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17 Creative Ways to Bring Company Leaders Together for Productive Conversation

Scott Gerber
Scott Gerber

Seventeen members of YEC share effective tactics for gathering together leaders that lead to effective strategizing and team building.

For a business to thrive, its leaders need to be able to communicate, plan and execute effectively. To do this, it's vital for leaders to gather together – whether in person or virtually – to discuss plans and exchange ideas. For most leaders, these meetings are a chance to have their say in how the business runs. And with companies these days looking at ways to pivot and take advantage of a new business environment, it's not strange to see companies branching out to find more creative ways to bring leaders together.

In the past, boardrooms or conference venues were the preferred meeting point for leaders. But as busy executives, it can be challenging to find a time that works for everyone. And even if you can get together, meetings that don't have a game plan may not always lead to the most productive conversation. Below, 17 members of YEC look at different creative ways business leaders can gather together for effective strategizing and conversation.

1. Plan a retreat somewhere interesting.

"Planning a retreat somewhere interesting gets the leadership out of the office and away from distractions so they can devote their focus to solving problems and enhancing the company. Booking the meeting toward the end of the week and giving people the option to have spouses or family join for a fun weekend after meetings are over is a great way to reward their hard work and boost morale." – Josh Awad, Flywheel Commerce

2. Do a virtual retreat via Zoom.

"Up until 2020, we would hold an annual retreat for the founders. Not only would this give us time to relax and bond, but we would also use time blocking to strategize for the next year. I found these sessions to be helpful and refreshing. If you're not able to do this because of Covid-19 restrictions, you could opt for a virtual retreat via Zoom." – Chris Christoff, MonsterInsights

3. Rent a beach house.

"'Purely business' planning meetings lack the spontaneity and vulnerability that catalyzes teams to take risks, think big and create new momentum. We rent a beach house each year, and everyone creates a personal 'vivid vision' for the next year. This helps our team see their purpose in our mission, and they find renewed passion for their work. The conversations afterward bring creative strategy for all of us." – Trivinia Barber, PriorityVA

4. Go camping with the team.

"Go camping, or have some other sort of outdoor retreat. What you'll find is that the great outdoors can be truly inspiring when it comes to having productive conversations. It's a totally different environment – it's exhilarating, and you can squeeze in some exercise and cool socializing." – Andrew Schrage, Money Crashers Personal Finance

5. Do an escape room.

"We usually do a team outing to an escape room. Currently, during the pandemic, we use virtual escape rooms. These games are perfect for team building (and fun) because everyone has to work together to win. By uniting in a non-business but fun forum, when you meet to tackle business problems you'll be able to use some of the same skills and alliances." – Matthew Capala, Alphametic

6. Take your team to the racetrack.

"Before the lockdown, I used to invite all my San Diego-based team members to a day at the Del Mar Racetrack. Although it's not the most ideal environment for strategizing, it's a great way for us to catch up and bring up any concerns with the company's operations and direction." – Bryce Welker, CPA Exam Guy

7. Go to a spa.

"We actually took our team to Glen Ivy to check out their hot springs. It was a fun bonding experience, and it allowed everyone to connect outside of the typical work environment and have conversations about life and goals, which inherently led to more enthusiasm and ideas when returning to the office. I think that sometimes stepping away from work mode with your team can be vital to growth." – Jennifer Buonantony, Press Pass LA and PPLA Social + PR

8. Host tech-free meetings.

"When leaders come together in person, host tech-free meetings. This means everyone leaves their cell phones and laptops outside the room. This opens everyone up to being fully present in the discussion and developing genuinely innovative ideas and strategies." – Matthew Podolsky, Florida Law Advisers PA

9. Organize quarterly 'issues and ideas' check-ins.

"We have an ‘'ssues and ideas' board that is full of ongoing opportunities to get our operations tighter and our products more polished. We review these together through quarterly check-ins. We talk about what's on our minds and what's been the recent wins and frustrations so we can all be in sync. Then we get to the board and see which of those items inspires us. It can get pretty fun." – Richard Fong, Ready Green

10. Set up networking events with breakout groups.

"Set up networking events for your top leaders through Zoom and then do breakout groups similar to a 'speed dating event, where top leaders get put into groups or one-on-one chats. They are then given topics of conversation and strategy to talk through. Then, for the last part of the event, the leaders will share their best ideas and takeaways with the group." – Diego Orjuela, Cables & Sensors

11. Include family in the activity.

"Pre-COVID-19, we used to bring our team together for working off-site. Spouses and kids were included. We'd have the entire trip planned out in advance, including nannies and workshops for kids and spouses. Being able to include the entire family brought us all closer, eliminated the stress of being away and gave our team the space we needed to focus while having fun." – Amber Anderson, Tote and Pears

12. Organize yearly hackathons.

"We enjoy having hackathons each year during our retreats. It's for the entire company, not just key leaders. It's a great mix of having fun while also getting creative and coming up with innovative new things we could be doing, no matter how 'out there' the ideas are. We break out into groups to develop ideas. After each group pitches their idea, we vote and decide which one to implement." – Dave Nevogt, Hubstaff

13. Hold brainwriting sessions.

"One strategy I've found that boosts creativity and collaboration between leaders is brainwriting. Before a leadership retreat or off-site, we each write down our strategic priorities and share our ideas for the company. Then, during our discussions, we seriously consider every idea. This way, our introverted leaders can more easily be heard, and we end up considering more diverse, unexpected solutions." – Diana Goodwin, MarketBox

14. Include a facilitator in your meeting.

"Have yearly council meetings with a facilitator who can help navigate the conversations, prompts and activities that way your meeting is constructive and organized. This is effective, because you can have a well-ordered meeting, which can lead to having more productive and strategizing conversations." – Riccardo Conte, Virtus Flow

15. Get together for storytelling.

"I love inviting the leads to tell a fantastic, imaginative story about where they see our company in five to 10 years. By pushing the end date far into the future, it encourages everyone to focus on outcomes rather than the individual steps that must be accomplished. The storytelling keeps them focused on the experience rather than the technical details. It's a lot of fun and yields powerful results!" – Carmine Silano, CheerSounds Music

16. Have monthly meetings for upper management.

"Company leaders should meet up at least once a month to go over content planning and marketing. You can create separate events for upper management, where they can host presentations and suggest new company ideas based on data from previous months. This is a good way to brainstorm ideas and get people talking about actionable changes." – John Brackett, Smash Balloon LLC

17. Leverage what your employees are passionate about.

"Organize retreats around activities your employees are passionate about so they're engaged enough to let go of the stress often associated with work. Business ideas and strategies are often a result of reflection on our goals and the effectiveness of our approach toward them. These are hard to come by when you're in the middle of execution. Engaging retreats are enabling environments." – Samuel Thimothy, OneIMS

Image Credit: Ridofranz / Getty Images
Scott Gerber
Scott Gerber Member
Scott Gerber is the founder of Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses. Gerber is also a serial entrepreneur, regular TV commentator and author of the book Never Get a “Real” Job.