In the first post of this series, I shared three proven steps in aligning people with strategy.

During times of significant change, alignment requires more attention from leaders and managers. This is especially the case when what is required to execute a new strategy involves more than small tweaks in people’s daily work.

How do you know when strategy must change?

John Caplan, former CEO of Open Sky, explained this well in a talk recorded on Inc. Only subscribers can view the article so I’ll just share a few notes from his talk.

He describes an ad agency in the early 2000s with a strategy to do cool work (mostly thinking about tech) but their strength was to do really great, but not cool, retail work. They changed their strategy, to focus on the retail work they were best at, and landed a deal with Starbucks. That deal put them on the map, so to speak, and they grew from there.

He also credits continuous iteration of a business, and even pivoting, as being what created a sustainably strong, relevant business. They sold to a well-known magazine and that magazine is generated over $80 million per year from that acquisition.

The business he was leading during the talk, OpenSky, was wildly successful in growing its registered members to almost 3 million by 2013 (from a start in 2009). Caplan will say that OpenSky opened the internet and the globe for small business. OpenSky provided software and data, and connecting consumers to the business’ products and services that well-known people (like Martha Stewart) love. [Update: OpenSky was acquired by Alibaba in 2017 and Caplan became Alibaba’s President of North America and Europe]


Next, in Alignment Series #3, I’ll get to the execution part of this and answer, “How do you re-align people when strategy must change in a way that changes their daily work?”

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