Effective Communication in the Workplace and Beyond: How to Bridge Gaps and Build (Genuine) Connections

The next time you find yourself at the start of a meeting with another?colleague that you don't know very well, instead of awkward silence, try asking this question to break the ice:

Ok, so… tell me: what's been your proudest professional moment, like, ever?

Note: You can also try this during a skip-level meeting with a senior leader, with whom we're going to presume there's a bit of power distance and/or you don't know that person very well.        

When formulated in the positive light, i.e., “proudest moment,” chances are you’ll feel a little weird about asking it, right?

But definitely not as weird as asking the negative version of that question:

What’s been your biggest professional regret?

Imagine that as an icebreaker question with an EVP sitting across from you?! Eeek.        

By the way, you’re supposed to also answer that question. After all, it’s a conversation, right?

You ask a bit, they answer the bit, and then you commiserate by answering the same question, yah? Pretty standard stuff. Except this one is (and that negative one is especially) difficult, right?

Yes, amigo, it is.

At the surface, it might seem a bit unprofessional to dig into a personal topic like someone's psyche and what drove them up a wall when you barely even know them.

But I'm going to try to convince you that this kind of exchange is both worthwhile to have and it can improve your relationships with all sorts of people, professional and otherwise. Also, when you combine “worthwhile” with “improved relationships,” you get a bump in overall work experience. Right?

People managers out there, the key for you here is: make space for this; your org will be better for it.        

Story Time

A few years ago, I found myself in a frustrating pattern with a mentor that was assigned to me.

Some folks saw that person's skill and experience, paired it up with mine, and thought:

Hey, Jareau and Soen So should link up and grow.

Win-win, I thought. I'd come to our one-on-one meetings full of optimism and enthusiasm to learn about the biz, flaunt a bit of the good work I've been doing, and hopefully bridge that gap by way of some stretch assignments. Instead, I walked away feeling unseen, unheard, and underappreciated

You've all been here, both at work and in person: the person you're talking to is looking at a screen, typing or doom-scrolling while you're in the middle of a story. Maybe they're tracking; mostly they're not. If it's inconsequential or informal, sure, you take it in stride.

But if you're opening up about something emotional, or, as it was in my case, chatting about good work with a hopeful eye on the future (which is, unto itself, an emotional topic), there's only so much "Uh huh... Hmmm... Wow.... Yeah..." you can take.

Why would you continually chat with someone who is looking and typing away into a second screen?

Interesting dynamic, right? We've all been there. Unsurprisingly, we've all been on both sides of that scenario, too.

And so, are there smarter people out there than me who know a thing or two about this stuff?

Yes, that was a rhetorical question.?

Enter "Supercommunicators", a book by Charles Duhigg about why some people are so much better at connecting with other people, and particularly through conversation.

One key insight from the book is this:?

What we might think of as a single conversation is actually multiple layers of communication. Here's what those look like:

1. Practical Conversations: these focus on what needs to be done, solutions, and action items.

2. Emotional Conversations: these focus on how we feel about a situation and our need for an empathetic ear.

3. Social Conversations: nonchalant conversations about our roles, identities, and how we relate to each other, the organization, and the world at large.

As you can imagine, if you're having one kind of conversation with a person who is having another kind of conversation (assuming they're actually conversing with you,) you'll both struggle to connect and understand each other.

This is the "matching principle" that Duhigg references in his book. Being a super communicator means you're able to recognize the type of conversation that's happening and you're able to align with it.

Ok, so how do I apply this in a professional setting??

Glad you asked.?

Your goal is to ask the right questions—specifically, you want to be asking "deep questions," as Duhigg calls them. These kinds of questions invite people to discuss their values, beliefs, experiences, and feelings.?

Let's take a perfect stranger as an example.?

Say you're sitting next to someone on a plane, and you overhear them talking on the phone to their team. You gather they are in project management of some sort. They end the call, and you ask:

Are you a project manager?

Too many of us expect that simple question to lead into a deep dive into their lives. Chances are exponentially higher, though, that the person will reply with a simple:

Yes.

And that's the end of the conversation, unless you ask a follow-up. Which, if a pattern of 1 can be called a pattern, you already have a pattern of asking binary questions. So, chances are you'll ask another binary question, right? "Do you like being a project manager?" Doh!

And, you guessed it, they answer with another "yes."

Now things are getting awkward. Three-time's the charm, eh? You're digging in your heels and going in with another binary question? Don't. You should have asked this in the first place:

Sounds like you're in project management; I've dabbled a little in that myself. What do you love most about a PM’ing?

Boom. You get a 3-5 minute answer. Now you're in a conversation.        

These types of questions allow people to open up, reveal who they really are, share what matters to them, and importantly, why things matter to them.

Why is an excellent question to ask.

This kind of vulnerability, when reciprocated, of course, is the key to starting a great conversation and then to building a strong connection and a lasting relationship with colleagues, family, and people in general.?

That airplane scenario serves to demonstrate how we can engage a stranger. Next, let's take a gander at how these principles apply in a more formal work setting.

A few years ago, I designed a skip-level meeting program for a VP that didn't have these in place. As part of the design, I provided the executive with a bank of open-ended questions to ask on their one-on-one's. Just the same, I provided them with a bank of questions that I was sharing with the individual contributors who would be meeting with that VP, also open-ended questions. Don’t wanna blindside your VP’s, ya know?

Here are a couple of examples of VP-to-IC questions:

• What would help you be successful in your role?
• If you were promoted to <insert role one or two levels above theirs>, what would you fix, change, or do differently?

Notice how those aren't "How's your week going?" questions. Also notice how those questions can't be answered with a yes, no, or single word.

And here are a couple of examples of IC-to-VP questions:

• How do you see our team growing, evolving, or changing in the next few years?
• What's your opinion about how the team I'm on is contributing to your goals??

If your VP is looking at their second screen, typing away in a frenzy on another matter, they'll probably pause, push away from that screen in annoyance, and turn to you. Frustration aside, you've captured their attention. It was their bad for multitasking while on your one-on-one. Now you have their attention. High five.

Leverage Deep Questions to your Advantage

Leverage deep questions to drive (and also shift) the conversation from a potentially stale convo, to a collaborative, problem-solving, or ideation session.?

You will feel heard and understood, which makes you more receptive to feedback and more willing to work on improvements. On the other hand, leadership will perceive you as engaged, which increases your chances of better opportunities.?

Leverage this everywhere—from an airplane seat to dinner with friends to that corporate holiday party. It's not just for formal or high-stakes conversations—instead, use it constantly to build better connections in your day-to-day, every day.

Here’s another tool for you:?

Duhigg talks about the concept of "looping for understanding." This technique is essentially asking a question, repeating back the answer you heard, and asking if you got it right. This is powerful because it shows the other person you’re genuinely listening to them. It shows you’re making a concerted effort at understanding what they’re saying to you.

A Word of Caution (for you too, leader)

What happens when a person mixes more than one style in the same conversation with someone who is only using one style?

As an example, someone brings in both Practical and Social styles to a conversation with someone who is only using one style.

Practical + Social = Mixed Signals . As a leader, you’re communicating that we’re working with both a hard deadline and that we can get it done whenever. No bueno.?

Another example: Practical plus Emotional

Practical + Emotional = Mixed Signals . As a leader, you’re setting a hard deadline and establishing that you’re going to be watching that person’s every move. Uncomfortable.

Why is this mixing of styles problematic??

Consistency and clarity are king. When you mix conversation styles, you're essentially sending conflicting messages. The fruits of your labor are confusion, anxiety, and misunderstandings.

In the Practical + Social example, the practical part of the conversation suggests urgency and importance—it’s work we’re talking about, right? On the other hand, the social side of things implies a more relaxed, less time-sensitive, laissez-faire approach. Which is it?

Your net-net here is a lack of clarity, misaligned priorities, and rather a stark amount of confusion down the line when you get emotional while outlying the practical, in an effort to rectify your initial mistake.

Similarly, in the Practical + Emotional mix, you're combining task-oriented communication with personal, feeling-based interaction. This pressures the listener to perform and makes them emotionally vulnerable, creating an uncomfortable work environment for both that person and the buddy they vent to. Yes, actions reverberate.

By sticking to one conversation style at a time, you ensure your message is clear, your intentions are understood, and your listener knows how to respond appropriately. This consistency builds trust and improves the overall effectiveness of communication, both yours and theirs.

As a communicator, it’s your job to listen.

Let me say that again for the folks in the back.         

Communication is both speaking and listening.

And “listening” is defined as interpreting, digesting, deciphering, understanding, internalizing, and empathizing. Without that, you’re just talking.

The next conversation you have with someone, try to figure out as early as possible, if they are engaging in a practical conversation, an emotional conversation, or a social conversation. And meet them where they are.

When you don't, you risk being perceived as distant, detached, uninterested, self-interested, and one-track-minded (which is kinda like saying narrow-minded, yah?) and you lower your approachability rating. One more drawback I guarantee: people will talk about it (read: you).

“Burr, you disgust me

- Ah, so you've discussed me”

And so, I encourage you to try this experiment.

In your next interaction with a colleague, especially someone you don't know well, or a senior leader, build up a little bit of courage and ask a deep question.

It might feel uncomfortable at first (correction, it will), but the potential for meaningful connection and improved working relationships is immense.

Effective communication isn't about being more charismatic, outgoing, or talkative. It's about learning and applying these listening skills; it’s about internalizing and empathizing. That’s how we truly connect with others.

Pop quiz: without scrolling up, what are the three types of conversations we spoke about here? And which of the three was this article written in??        

Work at understanding the different layers of conversation. Practice using deep questions to navigate those conversations. Be intentional about it.

Your result will be better, more honest, and more meaningful professional interactions. And you’ll yield stronger teams, better collaboration, and you’ll build and maintain a more fulfilling work experience. That’s the win-win.

And now, for the Wrap-Up: How to Become a Supercommunicator

If you’re not connecting, you’re not communicating.

Start by recognizing and engaging in practical, emotional, and social conversations whenever and wherever you can.?

• Recognize the type of conversation you're in and match it.
• Ask deep questions and invite people to share their values, beliefs, and experiences. The more you practice them, the easier they’ll be to ask.
• Practice "looping for understanding" to ensure you're truly hearing what others are saying.
• Be mindful of mixing conversation styles. You read my other article on mixed signals , yes?
• Be vulnerable and allow space for vulnerability. Vulnerability isn’t weakness. It’s strength.?

The beauty of all this is that you don't need to wait to start. And you’re never too old—I mean, you're never too set in your ways, to start either. Your very next convo is an opportunity to practice. Whether it's with a colleague, a leader, an individual contributor, your kids, or even a stranger on a plane, make it a point to apply these bits.

Charles Duhigg believes anyone can learn to be a supercommunicator. And I believe you can do it too.

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#EffectiveCommunication #WorkplaceSkills #Supercommunicator #ProfessionalGrowth #DeepQuestions