Building a Successful Team through Determined Optimism: Winners vs. Whiners

Determined optimists are Winners who are necessary to have successful teams.​ In this post, I argue that there are three types of team members: Winners, Warners, and Whiners. What are the characteristics that define a Winner? Why are Whiners so dang

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Some of the philosophies and lessons I've learned from my life experience don't have scientific backing but I have come to absolutely believe in through real world experience. More specifically, building a successful team through determined optimism is one such lesson.

The Power of Optimism

The belief in the power of optimism is not something new. Here in Silicon Valley, Steve Jobs was famous for his "reality distortion field" and willing his grandiose beliefs into reality. Hinduism has been around for thousands of years and has a notion of manifesting reality through belief.

And there's also this from Walden:

I learned this, at least, by my experiment; that if one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours. He will put some things behind, will pass an invisible boundary; new, universal, and more liberal laws will begin to establish themselves around and within him; or the old laws will be expanded, and interpreted in his favor in a more liberal sense, and he will live with the license of a higher order of beings.

So back to the primary topic at hand: How do you build a successful team?

I'm an old guy who has had the opportunity to work with many teams during my career. In my experience, three key characteristics define teams that have achieved great success:

  1. The teams worked long hours (e.g., work until 10:00 PM)
  2. Key members of the team have worked together for at least 4 years together
  3. Someone on the team was a determined optimist (aka "Winner")

There are many things that could be discussed when it comes to building successful teams from process to skill sets to work habits, etc. However, for the purposes of this discussion, I want to focus on just this last characteristic of optimism.

Types of Team Members: Winners, Warners, and Whiners

In my experience, three types of team members exist:

  1. Winners: Optimists who drive product vision and teams to success.
  2. Warners: Realists who foresee problems ahead of time and warn the team about them.
  3. Whiners: Pessimists who reactively complain about problems and remain focused on problems rather than solutions.

For a team to be successful, a team leader must ensure a team consists of at least 1 key Winner (ideally him/herself) and Warners, but to also eliminate Whiners from the team as quickly as possible. One or two Whiners on a team won't necessarily kill a project, but Whiners can certainly be a cancer that eventually kills the patient.

The Winner

I call the "determined optimist" on a team a "Winner" and believe they are absolutely critical to the success of the team.

Winners are:

  • Believers: Win through optimism and a strong belief in themselves, their team, and their product vision.
  • Fighters: Unfazed by obstacles and fight through adversity often times regardless of the personal cost.
  • Leaders: Lead their teams through example and are the engine upon which teams drive critical success.
  • Manifesters: Believe they can manifest their vision of reality through sheer force of will (very much consistent with ancient Hindu concepts) and find ways to win that others don't see.
  • Aware: Optimistic, but also grounded in the reality of their situation: the Stockdale Paradox (more on this further below).

Warners vs. Whiners

So what's the difference between a Warner and a Whiner?

The key difference between them can be characterized by three primary tendencies:

  • Proactive vs. Reactive: Warners typically have more experience and foresee problems ahead of time rather than just reacting to problems.
  • Problem vs. Solution Focus: Whiners tend to focus on problems whereas a good Warner will often propose solutions to problems instead.
  • Support: Warners can get behind a project or initiative even if they disagree with it. Whiners, on the other hand, try to undermine decisions or will not do their job to support a project that they view negatively.

Winners vs. Whiners

Let's now talk more specifically about Winners vs. Whiners and the specifics about one vs. the other. In the case of Warners vs. Whiners, there are often cases where the line between the two types may not be easily distinguishable. However, the distinction between Winners vs. Whiners is absolutely clear.

The following table denotes key differences between these two types:

Winners vs. Whiners

Determined Optimism

Let me clarify what I mean by a "determined optimist." Winners do not adopt blind optimism in which they live in an overly hopeful fantasy world. Instead, a "determined optimist" is differentiated from a general optimist in two key ways:

  1. Situational Awareness: The determined optimist is very clear on his or her specific circumstances. They fully understand their situation including both strengths and weaknesses no matter how grim the situation may be. Jim Collins describes this kind of awareness through The Stockdale Paradox described below.
  2. Manifests Reality: Determined optimists figure out ways to win. They focus on solutions and figure out how to win regardless of their specific situation.

1. Situational Awareness and The Stockdale Paradox

Jim Collins best describes the importance of optimism but with situational awareness in his book Good to Great in a principle he calls the Stockdale Paradox. The Paradox describes a lesson learned by James Stockdale who spent eight years in a Hanoi prison during the Vietnam War. He states of his experience in Good to Great:

I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.

But wait, there's a paradox: this is what Stockdale stated of the guys who didn't make it out of the Hanoi prison:

The optimists. Oh, they were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go.

Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.

Jim Collins explains the seeming paradox in the following way:

This is a very important lesson. You must never confuse faith that you will prevail in the end— which you can never afford to lose— with the discipline to confront the most brutal facts of your current reality, whatever they might be.

Winners are "determined optimists": they believe in themselves, they believe they will win, but they also realize the state of their current reality no matter how brutal it may be.

2. Manifesting Reality and Finding Ways to Win

Winners win. It's almost as simple as that. Winners find ways to win and Whiners wallow in negativity and can't think of "outside of the box" solutions. I know this can sound a bit vague but the difference with Winners is quite simply that they will figure out a way to make a bad situation work out.

Let's be more specific with a few examples to make this point more clear:

  • Situation: Your team is dependent on a key vendor for a product launch but they have been unresponsive. What do you do?
    • Whiners: Will report to their boss that unfortunately their hands are tied, the vendor is unresponsive so they can't do anything
    • Winners: Will call 20x a day, travel (regardless of location) to the vendor's office and camp out there until they are able to talk to the person they need to and get clarity on the vendor's services and timeframes
  • Situation: A remote development team has been consistently late on deliverables and producing software builds that are not up to your team's quality standard. What do you do?
    • Whiners: Will not have the nerve to have super direct confrontations with the dev team, will constantly complain to their boss and peers how incompetent the dev team is, and more generally make sure there are excuses when the team fails... just as they had predicted
    • Winners: Will immediately have extremely direct talks with the dev team, renegotiate contract terms including stopping payment if necessary, fly over and camp out with the remote team and directly manage that team until they produce what's necessary or cancel the project
  • Situation: A team member has been underperforming and dropping the ball on key tasks for a critical project
    • Whiners: Will not directly confront the team member but complain about that person to everyone else, will keep saying they need to "watch the situation" as the business continues to crumble around them
    • Winners: Will confront the underperformer to know what and how to improve performance and let them know that their job is at risk. If no immediate improvement occurs, Winners will let that person go quickly.

Hopefully, the point is now clear. Whiners accept situations at face value and throw their hands up. Winners don't accept bad situations and will do whatever it takes to figure out a way to win.

There's also this from Tony Robbins:

Unrelenting Will

What Can You Do Today?

Most of my early career was mainly academic, rather than with real world business experience building products. Until that time, I was largely a Whiner. In fact, most of my career has been spent as a Whiner or Warner rather than as a Winner (which I'm not even saying I am now but have had moments of and am aspiring towards).

So let's get back to practical reality: What can you do today given this information?

  • As a team leader:
    • You need to look yourself in the mirror and determine if you've got what it takes to succeed. Are you a Winner or a Whiner?
    • Evaluate your team. Who are the Winners, Warners, and Whiners? Isolate the Whiners and have direct one on one talks with them about what it will take to get them on board. If they continue to be Whiners you need to get them off your project.
  • As a team member:
    • Understand what kind of team member you are. You should have the self-awareness to be honest about yourself. If you are a Whiner, you need to change. Think about how you can help instead of hinder and realize that focusing on problems only will do nothing to change a situation: be solutions focused!

Whether you focus on optimism or pessimism, whatever you focus on is what you're going to find in life.

On that note, I want to leave you with the words of super entrepreneur and social media master Gary Vaynerchuk:

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