Should I break rank?
Is it cool if you chat up your boss’ boss’ boss? Likewise, should I grab coffee with the intern even though they’re two or three levels down the ladder? Let’s break it down by org size.
Small places: easy and natural
At a small org (say, less than 30 people), you talk to your boss and your boss’s boss, your report and your report’s report. That’s because there’s, like, 30 of you and you all know each other. It’s pretty cool: you can all stay in sync, and unless someone’s super insecure, it’s no big deal to ignore the “chain of command”, if there even is such a thing. Job titles are pretty fluid anyway. From the position of influencing such a culture, most of your thought should be on what happens as the org grows, since this arrangement is lovely but doesn’t scale.
Overall, this is the easiest size to navigate, albeit the least stable over time.
Crossing hierarchical boundaries: socially acceptable and effectively built-in, and so politically acceptable and built-in, too.
Large orgs: structured, political, and sometimes even regulated
At a large org (200+1, bigger…), there’s a bit more charge and a lot more politics, but if you don’t regularly connect with folks that aren’t directly adjacent to you in the hierarchy, you’re uninformed of what’s going on at the line level, and probably perceived as somewhere between unimportant and an easy target by folks higher up the ladder. A common adage among individual contributors in orgs like this is that the easiest way to get a promotion is to change employers. Whether this is easier I leave as a personal judgment, but an alternative path is to establish and nurture connections more than one step up in the hierarchy & communicate a hunger to grow. There’s some political risk in operating this way, but also there’s at least as much risk in being perceived as easily disposed of. Smart orgs intentionally enable and foster folks’ ability to cross boundaries this way so they can grow and promote aspirational people & reduce confusion across the board. They do this by establishing clear communication policies (including examples of exceptions) and transparency around folks’ connections, while still encouraging a socially connected environment. Enterprises attract people that are pretty open about ladder-climbing, which further normalizes this behavior for everyone.
There can be a lot to navigate, but most of the rules are established and available, and their change is relatively slow over time.
Crossing hierarchical boundaries: socially optional, but politically expected and expedient, albeit not without some risk.
The weird middle: complex, undocumented, and evolving
Mid-sized orgs are where you need to be a lot more adaptable, attentive, and deliberate about how you engage. It’s much harder to be prescriptive at this rapidly-evolving organizational scale, but here’s what you can keep in mind:
- Formal rules and relationships are starting to emerge, but may not be officiated or written yet. Further, different folks will have different ideas about what these rules actually are, and what can or should happen if they’re violated (and whether that’s a good thing).
- Folks that have been at the org since it was much smaller are likely to have relationships that would be hard or impossible for a newcomer to establish and grow.
- Different orgs will have different cultures around the acceptability of jumping ladder-rungs; this is all the more pronounced at scale.
When working to handle and influence cross-hierarchy comms, you need to keep in mind where the org’s going, more even than where it came from. Folks might miss the casual and informal structure of being small, but that ship has sailed. Past about 50 employees, communication by osmosis has already stopped working. You’ll need to look to the way organizations larger than your own have established the rules of engagement and communication & got more deliberate around making those relationships transparent. Since this size org is generally in cultural flux, the goal here is less to get it right in great detail, and more to remain attentive and adapt as things change—what was right for you, your team, or your org a month ago may already be a poor fit. This is the most difficult and involved size of org to navigate in terms of cross-hierarchical relationships. In my experience, it’s also really rewarding when you get it right.
Crossing hierarchical boundaries: nebulous everywhere, but to your great advantage if you can navigate these churning waters.
A pro tip: Consultants in such organizations also have fewer such constraints—without the obvious incentive to climb the ladder themselves & a more nebulous reporting structure, it’s generally accepted and often explicitly encouraged for consultants at these mid-sized orgs to dance up and down the org chart. If you’re entering an org in this capacity, you’ll be at your most effective if you can use this to connect individuals and teams that otherwise would rarely communicate. And if you’re working in an org that’s recently retained a consultant, it’s well worth keeping this exception in mind & playing it to your advantage.
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(Note: Ctrl+Shift will be on hiatus this coming Monday and Tuesday, returning Wednesday.)
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Yes, I’m considering a 100-person organization to be “midway” between 10 and 1000. This is more about culture than numeracy. ↩︎