Stereotypically, start-ups have small teams, who are flexible, informal, and fast. They can quickly test new ideas, or pivot their whole business. If a job needs doing, everyone will just jump right in, without worrying about things like roles or risk or even ROI (so long as they are unconcerned about that other all-important R: runway.) 

In large enterprises, it’s the opposite. People are arranged in hierarchy, with formal processes and decision-making authority. Nothing happens without a lot of meetings and a lot of PowerPoint, especially if it’s a departure from the status quo. The whole apparatus is designed to contain risk and deliver predictability. 

In theory, neither model is good or bad — they just make different trade-offs to prioritize different outcomes. In practice, most start-ups wear their agility and speed as a badge of honour, and go out of their way to eschew the trappings of large companies. Yet if things go to plan, a start-up will begin to scale and the trade-offs will change. That’s when the trouble starts. 

As a company grows, “everyone will just jump in to solve the problem” starts to look like kindergarteners playing soccer. The whole team converges on the ball, leaving nobody in position to score or play defence. Inevitably, the enterprise starts to bring in more formal structures, often based on best practices from large enterprises. There are new processes, roles, committees, policies, and they solve the kindergarten soccer dynamic — but at a cost. 

One such cost is over-engineering. A company scaling from 50 to 500 does need more structure and process. But it doesn’t need anything like the formality of a 15,000-employee global giant. Since most people work at a business that is either small or large, we lack reference points for companies between 100 and 1,000 employees. As a result, scaling companies tend to default to the best practices of large enterprises, even if they skew too heavyweight and bureaucratic for their needs. 

The second cost is cultural. Employees with a start-up mindset like the freedom and flexibility that comes with being small. They value things like a direct line to leadership and the ability to build first and ask questions later. When a new, more formal structure comes in, they will squawk. To them, it feels like the walls are closing in — now, everything has to go to committee, where it will be slowed down, watered down, dumbed down. Frustratingly, that reaction isn’t restricted to 10 or 20 O.G. employees. Just about everyone who joins a scaling firm starts to idealize the glory days of their first few months, back when things were less structured — whether that represents a team of 130, 1,300, or 13,000. 

Our hypothesis: the root cause of this phenomenon is a tendency to frame start-up vs. enterprise as a dichotomy. Either you are small and agile (subtext: good), or you are large and staid (subtext: bad). But what if we framed it differently? What if instead we talked about the skills of stakeholdering and organizational alignment, and treated them as something to be deliberately cultivated and levelled up as the organization grows?

Because Stakeholdering and Organizational Alignment (let’s call it SOA, for short) is absolutely a skill. If you have ever worked with someone who is skilled at navigating a large, matrixed organization, you can see what a difference it makes. Whatever they’re working on, they know who to involve, when to involve them, and just what context to share to move their initiatives forward. Compared to start-up speed, their projects aren’t moving lightning-fast. But compared to their enterprise peers without similar SOA skills, they accomplish astonishingly large amounts in astonishingly little time.

However, in the start-up world, we tend not to credit SOA as a skill. We see it as big-company horsepucky and congratulate ourselves for being so much more nimble and flexible. It is absolutely true that there is something wonderful and powerful about being on a small team, where you can cover off all the SOA you need by dropping a message in the group chat. But we shouldn’t valorize that as some Platonic ideal. It’s a unique property of small teams that they can get by without exercising any great effort or skill at SOA. However, once a team gets to the 25–50 range, skilled SOA becomes increasingly necessary — not just for leaders or the People and Culture function, but for the organization as a whole.

In a SOA skills-based framework, the goal is that every individual is able to:

• Clarify their own role and its boundaries.
• Identify interdependencies between their work and related work happening elsewhere in the organization.
• Exercise judgement on when and how to engage with others (input vs. feedback, high-level direction vs. detailed refinement, live discussion vs. offline notes).
• Communicate their work to others in ways that are salient, relevant, and efficient.

One nice thing about this skills-based framing is that it is consistent over time. At every stage in the organization’s growth, you are asking employees to exercise the same SOA competencies, doubling down on what has always been important. Sure, as the organization grows, SOA skills look different. When teams are larger and work is more ambiguous, SOA becomes harder, more complex, and yes, oftentimes more formal. The group chat isn’t going to cut it anymore, so collectively, we all need to level up by adopting new approaches. But at their core, these are the same skills the company has always valued. 

Another nice thing about skills-based framing is that it gives individuals more agency as the company grows and changes. It’s not new processes or policies being imposed by the organization, but rather an opportunity to grow and develop. These are skills you can work to improve: during 1-on-1s with your manager, in formal training sessions, through on-the-job practice. Even better, SOA skills are highly transferable. No matter where you go in your career, it will always be useful to have a toolkit of ways in which you clarify roles, identify interdependencies, exercise judgment on engaging others, and communicate relevantly.

Finally, when you are recruiting folks from larger companies, SOA skills help you map the cultural differences between start-up and enterprise mindsets. That helps enterprise refugees adjust their priors and adapt more easily, because they have explicit permission to depart from however SOA looked in their previous organization.

In an ideal world, SOA skills-based framing also helps inoculate against the heavyweight and bureaucratic, so you are instituting just enough formal process. You aren’t bringing in OKRs because that’s what Google does — you are figuring out how to adapt SOA for your current size. With luck, not only do you have people who feel agency over the skills they are building, but also approaches that are more incremental, more lightweight, and more fit-for-purpose.