Exceptional Leaders

Katerina Dimitratos
5 min readJan 19, 2021

Can we create them?

I once worked for both the most amazing leader and the worst manager of my career, all in the same year. This got me thinking about the qualities of great leaders and whether those leaders are made — contrived from nature and their surroundings or “born” (perhaps indoctrinated from a young age) and unmalleable. If the latter is the case, is it possible for a bad boss to change?

The exceptional leaders I have worked for have a few things in common:

Psychological Safety:

Exceptional bosses create psychological safety by communicating clearly and consistently. They provide frequent, steady, and transparent feedback; there aren’t any surprises — the feedback these leaders give is expected because of the consistency, frequency, and transparency.

In addition, these are the leaders that would “fall on a sword” for their troops. They protect their team and, though they can be tough, they are also kind and fair. In a psychologically safe workplace, employees do not fear making mistakes, challenging the status quo, or giving upward feedback.

An example of creating psychological safety is during a firm re-org, I remember one great boss who told me to focus on my work and “put blinders on” to what was happening around us. She was asking me to trust her to protect me — and she did. The opposite proved true a few months later, another employee expressed concern about their job stability on the team to a new manager — that manager responded “then you should be applying to jobs”, rather than hearing the employee’s concerns, empathizing, and reassuring them.

Stoic & Positive in attitude:

Though sometimes difficult, exceptional leaders attempt to practice stoicism and maintain a positive outlook for their teams. In doing so, they also convey strength and stability (and ultimately foster psychological safety through this behavior as well).

Positivity includes conflict management, diplomacy, care/empathy/friendliness, the ability to develop rapport, a willingness to help others, and respect. Most interestingly, a positive attitude includes humor.

Creativity:

The best leaders are creative — they are cognitively flexible, analytical, and curious. They evolve with technology and the regulatory environment, identify patterns, think critically, innovate, make abstract connections, observe, listen to others’ ideas, are agile and open-minded. Some may even call leaders with above-average creativity visionaries in their field.

Creative leaders also replace blame with curiosity, they encourage learning and outside-the-box thinking within their team.

Confidence (with self-awareness):

The best leaders I have worked with are confident in their decisions, but open to hearing opposing opinions. They are, as articulated above, self-aware of their weaknesses and hire individuals with the subject-matter expertise they lack and trust their judgement to lean on those hires for that expertise. The best managers are also collaborators rather than opponents and it is their self-confidence and awareness that keeps them from competing with their employees.

Self-awareness and self-reflection:

Studies show that the best of leaders self-reflect daily (and typically in the evenings) to assess their day, actions taken, and opportunities for change and development. The worst leaders typically have a flawed-confidence where they are not open-minded or aware of their weaknesses.

I remember an occasion where the worst manager of my career, who had been new to the team, called me for my expertise on a certain fintech/regulatory issue following a firm policy change. I had been the project lead for the impacted process for approximately four years by then and advised her following much research and collaboration with other teams (ranging from Data Analytics to the Office of the General Counsel Intellectual Property team for their input and expertise). She listened to my guidance, but proceeded with a course of action I advised against simply saying “well too bad, that’s what we’re going to do”. I ultimately left that team, my concerns fell through the cracks, and that manager proceeded with her original plan — which years later, did expose the company to unnecessary risk.

In another example, a high-level senior executive would call on me in a Steering Committee meeting simply because he was aware of his gaps and knew where my subject matter expertise was. To be honest, I would often sit quietly in those meetings because I was the most junior person in the room. However, he was confident in my skill set regarding that particular issue and confident in his hiring decision, so he would publicly ask for my opinion. This leader was confident in his skills and choices, but also had a keen self-awareness that never detracted from his confidence. He simply understood we all have strengths and weaknesses. One of my mentors says the best leaders identify people’s superpowers and leverage them. Strive to be that leader.

In these two examples, self-awareness is about identifying your weaknesses and selectively relying on team members that can fill those gaps. It’s about trusting your hiring selection and trusting that person to execute on their subject matter expertise.

In short, if you want to be a great leader, focus on cultivating psychological safety, stoicism, creativity, and self-awareness as they are all things that can be learned if a leader chooses to improve — most importantly though, keep an open mind, reflect often, and continue learning.

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This is a personal entry written and edited by Katerina Dimitratos. For questions about this post, please email katerinadimitratos@gmail.com. The views and opinions expressed on this blog are purely the author’s own.

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Katerina Dimitratos

Founder & CEO of Meddy Health, Strategist, Angel Investor, and advocate for women in business. I Believe in using business as a force for good.