The Overton Window — Why Some Ideas Stick While Others Struggle

Saumil Mehta
7 min readFeb 23, 2023

--

Over the last decade in tech, we have been inundated with talk of the empowered employee. In this fantasy, most of the stuffy hierarchy is shunted aside in favor of bottoms-up innovation. Employees are encouraged to bring ideas to peers, managers, even senior leaders, with an expectation that many of these ideas will get greenlit and become standalone products or key features of products.

The best ideas win, no matter who you are, we are told.

As far as platitudes are concerned, this is all wonderfully peachy. But the lofty rhetoric becomes problematic only when employees really try to push their ideas to become reality and find their beautiful, fragile ideas crashing into a wall of resistance and red tape. Typical big company bureaucracy, amirite?

Obligatory DALL.E digital art of red tape trapping an employee

Over the years, as I’ve scaled into leading increasingly larger organizations and P&Ls at Square, I’ve gotten versions of this complaint from many different people.

Why am I having so much trouble evangelizing what is obviously a great idea? We say our company priority is X, my idea Y fits, why isn’t it being supported? We claim to stand for Value A, my idea B is in line with Value A, why the resistance? Leadership doesn’t want to innovate and is too satisfied with incremental steps. Why?

There are many reasons ideas can peter out in companies with hundreds of semi-autonomous teams and thousands of employees. But one simple yet powerful concept can help demystify quite a bit.

Enter the Overton Window.

The Overton Window

Borrowed from the grubby world of retail politics, the Overton Window articulates the list of policies (i.e. ideas) that most politicians can reasonably support at a given moment in time given existing bottoms-up public support. Ideas that already enjoy somewhat widespread public support and are already popular are within the window — whereas ideas outside the mainstream will have a harder time getting support from the same political leaders and be considered too radical or unthinkable. As they say, political leaders frequently reflect society more than they lead it.

Of course, the key dimension here is time. Dynamic societies — much like dynamic companies — change over time in response to external stimuli and collective learning. Popular culture can win hearts and minds. As concrete examples in the United States, ideas that were rarely championed two decades ago (e.g. same sex marriage, recreational marijuana) started to enjoy widespread public support over time. Unsurprisingly, many politicians followed the public and suddenly “discovered” their own support for them. Why? Because the Overton Window had shifted and expanded over time and made them popular, plausible and sensible.

Grubby indeed.

It’s not hard to see how this translates to the world of fast-growing, scaling tech companies. While a company’s Overton Window isn’t dictated by widespread employee support, it is dictated by a combination of strategic priorities, industry platform shifts, ideal customer segments and competitive behavior. At Square, these priorities are Omnichannel, International Expansion and Upmarket Expansion and they were originally set by fiat. These strategic priorities are recursively rolled out across a handful of GMs with higher fidelity and eventually, with enough decomposition, wind up as individual projects for a given quarterly or annual roadmap.

The Overton Window is effectively set at this point — not just for most projects that are in flight right now but also the types of new ideas that are likely to generate actionable forward momentum vs. those that may drum up initial interest or even excitement but can’t really get off the ground. Initiatives that are widely and easily understood to have a direct impact on those priorities for those ideal customer segments are squarely within the Overton Window — these tend to get fast tracked and funded quickly. Initiatives or projects that claim to have a direct impact on those projects or those ideal customer segments but in fact have a more tenuous connection when closely scrutinized will get a lower shot. More importantly — because this trips up a lot of well-intentioned, creative earlier career folks — the burden of persuasion winds up falling on them to either tweak the idea to strengthen that connection or to reframe the idea in a way that persuades more people to get more clearly inside the Window. Everything else? Unspool the red tape.

This simple analysis helps explain why so many get frustrated when they see their idea sit on the shelf while someone else is off to the races. There was never anything wrong with their idea, really, nor is this a direct result of bosses being pointy-haired bureaucrats. But in the absence of a simple Overton Window analysis, they mistakenly assumed their idea was within the window whereas in reality it was on the edge — or just outside.

A case study may be instructive. Over the years, I’ve been able to serve as the exec sponsor for many major initiatives and a few company acquisitions. The role of an exec sponsor is to help teams shape their nascent ideas (or the case for an acquisition), frame how they communicate its value, build mindshare for them and eventually get them going. A few years ago, a smart Design lead paired with their Eng lead and came up with an idea to allow consumers to use Cash App as a payment method at our Point of Sale. It is now called Cash App Pay and has come a long way since its humble beginnings years ago.

Image Credit: Block

Sounds easy to get such a great idea going, right? Not quite. It took us a year of off-and-on persuasion, idea shaping, demos and conversations to get it off the ground. Why? Overton Window.

On the other hand, we’re in the midst of a compelling new idea now (which I won’t name yet!) which had a much, much easier time getting funded even though it is objectively less innovative/new than Cash App Pay. Why? Overton Window.

It’s easy to mistake these divergences as executives playing it safe and funding less innovative ideas over the more innovative ones. The truth of the matter, however, is that Cash App Pay (at the time!) was at the edge or outside the Overton Window.

So what’s an ambitious person with ideas working in one of these companies to do?

  1. Analyze the company’s Overton Window: First of all, analyze the company’s Overton Window. This isn’t just as simplistic as knowing strategic priorities — it also involves knowing ideal customer segments, key scars company executives carry around tied to past failures (since executives are all too human, failures can cast a long shadow) and major platform shifts or competitive shifts that are likely to have impact on priorities or customers.
  2. Map your idea to the Overton Window: The next obvious step is to understand where your idea falls — squarely within, on the edge or well outside. Since there’s no deterministic formula, follow the chain of reasoning step by step. What types of customers does your project benefit? How many of them do we already serve? Are these customer segments a key focus to acquire or retain? Which strategic priorities does the project impact and why?
  3. Iterate to fit the Window: Most ideas go through a process of shaping and iteration on the path from someone’s imagination to something customers can actually use. But an idea that is on the edge of the window can benefit from explicit tweaking to fit more clearly into the window. Sometimes that involves changing the idea to fit a new customer segment more clearly. Other times it involves taking advantage of an upcoming platform shift. Yet other times it may involve simplifying the experience to match what already exists — even if it’s less futuristic. Cash App Pay offers a good example yet again — the original concept involved using Bluetooth between the consumer’s phone and the point of sale device and was tweaked to use QR codes instead. The experience is likely less magical but fits more nicely since Venmo and Cash App both use QR codes already as part of their P2P experience.
  4. Build mindshare with Patience: Of course, tweaking can only take you so far. Some of these ideas are simply outside the Overton Window and it’ll do no good to pretend otherwise. These are ideas whose time has not come — yet. But this is not a call to passivity. It is a call, instead, for patient mindshare-building. Just like small groups of committed advocates work to change our society over a multi-decade time frame, culminating in success eventually, in cases like this the main guidance is to work patiently to win converts over time. And guess what? This applies to senior leaders as much as it does to a fresh-faced individual contributor 2 years out of college. In theory, I can greenlight a huge swathe of ideas with high autonomy. But even I have ideas that sat outside the Window 2 years ago and I’ve spent time patiently working to build the case, convince people and get into the Overton Window.

Outside of these 4 actionable suggestions, the final suggestion that applies above all else — stick with it. Getting frustrated and giving up too soon is highly common and understandable. But all good ideas were once fragile. All good ideas needed long-term nurturing by true believers when others wouldn’t or couldn’t see it. The Overton Window does shift and expand over time. Bide your time and make your own (tiny) dent in the universe.

--

--

Saumil Mehta

EVP and GM at Square (leading Point of Sale, Ecommerce, Workforce Management, Payments Partnerships). Former entrepreneur. Opinions obviously my own.