The Difference Between the Critic, Pessimist, and Optimist

By: Josh

Are you a critical leader, a pessimistic one, or an optimistic one? Let’s consider a thought by famed businessman and leadership author, Max De Pree:

“The first responsibility of a leader is to define reality. The last is to say thank you. In between, the leader is a servant.”

This has long shaped how I approach the act of leading, and still does today. But the first responsibility that he addresses, defining reality, has always fascinated me. What does that exactly mean? And what does it look like?

All leaders define reality for their organization one way or another. But I believe how we do is where the critical, pessimistic, and optimistic leaders diverge from one another. All leaders must understand, own, and convey reality for the organization. Nothing can or will happen if we don’t first realize where we currently are. But how a leader conveys that reality and what we do after that is what matters, and what can make us a critic, a pessimist, or an optimist.

The critic defines reality and…well, that’s really about it. Often through a negative and complaining lens, a critic merely identifies problems, but nothing seems to happen after that. They don’t take ownership or move onto the next steps of the problem-solving process to create and pursue solutions. A critical leader doesn’t bring the organization or their people much value.

The pessimist defines reality, acknowledges a potential future, but focuses on why we can’t do it or why it won’t work. Pessimistic leaders are doubtful, not giving much space to “what if” or “what could be.” They do make valuable red team members poking holes to ensure decisions are thorough and complete; these qualities are absolutely needed on a team. However, pessimists do not create a hopeful, possible future for the team. Without the balance of optimistic leaders, pessimists don’t make the hard, unthinkable things possible through change.

Optimists, though, define reality and then determine a way to make it a desired reality. Optimists deal in hope and possibility that people believe in; things that people become willing to commit to. Optimistic leaders are not blind to reality, no matter how bleak or challenging it is. They don’t blissfully convince others not to worry or that everything is good. But optimistic leaders do, however, make the unthought of and seemingly impossible into a new reality. Optimistic leaders create opportunity for learning, for a new standard, for improved organizational performance and results. Through their energy, commitment, discipline, and bias for action, optimists take an organization from “what is” to “what if” to “what can be” eventually to “it is.”

So, are you a critic, a pessimist, or an optimist?

More importantly, what do you want to be as a leader?

How to Be a More Optimistic Leader

I’m not trying to sell a belief that optimism alone is the solution. We need pessimists sometimes, realists to keep us grounded, and critics to help us identify problems. But none of those types of leaders take a team from Point A to an elevated, more desirable, and improved Point B. Leaders deal in hope, in change, and in organizational and human improvement. Leaders make things better. Leadership involves optimism.

What if optimism is not natural for us as leaders, though? We may recognize it is important but might not know really how to integrate it into our behavior. Or we may simply be looking for a few added ideas to be more optimistic. If so, here are some “habits of optimistic leaders” that we can work on applying today.

• Always consider opportunity: When making decisions, leaders must consider factors like risk, obstacles, cost, and value of course. However, add opportunity to those factors as well. Every decision or change in our environment creates opportunity. Making that a standard consideration creates room for optimism in the team’s decision-making process.
• Push others to think through “now what”: I use a simple framework of “what – so what – now what” to frame almost anything. It can apply to decision-making, understanding a problem, assessing the current situation we are in, and so on. It helps me make sense of the topic at hand and easily explain it to others. “What” defines the topic and fully explains what we are talking about. “So what” helps us to understand the importance and relevance of the matter. And finally, “now what” puts us into action mode, looking to determine a path forward toward a desired end state. Many leaders, critics and pessimists alike, tend to marvel and obsess over problems. Optimistic leaders are not ignorant of the problem or of reality. However, we aim to understand it so that we can do something about it. Push your team to understand the problem, but don’t let them marinate in it. Push them to “now what,” determining the necessary action to address the issue.
• Own, acknowledge, and learn from failure: Optimistic leaders don’t punish failure. We see it as an opportunity, both for ourselves and for others. Failure comes with disappointment, embarrassment, and consequences, sure. But that does not preclude the opportunity to learn, grow, and become better from failure. Own your failures, process them, and learn from them. Then, share about your failure with others to normalize continued growth. Help others through their failure too, processes and building back up from it. It builds resilience and a shared growth mindset.
• Celebrate small wins: Small wins are data points of progress toward lofty goals. Help your people see these small wins as indicators of success. They build momentum, buy in, and energy. It turns possibility into reality over time.
• Make molehills out of mountains: Change is hard. It can be scary and often overwhelming. Big, lofty goals that require change are intimidating. So, leaders need to help others frame the change, the growth, and the opportunity. I find it a little funny how often I use phrases like, “how do we eat an elephant?” or “how do you run a marathon?” with mentees and junior leaders. Sometimes, we just need to breakdown a thing into manageable pieces for us to see the possibility and to get moving. One bite at a time; one step at a time.

Our Challenge

Again, being an optimistic leader is not to blissfully ignore tough reality. We still have to have hard conversations and make hard decisions. But we don’t admire a problem. We are not hindered by it. We seek to understand it so that we can do something about it, always striving to make things better.

Optimism as a leader is a choice. It’s about taking responsibility. We can complain, we can make excuses, or we can own the issue and do something about it. Our organizations and our people need optimists; they deserve it. Through small, consistent commitments to optimistic leadership, we can make the seemingly impossible possible for others.

What is one small “act of optimism” we can enact today?

Think through if there are certain scenarios, environments, or topics that push you toward criticism or pessimism. What do you need to do to push toward optimism in those settings? What boundaries, reminders, or triggers do you need to put into place?

How can you inspire others toward optimism today as well?