The Awkward First Meeting

My colleague kicked off a new initiative and invited 15 members of all relevant teams. Once the meeting started, she outlined the objective, and explained the uncertainties. Then she admitted that the timeline will be very tight. As soon as she was finished, several people blurted out questions. “What do we need to build?” asked one. “Who is even responsible for which part?” exclaimed the next. Others just had a puzzled look on their face. Watching the room unravel, I realized this tension was exactly what surfaces the real gaps. After sorting out the chaos, we worked through all questions. Many were answered by silence, people looking down, shuffling through their notes or looking at others for help. It was not clear what the answer was, or even who should answer. My colleague offered nervous smile, and raised eyebrows through the awkward exchange. Sounds familiar?

Awkwardness is the doorway to stronger teams.

After the exhausting meeting, her shoulders slumped and she stared at her notes in silence. My response, sitting through the meeting was different. I told her that this is exactly what we needed. Now we know what the gaps are and we got everyone engaged. Next, we created a list of the questions and who can help to answer them.

Why you shouldn’t avoid awkwardness

If you are looking for advice online, you will find countless articles on how to fix or even avoid these situations. ¹ ² ³ While this might make you feel better in the short term, I think this is the wrong solution. Awkward situations happen when information is unclear and people do not know how to act. This is the textbook definition of every new collaboration. If we value exploration and innovation, we should embrace the awkward first stage, and not avoid it.

The science behind psychological safety

Consider Amy Edmundson, who coined the term ‘team psychological safety’. It’s the shared belief that a team is safe for interpersonal risk-taking. Her research ⁴ shows that teams where people feel safe to admit mistakes and experiment learn much faster. They test ideas openly instead of hiding errors. That accelerated learning translates into stronger collaboration, innovation, and ultimately more successful teams.

“Psychological safety is not about being nice. [… It’s] the belief that you can speak up, ask a question, admit a mistake, offer a different perspective without fear of embarrassment or punishment.” ⁵ - Amy Edmondson

Awkward meetings are where this plays out - people stumble through half-formed ideas, silences, and mistakes. That’s not failure - it’s the process Edmondson describes.

As a product owner, showing comfort with uncertainty nurtures psychological safety, for example, by admitting you don’t have all the answers. It signals leadership and encourages colleagues to open up in difficult moments. Not only does this help you reach goals faster, it also sparks cultural transformation, making teams more resilient and innovative.

When awkwardness unlocks connection

Let’s step away from the meeting for a moment. Uncertainty shows up in other places too - when a new colleague joins the team, or when you sense someone is in distress but hesitant to open up. Choosing courage in those moments can be a superpower. It helps you move past hesitation and unlocks opportunities for deeper connection.

At the same time, not every situation benefits from bluntness. Sometimes patience or a softer approach is what builds trust. The key is to weigh your options and choose the path that nurtures openness without shutting people down.

Navigating cultures that punish vulnerability

What if your company prizes certainty and treats vulnerability as a weakness? Even then, don’t shy away from it - leaning into openness can spark cultural change for the better. The key is to frame the awkwardness beforehand, showing that it’s the fastest path to clarity.

By doing so, you make it clear the meeting isn’t going off-track by accident. Instead, you’re deliberately using candor to move toward certainty, while still aligning with the values your company holds.

Conclusion: From Awkward to Authentic

Awkwardness isn’t a flaw in teamwork - it’s the signal that people are stretching beyond certiainty and into honesty. Whether it’s a meeting full of half-formed questions, a colleague hesitant to open up, or a culture that prizes certainty, leaning into discomfort is what unlocks connection and growth.

As a product owner, you don’t need to eliminate awkward moments. You need to frame them, embrace them, and show that they are part of the process. When you do, you create psychological safety, accelearte learning, and spark cultural change. In the end, awkwardness is not the obstacle - it’s the doorway to stronger teams and more resilient organizations.