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Great Leaders Are Confident, Connected, Committed, and Courageous

Peter Bregman

Peter Bregman is the CEO of Bregman Partners. He coaches, writes, teaches, and speaks mostly about leadership. His sweet spot is as a strategic thought partner to successful people who care about being exceptional leaders and stellar human beings. He is recognized as the #1 executive coach in the world.

Sanjay (I have changed his name and some details to protect privacy) was founder and CEO of a technology startup that grew rapidly to $50 million.

Then it stalled out.

Sanjay had not previously grown a company past that stage, and he was unsure what was wrong. He was hoping his team would pull together and figure it out but that had not happened yet.

"I think I need to change out my leadership team," he said to me, in anger and frustration.

"Or," I countered, "maybe you need to scale your leadership in order to scale the company."

Sanjay had not, to this point, done much leadership development work. He had ideas, told people what to do, and micromanaged the execution. He was impatient, angered quickly, and not very trusting. Turnover was high, employees felt unappreciated, and even the leadership team was unwilling to take risks for fear of the consequences.

Which meant that Sanjay was out of the communication loop (nobody was willing to disagree with him or bring him bad news for fear of his reaction).

In order to lead, you have to get your most important work done, have hard conversations, create accountability, and inspire action. Sometimes - especially at smaller companies - leaders can do that in very autocratic ways. But that's poor leadership, and poor leadership does not scale.

To scale, you need to show up powerfully and magnetically in a way that attracts people to trust you, follow you, and commit to putting 100% of their effort into a larger purpose, something bigger than all of you. You need to care about others and connect with them in such a way that they feel your care. You need to speak persuasively - in a way that is clear, direct, and honest and that reflects your care - while listening with openness, compassion, and love. Even when being challenged.

In 30 years of working with leaders to do all of the above, I have found a pattern that I share in Leading with Emotional Courage (Wiley, 2018 Peter Bregman), consisting of four essential elements that all great leaders rely on to rally people to accomplish what is important to them. To lead effectively - really, to live effectively - you must be confident in yourself, connected to others, committed to purpose, and emotionally courageous.

Most of us are great at only one of the four or maybe two. But to be a powerful presence - to inspire action - you need to excel at all four simultaneously.

If you are confident in yourself but disconnected from others, everything will be about you and you will alienate the people around you. If you are connected to others but lack confidence in yourself, you will betray your own needs and perspectives in order to please everyone else. If you are not committed to a purpose, something bigger than yourself and others, you will flounder, losing the respect of those around you as you act aimlessly, failing to make an impact on what matters most. And if you fail to act powerfully, decisively, and boldly - with emotional courage - your ideas will remain idle thoughts and your goals will remain unfulfilled fantasies.

Let's apply this to Sanjay and identify precisely where and how he was getting stuck.

Confident in Yourself. Strange as this may seem given how Sanjay presents, he actually struggled with this element. This might feel surprising since he seemed clear about what he wanted, micromanaged, and used intimidation to ensure his ideas were followed. But those things are not confidence, they're arrogance. Confidence is being secure enough to be wrong, to listen to other's opinions, and to be open to how others approach things. People who lack confidence always have to have their way. People who are confident can let others win and prioritize the best idea over their own idea. Sanjay obviously believed in himself - that's also part of confidence - but he wasn't confident enough to be vulnerable. He definitely had room to grow here.

Connected to Others. This was Sanjay's greatest weakness. He did not trust people enough to give them space to own things fully, and people did not trust him enough to tell him things straight. He showed little curiosity and quickly drew conclusions about others; once he made up his mind about someone, they would not get a second chance. He did have some strengths here: he was direct with people and did not procrastinate on difficult conversations. People knew where they stood with him. But he communicated so harshly that those attributes that could be strengths became weaknesses.

Committed to Purpose. This was Sanjay's greatest strength. He was clear about what needed to get done, and he was completely focused on the strategy and plan. He was clear about the small number of things that would move the needle and he was undistractable. And he had a reliable process for staying focused on the most important things, ensuring accountability and driving follow-through.

Emotionally Courageous. Sanjay had room to grow here, and it turned out to be an important element for growing his strength in the elements where he was weaker. Risks, by definition, make us feel vulnerable, and Sanjay avoided that feeling. He resisted the unknown and intentionally avoided uncomfortable situations. This made it hard for him to be open to other people's ideas and listen to their perspectives, especially when those perspectives differed from his. How could others feel ownership and risk offering innovative ideas when their leader was not courageous enough to listen and consider them?

So Sanjay's strongest element was "committed to purpose," which got him admirably far. But his weaknesses in "confident in yourself," "connected to others," and "emotionally courageous" were holding him, his team, and the entire company from achieving their ambitious objectives.

What we're seeing in Sanjay is actually fairly typical for aggressive and successful entrepreneurs. His commitment to purpose is inspiring to investors, employees, and other stakeholders. And it fuels his persistence through the inevitable obstacles every founder faces. Meanwhile, that irrepressible drive and focus prevent him from listening to others in a way that truly engages them, and his fear of failure (which is one psychological element that drives his commitment to purpose) diminishes his confidence. It takes tremendous emotional courage to let other people - and their ideas, perspectives, and disagreements - impact the baby to which Sanjay has given everything.

So I shared all of this with Sanjay.

Just knowing what was happening helped him immediately. We spent some time strengthening his emotional courage by taking small risks while feeling the emotions he had been trying to keep at bay. Each time he followed through, regardless of whether he succeeded, he obviously survived and also felt the accomplishment of addressing the risk itself, which, of course, built his confidence and helped him take bigger risks.

In a short time, he felt prepared (even though he may never have felt "ready") to be vulnerable with his team, apologize for the way he had been leading, and ask for their help in becoming a different type of leader so that they could become a different kind of team and, finally, scale their venture.

So Sanjay brought the team together. He was extremely uncomfortable going into the conversation - that's almost always the feeling you'll have when you do anything that requires emotional courage.

But using emotional courage builds your emotional courage. Sanjay emerged from the conversation with the team stronger in all four elements: he was more confident in himself, more connected to his team (as he listened to them without interrupting and without interrogating them), just as committed to purpose, and more emotionally courageous.

What's most important is how developing his own leadership impacted his team's leadership. They became more connected to each other (as well as to him) and far more committed to purpose than before. Their confidence and emotional courage grew as they brought challenges and obstacles to the team in a way that they were hesitant to do before. Which, of course, enabled them to address those challenges, as a team.

That is how you scale leadership. And that is how you scale a company.

Want to develop your own capability in each of the four areas? Here are four quick activities you can do - one for each element - that will have an immediate, positive impact and help you lead with emotional courage.

Confidence in Yourself. This is about staying grounded in the face of success, failure, ambiguity, complexity, or anything really. One of the best tools for growing your confidence is meditation - even just 30 seconds of it. Sit comfortably, close your eyes, take a deep breath, hold it for a second, and then exhale slowly, relaxing every muscle as you do. Repeat even for just a few breaths, and you will feel yourself more grounded. Try it now.

Connection to Others. People feel...