Ditch the stale questions: How to create deeper connections with thoughtful conversations

Have you ever casually chatted with someone and they asked, “So, how did you get started?” 

We’ve all been there…

It’s a common question, but let’s be honest, it’s not always the most engaging. Over time, it can feel repetitive, both for you and the person you're speaking with. But don’t worry, there’s a simple fix. 

By asking more specific, thoughtful questions, you can unlock deeper insights and create more meaningful conversations. 

You’ve likely had countless conversations with clients, partners, fellow entrepreneurs, people at networking events - heck even the person you chit chat with while you’re waiting in the grocery line where “How did you get started?” came up. 

And while building rapport is key, asking the same generic questions over and over, like “How did you get started?”, can feel stale. 

Not only does it get repetitive for you, but people often grow tired of answering the same thing time and again.

Here’s how you can ask the right questions that will not only make your conversations more engaging but also strengthen your connections.

Ask more specific questions that lead to richer responses

So, how can you spark more engaging, meaningful conversations? 

It’s about asking more specific, thoughtful questions that allow for richer, more detailed responses. These types of questions not only show genuine interest but also create opportunities to uncover shared experiences or insights that deepen your connection.

Here are some alternative questions that can open the door for more engaging conversations:

Has [insert industry, niche, profession, field of work] always been something you’ve been passionate about?

This question explores their long-term interests and motivations. By understanding whether their current field has always been a passion, you gain insight into their commitment and love for their work. It can reveal how their interests have shaped their career path and whether they are driven by a lifelong passion or if they found their passion later on. This also provides an opportunity for them to share stories about how their passion developed over time.

Was [insert industry, niche, profession, field of work] your dream job, or did you discover it along the way?

This question allows them to reflect on their career journey and how it aligns with their dreams and aspirations. It can reveal whether their current role was part of their original plan or if it was an unexpected but welcome discovery. This insight can lead to discussions about adaptability, unexpected opportunities and how they’ve navigated changes in their career path. It also opens up the floor for them to share any surprising or serendipitous moments that led them to where they are now.

What was the beginning of your journey like in [insert industry, niche, profession, field of work]?

By asking about the start of their journey, you're inviting them to share personal milestones, challenges and early experiences. This can provide a comprehensive backstory, revealing the hurdles they overcame and the lessons they learned along the way. It gives you a better understanding of their growth and development and highlights their resilience and determination in the face of challenges.

What initially sparked your interest in [insert industry, niche, profession, field of work], and how has that evolved over time?

This question delves into their initial motivations and how those motivations have transformed. It helps uncover the "why" behind their career choice, which can be deeply inspiring. By exploring how their interests have evolved, you can gain insight into their adaptability and how they have continued to nurture their passion over time. This can lead to rich discussions about personal growth and the factors that have influenced their career evolution.

What motivated you to take the leap and start your own business?

This question seeks to understand their entrepreneurial spirit and the driving forces behind such a significant decision. It can reveal their motivations, risk-taking ability and the vision they had when deciding to start their own venture. Understanding these motivations can provide insight into their values, ambition and what they hope to achieve with their business. It also opens the conversation to discuss the challenges and triumphs they’ve experienced along the way.

By asking these types of questions, not only are you discovering the details of their path, but you’re also likely to tap into common ground, be it shared experiences, similar challenges or mutual interests. These moments can serve as powerful connection points and help your conversations flow naturally, leading to deeper relationships and opportunities for collaboration.

The quality of your conversations can directly influence how your relationships grow. By using these questions, not only will the conversation feel more engaging, but it’ll also show that you’re genuinely invested in learning about the person beyond just the basics.

As you move forward with your conversations, remember:

Asking the right questions can dramatically shift the course of your conversations, making them more meaningful. The next time you're networking, skip the standard “How did you get started?” and try one of these alternatives instead. You’ll find that people will open up more, share their journeys, their values, beliefs and experiences, and you’ll create a connection that’s built on understanding and curiosity.

Give them a try and let me know how it goes! Share your experiences with these questions.