When I was a kid, I’d watch my Dad create weird-looking sketches.

“What is it, Dad?” — I asked.

“It’s a game plan.” — Dad said, looking up from his drawing.

“What is it for?”

“It helps you think about how to play a good game.”

That gave me a pause. I knew that Dad was a basketball coach; I knew that his team had recently won the National Championship. What I didn’t know was that his job entailed drawing. Now, that was puzzling — because, frankly, he was pretty bad at it!

“How could these messy squiggles help Dad’s team become national champions?” — I wondered.

Here is the story of my Dad and his approach to coaching his basketball team. It’s also the story of my first startup’s failure and the five lessons I learned from both.

Lesson 1: A playbook comes before a game plan.

When I asked Dad about his sloppy sketches, he was amused:

“A game plan doesn’t have to be beautiful — it just has to work. But even when it does work, it can only win you that set play. To win a game — and especially a championship — you need way more than a game plan.”

And then, he pulled out a leather-bound book from his bag. His playbook.

Dad’s playbook was where he’d clip in all his best game plans. But the most crucial part, he told me, were the first pages. They contained notes on his coaching philosophy and three simple rules he expected his players to live by. They were his North Star as a coach.

Key takeaway

We are hard-wired to solve problems. That’s why we love our game plans so much. We often act as if a good product-market fit, a great business plan, or a smart strategy are everything we need to succeed in business. But it turns out that tactics are not enough.

A playbook comes before a game plan. Before you figure out what you need to do to succeed, you need to know WHY you are in the game and HOW you want to play it.

Lesson 2: Practice for the game, play for the team, win for the fans.

In my late 20s, I quit my job, moved to Greece, married a guy I knew just for a few months, and set up my own business. All at the same time.

Many parents would freak out but my Mum and Dad seemed strangely unphased - at first.

But one day, as my parents were visiting us in Greece, my Dad said over dinner:

“I love it that you are so determined to make this business work, honey.”

I beamed.

“But you really need to take a step back,” — he continued.

“A step back?!”

“The way I see it, all business is, is a game,”- he said. — And he lost me right there. I couldn’t help but think: “Uh-oh, here comes the sermon. Dad is putting his coach hat on!” And so he did.

He talked for what seemed like an eternity. About how there was no point focusing on a game plan without a playbook — especially without those crucial first pages that would guide me in the long term. He insisted that the principles that he drafted for his team as a coach were 100% relevant here, too:

• Practice for the game
• Play for the team
• Win for the fans

I knew all that by heart by then but I humored my dad and pretended to listen. And then, true to my rebellious streak, I proceeded to… ignore all his advice. Entirely.

I was determined to succeed though and so I kept reassuring myself: “I have the product-market fit. I have a good business model. I have the talent to sell. I have many prospective clients. This will be great!”

Well, I was wrong. It didn’t turn out that great.

In hindsight, it’s pretty clear why: I violated every single principle on my dad’s list in my first business. I wasn’t thinking about who I was trying to serve. I was focused on winning, not on practicing to play my best game.

I hoped that “talent” was enough and I desperately wanted to believe that I had some. And to make things worse, I was a terrible ball hog — I tried to play solo, taking the impossible shots myself, instead of passing the ball to my team.

Key takeaway

Our culture fetishizes grit and determination, focus, and hard work and idolizes individual accomplishments. We want to be the heroes of our own stories, the ones who save the day and accomplish something against all odds. But here is what I learned:

Paradoxically, in order to win in business, we need to take the focus away from winning and zoom in on practicing our craft, creating the right environment for the team, and serving the people we care about.

As my dad said:

You practice for the game, play for the team, and win for the fans.

Lesson 3: Always course correct.

In Hemingway’s The Sun Also Rises, one of the key characters, Mike Campbell, is asked:

“How did you go bankrupt?”
“Two ways,” he answers. “Gradually, then suddenly.”

That’s exactly how I went bankrupt, too. Gradually, then suddenly.

I burned through all my life savings first. Then, I borrowed some money from my in-laws. I maxed out my credit cards. It still wasn’t enough. And after a year, my runway was gone. I had no money, no clients, no mojo. And at the end of it, all I was left with was a bruised ego and a crippling debt.

Key takeaway

When we veer off course by one degree, it doesn’t seem like much at first. But little things compound and can gradually lead to catastrophic results if we don’t pay attention early enough. It’s good to ask ourselves on occasion:

Where might we end up in a year from now if we keep doing what we are doing? Is it where we want to be?

My game was over. Prematurely perhaps. And it was all because I didn’t develop the right navigation tools. I was off-course and I didn’t even know how far off. If I were to give advice to my younger self today, I’d say:

Be crystal clear about where you’re headed but flexible on how to get there. And course-correct all the time.

Lesson 4: When you fail, own it, make amends and move on — asap.

I struggled to digest the failure of my first startup for years. My confidence was crushed. Facts were hard to accept. I was terrified of reflecting on the whole experience.

Because, how do you admit that you’ve given something your all — your heart and your soul — and you were still unable to pull it off? What does it say about you?

Like many failed entrepreneurs, I was in the grip of shame.

Shame is destructive on many different levels. But the worst aspect of being in the grip of shame is that it prevents us from learning and moving on. We get suspended in a limbo, held hostage by our own interpretation of what had happened and what it says about who we are.

The only way to break free is to look shame straight in the eye and say:

“Fine, you are right! I messed up pretty bad. But you know what? It doesn’t define me. I’m going to make amends to those I hurt and forgive myself for being human. I’m moving on and you are not coming along.”

Key takeaway

I wasted a lot of time not owning up to my failure. I blamed Greece, the market, lack of funds. Here is what I should have done instead: admit that I messed up, make amends to those who were hurt in the process, and learn everything I could from the whole experience. Looking back, hiding from my failure is exactly what held me back.

Failure sucks but we can make it suck less by embracing it, instead of hiding from it.

Lesson 5: Be in sync with your playbook.

I’m not sure whether something specific triggered the shift that finally allowed me to move on. But I have a strong, sensory memory of the moment it happened.

I felt like something has melted away. Suddenly, I had a sense of softness and warmth in my chest instead of the tightness and heaviness I felt before. It was like I was driven by a strange but friendly force that seemed to know what needed to be done.

I went to a bookstore. I breathed in all the smells I love — paper, books, fresh print. I browsed the shelves and finally got to a stand full of Moleskin notebooks. They looked beautiful. I pulled one out and took it to the cash register.

It was black. I paid for it and went outside. I sat on a bench, opened the notebook, and wrote the word “Playbook” at the front. As I turned to the second page, I wrote a couple of questions:

“Why am I in the game?”
“What impact do I want to have on those that I serve?”

It took me years to figure it all out. I added more questions on the way. But at that moment, as I was sitting on the bench near the bookstore, for the first time in a long time, I knew I’d be fine.

I had my playbook — it was right there, on my lap. All I needed to do was fill it in. And then, keep getting my life in sync with what was in it.

I guess that having failed at a business I wanted so much to work had something to do with my obsession with finding the answer to this question:

What sets a company up for success?

I joined consultancies like Hay Group (now Korn Ferry), and PwC to figure it out. Then, I struck out on my own again, this time as a consultant. And as I’ve worked with scores of teams, from VC-courting startups to Fortune 500, I kept being curious.

For almost 20 years I observed, tested, tweaked, and tested again. I wanted to know what works and what doesn’t — what needs to remain constant and what needs to evolve.

And I discovered that to grow successfully and make a true dent in the world, you need more than a great idea, loads of passion, capital, smart strategy, or even the most talented people on your team.

You need to bring everything and everyone that matters in sync. Like in a game. Because after all, my Dad was right:

Business is a game. And you can’t play it well without a playbook.

A playbook is not optional. Period. Not for an individual and certainly not for a business. Not if you want it to succeed. This is as true for a 10 people enterprise as it is for one that employes 10.000 team members. The more people there are, the more vital it becomes to have a playbook. When it comes to companies, I call it the Culture Playbook.

Elements of a Culture Playbook

A good Culture Playbook consists of:

1. A Mission Statement

It answers the questions:

• “What do you bring to the game?
• “How do you impact those you serve?”

2. A Vision Statement

It answers the questions:

• “What is your end-game?
• “How will the playing field be better after you’ve accomplished your mission?”

3. The Core Philosophy

It answers the question:

• “What is the core belief that got you in the game in the first place?”

4. The Core Values

They answer the questions:

• “What do we value most?
• “What are the principles that help us play our best game?”

5. The Core Desired Feelings

They answer the question:

• “What is the emotional impact we need to have on the employees and customers to play our best game?”

They are what I refer to as the Big Five.

Key takeaway

In combination, the Big Five can become the most essential enabling constraint for a business. While your company grows and evolves, they are the elements that help you navigate the uncharted territories in a way that is consistent with what you stand for and who and how you want to serve.

There is a sweet spot from which you can maximize success: it’s where your brand promise, your products, your employees, and the people you serve are in perfect harmony — in sync. A good Culture Playbook helps a great deal to make it happen.

Invincible cultures and businessed are a by-product of discovering, articulating, and operationalizing their Culture Playbook.

P.S. My dad (second from the left in the picture below) is almost 80 today and he still coaches a team near his hometown — and still uses his playbook (which he has now fully digitalized)! So here is to never giving up, always learning, playing a good game and letting our playbook guide us on the journey!