Self-Awareness and the Art of Challenging Conversations

I’m Andy Temte and welcome to the Saturday Morning Muse! Start to your weekend with me by exploring topics that span leadership, business management, education, and other musings designed to support your journey of personal and professional continuous improvement. Today is December 14, 2024.

This morning, I’m going to read an excerpt from my first book, Balancing Act: Teach, Coach, Mentor, Inspire. The point of today’s Muse is to shine a bright light on our responsibility as leaders to hone the skills of self-awareness and engaging in challenging conversations.

I am a boater and have been plying the waters of the Upper Mississippi River since I was a boy. One of the most important lessons you learn as a boater is that you are responsible for your own wake. The wake you throw off depends on the size, weight, and speed of your vessel. The waves that your boat generates can damage the environment, destroy property, and cause personal injury. Therefore, as an experienced boater, you are constantly evaluating your surroundings and anticipating the impact your wake will have on other boaters and the shoreline.

On balance, boaters are a curiously courteous and helpful group of people. On the water, people wave at total strangers as if they’re best friends, and they look out for one another when they find someone in distress. This makes sense when you realize that any body of water can turn from idyllic to treacherous in the blink of an eye. The wake your boat creates is an integral part of the ecosystem and can be quite damaging if not managed carefully.

One day we were enjoying a beautiful Sunday afternoon on the Mississippi with a few of our friends and family, including my wife’s then 101-year-old grandmother. Our boat is classified as a cruiser, which is basically a motorhome that floats. As we were putting along, another large vessel approached from our stern at full speed, and it was throwing off a huge wake. It passed me with just seventy-five feet of clearance on our starboard side, leaving me no time to course correct or prepare for the impact of its wake. Our boat rocked violently, sending appetizers—and grandmother—flying. Fortunately, no one was injured, and no damage was caused, but it could have been much worse. If it had been, both the pilot and the owner of the other boat would have been directly accountable for any damage that occurred.

A boat’s wake is a temporary but potentially powerful reminder of its presence on the water. The bigger the boat, the greater the level of responsibility that the captain bears.

Here’s the point: Leaders at all levels leave a wake as they interact with the organization—the higher up you are in the company, the bigger the wake you throw off. It’s your responsibility to be aware of your wake and the impact it could have on individuals and teams, both within your immediate surroundings as well as further downstream.

Most experienced leaders will immediately connect with the point of this parable. If you’re an experienced leader, I’m sure you can recall times where something you did or said inadvertently had a lasting negative impact on a team or team member. You likely learned from that experience and vowed to improve your level of awareness of the impact you have on others.

However, there are those senior managers whose egos and lack of behavioral training limit their ability to understand how their wake impacts their surroundings. These managers likely reached their level in the organization based on technical expertise but never invested themselves in grooming their emotional intelligence skill set.

The best managers continually optimize the balance between their technical and behavioral skills. They have a keen understanding of their surroundings and the impact they can have on others. High-performing leaders also carefully balance their views as they look into the future by ensuring that previous decisions and interactions have not had unintended negative consequences on their environment.

Now think of your role as a manager or an influencer in a business. You are responsible for a team and are in a position of authority. … Imagine the impact a few carelessly uttered words can have on your colleagues. Whether you like it or not, your voice is loud and leaves a powerful wake. As you speak, those around you will pick your words apart for context and subtext.

Now let’s apply the concept of your “leadership wake” to the need to engage in challenging conversations. Back to the story.

Some of your key roles are to teach, coach, mentor, and inspire. Others are to assess talent and provide constructive feedback to your team members so that one day they can surpass you. As an influencer, you walk a fine line. You need to find a balance that allows you to judge without being judgmental—to criticize constructively. Sometimes you need to take control of a situation and be the smartest person in the room. It’s much harder—but equally rewarding—to help others develop and grow by allowing them to shine.

To minimize the risk of inadvertently hurting your work partners with your words, it’s important to provide them with regular and consistent coaching and feedback. Unfortunately, those who have put little effort into developing skills like emotional intelligence and effective communication will likely struggle with this quintessential managerial function.

Challenging conversations are called “challenging conversations” for a reason. A feedback session can be difficult for both the sender and the receiver. To make them less challenging, make the time to provide coaching and feedback more often—optimally in the flow of work.

If you’re waiting for the annual performance review to provide feedback, anxiety will build on both sides. The sender will do a less-than-effective job of providing feedback, and the receiver will likely be so nervous that they hear very little of what’s being said. When you provide feedback more often, the receiver will digest it more readily, and you’ll do a better job as a sender because it will feel more natural to do so.

If you’re well-balanced, objective, and data driven, a coaching/feedback session is likely to go much better for both parties.

It’s incumbent on leaders to create opportunities for personal and professional development for their team members. Nothing says “I care” more than helping another human develop and grow. If you create learning opportunities for your team, both formal and informal, it will pay dividends for both individual and team performance for years to come. Speak the truth in your constructive criticism and follow it up with action to help the recipient get better.

I urge you to pick up a copy of Balancing Act on Amazon today.

Grace. Dignity. Compassion.