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Why Leadership Development Has to Happen on the Job

Melissa Daimler

March 16, 2016

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.

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. Despite being in different

buildings, different time zones, and even different countries, everyone always

knew the project status, which decisions were open, and when we d reached

milestones. That s an accomplishment of contextual leadership, as well as smart

use of technology tools.

To help develop a workforce s contextual leadership skills, those of us

responsible for training and developing our firms next leaders have to think a

little differently about learning. Organizational learning has to become less

about the kind of learning done in a training session or online tutorial and

more about continuous learning on the job. That means creating a work

environment that supports and encourages learning, one that s less about

individuals learning new skills on their own, and more about using their

environment to learn and learning from one another.

Done right, this kind of learning teaches employees new skills and results in

knowledge being shared across the company. Perhaps even more importantly, it

also satisfies the deep desire expressed by so many employees to be part of

something bigger. In the past, people I managed preferred to focus their time

and energy on work they could take sole ownership of; now people emphasize

their desire to work on projects that they can see will make a significant

difference for their own growth and for the company s.

Once the context shifted at our summit, we could have continued with the agenda

as planned, but we instead chose to address the departures and all the issues

they raised. The conversations that ensued were more candid than any I d

experienced in my career. We directly addressed the challenges of the new

situation, engaging in healthy debate that balanced, as one leader put it,

optimism with sober reality. At the end of the two days, we were aligned

around a clear set of priorities and were inspired about our future. We were

also better prepared to provide context to our teams about the challenges and

opportunities ahead and to inspire them in turn.

Technology tools are evolving, and the way we work and learn must also evolve.

People s desire for more inclusion and agency and the increasingly rapid

evolution of the business landscape both require that we find ways to create

more collaborative teams, facilitate richer, more continuous learning, and

involve all employees in their quest to adapt and seize the abundant

opportunities our fast-changing world offers.

Melissa Daimler currently heads the Global Learning & Organizational

Development team @Twitter, integrating interests in learning, coaching, and

organizational dynamics into a career. Follow Melissa @mdaimler