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How to Build Connections and Create Boundless Opportunities

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Even if you meet someone 30 times for coffee, it’ll never equate to the connection that forms when you’re trying to change a flat tire together on a remote island without cell service. (Yes, that happened to me.) That’s why I’ve made it a personal mission to create memorable group trips that provide space to share experiences and grow relationships (ideally with no flat tires).

I started hosting curated trips in college for my business society. As I entered the workforce, I began theming trips around learning new skills, bonding over specific topics, or going on unforgettable experiences. My goal is to handpick professional contacts for trips that accelerate bonding and promote collaboration.

If you’re thinking you’d love to go on a trip but don’t have the time, I challenge you to reframe your thought process. These trips aren’t just vacations — they’re opportunities to learn something new, build deeper relationships, reflect, recharge, and invest in your future success. Group trips are a way to access people for longer periods than you otherwise would and bond over topics outside of work. Plus, you can outsource a lot of the planning, which is a huge benefit as a busy professional.

How Group Trips Prompt Self-Reflection, New Opportunities, and Growth

For years, I attended Jeff Bezos’ annual, invite-only MARS retreat. At this event, top leaders in machine learning, automation, robotics, and space gather to listen to thought-provoking lectures about the future of technology, bond over meals, and engage in activities such as hiking and martial arts. In just a few days, people with similar professional interests meet and form long-lasting connections.

These retreats are some of the most productive “workcations” I’ve attended. They gave me time to self-reflect on my own work, learn from thought leaders, and turn professional contacts into friends. After every MARS retreat, new businesses form and people change roles. These retreats are fun and successful, driving new ideas, strong partnerships, and individual growth.

The MARS retreat resembles many of the trips I’ve been doing for 15 years, and it’s the perfect playbook for planning a professional getaway. 

Here are the five key ingredients for success:

  1. Curation. Curate a group based on a common thread: an interest in meditation, experiences as women finance executives, etc. It’s important to handpick the right mix of people to ensure they get something valuable out of the trip.
  2. Purpose. There must be an explicit purpose for the trip. For example, if you want to host a meditation retreat, you should plan to spend three hours each day meditating and bringing in teachers. You can use the rest of the time for general bonding and group activities.
  3. Length. The trip should be at least three and a half days to give people time to build meaningful connections. (This does not include travel time.)
  4. Quality. My recommendation for a three-to-five-day trip is about 20 people. But if you want to maximize your efforts, you could invite up to 100.
  5. Downtime. Each day should have a few hours of downtime for the group to recharge and connect.

“The time to build a network is always before you need one.” – Douglas Conant

Group Trips Aren’t as Difficult to Plan as You Might Think

Remember, group trips are an investment in your future success. To make them more feasible from a planning perspective, try out these three types of trips:

1. Center your trip on learning a new skill for self-development.

Everyone has hobbies and skills they want to learn, so use those as conduits to bring people together and bond with professional contacts. For instance, pre-pandemic, a group of entrepreneurs in Silicon Valley went on annual kitesurfing trips around the world (including Richard Branson’s Necker Island). Hire a company that does custom tours to learn something new, such as mountaineering, sailing, or cooking. These companies will set a price and then usually take care of everything once you touch down — all you have to do is book a flight.

I did a four-person girls’ trip to French Polynesia, where we spent a week getting our catamaran skipper certifications. It was one of the most fun trips I’ve ever taken. We all studied together to take tests, practiced our skills on the catamaran, and bonded over a common goal. We also had a blast swimming with sharks, cooking meals together off the boat, and sailing around Bora Bora. We still regularly chat on our WhatsApp group about sailing and have been looking for more ways to put our certification to use.

2. Use pre-planned trips to meet new people.

Many companies offer incredible journeys with set dates, prices, and itineraries. You can travel at a better rate by inviting specific people you’d like to get to know on these trips. A couple of examples of ones I personally like are El Camino Travel (small group travel for women); For the Love of Travel (small group travel for Millennials); Modern Adventure (luxury culinary and wine tours); Abercrombie & Kent (global luxury tours); &Beyond (small group safaris); Nat- Geo Expeditions (history- and culture-themed trips); and Healing Holidays (wellness retreats).

“Your communication skills are your greatest strength as an entrepreneur. You have to know what to say when networking, team building, and talking with investors. Going on a group trip expands your professional circle and allows you to encounter new social situations that can help you grow as a communicator” – says Milosz Krasinski, Managing Director at Chilli Fruit Web Consulting.

3. Book a villa at a destination with many bonding activities.

I recommend the Caribbean for this approach! Look for homes that have a concierge or staff. These individuals can help you with responsibilities such as cooking, cleaning, or booking activities to remove those day-to-day stresses so you can focus on bonding with the people you’re traveling with. I curated a five-night trip to the Cayman Islands with 20 handpicked people where we all stayed in the same house. It was basically a summer camp for adults. We did night kayaking in a bioluminescent bay, sailing, and group yoga.

Many people on the trip didn’t know one another, but they were all Millennial tech professionals. This common thread created an opportunity for folks to have hours-long conversations. Have your guests facilitate events or conversations that play to their strengths. While on our trip, one individual hosted a yoga class, another taught everyone about body posture, and a third gave a lecture on trends in the tech industry. By planning daily events and topic-based meals, you force people to open up, reflect, and be vulnerable in front of each other.

Making time for group travel — not to mention handling the logistics — can seem daunting with your busy schedule. But you will be glad you took the leap. The growth you’ll experience will be more than worth it.

Sasha Hoffman is a travel expert, business strategist, investor, and entrepreneur who’s worked for companies such as Uber, Piaggio Group, and Goldman Sachs. Sasha has been to over 100 countries and has married her innate ability to find great deals and design unique experiences with her passion for travel, curating luxury, purpose-driven trips for professional women to learn new skills and see remote parts of the world. Connect with Sasha on LinkedIn.

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Success Advice

Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)

The surprising truth about leadership styles that can make or break your team’s success.

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Why one-size-fits-all leadership doesn’t work
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Leadership has always been as much about people as it is about performance. Ken Blanchard, in his influential book, “The One Minute Manager”, put it simply: different strokes for different folks. (more…)

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Success Advice

What Every New CEO Must Do in Their First 100 Days (or Risk Failure)

Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

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When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Entrepreneurs

What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators

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