Why You Want to Instill a Culture of Learning in Startups

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People often ask why I chose to pursue a career in business after serving in the military. One of the reasons for my shift is that I wanted to forge direct, meaningful change in a small and agile organization. The startup environment, which is fast-paced and dynamic, became the perfect place to do that.

After starting Wing Assistant, it became apparent that training is vital not only to our own organization but also to all assistants serving our clients (of which many are young startups, too). Based on this vast experience, I want to share my insights through this article for other entrepreneurs to leverage.

Training in a startup: How is it special?

In early-stage startups, employees often learn on the job. They solve problems on their own and come up with initiatives to meet business goals. This differs from the training that corporate workers often get when they first join an organization, which is typically more structured.

Startups are also more likely to leverage remote work. Having teammates in different time zones or regions could impact collaboration and communication. These realities present unique challenges to entrepreneurs tasked with continuous learning processes.

Related: 4 Great Things That Happened When We Went Remote

Shifting paradigms: From training to learning

Modern organizations must embrace a paradigm shift. They must cultivate a culture of learning. Traditional onboarding focuses on skill acquisition through standardized sessions. These sessions may help a new employee grasp the basics but have a limited impact.

Our rapidly evolving world necessitates an openness to change. Focusing on what one can learn encourages constant personal and professional development. It keeps employees balanced—successes are signposts of doing the right thing, while failures are learning opportunities.

Learning by doing helps employees focus on addressing the company’s immediate needs. They must quickly acquire knowledge and skills that help them manage emerging issues, new technologies and changing customer needs.

Related: Managing Your Customers Through Change

How to build a learning culture

Building a team that puts a premium on learning doesn’t happen overnight. For one, leadership support is crucial. Leaders must set the tone by actively supporting and promoting learning over training. A plan is essential — not a module for strict, by-the-book implementation, but a list of milestones trainees should meet. Create inclusive and supportive learning environments where new employees feel comfortable taking risks, sharing knowledge and experimenting.

Like a cross-functional team, establishing a learning community is one way to develop a supportive space. Within a team like this, peer-to-peer learning isn’t forced. It’s an organic offshoot of working together.

Designing engaging learning opportunities

Changing training methods to suit today’s changing work environments involves leveraging technology and tools to engage workers remotely. Even if you have a hybrid or in-office work setup, these tools will enable your new team members to keep learning.

For instance, video conferencing and multimedia tools encourage engagement with educational content. Video-on-demand tutorials can also enable employees to pick up skills as needed and return to lessons for individual refresher training. Consider allowing employees to learn remotely to incentivize them to engage in educational activities.

These adaptations allow companies to create learning experiences that adequately support skill development and employee growth.

Agile methodologies

In a startup, rapid prototyping is common. Managers can apply this principle to employee education. Continuously improving training materials by testing and iterating based on employee feedback will refine content and delivery methods.

In rapid prototyping, having regular feedback loops in the learning process is vital. Feedback, whether through surveys, focus groups or 1:1’s, enables managers to gather insights and make timely adjustments. Implementing feedback keeps learning content adequate and relevant.

Lean teams or startups can also leverage Scrum, Kanban or other agile project management frameworks for managing and improving the learning environment. Frameworks like these make the learning process efficient and promote accountability for new employees, thus, ensuring teams stay on track.

Using these frameworks also generates data. For example, managers can match their milestones to time stamps when new employees use Kanban to progress through a learning plan. They will know exactly when their new team members complete certain tasks. Managers can use learning analytics to track everything from engagement to knowledge retention. This means data-driven, purposeful changes can be made to learning plans.

Addressing the challenges of remote learning

While having a remote-focused learning environment has its advantages, it also has drawbacks. For one, connectivity and technology challenges may disrupt remote learning. Overcome these hurdles by ensuring that employees have a stable internet connection. Recommend backup options for remote employees, like mobile hotspots. You may even consider providing access to workspaces such as WeWork. Addressing remote learning challenges and providing support ensures all employees’ learning experience is as smooth as possible.

Encourage continuous learning among employees

Finally, learning shouldn’t stop when the onboarding period does. Organizations can solidify their culture of learning by encouraging employees to seek out new knowledge and skills actively. Empowering self-directed learning allows employees to shape their roles (and, by extension, their careers) to suit their natural talents.

Rewarding employees for reaching milestones also bolsters this culture. Celebrating team members’ commitment to learning by spotlighting their achievements further motivates continuous development. Simple examples of fostering this are nicely designed learning certificates or LinkedIn certifications.


Effective training and development no longer rely on how well a new employee scores on a standardized assessment. Today, companies should embrace agile principles in delivering educational content. Create flexible learning plans, implement feedback loops, use agile project management tools and empower self-directed, on-demand instruction.

Doing these things ensures new employees take ownership of their learning and will be ready to take on whatever challenges come their way.

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