Sparking Meaningful Dialogue with "Highs & Lows"
and Powerful "Why" Questions
How many times a day do you ask, or get asked, "How are you?" And how often does that simple question actually kickstart a truly engaging conversation? Chances are, it's usually met with a quick "Fine, thanks, you?" and just like that, the interaction flatlines before it even gets a chance to breathe. If you're a professional who sometimes feels a bit socially awkward, or really anyone looking to deepen their connections with colleagues, figuring out how to move beyond these conversational autopilots is a game-changer.
The great news? There are some simple, yet incredibly effective, strategies out there that can transform those everyday, mundane exchanges into genuine opportunities for connection and understanding. Today, we're going to explore two such power tools: the "Highs & Lows" check-in, a technique that speakers like Vinh Giang famously champion for its ability to instantly add depth, and the art of asking thoughtful "Why?" questions to gently uncover the motivations and stories that lie just beneath the surface.
Now, this isn't about becoming nosy or making people feel uncomfortable. It's all about signalling your genuine interest, fostering a more open and communicative environment, and ultimately, building stronger, more influential relationships, both in your work life and beyond.
Breaking the Ice and Building Bridges: The "Highs & Lows" Strategy
Picture this: you're starting a team meeting or a one-on-one chat. Instead of falling back on the usual "How's it going?", you offer a simple invitation: "What's been a high point and a low point for you this week?" That, in a nutshell, is the "Highs & Lows" strategy. It might seem deceptively simple, but this framing can radically change the quality of your interactions.
Vinh Giang, a renowned keynote speaker and communication coach, often talks about this technique as a fantastic way to quickly build rapport and create a space where people feel comfortable sharing more authentically. Instead of prompting a generic, one-word answer, asking for "Highs & Lows" encourages people to pause, reflect, and share something specific – and often a bit more personal, always within professional comfort levels, of course.
So, how does this play out in a professional setting? Well, kicking off a weekly team meeting by having everyone share a professional high and low can be a brilliant way to get a real sense of team morale, spot any hidden challenges, and also celebrate those important small wins. For instance, a high might be, "My high this week was finally getting that tricky client proposal submitted ahead of schedule. It was a real team effort," while a low could be, "A low for me was hitting a roadblock with the new software integration; it’s taking longer than I anticipated."
In one-on-one check-ins with direct reports or even peers, using "Highs & Lows" can open up a much more meaningful dialogue than your standard status update, allowing for a supportive discussion of both successes and challenges. Even at networking events, while you might not lead with "What's your high and low?" to someone you've just met, a softer version like, "What's been the most interesting thing you've worked on recently, and perhaps something that's been a bit of a learning curve?" can achieve a similar, more engaging effect. And after a project wraps up, asking about the highs (what went well, what are we proud of) and lows (what were the challenges, what could we improve) provides a really structured and valuable way to gather insights.
But why is this technique so effective? Firstly, it encourages specificity, moving people beyond those vague responses like "good" or "busy." It also promotes balanced sharing, acknowledging that work life naturally has its ups and downs, which makes the conversation feel more relatable and human. Hearing about colleagues' challenges, their lows, can foster a great deal of empathy, while celebrating their successes, their highs, really builds camaraderie. What's more, it creates an atmosphere of openness; it normalizes talking about difficulties, making it easier for team members to flag issues before they escalate. And perhaps most importantly, sharing even small personal highs and lows can significantly accelerate the process of getting to know your colleagues on a more authentic level.
It's important to remember this technique isn't about forcing deep emotional disclosures. The level of detail people share will naturally vary depending on the individual and the existing team culture. The real power of "Highs & Lows" lies in creating that invitation for more meaningful sharing.
Digging Deeper with Purpose: The Art of Asking "Why?"
Once a conversation is flowing, how do you take it from just interesting to genuinely insightful? This is where the art of asking "Why?" truly shines. Now, this doesn't mean you should start peppering your colleagues with a blunt "Why? Why? Why?" like a persistent toddler – that would get old very quickly! Instead, it’s about thoughtfully using questions that help you get to the underlying reasons, motivations, passions, and thought processes behind what someone is saying or doing.
Vanessa Van Edwards, in her work on social dynamics, also really emphasises how crucial understanding the "why" is if you want to truly connect with people. These kinds of questions are your tools for gently uncovering the layers that lie beneath the surface of a conversation.
Often, the most effective "why" questions don't even use the word "why" directly, especially if you're worried about sounding confrontational. So, instead of asking something direct like, "Why did you choose that approach?", which can sometimes put people on the defensive, you could try softer, more exploratory alternatives. For example, you might ask, "What was your thinking behind that decision?" or "What led you to that particular conclusion?" Other great options include, "What makes that aspect particularly interesting or challenging for you?", "Could you tell me more about what motivated you to get involved in that project?", "What’s the story behind how you developed that skill?", or even "What values guide you when you're making those kinds of choices?"
These thoughtful "why" questions can really enhance your professional interactions. If a colleague says, "I'm really passionate about our new sustainability initiative," you could explore their 'why' by asking, "That's great to hear! What is it about sustainability that particularly resonates with you, or what do you feel is most critical for our industry right now?" If a team member, during a debate, states, "I think we should prioritise Feature X over Feature Y," you can seek to understand their reasoning by saying, "Interesting point. Could you walk me through what makes Feature X the higher priority in your view at this stage?" This approach is also invaluable in mentoring or coaching. If a mentee says, "I'm not sure which career path to pursue next," you can help them explore their 'why' with a question like, "When you think about the different options, what aspects of each one feel most aligned with what you truly enjoy doing, or what you want to achieve long-term?" And it’s just as useful for problem-solving. If a report shows that "Customer satisfaction scores have dipped this quarter," you could dig into the 'why' by asking, "What are our initial thoughts on what might be contributing to that dip? Have we seen any specific feedback patterns?"
The benefits of this kind of thoughtful "why" exploration are numerous. You'll find you uncover much deeper insights, moving beyond just surface-level information to understand the core drivers and reasoning behind things. Taking the time to understand someone's "why" is also a powerful signal that you genuinely value their perspective. This, in turn, fosters stronger connections because understanding motivations and values is absolutely key to connecting with people on a more meaningful level. For teams, understanding the "why" behind different viewpoints can lead to more informed and robust decision-making. And perhaps surprisingly, when you understand what truly motivates someone, you're much better positioned to communicate with them in a way that resonates and, ultimately, persuades.
The real skill here lies in asking these questions with genuine curiosity and respect, creating a safe and open space for the other person to share their thought process without feeling judged or put on the spot.
Bringing It All Together: "Highs & Lows" Opens the Door, "Why" Invites You In
It's helpful to think of these two strategies as working in tandem, like a well-coordinated team. The "Highs & Lows" check-in is a fantastic way to open the door to more authentic sharing; it gets those initial, specific details out on the table. Then, your thoughtful "Why?" questions (or their softer equivalents) are what allow you to step through that door and really explore the landscape within.
For example, if a colleague shares a "high" about successfully launching a new feature, you could follow up with something like: "That's a fantastic achievement! What was the most rewarding part of that process for you and the team?" This helps you explore the positive 'why' behind their success. Similarly, if they share a "low" about a communication breakdown, you might ask: "That sounds frustrating. From your perspective, what do you think were the main factors contributing to that breakdown?" Here, you're exploring the 'why' to understand the situation better and potentially help with problem-solving.
Navigating for the Socially Awkward Professional
If you're someone who sometimes feels a bit unsure in social or professional interactions, these structured approaches can be particularly empowering. The "Highs & Lows" strategy, for instance, provides a kind of script; it gives you a concrete, easy-to-implement way to initiate more meaningful small talk or kick off meetings, so you don't have to guess what to say. Then, "Why?" questions offer a clear path forward. Instead of wondering how to keep a conversation going after the initial facts are shared, these questions give you a natural next step to show your interest and learn more.
It can also be helpful to start with observation. Notice how others react when you use "Highs & Lows." See how people respond to different types of "why" questions in meetings. And don't forget to practice in lower-stakes settings first. Try "Highs & Lows" with a friendly colleague, or even adapt it for conversations with friends and family to get comfortable with the flow. Most importantly, remember to focus on listening. Both of these techniques are powerful because they encourage active listening; your primary role is to create the space for the other person to share.
Beyond the Office Walls
While these strategies are incredibly useful at work, they also have the power to enrich your personal relationships. Imagine using "Highs & Lows" with your family or partner. Instead of the standard "How was your day?", try asking, "What was the best part of your day and what was a bit tough?" This simple shift can lead to much richer sharing around the dinner table or at the end of a long day. Similarly, when a friend shares news or an opinion, gently exploring their "why" can deepen your understanding of them and significantly strengthen your bond. You could ask, "What made you decide to take that leap?" or "What is it about that particular author that you connect with so much?"
By incorporating "Highs & Lows" and thoughtful "Why?" questions into your conversational toolkit, you're not just learning new techniques; you're cultivating a more curious, empathetic, and engaging way of interacting with the world. You’ll likely find yourself building stronger connections, gaining deeper insights, and feeling more confident in your ability to communicate effectively – skills that are truly invaluable in any professional or personal setting.
Key Takeaways for Readers:
Implement "Highs & Lows": Use this simple check-in (asking for a high point and a low point) to move beyond generic greetings and foster more specific, balanced, and authentic sharing in team meetings and one-on-ones.
Master Empathetic "Why" Questions: Go deeper than surface-level facts by asking thoughtful questions (often phrased without using the word "why" directly) to understand the motivations, reasoning, and values behind colleagues' statements and actions.
Combine for Deeper Connection: Use "Highs & Lows" to open the door for sharing, and then employ "Why?" questions to explore the insights and stories that emerge, building stronger rapport and understanding.