The Criticality Of Timing

Timing is the factor that is most absent in conversations I have with investors, with other leaders of products, and with fellow entrepreneurs. While there is so much focus on trends, new technologies, data, and human tendencies, the criticality of timing is seldom discussed. Perhaps, because timing is so out of our control, we talk about it less. But the outcome of your work is determined by timing just as much as other variables. Timing is worthy of our respect and attention.

The Right Leader For The Right Time

It’s humorous how quickly we — and even professional headhunters — focus on the fit of a particular leader in a company without factoring in timing. At any point in time, companies have a unique set of needs and opportunities (and insecurities). Sometimes you need leaders that will drive product innovation, other times you need leaders that will masterfully sustain incremental growth. Sometimes you need a finance-CEO that brings margins and expenses in-line and transforms the business model. Other times you need a vision and product-CEO that will create a new narrative and reposition the product for entirely new purposes. In my experience, these leaders are rarely the same people. Like meeting a loved one, a great match is as much about timing as it is about capabilities and shared values. While at Adobe, the transformation to Creative Cloud required a regime of leaders focused on the business model (and the stock price went up over 100% within 3 years as a result). Of course, with the new model in place, the focus must shift back to product.

To lead an industry, companies require different leaders (or different leadership styles) at different times. Easy to say, hard to do. The default of most companies is to cling to a playbook that has already proven successful. Every playbook gets old, and the more successful it is the harder it is to deviate — especially for the coach who wrote it. When I help companies recruit an executive — or hear about a CEO transition — I try to reconsider the company’s position with a blank slate. Where is the company coming from and where must they go? Who is the right leader…now?

The Right Decision At The Right Time

As a generally impatient person with idealistic tendencies (I call it “process intolerance”), one of the most important lessons I have learned over the years is waiting for process to unfold. Achieving a vision without breaking the system requires periods of generating buy-in, exhaustive testing, and allowing time to pass for ideas to sink in and folks to get on board. It is frustrating but true that, in most cases, companies and products should only change in careful increments. Pacing is important, and most new ideas should be killed for the sake of focus. But sometimes your team and product are at an inflection and a trigger must be pulled quickly and all the way. Only the best leaders can maintain healthy incrementalism while imposing the occasional transformational jolt when needed.

My rough illustartion of the local maximum problem, which also appears to be a holiday greeting card.

The inevitable outcome of any business governed by incrementalism is a limited market size because the local maximum (the closest hill) becomes the limit. Evernote is a good example. The company addressed a real problem (saving your notes in the cloud) with a solution that has only incrementally improved over the years. It is now at the top of a hill. Some say Twitter is liable to suffer a similar fate (although I still have hope). In contrast, companies like Google, Amazon, and others have consistently increased their scope and ambitions by a step-function, and made the difficult decisions to execute.

Given the criticality of timing, incrementalism kills too many great ideas by pushing them to fruition too late.

Given the criticality of timing, incrementalism kills too many great ideas by pushing them to fruition too late. Yes, I am a big proponent of taking small steps in cautious terrain, and carefully testing and validating new improvements before going all in. But some new ideas are inflections and must be executed in full before they function. The best teams know when to do this and can reorganize to pull it off.

The Right Investment At The Right Time

Investing is a discipline focused on the future that can only be determined by the present. While you’re forecasting and attempting to bet on the future, it’s impossible to predict how the variables (the ones you know of) will interact over time. Therefore, forecasts for the future (a good exercise for everyone) should be grounded with a deep and accurate understanding of present day problems and humanity at the moment. Otherwise, you may be betting on a future that is off by an order of magnitude.

The other key to timing is tracking the tail winds. My criteria for investing at the right time is whether the team is attempting to defy a likely outcome or make it happen in a better way. I invest in the latter. The best teams I come across are parlaying forces already underway to their favor. They are grounded by the present and are capturing a tail wind.

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