Success Advice
How To Socialize Like A Pro

It was late on Friday night.
I couldn’t really be bothered socializing
The energy wasn’t there, but I did it anyway.
Last time I went to this social event I hated it. It was full of pretentious ex-Harvard / Stanford snobs that loved to compare whose daddy had a better car. Inside, I was shaking my head the whole time. This time, though, it was different.
This time I met game changers who were doing seriously cool sh”t – cool because they were solving real problems. One thing I find hard to deal with is shallow conversations. There’s nothing better than going all in and going in deep.
Ok, don’t look at me like that.
If you want to socialize like a pro you’ve got to make an effort and think about what you’re doing. Here are a few hints to get you on the right path:
1. Don’t be scared to ask for a phone number
Never leave a place where you have connected with some interesting people you like, without doing this step: ask for a phone number. You’ve put all that work in and then to walk away and not continue the conversation would be a major loss.
Avoid trading social media details if you can because there is a good chance they may not respond when you reach out. SMS is near impossible to ignore and we all read them (let’s face it).
It’s like spending considerable time showing someone your business and then not asking if they would like to be a customer.
“Closing the deal is what all successful people do and do well. Have confidence in yourself and do the same”
2. Put your phone on flight mode
The quickest way to kill a socializing opportunity is with that damn phone you always have on you. Put it on flight mode so you can focus on the people you’re connecting with. The world is not going to end because you didn’t see a “like” or reply to a comment.
3. Introduce mutual connections
Meeting new people in a social context is one of the key skills in socializing like a pro. The fastest way to build rapport is to leverage the mutual connections you have in common with someone you have just met.
You can discover these mutual questions by having a friend introduce you to someone new, using social media, or by simply asking questions that reveal mutual connections.
There’s a reason that social platforms make the most of mutual connections and you should do the same when socializing.
4. Ask quality questions
The questions you ask will have a lot to do with your socializing success.
– Ask the questions everyone’s thinking, but too scared to ask
– Ask follow up questions to interesting answers
– Ask lots of questions
Be like a detective and go all in on your test subjects (the people you’re talking with). Find out what makes them tick and what get’s them out of bed in the morning. Here are some great questions to try:
– What’s the scariest thing you’ve ever done?
– Where was the coolest place you traveled to and why?
– Why did you choose that way of making a living?
– What are you most passionate about above everything else?
– Who’s one person that has taught you more than anyone excluding family?
5. Look people in the eye
What I realized I do a lot of is look people in the eye. Now I’ll admit that girls tell me I have very nice eyes, so my reason for doing this is to exploit this “so-called asset.” I don’t believe what these girls say about my eyes by the way so calm your horsey.
Looking people in the eye creates a connection and shows you’re truly interested in them. It’s a way to be completely, 100% vulnerable.
“When you look into someone’s eyes, you’re showing all of yourself. That’s what socializing is all about”
Don’t hold back and be prepared to go the extra mile. By looking at someone in the eyes, you can see their heart, passion and human nature. You can feel them in a totally different way.
6. Inspire
The way you talk to people in social situations matters. I find that by talking in a way that inspires, you bring people in. Make the people you’re chatting to believe that they can do what you have achieved or that there is another perspective about a topic that they may not have thought of.
Try to leave them with a lasting impression of you. Hear about what their goals are and then see if you can find a tool or strategy that they haven’t thought of to try. Then challenge them and inspire them to give it a go.
7. Talk about what you’re passionate about
There’s a lot of nonsense people talk about when socializing. Try to focus social situations around your passion and the passion of those you’re talking to. From this place, there’s always more to talk about. Your passion is what makes you light up and people remember that feeling.
Share some stories of things you’ve done which are related to your passion. The other people around you may have different passions, but that doesn’t mean you can’t relate to them through your own passion.
I’ve found, that when you find people who have similar passions, the conversation becomes addictive. It’s those social moments that make all the energy and effort worth it.
When you find a conversation like this that has all of those ingredients, stick around for a while. Don’t feel like you have to talk with everyone in the room.
8. Be humble
We’ve all achieved a hell of a lot in our own little worlds. We all think we’ve got some awesome story that will blow people away and impress them. Reframe from thinking like that. If you’re intent is to get people to like you, they’ll run the other way.
The key is to be you and be gracious. Talk about what you’re good at, but don’t go over the top. The same goes in the other direction. Make sure you’re not afraid to talk about things people might like about you. Just don’t do it like a wanker. There’s a subtle difference between the two.
What else do these tips apply to?
These are the same tips for dating. That’s not the intent of this post, but I thought I should point it out. You can also use these same tips in a job interview to get yourself ahead of the game.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
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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.
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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.
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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.
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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.
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Simplify HR processes
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Redefine the value HR brings
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Treat Employees Like Associates, Not Just Staff
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Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
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