Asking the Right Questions: Connecting Knowledge Holders and Seekers
In every organization, knowledge lives in two places: in systems and in people. We often spend significant energy refining our systems and building databases, launching collaboration platforms, or now, experimenting with AI-driven knowledge assistants. Yet, the true artistry of knowledge transfer happens elsewhere. It takes place in the conversations between people who hold knowledge and those who seek it.
Too often, we seek the easy answer. It’s faster to search an intranet or ping a chatbot than to engage with your coworker. But convenience can come at a cost. When we skip the conversation, we miss the context, the “why,” and the nuanced reasoning that shapes professional judgment. In the architecture and engineering world, this is where tacit knowledge (understanding gained through experience) resides.
The most valuable knowledge exchanges don’t happen when someone seeks a quick answer. They happen when someone asks the right question. Questioning is not a sign of weakness; it’s an act of engagement and curiosity. A well-posed question invites a story, sparks reflection, and opens a pathway to shared understanding. It’s how experts articulate the thinking behind their expertise and how learners develop true understanding.
Technology plays an essential role. It helps us access information quickly and handle routine tasks efficiently. But its greatest value is in setting the stage for deeper human learning. When technology gives us a foundation of understanding, we can use our time together to ask better, more meaningful questions. The heart of knowledge transfer still lies in conversation and those interactions where people explore uncertainty, challenge assumptions, and wrestle with the classic “it depends” moments that bring real expertise to life.
The Multi-Generational Moment
Right now, this work has never been more critical. Many organizations face a narrow window (e.g., 1-5 years) to capture the experience and insights of professionals nearing retirement. The wisdom built over decades of solving complex problems can’t be downloaded in a week or summarized in a database; it must be shared through dialogue, mentoring, and storytelling.
At the same time, younger generations bring new energy, digital fluency, and fresh perspectives. But they often crave understanding of why things are done a certain way, not just how. Good knowledge culture bridges that gap and connects generations through shared curiosity and conversation.
To capture attention across all generations, make knowledge sharing top of mind and relevant to the work:
Tell stories that show how experience shapes outcomes and builds resilience.
Share lessons learned not just as reports, but as conversations on what worked and what didn’t.
Make it personal and reciprocal. Help both knowledge seekers and holders see “what’s in it for me.” For seekers, it’s faster growth, building confidence, and fewer repeated mistakes. For holders, it’s recognition, legacy, and the satisfaction of shaping the next generation of expertise.
Focus on purpose. When people see how knowledge sharing strengthens teams and leads to better client outcomes, they’re more likely to engage.
Turning Insight into Action
So, how can organizations shift from good intentions to sustained behavior?
Model curiosity from leadership. Leaders who ask great questions and make time for reflection signal that learning is ongoing throughout their careers.
Design learning moments into daily work. Create structures such as peer design reviews, project debriefs, and mentoring circles where the goal is knowledge exchange, not performance evaluation.
Recognize and reward inquiry. Celebrate when someone takes the time to learn from a colleague or documents lessons learned, especially after challenges.
Balance metrics with meaning. Move beyond analytics like search counts or number of platform users. Instead, assess whether teams are collaborating more deeply, whether curiosity is encouraged, and whether people feel safe admitting what they don’t know yet.
Building a Learning Culture
Ultimately, a strong knowledge culture underpins an organization’s ability to learn, adapt, and innovate. By connecting knowledge holders and seekers, encouraging small and complex questions, and valuing rich conversation, firms build a living system of expertise that continually renews itself with each generation.
When knowledge becomes a shared responsibility and led by those closest to the work, it moves beyond being a single process or platform. It becomes part of how decisions are made, how projects evolve, and how people learn and grow. A strong knowledge culture doesn’t just preserve what a firm knows; it expands what it’s capable of becoming.
The organizations that thrive in the future will be those that invest not only in technology, but in the curiosity, trust, and dialogue that sustain learning.
Start by asking yourself and your teams: Are we creating the conditions, trust, and expectations for our employees to truly share what they know and to keep learning from one another?
The future of your organization lives in the questions your people are asking today.