How Square set L&D docus areas in a time of ambiguity with Oliver Liao

Estimated reading time: 4 minutes


Every month, PlusPlus gathers together leaders working at the intersection of technical training and learning and development for the TechKnowCon Roundtable to explore topics top of mind for the industry.

Square helps millions of sellers to run their businesses and was one of the two organizations to present their ideas at the July 2020 discussion. Here, Oliver Liao, learning and development lead at Square, explains how his team found their focus during a challenging year.

A focus on now

Oliver begins by explaining that for organizations to thrive, they need to focus on the moment and accept that we are all in a transitional phase.

“We now live between two boundaries. Where we were and where we are heading. Yet, we are all stuck in the middle right now. It’s all of our common grounds.”

“What’s great about being in the middle is that we know these two truths. Some organizations will go back to business as usual pre-COVID-19, back to the offices. Others will not, instead they will find a new normal, such as having fully or partially distributed teams.”

Developing the Square approach

When COVID-19 hit at the beginning of the year, it was critical for Oliver and his team to learn and hear from organization leaders at Square and HR business partners to determine their learning and development focus areas. The team also looked closely at people analytics and industry news.

Four areas to focus for L&D at Square

After gathering up-to-date research and information, Oliver and his team decided to focus on four key areas to develop a new learning and development strategy:

1. The distributed workforce

To support the distributed workforce at Square, Oliver explains that onboarding at the company is now 100% virtual.

His team will also add ten team effectiveness exercises for those in leadership to have at their disposal for their remote teams. These will be made available to everybody in the organization.

“These exercises are inspired by the Tuckman phases of team development,” Oliver explains. The framework serves to enhance a team’s effectiveness by increasing their commitment to reflection and on-going evaluation.

Oliver and his team are also focusing on how they navigate career development. They are exploring methodologies to focus on helping employees develop their values. Oliver explains that this is particularly important when people’s values may have shifted as they transition into a remote workforce.

2. Talent management

“For anybody who has worked in organizational development, talent management is a critical area,” Oliver says.

“In light of current events, we are reassessing how to approach, document, and assess performance conversations.

“We are also providing guidance around navigating difficult conversations, and setting a cadence for accountability.”

3. Leadership

“We recently launched a coaching offering for our managers focused on the three levels of listening, powerful questioning, and accountability,” Oliver explains.

Oliver and his team at Square worked with BetterUp on this initiative, an organization helping people, teams, and companies thrive through change.

Oliver adds that his team launched an offering focused on embracing the five levels of distributed teams, a concept developed by Matt Mullenweg, founding developer of WordPress and Automattic.

“Matt’s work inspired us,” Oliver says. “He explains how to create the right environment and what makes distributed teams effective.”

“We also continue to partner with our diversity and inclusion team and communicate within our internal channels.

“Following the recent events of systemic racism and police brutality, we assessed and realized the value in talking about events together.”

4. Learning experiences

“Similar to our onboarding processes, we also made all of our learning experiences virtual. Our current goal is to convert a two-day in-person leadership program for managers into two virtual half days,” says Oliver.

“We’re also looking at how we can make our existing and future offerings shorter.”

Additionally, Oliver’s team is focused on developing communal and peer learning.

“In the spirit of experimenting and learning, we recently launched our first learning and development speaker series focusing on leadership. Everyone is invited, it’s virtual, and it’s an unscripted dialogue with a high-profile leader in our organization.”

“In addition, we have launched a ‘train the trainer’ program, which will act as a foundational structure for peer-to-peer learning in the future.”

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