Technology has given us more ways to connect than ever before. We can collaborate across countries, collect employee feedback in seconds, measure nearly every digital interaction, and use AI to uncover patterns in enormous amounts of information. And yet, more technology does not automatically create more connection.
In fact, the sheer volume of digital tools, channels, metrics, surveys, and notifications can create what might be called a digital veil, a layer of noise between people that makes it harder to understand what they actually think, need, and experience.
For leaders building meaningful workplaces, the challenge isn’t choosing between digital and human. It’s learning how to use technology in a way that strengthens the human experience rather than obscuring it.
Connection Is About More Than Where People Work
It is tempting to make workplace connection a debate about remote versus in-person work, but location alone doesn’t determine whether people feel connected. A fully remote team spread across countries can develop a strong sense of community without regularly sharing a physical space. At the same time, employees who see one another every day can still feel disconnected from their coworkers, leaders, and organization.
The difference is intentionality.
People, process, and technology have to work together. The right approach also depends on the organization, the work being done, and the people doing it. There is no universal formula for where or how people should work.
That is why absolutes can be dangerous. Sending everyone remote without preparing them to collaborate effectively can create problems. Requiring everyone to return to an office without considering how they work best can create different problems.
The better question is: What are we trying to accomplish, and what will help these particular people accomplish it together?
The Limits of Measuring Human Experience
Organizations have become incredibly good at collecting data. Clicks. Scores. Surveys. Reports. Engagement metrics. Customer feedback. Employee experience data. These signals have value, but they don’t necessarily tell us why something is happening.
A survey, for example, typically answers questions the organization has already decided to ask. Even when a survey is anonymous, employees may question whether it truly is. They may choose the safest answer, rush through the questions, or simply stop participating after being asked for feedback too many times.
The result is technically data, but it may not represent someone’s complete experience.
Trust Changes the Quality of the Answer
If leaders want authentic insight, they first need an environment where people trust the process enough to respond authentically. That means considering the experience from the employee’s perspective. How often are they being asked for feedback? Do they understand why they’re being asked? Does the process feel genuinely anonymous? Does it feel different from every other survey sitting in their inbox?
Most importantly: Do people believe their voice actually matters?
Trust isn’t simply a nice addition to employee listening. It influences the quality of what people are willing to share.
From Information to Insight: Population, Prompt, Product
One way to move beyond surface-level data is to think about human insight through three interconnected elements: Population, Prompt, and Product.
Population: Know Who You’re Trying to Understand
The first step is understanding the population.
A broad group may contain several distinct populations with very different experiences. Within an organization, for example, new hires, hiring managers, frontline employees, and senior leaders may experience the same workplace very differently.
Leaders need to ask: Who are we trying to understand? How accessible are they? What matters to them? And do they trust us enough to tell us what they really think?
That last question matters because insight begins with more than access to people. It requires connection with them.
Prompt: Create Space for the Unexpected
The second piece is the prompt.
Traditional surveys often begin with the organization’s questions. A thoughtful prompt does something different: it frames a topic broadly enough that people can reveal what matters to them.
Consider exercise. You could ask how many times someone exercises each week, what shoes they wear, or what equipment they own. Those answers may be useful, but they won’t necessarily explain why exercise matters to that person.
Asking why someone began exercising, and why they continue today, creates room for very different answers. Exercise could be about health, weight loss, therapy, confidence, enjoyment, or something else entirely.
The goal is not simply to collect an answer. It is to give people enough space to reveal something you may not have known to ask about.
Product: Let What You Learn Influence What You Build
The third piece is product: the outcome, service, process, or experience the organization creates through its efforts.
Once you understand a population more deeply, what will you change because of what you’ve learned?
The insight may confirm that you’re meeting the right need. It may expose a gap. It may reveal that one part of the population needs something different or even uncover another population you hadn’t considered.
The value isn’t in collecting more information. It’s in allowing that information to influence decisions.
Employee Experience Gets Better When People Have a Real Voice
This approach becomes especially powerful inside organizations.
Employees are often asked to provide feedback about engagement, onboarding, culture, or retention. But understanding employee experience requires looking beyond whether someone stays or leaves.
There are also employees who remain but don’t care as much as they once did. Connection, belonging, and energy matter here.
Consider onboarding. New employees can spend months wondering whether they’re keeping up, fitting in, or meeting expectations. That anxiety consumes energy that could otherwise be directed toward learning, contributing, and building relationships.
Now imagine new employees hearing experienced leaders openly share that they once felt the same uncertainty, and what helped them move through it. That changes the experience.
Instead of forcing every new employee to figure out the unwritten rules independently, organizations can use the experiences of people who have already navigated them to create stronger mentorship, clearer expectations, and greater connection.
The People Closest to the Work Often See What Leaders Can’t
The same principle applies beyond onboarding. Frontline employees are often closest to the problems an organization is trying to solve. They experience patterns, customer challenges, process breakdowns, and opportunities every day.
When those employees feel like “just a number,” organizations risk losing valuable insight. When people are given meaningful opportunities to share their experiences, leaders gain a clearer view of what is actually happening, and employees can see that their perspective contributes to something larger.
Listening can improve the employee experience and the business at the same time.
Storytelling Can Reveal What Metrics Miss
There is a reason stories can be particularly powerful in this process. Storytelling is deeply human. Long before dashboards, surveys, or digital platforms, people used stories to communicate experiences and make sense of the world around them.
When someone is given room to tell a story, they have an opportunity to process their experience instead of selecting a predetermined answer from a list.
The person receiving that story also interacts with it differently. Stories encourage active listening. They provide context. They can create empathy and compassion between people whose experiences may initially appear very different.
For organizations, analyzing stories across a larger population can reveal recurring themes and patterns. Instead of simply knowing what people selected on a survey, leaders can begin understanding why those experiences matter.
Data Needs Context, Especially in the Age of AI
None of this means organizations should abandon quantitative data. The challenge is using data within the right context and with the right intent.
A metric can be accurate and still be misused if it is taken outside the context in which it was collected. Leaders therefore need to understand not only what the data says but what it was originally intended to help them understand.
The same principle matters as AI becomes more embedded in workplace decision-making.
AI’s output is heavily influenced by the information it has been trained or instructed to work with. When its context is poorly defined, results can become unreliable. When the context is deliberately constrained to relevant information, AI can become a powerful tool for analysis.
For example, AI can analyze hundreds of employee stories to identify recurring themes, compare patterns across groups, or surface topics leaders didn’t think to ask about.
That last capability may be one of the most valuable. Instead of only asking AI to confirm what leaders already want to know, organizations can ask: What are people consistently talking about that we haven’t considered yet?
Used that way, AI doesn’t have to replace human insight. It can help us see more of it.
Bringing Humanity Back to Digital Work
As work becomes increasingly digital, leaders need to remember the basics.
What is the organization’s mission? Who are the people it serves? Who are the people doing the work? Do those people know that the organization cares about their experience?
Technology, branding, metrics, automation, and AI can all support the work, but they shouldn’t cause leaders to lose sight of why the organization exists or who makes it possible.
The future of work isn’t about rejecting digital tools. It’s about becoming more intentional about how we use them.
Know your people. Give them meaningful opportunities to use their voice. Understand the context behind the data. Then allow what you learn to shape the processes, experiences, and products you create.
Meaningful work won’t come from measuring more clicks. It will come from remembering that there are humans behind them.
Listen to the episode: Gut + Science | 331: Beyond Clicks and KPIs: Bringing Humanity Back to Digital Work with Andy Sitison
Key Takeaways:
- Technology doesn’t create connection, people do.
- Trust unlocks honest and useful feedback.
- Know your people to serve them better.
- Data without empathy risks missing the human story.
- Surveys ask, stories reveal the real truth.
Things to listen for:
- [00:02:00] How the “digital veil” can create disconnection in both our personal and professional lives
- [00:03:00] Why remote versus in-person work isn’t the real question when it comes to connection
- [00:07:00] Why leaders should avoid absolutes and design work around the people, mission, and outcomes involved
- [00:09:00] The limits of digital activity data and why trust is critical for authentic employee feedback
- [00:13:00] The three Ps framework: Population, Prompt, and Product
- [00:15:00] How thoughtful prompts can uncover the deeper “why” behind people’s experiences
- [00:21:00] Applying deeper listening to employee experience and engagement
- [00:23:00] How shared stories can reduce anxiety and strengthen the new-hire experience
- [00:26:00] Why storytelling creates connection, empathy, and a sense of being heard
- [00:31:00] How AI can identify themes and unexpected patterns when it is given the right context
- [00:36:00] Why leaders need to return to the basics of mission, intent, and caring about the humans behind the work