What’s in a “Win”?

A Rare Pocket of Time for Changing the Game

Reading Time: 6 minutes


2020 has been a year of unprecedented challenges. Whether you’re a solo entrepreneur, a creator, working in or running a small organization, wins have likely been rare. Or they have paled in comparison to the 2020 context. 

A “win” moment is a sweet pocket of time for taking a systems view. Taking advantage of a “win” moment in such a way is critical. Without it, we risk letting our initiatives and organizations take on wasteful habits and norms.

What’s in a ‘Win’?

2020 wins for being the most unprecedented year. Hands down. In 2020 an actual ‘win’ moment is rare. So many losses. So many setbacks. So much chaos and noise.

All of this background spurred my thinking about what an opportunity a ‘win’ can be. For our small businesses in particular, what’s in a ‘win’?

You reach Inbox Zero on your work email. 

You reach 1000 subscribers on your new Substack.

Your team ships the product on time. 

Your e-commerce company surpasses its monthly conversion goals. 

These win moments release pressure as though in a valve. Under pressure, we hold onto our standard operating protocols like a crutch. With the release that comes with a win, our routines get less sticky. For a moment we are freed. 

The win is a liberating moment not to be squandered.

For many initiatives and organizations, 2020 has brought challenge after disruption after hurdle. All of this on a meta-crisis backdrop of the unprecedented pandemic and economic shock. 

In the food business I helped start, 70% of our revenue in February came from selling to restaurants. As of April all of those restaurants were closed. We had to pivot hard back to e-commerce, which was fraught with its own challenges. 

In such a context, in such a year, it’s critical to make the best of a rare “win” when it comes. But how do you do that?  

Here’s an example standard game plan of a win on an organizational front: 

Your team sets audacious revenue goals for the quarter. You convene for a strategy meeting, delegate, and decide to bring on some consulting to help with a search engine marketing boost. You find the partner, set the systems, marshall the resources needed to make goals achievable. You go after it, iterate, report back, pivot, debrief, stretch, make mistakes, grow. 

You do the damn thing. 

The quarter ends and the returns show up big.


What next? Do you repeat what just worked? Do you double down? 

The Bureaucratic Becomes More Automatic

Many renowned organizations suffer from bureaucratic sloth. It’s a drag. To solve or even weather the meta-crisis of our time, we need more people to be lit up. Impassioned, empowered people create conditions for positive change. Business should be an expression of its lit-up change-makers. Instead, many businesses have systems and cultures that hamper this engine of grassroots innovation.

Some of this is unavoidable. 

Some of this is by design. 

But all of this is disastrous. 

For the products shipped and the people involved, business can fit like a tight, chafing wool sweater. 

To be sure, this is complex. 

Cracking the nut of how business can make products better and people more fulfilled will take longer than a newsletter. But cracking a chink in the armor is a simple task made synchronous by a “win” moment. When there’s a gap in the pressure, it’s time to look under the hood. 

Author and organizational design thinker Aaron Dignan developed a simple thought exercise to highlight the bureaucracy of our time. In his book Brave New Work: Are You Ready to Reinvent Your Organization?, he asks us to think of our experience and see if any of the following guidelines remind us of colleague behavior or organizational norms: 

  1. Insist on doing everything through channels. Never permit shortcuts.

  2. When possible refer all matters to committees.

  3. Haggle over precise wordings of all communications.

  4. Reopen matters already approved at previous meetings.

  5. Advocate caution.

  6. Require three approvals where one would do.

  7. Apply this and all regulations to the letter.

We’ve seen some or all of this before in our organizations. It’d be laughable, were it not so true and troubling. Business moves fast and there’s constant pressure, and systems get put in place piece by piece to manage for that. 

In business, growth is the game. Unfortunately, waste is a natural output of growth. To clear out the waste, we need to flush out the parts that no longer serve their function. We need to take a look at our norms like those listed above. 

But here’s the kicker: these seven steps above, which I’m sure resonated hard for many of us, are taken from an actual playbook—I kid you not—on sabotage.

Literally. Sabotage.

They are excerpts from the Simple Sabotage Field Manual developed in the 1940s by the precursor to the CIA: the United States Office of Strategic Services. This is the playbook used for going into enemy states and destabilizing day-to-day business operations from the inside out. 

Our businesses are saddled with such bureaucracy that the norms resemble actual, legit sabotage.

We find only rare opportunities to assess these organizing principles, the “operating systems,” as Dignan calls them.

It’s normal for business to grow. As it grows, it’s natural to set up departments. Then, the departments need communication systems to coordinate activities. Then, more people are hired to fill those departments and piecemeal the systems. So, incentives schemes are devised to draw out the purpose of the organization. 

A culture emerges that serves a hierarchy meant to serve the company purpose

But often the hierarchy is a drag on the purpose. 

Often, the hierarchy starts looking like the sabotage playbook. 

When the culture becomes a drag, the experience turns sour. 

The norms of protocol seem to prioritize top-down control over workers. They are assumed to need rewards structures to manipulate productivity and innovation out of them. Once this sets in, the legacy, bureaucratic companies are doomed. Particularly in an era of ever-greater pace of change and disruption. As Dignan notes:

The organization begets systems. The systems are meant to nurture innovation. Instead, the system sabotages from the inside out. The small startups and initiatives of today may take on this growth flaw. 

I hope the meaningful ones don’t.

What to Do with a ‘Win’ Moment

A win sets the wind at your back for a moment. When the pressure’s off, it’s good to take a moment and slow down. Assess the assumptions and operating principles that make each successive game a loss before it’s begun. 

Whether you’re in such an organization, starting or running one, or a solo entrepreneur, a win is an awful thing to waste. Here’s a starter set of five key activities that could change the game during a ‘win’ moment: 

  1. Set up an unplanned off-site retreat to get bottom-up feedback

  2. Take any so-called sacrosanct norm of the business (a regularly scheduled meeting or presentation, for example) and ask why it’s done the way it is, what problem it’s solving, and keep asking “why” to each successive answer. Note what comes up from this more informal Five Whys process. We often find we’re going to the hardware store to buy milk. 

  3. Undertake a Scenario Planning workshop. It’s a powerful framework for recognizing and adapting to change over time, ahead of time. By conjuring the details of possible futures and how they will impact the world of our organizational concerns, we can develop resilient strategies.

  4. Brush up on the Mental Models that Every Founder Should Know

  5. Take a deeper pause to undertake a Blue Ocean Strategy Canvas. It’s a superpower exercise where you look closely at your biggest competitors and assess the attributes of their offering. What key factors are they competing on? You map those attributes to see how well the competitors do at each of them. In so doing, locate where they’re not competing, and aim there.

These are just a few examples of ways to uplevel when the wind of a win is at your back. You, your team, your culture, and your customers will feel the benefits.

Innovators and creators that re-write the code of their culture are creating value at logarithmic levels. They’re making virtually automatic what can barely be achieved by organizations of the old guard. In such an unprecedented year as 2020, we need to be nimble and resilient. And people deserve to feel a part of something electric. 

What else is a “win” for if not to change the game? 

Thanks for reading. If this resonated, please hit the heart button below, or share it with someone else who might feel it too.

Special thanks to Team Hotel @beondeck and Tom White for critical feedback and editing prowess on this.