times. That is a mistake. Humiliating others makes you look weak. Being arrogant makes you an asshole.

For whatever reason, people are choosing to follow your leadership. Stop complaining. Leadership is not a chore or burden. It is a privilege.  When people ask you how things are going, focus on a positive development that has happened or a new idea that you are working through. Do not answer, “How are you doing?” with “Busy”.

Listen. It is an underappreciated part of communication and leadership. Spend 60% of your time listening and 40% of your time talking (unless, of course, people are asking you to talk all day). Speak at invitation and at strategic times only. Leaders do not spend all of their time listening to their own voice.

Stop being worried about people leaving you or your organization. Train them so well that they can leave and have an impact on other organizations. Treat them so well they never want to.

People being afraid of you is not working. The people that are following you need to be fearless. Not fearful. Know the difference.

Want to measure the bottom line? Start measuring the outcome of your work, not wondering about the income of your salary. As soon as you learn that this is about making a difference and not about making money, everything will change.

Be brave enough to not only make mistakes but to own them as well. If you are pretending to be perfect you will alienate others around you. Encourage others to make mistakes too, including people that report to you. Do not punish people for trying. Praise them and ask what they are learning.

Competition is bullshit is leadership. Creating competition amongst your followers will only get already competitive people going, and mediocre and low performers to quit. Tearing each other down will only bring all of us no where fast.

Find time to be still. Be quiet. Write out your thoughts. Carve time out of your schedule to do these very things. You think this is a waste of time, but you will learn this is key to innovation, reflection, understanding, and deepening your awareness.

Ask for forgiveness when it is necessary. You will harm people. Sometimes intentionally. Often not. Nonetheless, empathise and offer a heartfelt apology. And if you don’t understand the value of forgiveness think of one of the many things people would forgive you for and measure the value you place on wanting that forgiveness.

Let go of the small stuff you have no control over. Losing sleep over things that you cannot influence makes you a worse leader, not a better one.  Influence the big picture and the overall direction. Spend less time in the weeds.

And finally, learn to love your work. Find joy in the privilege to do what you do. If you stop feeling in love, move on and let someone else lead.

About Iain De Jong

Iain is a playful nerd, hellbent on ending homelessness, increasing affordable housing, creating vibrant communities, and expanding the knowledge amongst leaders that influence social issues. Having held senior management and professional positions in government, non-profits, and the private sector, Iain has a wealth of experience and has garnered dozens of awards for his work across Canada and internationally. His work has taken him across Canada, the United States, and to Australia. In 2009, Iain joined OrgCode as its President & CEO, and in 2014 assumed full ownership of the firm. In addition to his work with OrgCode, Iain holds a part-time faculty position in the Graduate Urban Planning Programme at York University.


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