Part II: The Long Game: A Master Class in Strategic NetworkingAccording To Shane Winn

From different ways to network to follow-up tips, my conversation with Shane continues with more great tips we can all use!

6. Beyond Traditional Events: Creative Networking Approaches When we think of networking, cocktail parties, networking events, and dinners all come to mind. However, they are not the only way to network. Shane gives us some great ideas to take the ick out of networking to a different level.

Shane has made some of his best connections in non-traditional settings. Some of the most effective relationship-building happens in relaxed, enjoyable settings:

• Sporting events or concerts provide hours of one-on-one conversation time

• Shared hobby activities create natural bonding opportunities — why do you think there are so many golf outings?

• Casual meals or coffee meetings allow for deeper discussion than cocktail party small talk

The key is creating environments where authentic conversation can flourish.

7. The Two-Tier Follow-Up System

Maintaining your network requires intentional effort. Here’s his systematic approach:

Tier 1: Your Core Network

Keep a literal list of your top 10-15 most important professional contacts. Reach out to each person at least once per quarter through their preferred communication method (text, email, phone call, or in-person meetings).

The key is sharing something relevant to their interests or industry, not just checking in to say hello.

Tier 2: Broader Brand Awareness

Use platforms like LinkedIn to maintain visibility with your broader network. Regular posting and engagement keeps you top-of-mind without requiring individual outreach to hundreds of contacts.

8. The Gen Z Challenge: Overcoming Digital-First Communication

True connections that are nurtured in person will always be the path to success. For younger professionals who grew up with digital communication, networking can feel particularly daunting. The solution isn't to avoid in-person interaction but to build up to it gradually.

Start with low-stakes social interactions with colleagues—even something as simple as "it's just one beer" after work. If you can't feel comfortable in social settings with people you work with daily, networking with strangers will be nearly impossible.

The hard truth is that there's no substitute for in-person relationship building. Technology has made many things easier, but authentic professional relationships still require face-to-face interaction.

The Missed Opportunity That Haunts

Sometimes the best networking lessons come from mistakes. Shane had to skip a sports marketing conference in New York due to personal issues. Four months later, his company pitched for business with the company whose CMO had been the keynote speaker at that conference—and they lost.

“Would me being there have made a difference? If I had met that person and had two minutes with that person, would that have swayed anything in the decision-making?" He really won't know. However, I do know he made the right decision.

The Bottom Line: Networking as a Worldview

Effective networking isn't a skill set—it's a worldview about how you interact with other people. It's about being genuinely curious about others, generous with your time and knowledge, and patient enough to invest in relationships without expecting immediate returns.

The professionals who master this approach don't just build networks; they build communities of mutual support that accelerate their careers and create opportunities they never could have imagined.

Whether you're an extrovert who thrives at cocktail parties or an introvert who prefers one-on-one conversations, the principles remain the same: be authentic, be generous, think long-term, and always remember that the person you meet today might change your career trajectory five years from now.

Shane’s closing remark is true: “The question isn't whether networking works—it's whether you're willing to play the long game to make it work for you.”

Here’s a challenge:  Take one of these tips and implement it.  Let me know how it works. Contact me at janvkostner.com. I look forward to hearing from you.