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Boosting Learner Engagement for Data Upskilling Programs: A Comprehensive Guide

Discover how to boost learner engagement in data upskilling programs with actionable strategies from the 2023 State of Data Literacy Report.
Apr 2023  · 5 min read

As the world becomes more data-driven, the need for data-upskilling programs is becoming increasingly important for businesses. Ensuring your workforce is engaged and committed to these programs is crucial for their success. In this blog post, we'll use findings from our State of Data Literacy Report 2023 to explore various strategies to drive learner engagement and overcome common challenges in implementing data upskilling initiatives. 

data literacy framework

Overcoming Cultural and Employee Resistance

One of the major challenges in implementing data upskilling programs is overcoming cultural and employee resistance. In fact, in our State of Data Literacy 2023 report, 27% of leaders engaged in data upskilling cited employee resistance as their biggest challenge to success. To address this issue, thinking like a marketer and focusing on creating buy-in from your workforce are essential. 

Think Like a Marketer

Arguably, one of the most important elements of building engagement for data upskilling programs is evangelizing the program throughout the broader population. Leaders should consistently articulate the value of picking up data skills. 

The value shouldn’t be constrained to how data upskilling can benefit the organization’s bottom-line metrics but also how developing data skills can enable better career outcomes for individuals. In many ways, this necessitates leaders engaged in upskilling to think like marketers.

One common marketing tactic to undertake is by developing your organization's data personas is key to articulating and tailoring this messaging. 

Our data personas were really important for helping us create demand amongst colleagues. It helped us really understand what learning they needed, and we could justify why we've given them some learning content over others based on their persona and their role. It also helped us in our communications because it helped us personalize our messaging and our approach. Our persona work helped us answer “What's in it for me,” because I guarantee you that's all people really care about. How is it going to help them be smarter, quicker, better, and more productive at their job? Part of the persona work really helped bring that to life for people.

Emily HaywardData & Digital Change Manager at CBRE

In a nutshell, data personas are archetypes that represent different individuals within your organization and their relationship with data. In the quote above, Emily explains the importance of data personas in evangelizing learning programs. 

Data personas help program managers personalize their messaging and approach, making it easier for learners to answer the question, "What's in it for me?" This way, they can understand how data upskilling will help them be smarter, quicker, better, and more productive at their job.

The data science academy is one of the most popular programs at New York Life, and that supports our branding efforts. Whenever the data team works on data projects,  we actually create videos that will have people from our team and partners speak, and it's like a three-four minute video, easy to digest and be consumed by anybody. And in fact, we use these videos in our executive officer training.

Glenn HoffmannChief Data & Analytics Officer at New York Life Insurance

Another is by creating excitement around data initiatives with engaging communication plans for each initiative. Glenn shares some ways New York Life evangelizes its learning program and data products in general. For example, they create short, easy-to-digest videos featuring team members and partners, which are then used in executive officer training.

Other Tactics to Evangelize Your Program

There are a variety of tactics you can adopt to evangelize your learning programs:

  • Link to your data literacy program in all your communications: This includes internal newsletters, email signatures, and other relevant documents. By making your program consistently visible, you increase the likelihood that employees will recognize its importance and consider participating.
  • Launch an internal podcast on the importance of upskilling: Develop a series of podcast episodes that discuss the value of data literacy and feature interviews with industry experts or successful learners from within your organization. This will raise awareness about the program and helps build a culture of continuous learning.
  • Create learner testimony videos from your pilot program: Showcase real-life success stories by having participants from your pilot program share their experiences in short video clips. Creating social proof allows potential learners to see the benefits and impact of the program on their peers.
  • Begin a learner-of-the-month program: Recognize and reward the top learners each month by featuring their achievements in internal communications or social media platforms. This approach can help motivate individual learners and encourage healthy competition and engagement.
  • Launch a lunch-and-learn initiative with data experts within your organization: Organize informal lunchtime sessions where data experts share insights and best practices with employees interested in upskilling. Such events help to build a community of learners and reinforce the importance of data literacy within the organization.

Making Data Human

A significant aspect of cultural and employee resistance to data upskilling initiatives stems from common misconceptions about why and how data is becoming a priority one agenda item.

Data science and its related fields, like machine learning and artificial intelligence, often create fear within the broader population of the organization. These fears are skills-related, where individuals are worried that their skill set may become obsolete, or automation-related, where they tend to believe that machine-learning-based solutions will automate large degrees of their job.

I think culturally, we have a fear of math. Numbers aren't necessarily where we feel the strongest in general. So workforces are naturally worried that their career won't be able to keep up with the coming data demands. And a large part of that is how we, learning and data leaders, choose to communicate. If we're not paying attention to whom we’re speaking to and jumping into a technical conversation with business audiences, that will just add to the fear of math.

Megan Brown, Ph.D.Director of the Global Center for Excellence for Advanced Analytics and Data Science at Starbucks

Megan explains how leaders can assuage data fear by paying attention to their communication style. Avoiding overly technical conversations with business audiences can help reduce the fear of math and make data more approachable.

Setting Expectations About Data Usage

Another crucial aspect is setting clear expectations about how data will be used in the data transformation program.

No one wants to feel belittled, and when you make data hard and inaccessible, that’s the first feeling folks get. Moreover, leaders shouldn’t use data to punish individuals. We need to use data to improve business processes, to keep teams accountable, but we need to ensure people feel confident surfacing data to discuss business outcomes.

Cindi HowsonChief Data Strategy Officer at ThoughtSpot

Cindi explains that while data should be used to hold teams and individuals accountable, it shouldn’t be used to punish individuals or disincentivize the use of data. Instead, data should improve business processes and foster a data-driven culture where people feel confident surfacing insights to discuss business outcomes.


Boosting learner engagement for data upskilling programs requires overcoming cultural and employee resistance, thinking like a marketer, and making data more human. By adopting various tactics to evangelize your program, addressing data-related fears, and setting clear expectations about data usage, you can create a thriving environment for your workforce to embrace data literacy and drive your organization's success in the data-driven era.

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