The Evolution of Leadership Training

coaching employees Learning & Development Talent

The leadership development and coaching industries are undergoing a major transformation due to the dramatic shifts in remote workforce policies in response to COVID-19.


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With many companies canceling events and tech employers like Shopify, Twitter, Square, and Facebook enacting permanent work-from-home policies, it appears that technology and knowledge workers could be waiting a long time to return to the office. This shift will permanently change the way leadership coaching and training are delivered.

While working from home has increased the demand for leadership guidance and coaching, the traditional methods of delivering these services have been shut down.

Facing Leadership Training Challenges in the New Normal

Companies are unable to bring speakers into the office for events or workshops, and they can’t send their employees to training seminars. Periodic “one and done” trainings and yearly seminars are often not effective because people struggle to retain the information and skills they learn without regular reinforcement. Companies that are having employees work from home permanently will find it even more challenging to train and coach them.

While one-on-one human coaching can be done remotely via videoconferencing, it’s often too expensive and time-consuming to be a realistic option at scale for most companies. These videoconferencing sessions also take up valuable time in days already packed with back-to-back video calls (not to mention the energy-draining “Zoom fatigue” from too many video calls). And we already know that the #1 reason employees don’t engage in workplace learning is because they don’t have the time.

Putting an additional burden on managers who are already stressed out is not likely a recipe for success. The reality is leadership training needs to evolve. The best types of coaching include regular and consistent “touches.” Unfortunately, most organizations can’t afford that approach. But digital coaching platforms could offer a possible solution.

New Technologies Help Solve Problems and Empower Leaders

These platforms (more akin to people analytics technology) have the ability to provide all people leaders (not just executives) with cost-effective coaching at a global scale. They take in data from HR tools’ feedback platforms and digital communications like e-mails, instant messages (such as Microsoft Teams and Slack for Business), and calendar meeting invites and use them to find patterns and trends to empower employees.

Some platforms even use artificial intelligence and machine learning engines to measure users’ digital behaviors, like how often they ask their team members for input and how many messages they send after hours. This kind of analysis can offer valuable insights, like what types of behaviors tend to correlate with more high-performing employees and how managers’ communications with their teams change while working from home.

These platforms also use this data to provide real-time analysis and feedback to managers to help them become more self-aware and improve their leadership skills. This feedback is delivered in a format that’s accessible, private (completely opt-in based), and affordable and that requires zero input from the user to get started (because it’s all based on analyzing existing digital data).

By providing feedback in the flow of work (using Slack bots or e-mails, for example), these tools reinforce lessons repeatedly over a long period of time to produce actual changes in behavior and improved self-awareness.

Perhaps most importantly from a cost-benefit perspective, digital coaching platforms cost a fraction per user of what in-person training does and can scale up easily to support everyone who needs it. Now, multinational corporations with global teams don’t need to pick and choose which managers to support. These platforms allow them to do more with less and create change across all levels of the organization.

In the short term, digital coaching platforms present an amazing opportunity for organizations to offer leaders and managers powerful tools for empowerment and support during this health crisis.

While the U.S. economy will eventually recover and many workers stuck at home will return to the office (although possibly for fewer days per week than before), this shift toward digital training and coaching platforms won’t stop. These platforms provide extremely effective coaching that fits into existing workflows. Their relatively low cost and scalability democratizes leadership development and training in a way that in-person coaching will always struggle to achieve. It’s the next step in the evolution of leadership training.

Joseph Freed is the CEO and cofounder of Cultivate, an artificial intelligence-powered platform for leadership development and employee experience. Freed has led several start-ups focused on online learning and HR technology and lectures at UC Berkeley Extension. Cultivate has raised $10 million in funding to develop future-of-work technology. Follow Freed on Twitter, @josephfreed79.

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