The 40-Day Leadership Challenge

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Wouldn’t it be nice if in life you could yell “do over!” after a major blunder and start with a clean slate, like you did as a kid playing kickball? The good news is that, while you might not get a totally clean slate simply by declaring the “do over,” I think it is possible to start the next round on a clean page. How? Take my 40-Day Leadership Challenge.

For many Christians, the period of forty days before Easter is known as Lent, representing the forty days during which Jesus fasted and prayed in the desert before his crucifixion and subsequent resurrection. It is a season that is often observed by people making forty-day sacrifices such as giving up chocolate, alcohol or television; or making a special effort like praying more often or doing volunteer work in their community. The idea is for it to be a time of purification, emerging as a better person and closer to God. But at a deeper level, it strikes me that there is a much more universally valuable leadership challenge and lesson to be learned from this kind of experience.

Just about everyone is aware of some relationship in their professional or personal life that could be improved. It could be on an individual level such as if you always seem to get into disagreements with the same person, or someone just perpetually rubs you the wrong way. Or on a grander scale, maybe you realize you need to polish some aspect of the leadership image you project in order for your team or even family to see you as someone not just to follow, but to admire. Relationships are made and broken through the value of the communication they use, and while all communication is a two-way street, change begins with the first step, the way you choose to communicate.

What if you were to choose to take that first, single step today, and then one more step each day for the next 39 days, as your 40-Day Leadership Challenge? The idea is to commit to doing something that improves your communication – and ultimately, your relationships – for 40 days. Pick something that is difficult enough that you have to make a conscious effort in order to do it successfully. By, replacing old, bad habits with positive new ones, not only will it make you a better person, but it will improve the lives of those around you.

For your challenge, you could choose to “fast” or abstain from gossip, sarcasm or snarky comments, whether in conversation or email. Bite your tongue and opt not to share a criticism of someone publicly even when others are doing so, or let the other person get the last word even when you don’t like what they said.

Perhaps you are very conflict averse. Your challenge might be to muster the courage to address problems when they arise rather than letting them fester. Instead of delegating the responsibility of handling it to someone else simply because you don’t like the discomfort, you choose to take the responsibility for yourself. There may not be relevant “conflicts” every day for 40 days, but the idea is that within that window, when they do arise, you commit to handling them directly and efficiently.

Alternatively, maybe you have the opposite habit: you can be a bit too blunt, dramatic or insensitive in some contexts. In that case, you could commit to a 40-day period of diplomacy. Ask the other person to share his perspective first, and actually listen, before you launch into yours. Try to abstain from making assumptions, and ask people more questions instead of giving them your answers. Put a 40-day moratorium on exaggeration, swearing, or drama, or decide you’re going to walk away from a conversation when you feel yourself starting to get heated, then follow through by setting a time to resume the conversation when cooler heads prevail.

It could even be a simple question of knowing deep down that others wish you would respond to their email or voicemail more expediently, so they could move forward with their own work. You could commit to responding to all critical messages by the close of business, or within 24 hours, even if it’s just a brief acknowledgement of their inquiry and a promise to get back to them by a certain date with more information.

Your 40-day leadership challenge could also be something as subtle as an intent to give people the benefit of the doubt that if they say or do something you don’t like, there’s a valid reason or concern behind it. Then make an effort to elicit what that concern is, so you can move forward with collaborative problem solving since you both have the same understanding of the situation.

Want to keep it simple? You could just make an effort to remember to explicitly thank people for their efforts, big or small. You’ll be amazed at what a big impression such a small gesture can make. I promise you it won’t go unnoticed.

Even if it’s difficult, and you fall off the proverbial bandwagon from time to time, that’s okay! You could put a dollar in an envelope or jar every time you realize you’ve broken your commitment, then after 40 days, take however much money has accumulated there and donate it to charity.

However, even if you find that you keep putting money in the “oops” jar, you get to call a “do over” each and every time: get right back up there and start again the next day or meeting. It doesn’t have to be 40 days of consecutive perfection; it’s about 40 days of conscious effort to be a better person and a better leader, leading by example. What’s most important is that others will feel the difference through lessened friction and greater transparency and be more inspired to follow your lead.

And the best part? It doesn’t matter which 40 days you choose, whether at the start of the new year, during your summer vacation or any other time. By the end of your 40 days, your new behaviors should start to become second nature, replacing the old ones. Now that you have your “do over” you can work on the foundation of a new kind of leadership that makes others want to follow suit.


Want to discuss your potential 40-Day Leadership Challenge? Email me at or click to set up a 20-minute focus call with me personally.

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