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Integrating Thoughtfulness into Leadership

Dear Leaders,

Almost by definition, an executive is responsible for serving a group of people.

Whether it’s identifying opportunities, problem-solving, decision-making, conflict resolution, collaboration, delegation, etc. – all involve people. And the higher the quality of your relationships, the more effective you are as an executive.

Technology makes organizing oneself easier, tasks more automated, reminder notifications – for big events like birthdays and such – easier to “remember”, and even associated delivery services that, without any active involvement from you, automatically ship the person of your choice the appropriate gift.

Regardless of technological advancements, being thoughtful always was, and still is, an invaluable skill. An ace card, really.

And that’s because beyond a certain point, it can only be done, highly effectively, by a human being.

The Challenge? Time.

It moves so fast that we can barely process our interactions fully, let alone in-depth.

How can we act in a consistently thoughtful manner so the people we work most closely with, rely on, or rely on us, experience a high-quality interaction despite our fast-paced lives?

The Solution? A pen, paper, and a short window of time.

Allocate 15 minutes once a week (literally) to writing about one person that you work most closely with.

Write your general thoughts about them, what they might have shared with you recently, your expectations of them (and why), their expectations of you (and why), what makes them tick, and so forth.

Write freely and put whatever comes to your mind about them, or situations related to them, on paper. The goal is to get to know them better on paper, even though you might’ve known and worked with them for years.

If you’re happy with their performance, write it down.

If you have a resentment against them about something minor (or major) that you’d rather not bring up so as not to rock the boat, write about that too.

At the end of 15 minutes, rip up that paper and throw it away.

After a few weeks – about 45 minutes to an hour of total writing about a person or a complex situation – you’ll notice a few things:

1. You have a much more in-depth understanding of that person and, as a result, that relationship. If you wrote about a complex situation instead, well, you won’t find it as complex anymore.

2. If some of your writings are done with you imagining yourself to be in that person’s shoes, you’ll begin to think about and understand their perspective a lot more clearly. You still might not agree with them on a given matter, but you’ll certainly have a better understanding of why they might feel that way and the behaviors associated with it. That clarity and understanding will start showing in your day-to-day interactions with them, leading to more thoughtful comments and actions by you, which in turn will lead to a higher-quality relationship.

3. The biggest advantage, though, will be your newly found habit of thinking about and nurturing your relationships on paper as opposed to doing the best you can as you move fast through the day. That weekly time and thought investment into the relationship on paper will lead to caring more about little things, clarity on specific situations, and you responding more articulately than simply reacting.

And it won’t just be limited to this relationship or situation, it’ll become your standard mode of operation across all relationships and situations. In other words, it’ll lead to you consistently being able to think and behave in a more thoughtful way.

Bonus Tip: Hand-Written Notes.

Write thoughtful, hand-written notes often.

I realize this isn’t a breakthrough idea. But the fact that an employee, or a peer, can feel so deeply moved by a hand-written note received from their boss that they place it next to their family’s pictures on their work desk makes this simple yet thoughtful practice worth the reminder.

Until next time, stay Thoughtful!

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