Why Leadership Development Has to Happen on the Job

At a recent leadership summit we held at Twitter with 100 of our top global leaders, our agenda was to talk about our strategic direction and get aligned as a leadership team. Then, the day before the summit, news leaked of several executive departures. The context of our discussions had shifted.

You’ve surely experienced such context shifts as a leader yourself. Over the last 10 years we’ve seen the command-and-control style of leadership give way to a flatter, more collaborative approach. I’m now seeing another shift happening — to more and more discussion of contextual leadership. As Tony Mayo, director of the Leadership Initiative at Harvard Business School, has put it, “Success in the 21st century will require leaders to pay attention to the evolving context” a business is operating in. Contextual leaders facilitate adapting to change by helping their people understand the nature of new challenges and opportunities and how to address them in the moment.

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Why are we hearing more and more about the importance of “context” now? One reason is that the context around us seems to be shifting more rapidly, due in part to major technological shifts. This means more of us are operating in more contexts, more of the time. To take a simple example, when you’re in touch with your colleagues on Slack or Google Hangouts outside of normal work hours, you’re operating in multiple contexts — “work” and “personal” — at once. At work alone, though, contexts have proliferated and shifted as well. For instance, more of us work with more people, as technology has opened up collaboration to more people, departments, and business units. More of us work on cross-functional teams or across time zones. A 2014 research study by CEB showed that 60% of people coordinate with at least 10 people daily in their work.

This means that leaders have to be aware of all these contexts — and more — as they try to move projects forward. For example, at Twitter we wanted to transform our feedback and talent management processes, and we wanted to involve cross-functional teams from all across the company, including designers, engineers, and data scientists.;

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