TBM 353: Conversation Quality and Scale

Help Needed!

If you enjoy my newsletter, and want to help me out somehow, please take a couple minutes to fill out this quick survey on meetings/rituals at your company.

Fun Stuff!

• TBM posts are now searchable all in one place. This is an experiment. What do you think?

• I used AI to extract 270 specific behaviors and 180 rituals mentioned by ~10 guests of the

  Lenny's Newsletter
  podcast. Check it out!

---

I've been on a kick recently about conversations and interactions. You can often "just tell" how a team (or company) is doing by listening deeply to their conversations and observing how they interact. You can also boil an operating system down to how intentional people are about creating conditions where awesome conversations can happen at the right time and with the right people involved.

In this post, we will consider the "quality" or "maturity" of conversations and interactions on several different levels.

Conversation and Interaction "Maturity"

First is something that looks like your standard "maturity model." I'm not a big fan of maturity models since they 1) assume things are linear and 2) are often created "backward" (the five columns) vs. any real theory of causality, a performance goal, and a sense of the actual distribution across the levels.

But I'm going to fight my normal bias and share this overview of different classes of conversation/interactions and what they look like across a spectrum of absent/ad-hod all the way up to reflexive and integrated.

Be kind here, this is a V0.1.

A couple of points and probing questions:

• Yes, being at a five sounds great. But is it required in your domain?

• Assuming you have gaps—we all do—how will you decide where to focus?

• Is where to focus a strategic decision?

• Are there related discussions? Could a company with two on Strategic Depth be a four regarding Customer Value?

• There are plenty of "high-performing companies" (by some measure) that are somewhat pathological (Levels 1-3 in terms of Org Health & Tensions). Are they truly high-performing?

Scale

I looked at this table for a few minutes, and while I found it helpful, something was nagging at me.

There's very little sense of scale. What if you have a company where excellent conversations are happening locally but struggle to scale—either vertically (up and down reporting lines) or horizontally (across teams and functions)? The table above doesn't capture how local excellence might still fall short.

So, I took a stab at a companion lens:

You could imagine this as an extra dimension for each row I referenced in the first table.

An interesting caveat:

It is easy to look at the upper right cell (Org-Wide/Integration and High Performance) and imagine this is where everyone should aspire to be. However, one might argue that it is extremely difficult to get to that level, especially during periods of rapid scale. You risk a certain fragility if you push too far to integrate everything. You should really be seeking minimally viable global consistency. If there's too much need for org-wide clarity, you might be experiencing too many dependencies.

On the flip side, many rapid-growth tech companies struggle with being too far in the other direction (High Performance / Local). There's so much emphasis placed on team autonomy and moving fast that very few effective conversations happen between teams (even when they need to happen). As we learned recently, many companies were caught flatfooted when the ZIRP wave ended—they had no real OS for org-wide coordination.

Implicit Vs. Explicit

Interestingly, depending on the organization's culture, this maturity can take different forms. Some teams at this level may still lean on explicit frameworks and structured approaches because skilled people still use scaffolding. But others become much harder to pin down. They pivot quickly between different methods, remix tools as needed, and rely on shared instincts and trust to navigate complexity.

Here's a quick overview of that 9-box.

Some interesting things to note:

• There is nothing inherently good/bad between high formalization and low formalization, BUT you'll need some formalization in scaled settings.

• There ARE fluent teams that use high formalization and shared language. And there are early/struggling teams that use intentional scaffolds. Knowing the difference between these contexts is important. So is when to release those scaffolds.

• Even fluent teams may need scaffolding during periods of rapid change or disruption. But they do so with the explicit plan to release that level of formalization.

Skills, Or Something Else?

I've written in the past about focusing on behaviors. Conversations and interactions are behaviors.

There is a skill component to this—but it is only part of the picture. Imagine you worked at a company that had figured out how to design and build great products. You are used to certain conversations happening. You walk into a new company, and none of those conversations happen. One possible hypothesis might be that the people at this new company lack certain skills.

In the linked post, Julie Dirksen provides a great list of reasons why it may not be a training issue.

The following are problems that may have a training component, but they're not first and foremost about teaching learners how to do the behavior. Sometimes training can help, but often, other issues in the environment or the system also have to be addressed for the behavior to change:

• Lack of feedback

• Unclear goals

• Unlearning an existing behavior

• Unawareness of consequences/ bigger picture

• Lack of environment or process support

• Anxiety/ fear/ discomfort

• Lack of confidence/ belief about capabilities

• Mistrust

• Social proof

• Lack of autonomy/ ownership

• Learned helplessness

• Misaligned incentives

• Lack of identity or value alignment

• Emotional reaction

Of course, you could try to tie any of the gaps above into a manager's or leader's skill set, but that's a topic for another day.

There are other explanations. If you have only worked at a handful of companies, you may be biased to how people in those companies, in context, did their work. Maybe your new company has more of a writing culture. Maybe there is less disagreement in groups. Maybe UX Research doesn't feel the need to formalize everything.

Sometimes, the most skilled people—assuming their experience is narrow—are the most stubbornly opinionated and close-minded about ways of working.

Questions to consider

• When I reflect on my team's conversations, what do I hear? Do they sound rushed? Safe? Curious? Avoidant? What's the overall tone, and what might it reveal?

• Are we designing for the conversations we wish we were having or the ones we have? Where is the gap between aspiration and reality—and is anyone naming it?

• What kind of scaffolding do we rely on, and have we outgrown any of it? Are we holding onto frameworks or rituals that served us once but are now getting in the way?

• Where do great conversations already happen in my company, and why are they there? What conditions made those spaces possible, and could those be replicated or protected elsewhere?

• Have we confused autonomy with isolation? In our pursuit of team independence, have we lost the ability to coordinate when it matters most?

• Are we so fluent and reflexive that newcomers are left behind? What might feel natural and seamless to us could feel invisible and exclusive to others.

• Are the "bad conversations" really about skills, fear, friction, or lack of trust? What's underneath the silence, avoidance, or tension?

• What conversations don't happen at our company—but should? And who's missing from the ones that do?

• What would change if we saw every interaction as a reflection of our operating system? What are we broadcasting?