Democratizing Storytelling in Mid-Sized Organizations

Angelina Gennis studies what happens when organizations cross the threshold from small to medium-sized. As a principal analyst at Forrester leading research on culture and change management, she’s watched countless companies navigate the transition—and the patterns are consistent.

In small organizations, culture operates almost automatically. Founders model behavior, tell stories, and everyone absorbs how things work through proximity. But as companies grow, that informal transmission breaks down.

“From a change management perspective, we also see, as you go from small to medium, that there needs to be more policy, more governance, more structure in place—that the ‘I wear every hat’ needs to get yielded to ‘what’s my lane in this, and how do I ensure that everyone understands their role in collaborating?’”

Growth does bring positive changes that feel great. B2B companies start feeling like legitimate competitors and can walk into major potential customers with a strong track record and reputation. B2C companies finally get breathing room to think strategically instead of just sprinting to execute. Growth creates the space to ask: Who do we want to be?

But growth also creates tensions. Some people who were heads of departments realize they don’t want to be executives; they want to stay close to the work.

“I’ve seen this happen in rapid growth—someone in that lead role says, I don’t want to be an executive. I want to be an individual contributor. I want to do what I love, and what we’ve been doing so far has been the real work, and as we expand, I see myself moving further and further away from the real work.”

Others get pushed down a level when more experienced leaders are brought in. And when new leaders arrive with their own playbooks, the culture can shift significantly.

The managers caught in the middle face a particular bind. They rose because they were good at the work, not because anyone prepared them to lead. New hires arrive asking for best practices, and managers realize those practices exist only as unwritten knowledge.

“What usually tends to happen is you’ve got folks holding onto an old culture. Teams that are growing, coming in, looking to say, ‘What is the culture? What’s important here? What are our best practices?’ A lot of those aren’t defined, they’re just kind of known or felt. They’re just expecting folks to understand how to behave, what to do, and there’s a lot of gaps that they don’t see.”

As teams get bigger, managers can’t operate the way they did before. They need new skills—coaching, understanding delegation, tapping champions to support the culture.

“We like to say at Forrester, managers can’t be coaches, but they can be coach-like. Because they have this top-down accountability which prevents them from being purely coaches. But they should be coach-like, and they should encourage their teams to figure things out rather than micromanage the way they may have been able to do in smaller organizations.”

When Angelina works with struggling organizations, she finds the root problem is often surprisingly simple: executives aren’t having real conversations with their managers. They default to surveys and focus groups instead. Speaking of one large organization, she laments the lack of those informal one-to-one conversations.

” I don’t think that leaders are asking managers what they need. So there is a lack of employee listening to determine the right tools, the right resources that are best fit for that individual and that team. The idea of the executives just having a few conversations with employees to figure out the problem they’re trying to solve seemed ridiculous in their culture, which is unfortunate.”

The same dynamic plays out in many organizations as they get larger: employees don’t want to look like they messed up, so they hide problems. Managers don’t want to appear weak, so they stop asking for help. As organizations grow, walls accumulate between what people know and what they’re willing to share.

Leaders break through by modeling openness themselves. And sometimes the answer isn’t a resource-heavy program at all.

“Leaders set the example: by being an open book, by modeling, by storytelling. And then they invite the middle management to do the same. And in that you’ll find a unique answer to what the managers need most. And it doesn’t need to be a resource heavy answer. It might just be ‘we need permission to say no. And when you give me permission to say no, it gives my people the permission to say no.’”

If Angelina had a magic wand, she would give every leader full change management capabilities (the skills, resources, and time)—the ability to see all the change ahead, assess risks and skills gaps, and communicate authentically. That’s what growing organizations need most: not to fight the change, but to embrace it.

Her advice for leaders approaching mid-size carries a warning about what happens next.

“As you grow, you’ll feel like you should succumb to metrics, to defining success by numbers, to living and dying by a metrics target, and to shifting the pressure to achieve those targets to the folks below you, and they will shift that pressure to the folks below them. But there is no metric or index of metrics that will tell the full story. So you always have to have a system for explaining and thinking.”

Metrics obsession is rampant in larger organizations. But no index tells the full story.

“Being realistic and being human centric as numbers start to take over your life is critical. Have a process for designing your own metrics. Have a process for requiring everyone to explain when they put a number out there, and have a process for protecting people from metrics obsession.”

This means that the transition from small to mid-sized is not just about transformation but about preservation—holding onto the human element that made the early days work, even as everything else changes.