Why you should upskill your internal staff for greater success

As job descriptions evolve rapidly in response to the ever-changing requirements of our modern workplaces, the scramble for talent feels like an unwinnable race. But rather than looking for external talent to join the business, exploring the potential of the people already in your organization is a powerful opportunity.

Not only could internal upskilling save you the cost of external hiring, it also means benefiting from the loyalty and trust of your existing people.

Nowhere is this more obvious than in the talent of the members in your administrative team, who are often keen to progress – if given the opportunity.

Untapped potential

Start by looking at executive assistants (EAs) and senior administrative staff as individuals with a deeply embedded understanding of company culture and organizational dynamics. Not only are they immensely loyal, they’ve also already established trust with people across every level of the organization. 

Despite this, many leaders still overlook and undervalue EAs and administrative staff in development discussions, causing a miscommunication gap in career progression. Leaders fail to see the untapped potential – and those administrators who are eager to progress don’t want to ask about other roles, for fear it might jeopardize their current position.

So how can we make these opportunities more obvious for all involved?

When you have catch-up meetings with your assistant one-on-one, don’t just focus on their day-to-day tasks. Discuss their ambitions and potential interest in career growth as an agenda item, as well. Transparent communication about the company’s direction and the EA’s role in it can foster a sense of purpose and belonging. 

And don’t overlook these people for cross-departmental projects, development opportunities or leadership programs, as these are an obvious stepping stone to upskilling them into a more strategic role that benefits the business and fulfills their ambitions.

Encourage exploration

Create a culture where it’s safe to explore and even fail. Leaders should encourage EAs to step out of their comfort zones, attend client meetings and take on projects that stretch their capabilities.

Small opportunities to explore and experiment, safe in the knowledge that there is no risk if they don’t succeed, might uncover a clear direction or a valuable strategic skill that makes their path to progression even clearer.

These small explorations and experiments are often the secret to the success of some of the world’s most profitable companies – for example Amazon, where Jeff Bezos encouraged this kind of small-scale experimentation to get clarity on which ideas were worth progressing.

Organizations that successfully upskill their administrative talent often see remarkable outcomes. For instance, by encouraging EAs and administrators to take part in graduate programs or to rotate through various departments to broaden their experience and knowledge, your organization will ultimately benefit by fostering loyalty and rapidly advancing the strategic value of these employees.

This is the kind of thing many startups do well, as it’s natural within a new or scaling business for people to wear many hats. But the more established the business, the more rigid the roles. It takes a proactive approach to create these opportunities and help people see the wider opportunities that might be available to them.

Recognizing the value of involving EAs in the organization’s core operations leads to quicker promotions and more dynamic career paths. For example, an EA in a startup might transition to an operations manager role within a year, leveraging their deep understanding of the business and its network.

Return on investment versus risk

In my role as a coach to ambitious EAs, I’ve worked with administrators in large companies who’ve been able to express their ambitions and have accelerated their career progression as a result. If leaders can encourage transparency around what those ambitions are and how the business could support them, they’re more likely to reduce the risk of losing talented people who feel they have nowhere to grow.

And this risk comes with a significant cost.

Data from the Work Institute estimates that each lost employee costs the company, on average, one-third of their annual salary. Hiring externally involves recruitment fees and training costs, not to mention the time taken for a new hire to acclimate and become fully productive. The cost of hiring employees is also on the rise, more than doubling between 2020 and 2021 from approximately US$7,000 to US$16,000​​ according to research from the Australian HR Institute.

Upskilling internal staff is not merely a cost-saving measure, but a strategic investment in the future of the organization.

By recognizing and nurturing the potential within their administrative teams, leaders can create a more loyal, skilled and motivated workforce. The key is to foster an environment where employees feel valued and supported in their career aspirations, ensuring that the organization can meet the evolving demands of the modern workplace while retaining its most dedicated talent.

Not every EA or administrative person is going to have lofty career aspirations, but many are ready for a new challenge, and you might be surprised at the potential of the talent already in your workplace.