From Awkward to Advantage: Building a Culture That Evolves
Rich Allen
Helping CTOs, CPOs, Engineering Leaders, and teams optimise for faster flow of value | Author of User Needs Mapping | Team Topologies Valued Practitioner
Over the last few posts, we’ve explored how awkward team interactions can be frustrating, but also incredibly useful. They expose where responsibilities are unclear, where dependencies feel painful, and where current structures no longer reflect how work actually flows.
But awkwardness doesn’t just show us what’s broken. Handled well, it can become a source of ongoing learning and adaptation, a cue for teams to pause, make sense of the tension, and evolve in response.
This final post is about building the habits and conditions that make that possible, so that teams don’t have to wait for permission or a burning platform to make meaningful changes.
Awkwardness as Feedback
Most of the time, we smooth over awkwardness. We normalise it, joke about it in retros, build workarounds and move on. But in organizations that stay adaptive, awkwardness isn’t ignored or joked away. It’s treated as a feedback signal; a prompt to inspect the structure, not just the symptoms. If you want your teams to evolve without waiting for top-down change, here are five habits to help make that happen:
1. Notice More
Start by making it okay to notice. Encourage teams to name friction when they feel it; not with blame or defensiveness, but with curiosity. The goal isn’t to find fault, but rather to spot patterns.
You could ask:
2. Start Small
Once a pattern becomes visible, you don’t need a big fix. You need a small, thoughtful test.
Examples:
Safe-to-try experiments like these create the space to learn without making irreversible changes.
3. Reflect Regularly
After any such experiment, build in a reflection point. Don’t just assume it worked; learn from what actually happened.
Ask:
Reflection turns one-off tweaks into long-term capability. It also helps teams develop team interaction literacy, recognising how work, ownership, and interactions influence their experience.
4. Share What You Learn
If something works, make it easy for others to learn from it. When teams share how they spotted a signal, what they tried, and what they learned, it creates a distributed sense of awareness. It becomes easier to spot similar patterns elsewhere, and easier to ask for help when you're stuck. Aim to develop a way to spread useful stories.
5. Normalize the Evolution
The most adaptive organizations treat change the same way high-performing teams treat code: as iterative, testable and collaborative. They don’t wait for annual reorganizations; they notice, adjust and evolve. By treating awkwardness as a signal rather than a flaw, you can create a culture where continuous change isn’t scary, it’s expected.
Series Recap
This is the final post in my 'From Awkward to Aligned' series. Here’s what we covered:
Final Thought
If something keeps feeling awkward, there’s probably a reason, and it usually isn’t “people need to try harder.” It’s often a misfit between the structure and the flow of work. You don’t need a senior title to spot that, or a giant budget to act on it.
You just need to pay attention and be willing to try something small. To steal a line from everyone’s favourite philosopher-coach, Ted Lasso: “Be curious.”
Start with what you can see, try something safe, learn, repeat.
If you'd like help acting on awkward interactions you are noticing in your organization, feel free to connect and DM me.