What is great leadership?

It’s a lot of things, but it’s mostly listening and embracing change

Hello everyone! Thank you all for the helpful feedback from the Gridology survey (you can still take it here). First, I will opt for a less frequent cadence—I plan on aiming for 2-3 posts per month. Second, I’m going to anchor the majority of my posts on the following topics: career development, self-help, growth mindset, and prioritization. Third, I will start to expand outside of just the 2x2 grid to other types of frameworks and mental models.

For my first post back from my mini-hiatus, I’m sharing my takeaways from my first completed class at NYU Stern. Special shout out to Professor Nate Pettit for teaching such a terrific course.

And here we go:

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Great leadership is having the courage and ability to drive change in a compassionate, inspiring, and inclusive manner. Great leadership, then, is a lot of things all rolled into one. It’s not a skill you can learn but rather a goal and mindset you can strive to achieve. Becoming a great leader requires many different abilities working together for a higher-order cause.

A younger version of me also wrote a post on leadership. If you want to save the five minutes reading it, here’s younger me’s thesis:

“When your successors outperform you, that's when you know you've done right by them.”

This misses a lot of the nuance. For one, the team could have outperformed you because you were holding them back. It goes without saying that many leaders strive to leave teams better than how they joined them. However, assuming you’re a good leader just because your old team outperforms without your presence misses a few dots between points A and B. There’s more to the story.

I filled in many of these gaps in the last three weeks after finishing my first class at NYU Stern. As you could probably guess, it was a class named Leadership, and it was taught by Nate Pettit. It forced me to rethink many of my views on how to be a great leader. 

Most importantly, I learned being a leader is less about gaining new skills and more about refining ones we practice every day. It’s about being a great listener, having courage, and embracing change. It’s about having the right mindset on how to collaborate with others. These things, right now, are 100% in your control.

Let today’s grid be a tool for us all to strive to be the leaders we want to be.

On the x-axis, we have an individual’s level of emotional intelligence (EQ). I wrote about EQ back in March, but I applied it to the concept of managing your friendships rather than leading people. Great leaders have a high EQ. Full stop. As Professor Pettit puts it, “EQ does not just mean you are nice.” He goes on to say that EQ is characterized by five traits:

  1. Self-awareness — How do my actions affect others?

  2. Self-regulation — How am I able to monitor and adjust my emotions across different situations?

  3. Motivation — Do you have an internal self-drive for improvement?

  4. Empathy — Can you know/feel what others are feeling? I’d make the argument here that compassion is probably better to use as it’s based more on your ability to combine action and empathy rather than to just know/feel what others are feeling.

  5. Social Skills — Are you generally a tolerable person with good people skills?

For the sake of simplicity, I’d like to narrow the focus for identifying EQ to the most observable indicators: a person’s ability to listen and be honest.

When you listen, and I mean deeply listen, to the point where you provide others the space to solve their own problems just by affording them the opportunity to be heard, it’s an indicator you have strong social skills and are an empathetic/compassionate person. Take any conversation: you have a speaker, and you have a listener. Often when someone speaks, the listener is thinking more about what to say next than what is being said to them. When the listener stops evaluating and starts actually listening, it allows the person speaking to feel more open and cooperative.

When you’re honest—not just with others but with yourself, too—it indicates self-awareness and self-regulation. You can make better decisions from a place of transparency and openness rather than through lies and deceit.

On the y-axis, we have an individual’s tolerance for change and failure. As I alluded to earlier, great leadership is about having the courage to drive change and respond to failure. The best leaders are ones who don’t resist change but seek it. Change is a constant: we can count on the fact that 10 years from now will look nothing like 10 years ago. The best leaders prepare for this reality by shifting priorities, dreaming new strategies, and aligning individuals accordingly. Change, too, is a lot like Rome. It’s not created in a day. Sure, there are seismic, black swan-type events that can rock our system (COVID-19, cough). Those are not the norm, however. That said, great leaders embrace change—however and whenever it comes.

Great leadership also appreciates the power of failing. Not every idea can be a winner, but every failed idea helps lead to winning. Simply put, “failure is a prerequisite to invention.” Great leaders encourage their employees to innovate, fail, and try again. When I worked at LinkedIn, this point was made clear through the company’s culture. Communication from executives to middle managers encouraged every employee to “take intelligent risks.” This provided a safety net for failure. Rather than being scolded for trying an idea that didn’t work, employees were generally recognized for innovating on the status quo.

Understanding the Grid

The objective of this grid is to land in the top right quadrant. The more you can improve your EQ, encourage failure, and embrace change, the more impact you will have as a leader.

Transformation

You have high EQ, and embrace change and failure. Think about the best leaders you’ve known. Here are a few guesses: They don’t only care about your work. They also care about you as a person. When they ask you how you’re doing, responding “good” is considered inadequate... they did deeper. These leaders share their own shortcomings. They don’t pretend to be god-like figures or business messiahs. As Richard Farson and Ralph Keyes wrote in The Failure-Tolerant Leader, “[a]dmitting mistakes show’s a leader’s self-confidence… a blunder admitted is empathy earned.” Transformational leaders build a culture that’s diverse and inclusive—one where all team members can act like themselves and feel like they belong.

These leaders are transformational because of their ability to shape both their business and their people. On the business side, transformational leaders embrace the hunt for new ideas… not necessarily good ideas. Every idea to these leaders can offer essential learnings needed to achieve their vision. When it comes to people, they use their ability to listen and understand rather than speak and demand. This garners respect amongst their team and improves collaboration.

Conservative

You have high EQ, but avoid change and failure. These individuals tend to act more like managers than they do leaders. According to John P. Kotter, managers “cope with complexity” while leaders “cope with rapid change.” This division is profound. When individuals fall in the conservative quadrant, they prefer to resist change rather than embrace it. That’s because the systems they’ve set up to manage current business complexity do not apply to future business complexity. Change creates new obstacles, upsetting the status quo. While these managers care deeply about their team, they don’t accelerate the growth of the business. They prefer to optimize for here and now rather than tomorrow and the future.

Because of their high EQ, these individuals fear upsetting others. However, to enact change, you’re going to upset someone. As Ginni Rometty, former executive chairman and CEO of IBM, says, “growth and comfort do not coexist.” Making people feel comfortable with uncomfortable situations is a large part of being a great leader, and conservative individuals have a hard time operating in uncomfortable environments.

Cures: Demonstrate that doing nothing is more dangerous than pursuing new strategies; showcase how failures are not really failures, but opportunities to learn and find the right solution.

Pushy

You have low EQ, but embrace change and failure. Leadership stereotypes often apply to these people. They can be loud, assertive, demanding, and action-oriented. These traits are considered the “push” elements of leadership—activities that compel others to act. Where these people lack is in the “pull” elements of leadership—activities that build credibility and garner respect through listening. I’m sure you can think of some pushy managers you’ve had… they probably don’t do a good job listening to your feedback. They may be micromanagers. As Maslow said, “To a man with a hammer, everything looks like a nail.” Pushy managers only have a hammer in their toolbox. They must solve problems any way they can. I’ve had managers like this. It’s a painful experience. Things need to be done their way and on their timeline. They do a poor job of listening. When you speak, they evaluate and critique as a means to convince you to see it their way rather than trying to understand your point of view.

Cures: Listening; self-reflection; receiving open, honest, and constructive feedback

Stationary

You have low EQ, and avoid change and failure. These individuals believe they know best and are desperate to protect the status quo. After all, the present is the environment where they have thrived. These individuals may be more extrinsically motivated than intrinsically motivated, meaning they care less about seeing the company succeed than they do cashing (large) paychecks. They lean into their titles to assert their leadership ability, too. As a general rule, when you have to tell others to listen to you because you’re the “leader,” you’re not really the leader you think you are. Leadership isn’t bestowed through titles. It’s granted through courage, conviction, compassion, and action. This quadrant could have been named regressive, as these stationary people can cause teams to move backward through intra-team drama and/or poor results.

Cures: Pursue strategies listed in the Stationary & Pushy quadrants.

Grid Shortcomings

  1. This grid ignores results. Leaders are ultimately deemed effective when they can drive positive outcomes. Part of driving success is making good decisions. However, every great leader must account for different biases and shortcomings that can negatively affect decision-making (i.e. overconfidence or prospect theory).

  2. This grid ignores personality. That’s because it isn’t a strong indicator of what makes for a great leader. Great leaders can be introverted or extraverted, Type A or Type B, ESTJ or INFP. What matters more is someone’s EQ, as discussed.

  3. This grid ignores company culture. A strong and healthy culture is a byproduct of great leadership, not an input to it. Transformational leaders build a diverse and inclusive team where everyone has the opportunity to grow.

  4. This grid ignores team development. While I didn’t specifically call it out, great leaders help their team become better professionals (and people). As Pettit said in a class lecture, “the higher you go, the more you are judged by the performance of those beneath you.” Great leaders build their team while aligning each member towards achieving a shared and urgent vision.

When you reflect on the best leaders you’ve known, what made them so great? Did you feel like they cared about you as a person and as a professional? Did they listen to you? Did your career accelerate after being on their team? My guess is the answers to all of those questions are yes.

Everyone can be a leader. However, we often default to not rising to the occasion. Being a leader is scary, and it’s not for everyone. However, if you strive to be a great leader there are simple things you can start doing right now to improve.

You can listen better. Rather than interrupting others or “trying to be a good conversationalist,” ask follow-up questions and give them space so they can take their time to speak.

You can pursue the right thing rather than the popular thing. It takes bravery to stand with conviction against the norm for what you believe is right. Conformity is not leadership. It stunts a team’s potential.

While these things are hard, they’re not impossible. All it takes is a bit of courage to get going.

Life’s only as confusing as you let it be,
Ross


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