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What else does an organization need to do to upskill employees successfully?

What else does an organization need to do to upskill employees successfully?

To make upskilling efforts successful, companies should establish measurement infrastructure, make programs inclusive and set up career paths for employees who take advantage of the programs, members of the Braintrust say.

Good afternoon! As companies look to add new technical skills up and down the org chart, programs and services to teach employees while they're on the job have grown significantly. In this week's Braintrust, we asked experts to let us in on what successful companies do before they start upskilling their staffs to determine the best ways to prepare an organization. Questions or comments? Send us a note at

Cathy Gao

Partner at Sapphire Ventures

Twitter announced this week that Parag Agrawal is taking over as CEO. Parag started at Twitter 10 years ago as an engineer and worked his way up to the top seat. While this kind of meteoric rise is uncommon, it is an excellent example of how an organization can provide employees with meaningful upskilling and reskilling opportunities.

As an investor who funds the next generation of tech companies driving forward the future of work, I spend a lot of time talking with innovative organizations actively seeking to implement best practices and adopt technologies that institutionalize up/reskilling. Three common themes I see across successful programs are personalization, microlearning and inclusion.

  • Personalization. While traditional learning solutions are often one-size-fits-all and corporate-centric, newer technologies deliver personalized content to the right person at the right time. For example, modern learning experience platforms (LXP) recommend curated content to individuals based on its algorithm and social recommendations.
  • Microlearning. Often the biggest enemy to upskilling and reskilling programs is time — employees are often working full-time jobs without time dedicated to learning. Companies that leverage engaging and bite-sized content that can be delivered on any device and in various media formats allow employees to learn when and how they want.
  • Inclusion. Up/reskilling and inclusion go hand-in-hand. Providing broad access to learning opportunities is fundamental to successful programs. Pairing self-guided learning with mentorship and community amplifies and enhances both retention and efficacy. Effective programs help close the skills gap and improve diversity and inclusion.

Aaron Skonnard

CEO and Co-Founder at Pluralsight

Pluralsight’s most successful customers understand that upskilling programs that have a meaningful impact on the business and its people require a visible investment and commitment from the top down and an organizational culture that embraces skill development.

Successful upskilling programs are customized and designed around the organization’s specific needs. This is especially true when developing technology skills. Skill development programs must mirror technology investments made at the organizational level to ensure ROI. To make this happen, alignment between HR, L&D and technology leaders is especially important.

Strong skills development programs need curriculum that can be customized in terms of scope, breadth, depth and delivery. Some teams require a broad curriculum that helps individuals understand technology at a high level. Other highly specialized teams need content that can go deep into the intricacies of the topic. Different learning modalities must be considered so organizations can avoid a one-size-fits-all approach by using a combination of on-demand video content, customized instructor-led training and specialized hands-on learning opportunities that align to business objectives.

And measurement is critical. Traditionally, metrics such as usage or course completion have been used as indicators of success. However, a more accurate picture of success emerges when programs consider metrics such as rate of product development, accelerating onboarding of new team members or ability to align team skill sets with new technology investments.

The companies that win in the digital era will be those that see their skills inventory as a competitive advantage and make skill development a priority.

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Ken Eisner

Director, Business Development, Learning Systems at Amazon

Is your organization trying to solve a near-term need such as getting software developers quickly up-to-speed, or are you trying to create long-term career paths for your employees? While both use cases are vital, there are likely different “customers” and different problems to solve in each scenario, and the learning solution needs to support employee knowledge and capability development to that given goal.

Too often, learning providers fail to define the customer problem and the knowledge and capabilities required to address that problem. Instead, they focus on compliance, where learners click toward the “I’ve completed” page without any ability for the learner or employer to know whether the initiative was successful, and leverage corporate training solutions that perpetuate this ineffective and inefficient state.

Organizations need to adopt an infrastructure for learning, where knowledge and capability development is explicit, clearly linked to the business or personal goal and measured to determine effectiveness.

In line with Gallup’s survey that shows over half of U.S. workers surveyed were “extremely” or “very” interested in participating in an upskilling program, applications have surged to Amazon’s upskilling programs, reflecting the interest in bolstering skills and future-proofing careers. We’ve listened to our employees and have responded with a $1.2 billion Upskilling 2025 pledge, to meet our employees where they’re at and provide pathways to in-demand, higher-paying jobs. As the fastest job creator in the U.S., we believe that investing in employee skill-building will have a positive ripple effect for hundreds of families across the country.

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Suneet Dua

Chief Growth Officer at PwC US

Since people and technology are crucial to a business’ success, it’s important that businesses bring those two powerful forces together to unlock a future that is human-led and tech-powered. At PwC, we have seen firsthand that putting the right technology into the hands of our people and empowering them to leverage that tech changes how work gets done — creating the perfect condition for innovation and improved business outcomes.

This is especially critical today, with increasing competition for highly skilled candidates. Companies that don’t plan to digitally upskill their workforce will struggle to attract and retain top talent, and to deliver the increasingly complex work customers require. Investing in future-forward skills not only helps boost talent acquisition and recruiting efforts, it also contributes to greater social stability. When successfully implemented, upskilling initiatives have the potential to help create 5.3 million net-new jobs globally by 2030. To make this possible, access to learning will be key. By making microlearning and credentialing experiences available to all staff, employers can level the playing field by providing equitable access to learning opportunities.

In addition, when businesses provide an environment where employees feel valued and offer upskilling opportunities and resources for everyone, people are empowered to invest in themselves. Upskilling contributes to economic sustainability by keeping people employable and creating a culture of infinite learning that fosters digital citizenship and inclusivity. Those who need digital skills the most are the least likely to get them: If this trend continues, we risk allowing the digital divide to widen.

Learn more.

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Kathy Kay

SVP and CIO at Principal Financial Group

For upskilling to be successful, it’s important to understand and address the challenges that might derail efforts. For example, because Principal is a global company with four business units, multiple product lines and distinct customer audiences, we recognized the need to break down our silos and work together to drive cloud adoption using consistent language, reusable components and success metrics. We leveraged our internal cloud community and partnered with AWS Training & Certification services to create a centralized training approach to help our teams develop the skills needed to innovate.

Experiential and hands-on learning opportunities and creating a culture of continuous learning are critical to upskill employees successfully, too. For example, we’ve hosted weekly demos and office hours, developed inner source models and rolled out a certification process that allows employees to study and test on their own timeline. We hosted over 20 lunch-and-learns in seven months and used immersion days, sandbox accounts and hackathons to accelerate learning and provide practical skill application.

Finally, it's important to create a culture that includes both the expectation of learning being part of the job and embraces experimentation. People need the time to learn. Then, they need to feel safe experimenting with what they’ve learned. When trying something doesn’t work out, we benefit because we’ve learned something new in the process.

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Tom Clancy

SVP of Learning at UiPath

In the age of the Great Resignation, it’s critical that companies provide broad-based, continual upskilling and reskilling programs. Our survey of 4,500 global office workers found that 73% of respondents said they’d be more willing to work at a company that offers training and upskilling opportunities, and 76% feel that upskilling offers job security.

Democratizing access to technology is key to ensuring widespread enterprise adoption and understanding for both business and technical users. As software robots take on lower-value tasks and roles and higher-value jobs emerge to take their place, HR departments need to identify the skills of the future of work and embark on a massive training effort. This includes training to work with tools like AI and automation and building soft skills like leadership, critical thinking and adaptability. It’s important for the C-suite to make strong investments in digital upskilling for their employees to foster career development and employee satisfaction, which creates a competitive advantage for their company.

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Leah Belsky

Chief Enterprise Officer at Coursera

The accelerated pace of automation and increased demand for new digital skills is creating a growing sense of urgency within enterprises to upskill employees and ensure they are prepared for jobs of the future. However, building a high-quality skills development program from scratch and effectively deploying it across an organization is challenging.

To ensure success, enterprises must start the process by carefully mapping their business goals to skills objectives. It is critical to identify what you want to achieve as a company and what skills are needed at the most macro level to get there. Organizations must then take an objective look at their employee base to inventory existing capabilities. The goal at this stage is to gain a deeper understanding of where your teams are today relative to the skill proficiency goals you have identified. From there, companies will need to assign specific job roles to the specific skill objectives.

Lastly, it is important for organizations to focus on establishing programs that can provide job-relevant skills training for employees at all levels throughout the company. The most successful companies deploy learning solutions with the depth and breadth required to upskill existing experts, and to develop literacy for frontline, entry-level talent — all while measuring their progress along the way.

By taking a methodical approach to developing learning solutions, and providing clear development paths for employees at all levels, enterprises can ensure their teams have the high-demand skills needed to succeed in the digital economy.

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See who's who in the Protocol Braintrust and browse every previous edition by category here (Updated Dec. 2, 2021).
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