Observation: An Often-Overlooked Leadership Trait

Steve Schloss
5 min readJun 28, 2023


Photo by Puwadon Sang-ngern

“All of us are watchers — of television, of time clocks, of traffic on the freeway — but few are observers. Everyone is looking, not many are seeing.” Peter M. Leschak

When I started my ListenForward coaching and advisory practice three years ago, I was principally looking to assimilate three and half decades of learned leadership lessons that could best help and empower CEOs, executive leaders, and teams.

Along the way, I have personally witnessed and continue to advocate for five essential ListenForward building blocks that differentiate the most effective leaders and teams regardless of company size or growth stage:

Recently, I was thinking about the building block of context and the added importance of observation while attending the Edison Partners Annual Meeting in Nashville (a firm on which I also serve as Operating Partner and Head, Leadership Center of Excellence).

In this particular case, meeting attendees heard from a thought provoking and diverse panel representing disparate points of view from the worlds of government, industry, and journalism. I was particularly impressed by the facilitator and panelist members’ innate gift of observation as they covered a wide array of topics ranging from policy to economics, and culture. Their individual and collective ability to process and probe on said (and unsaid) elements of the dialogue, while blending in their own personal life experiences and context, was quite impressive.

A Non-Obvious Trait for the Day-To-Day

As an executive leader, the practice of observation and the discipline to be a more observant leader (defined as the ability to effectively interpret the world around us), is an overlooked skill, and one that is especially important for understanding and operating in the highly connected and ever-changing world in which we operate.

Too often, executive leaders focus on “doing” their jobs through the lens of task and execution. Like watching a sporting event through the lenses of our iPhone cameras they see what is in front of them rather than focus on “being” and taking in the world and surrounding environment. Making the conscious choice (like putting the iPhone camera down) and actively seeking to understand the many facets of our world by being present, and engaging “in person” without a filter, bias, or assumption, takes effort.

When coaching and advising individual and team clients, conversations often vector toward a common list of leadership challenges: including being more effective communicators; influencing tactfully and strategically; being more resilient or adaptive; becoming more aligned as a team; or gaining new insights and best practices for how to let go and delegate or deliver performance feedback to peers, teams, and direct reports.

In contrast, observation (or the absence thereof), is a subtle and often beneath-the-surface skill that may only reveal itself through intentional action and behavior, and a leader’s ability to be present and connected during in-depth conversation.

Being a more observant leader will make a meaningful difference.

1. You will create a heightened sense of awareness. By paying close attention to dynamic connections in your environment, and the behaviors, attitudes, and needs of various stakeholder groups, you are better able to identify trends and anticipate challenges. You will also develop a greater sense of and foster empathy and understanding.

2. You will improve your decision-making and problem-solving skills. By carefully observing situations, you are gathering relevant data in the moment, identifying patterns, and recognizing underlying causes. You are more apt to consider multiple perspectives before making critical choices.

3. You will nurture a culture of continuous learning and innovation. By encouraging your team to be curious, observe, question, and explore, you unlock or discover the gifts of others, as new perspectives or creative insights are raised.

4. You will strengthen your relationships. By keenly observing individual styles and behaviors, you can provide targeted guidance that support growth. Combined with the power to listen attentively, you foster trust and open lines of communication.

Grooming Your Observation Skills: Where to Start?

Below are a few ways to become a more observant leader.

1. Cultivate a mindset of curiosity and openness.

Approach each situation with a genuine desire to learn and understand. Model behavior by training yourself to ask questions, invite different perspectives and challenge assumptions. By adopting a curious mindset be willing to actively seek out diverse points-of-view and experiences to broaden your observation lens and enrich your leadership perspective. For example, in the Medici Effect, by Frans Johansson, he speaks of the “intersection”–or the place where ideas from different industries and cultures collide to create innovation.

2. Practice active listening and non-verbal observation.

When engaging with team members, clients, or other stakeholders, give them your full attention and listen actively to what they are saying. Observe body language, facial expressions, and tone of voice as these non-verbal cues often relay valuable information beyond their words.

3. Develop situational awareness.

Situational awareness is critical to effectively navigate complex environments. Train yourself to observe and absorb details about your surroundings, including the physical space, organizational dynamics, and interpersonal dynamics. Develop an understanding of the interplay between those internal factors and external factors such as customer behavior and industry developments. The advent of AI hastens the need to be more situationally aware.

4. Encourage feedback.

Create platforms and opportunities for team members and other stakeholders to share their insights, ideas, and concerns openly. Actively seek input and encourage constructive feedback. Create a space for dissenting opinions as they can provide valuable and actionable insights that may otherwise get overlooked or unnoticed.

As an executive leader, honing your observation skills to better support and serve the the stakeholders you lead and partner is an essential trait for your ever evolving leadership toolkit.

Early in my career, I was taught that less is more. Or, more specifically, to talk less … and listen and observe more.

I live that mantra every day.

I encourage you to do the same.



Steve Schloss

Coach and advisor to CEOs, executive leaders and teams. Sharing thoughts, observations, and ideas around leadership and culture. Trying to break 80 more often.