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To Create Culture, Ditch the Playbook and Embrace Contradiction

Michael Wanderer, SVP of People, Handy

Michael Wanderer, SVP of People, Handy

Most of the best phrases you read are brilliant for a moment and lose their shine the longer they’re exposed to the elements. In this case, the phrase in question is about that phenomenon: being the best at anything is only a moment in time. Jason Preston wrote that in his recent piece for HBS Digital, “Culture Eats Strategy for Breakfast,” and it illuminated a particular characteristic of successful companies. Invariably, business dynamics change and teams find themselves clamoring to stay ahead of the curve and adapt. Successful companies, Preston notes, are able to motivate highly competitive team members to set their egos aside and put organizational priorities first. When this alignment is seamless, organizations can pivot smoothly when the time is right.

This insight is well and good, but how can a company achieve this sort of flawless parallelism? Especially in a tech start-up, where everything is moving so fast that it’s nearly impossible to see beyond immediate concerns, how can a team develop a work culture that fosters such perfect alignment? Is the answer a series of inspirational speeches? Trust falls and potato-sack races?

Just about everyone has something to say about ‘the culture factor.’ Yes, it needs to be defined. Yes, it’s learned. Yes, it’s adaptive. Whatever you come up with needs to be shared, pervasive, and enduring. These are all true. But how you understand culture is critical to developing culture. And to understand culture, there are three essential points to consider.

The Contradictions of Culture

There are academic definitions of culture and colloquial definitions and they all essentially say the same thing. “A secret language” is an exciting one, but culture shouldn’t be secret — once experienced, a given culture feels all but inescapable. What’s important to take away from these definitions is that there’s a broad gap between the phrases we use to capture the essence of culture in the abstract, and the concrete expression of that culture.

"Part of building culture is voyaging into uncertainty"

“Our meetings always end on time” is not how most people would respond if asked to summarize their present work culture. If anything, emphasizing something so tactical feels like it trivializes the nature of culture. And yet, when you think about all of the things that would have to happen in concert across an organization for all meetings to end on time — agendas created and distributed in advanced, a shared understanding of issues, prioritization, ownership, the ability to make tradeoffs, time management, role clarity, effective consensus building, etc. — you realize that single tactic is a poignant expression of a well-articulated culture.

But regardless of what it took to get every meeting to end on time, what becomes clear is that a culture is only ever defined by a collection of tactical moments that coalesce into something greater. It might be a very, very big list, but ultimately a finite list consisting of items that are concrete and knowable. A list that can be understood and prioritized and acted upon. And critically, a list that can be influenced. Which leads to the second point of understanding culture: decisions create culture. Each and every one. So make them consciously.

Decisions Create Culture

At every start-up, a new work culture will be created from scratch. And once it’s created, it will evolve. Continuously and whether or like it or not. Work culture — any culture — is incapable of sitting still.

So the only question is whether this process of cultural development will be deliberate and active, or if it will be reactive, the consequence of chance or a lack of prioritization.

Football or a pool table? Pets in the office? Unlimited vacation? On-site baristas? These are all decisions that influence culture, and the decision-making process itself has as much of an impact on culture as the end result. Crucially, while the impact of in-office amenities does matter, the process of weighing what matters in an organization beyond the facts and circumstances is far more telling about and more influential of the work culture overall.

One of the hardest decisions a manager ever makes is when to let an employee go. Not just the true underperformers; that’s easy in the grand scheme of things. The hard part is when you have to decide whether to cut ties with someone who was instrumental in getting an organization from A to B, but isn’t as successful in the context of moving to C. Or, someone who you are personally close with, and works hard, but just can’t keep up with their peers. These modest deltas in performance can create a fault line. It’s small at first, but it’s increasingly visible — if unaddressed — to the rest of the organization.

Typically, when people are let go in this context, the action is overdue. Months overdue, if not longer. And the cultural damage caused by indecision is already done; the lack of decision-making has already itself become woven into the fabric of the culture. It was blindingly obvious in hindsight, but excruciating in the moment. How do you avoid that? How do you avoid both the personal anguish and cultural damage? This is where there third point comes into play: the fact that there is no playbook.

There’s No Playbook

Or at least, there’s no set of guidelines, no textbook, that’s specific enough to guarantee an amazing culture that’ll endure through time. There are best practices — high engagement, consistency, adaptability, transparency — but nothing that can make a choice for you or guarantee that it’s the right move.

But that’s okay. Part of building culture is voyaging into uncertainty. The right way to build culture is the same as the right way to build anything without a definitive blueprint: you anchor yourself in mutually agreed-upon values. You align around a shared mission. You test. You develop strong feedback loops. You pivot when necessary. And you handle all of your decisions, particularly the ones that involve people, as if they will make or break the company culture you’re envisioning — because they will.

There’s no playbook that’ll make decisions for you. And your decisions are the essence of culture. And the essence of culture is a concrete list of decisions. This apparent contradiction is your challenge, because leadership — especially cultural leadership — requires vision and balance and willingness to learn, take risks, adapt, and create something new.

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