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Developing From Within: Upskilling and The Great Resignation
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Developing From Within: Upskilling and The Great Resignation

At this point, The Great Resignation is almost a cliche. We’ve been notified time and time again–maybe one too many times–that people are leaving their jobs in droves, dissatisfied with their work and struggling with motivation in their careers. Similarly, it’s hardly a revolutionary idea that continuous learning in the workplace is a worthy pursuit and valuable investment for many companies. However, increasingly over the last few years, workplace learning, or upskilling, has been suggested as a strategy for overcoming many of the attrition and retention issues plaguing organizations. 

In a recent conversation with our founder and CEO, Kian, Shelley Osborne, Head of Learning at Modal and author of The Upskilling Imperative, offered insights and recommendations regarding how leaders can develop their organization from within–that is, how they can grow their organization by investing in its people rather than relying on hiring to fill skill gaps and acquire talent.

According to Shelley, “We have to realize that talent is human, that these are human beings, and it is really expensive and really inefficient to look for talent outside an organization.”

By supporting upskilling, leaders can help their people build rewarding careers within an organization, which will in turn assist the organization in retaining and developing talent instead of spending on unnecessary hiring.

The question we have to ask though, is: what does supporting upskilling look like? While it’s easy enough to understand the theoretical benefits of upskilling, how can leaders actually begin “developing from within”? Here are Shelley’s top three insights:

1. Be willing to reskill

It is relatively clear how upskilling will help your organization’s efficiency and, ultimately, its bottom line. As an organization’s people become more knowledgeable and skillful, they can complete more tasks and build solutions that are more creative, leading to improved outcomes for the organization as a whole.

However, Shelley is adamant that leaders should also embrace “reskilling”, allowing an individual to develop new sets of skills that will qualify them for a role that is different from the one they hold. There is a tendency among leaders to “pigeonhole” their people by keeping them on a career path that reflects the skills on their resume when they were hired. But an individual’s curiosities, self-knowledge, and aspirations develop over time, so embracing internal mobility and career transformation is key. Organizations that want to retain their people need to be willing to let their people change–and provide support for that change.

2: Have career conversations with your people…often

Internal mobility counteracts attrition and supports retention among an organization’s people, but it depends entirely upon a consistent line of communication between leadership and employees. Shelley recommends beginning the conversation about upskilling and reskilling during an initial performance review six months after an employee’s hire, and then to continue these conversations on a biannual basis.

Leaders should seek to identify three major things in these career conversations:
Peaks: When an individual felt proud and successful in their role
Valleys: When an individual felt like their work was not meaningful
Values: What an individual is working for (for example, financial reward, collaboration, purpose, personal growth, etc.)

With the knowledge gained from these conversations, leaders can guide individuals into roles that will allow them to enjoy a long, satisfying, and productive career in an organization.

3. Talk about the learning you are doing

A final strategy for “developing from within” is to create a culture of learning by making learning public. Strange as it may seem, learning can be a source of shame, often felt to be something more properly confessed than encouraged. From this perspective, learning means little more than acknowledging a lack of skill.

To battle this perfectionistic perspective, Shelley encourages leaders to be honest with their team about what they have been learning and to provide regular opportunities for employees to do the same. For Shelley, this has meant instituting “Wins and Learnings” discussions during team meetings, where each member reports something that has gone well and something learned over the last week. Strong leaders should also participate, admitting where they need and desire to grow in order that the rest of their team can feel comfortable admitting the same. 

As Shelley says, “When you think you have to be perfect, you don’t give yourself space to grow and develop.” “Developing from within” requires an openness to change–embracing the flexibility of internal mobility, instability of career changes, and vulnerability of honest conversation. By embracing these (sometimes uncomfortable) contingencies, a leader puts the best interest of the organization and its people first.

Key Quotes 

  • “A culture of learning is the very first thing [data leaders should establish in their organization]. You need to create this expectation and perspective that people are learners first…everyone has to be learning all the time.”
  • “One of the things I like to do is battle perfectionism because I think that can be a real learning killer. When you think you have to be perfect, you don’t give yourself space to grow and develop.”
  • “When we’re dealing with a talent market like we are, where we have massive potentials for attrition, and we have important retention issues, we need to get a lot better much faster at identifying [the skills] we have, we don’t need, and we need to develop.”


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