7 Innovative Leadership Development Activities From Udemy, HubSpot, and More

When you think of the leaders you admire, what kinds of qualities do they possess? Inspirational, hard working, and committed are probably just a few that come to mind. Yet, becoming a great leader doesn’t happen overnight — it takes feedback, mentorship, and effective training.

While most people agree that  professional development is important, many companies aren’t investing in these programs. In Inc.’s article, Much Potential, So Little Investment: Why Great Talent Languishes, Adam Vaccaro says, “Executives overwhelmingly agree that talent can make or break a company; yet only a minority actually say they invest in leadership development programs.” This disconnect might be because “the ROI is not clear, so companies don’t invest much effort or money into them.”

To get the greatest ROI from these activities, we talked to experts from Udemy, Hubspot, and even Peerspace’s founder and CEO to learn about what kinds of programs they implement to create successful leaders in the workplace. Forget the trust fall and awkward icebreakers and try these leadership activities that actually work.   

1. Implement leadership shadowing programs

On HubSpot’s Marketing Team, we’ve rolled out leader shadowing as part of our Emerging Leaders program. Each program participant shadows a leader outside of the marketing business to observe their day-to-day. Through this activity, the group learns to identify different leadership behaviors and understand their impact on the people around them.
Rebecca Corliss
Director of Marketing | HubSpot

2. Create a curriculum that let employees lead teaching sessions  

Giving employees teaching roles makes learning part of the way employees work together rather than something HR is making them do. By offering a wider curriculum, we’re able to meet the wider range of their needs and interests. I think that makes people feel like they can be their whole self at work, whether we’re looking at photography or mountain climbing or mindfulness. (Source: Fast Company
Karen May
Vice President, People Development | Google

3. Hold quarterly offsites that foster interdisciplinary development

One of our core employee values is that “everyone is a manager.” We look for team members that are self starters and strive to take ownership of processes and tasks. We hold weekly team meetings and quarterly offsites with the goal of fostering cross-collaboration and interdisciplinary development. During these meetings, team members have the opportunity to lead sessions and present to a broader group. Overall, I place an emphasis on each team member having an entrepreneurial mentality and to lead by example.
Rony Chammas
CEO and Founder | Peerspace

4. Organize manager discussion groups and keep groups small  

Artsy organizes regular “Manager Discussion Groups” themed around different people management issues (ie, “Facilitating Effective One on Ones” or “Inspiring & Motivating Your Team”). All people managers are invited but we keep the groups small (8-15 people) and ask people to do some prep work in advance. This leads to meaningful discussion and peer learning and helps us align our values around around leadership expectations.
Elisa Colombani
Director of People | Artsy

5. Schedule follow-up sessions to hold people accountable  

As a decentralized organization, it’s essential that our directors and managers are able to establish cross-functional connections with their peers. We hold group leadership training sessions with these team members, and schedule follow-up lunches for each cohort to meet monthly. We ask them to develop action plans resulting from their training and discuss not only which leadership skills they’re working on, but also how and when they’re implementing them. The follow-up sessions ensure accountability for applying best practices to day-to-day work at Udemy.
Lisa Haugh
VP of People and General Counsel | Udemy

6. Ask for feedback to build trust    

I recommend that you ask people on a regular basis how your feedback is landing for them. You’ll learn whether people think you’re pulling your punches or punching too hard, and that will allow you to adjust. Not only will you get better at feedback, but asking for this gauge and showing you appreciate it builds trust and makes you a better leader.
Kim Scott
Co-founder | Candor Inc.

6. Role-play to deepen leadership styles 

I often use the DiSC Personal Profile to help people explore group dynamics and the different ways people approach collaboration and problem solving. One of the activities in the session is to sell a randomly chosen item to someone who has a style very different than your own. It helps people recognize that “different” does not mean “wrong.” It also puts them on a path to develop a wider range of leadership styles that helps them be effective with a diverse set of people. 
Chris Holmberg

Need a creative space for your leadership building activities? Explore these venues in San Francisco, New York City, Los Angeles, Chicago, Seattle, or Austin.