How Your Org Chart Decides For You

Without knowing anything about your company, I’d bet your lawyers aren’t advocating for taking on more risk. And your Customer Success team probably isn’t pushing you to deprioritize a feature their client wants. It’s not about personality quirks; it’s the role. The same predictable tug-of-war plays out nearly everywhere.

Often this starts with incentives. As much as your CEO wants everyone to prioritize the long-term health of the company, the humans making up the company tend to have conflicting priorities. If a Customer Success rep is quietly angling for a job at the client’s firm in two years, they’re going to have a hard time saying no to them. Doing so would require putting their current company’s needs above their own long-term career aspiration. And even if the company succeeds, they’re only going to make a sliver of what the CEO does.

The simplest way to avoid this is to hire incredible individuals who can see past the incentives their roles try to force on them. At AngelList I had the privilege of working with both lawyers who viewed the legal as something to be engineered around and customer support reps who delighted in getting on the phone with an upset client. But such people are rare, and any role that relies on consistently making 10/10 hires is unlikely to be durable. It’s a bit like a struggling football team using its top draft pick on a star quarterback and hoping he’ll fix everything. Maybe he will! But far more often, even great talent will crumple without support (offensive line, receivers, etc.). When that happens, the team is right back where it started, burning another high pick on the next supposed savior.

So it’s often better to manage these incentives at a macro level. Since each department has its own objectives, healthy companies can effectively crowd-source across all of them to arrive at the right decision. You could probably map this out for every department at your company if you spent 5 minutes thinking about it: Your sales team wants to support every possible product customization and adds yes energy. Your compliance team doesn’t want to miss a critical gap and adds no energy. Etc. etc. Then, the company just needs to decide the balance it wants. If growth stalls, add more “yes” energy. If quality slips, do the reverse.

A more insidious danger occurs when specific departments become predictable. If security says no to every single request, people are going to realize that and route around them. That’s how you ship a product that has a critical zero-day exploit and a front-page feature on Troy Hunt’s blog.

As companies grow, they naturally tend to accumulate more no energy. Beyond introducing guardrails and process, there are also simply more people who want to review decisions. 12 people reviewing a product brief or hiring decision means 12 people who could veto it.

That no might be for an entirely legitimate reason, but often it’s a reflection of risk-aversion. A bad yes is a visible failure: a production incident, a product launch that flopped, a buggy system design. A bad no quietly disappears.

Institutions like the FDA illustrate this perfectly: they’re punished for approving a harmful drug, but rarely for delaying a helpful one. This dynamic is so entrenched that they can only overcome it when the downsides are incredibly apparent (like COVID). Most companies inherit this same asymmetry. You never see how good that candidate would’ve been or how much your customers would’ve loved an aborted feature.

When a company settles into this state, it typically falls to the company’s management chain to restart the machine. To tease out the truly critical product gaps from your boy-who-cried-wolf sales team and navigate the blockade on new requests your engineering team has set up. It’s a hard job, and any mistakes will be immediately visible — wasted quarters of work, people you have to fire, and flopped product launches. It’s easy for smart, talented people to retreat into safe decisions and wins for their team. Over time, this calcifies into a stasis where everyone is busy but nothing important gets done.

In my mind, this is the core difference between management and leadership. Management implies keeping people reasonably content. Leadership implies striving towards some difficult goal, which necessitates taking risks. Yes, leaders will make mistakes, but honestly picking the wrong direction and marching towards it in unison is often a better option than keeping the status quo. Even if you’re wrong, at least you’ll learn something from it.

As a visceral example, I don’t think a manager is truly a leader until they’ve fired someone. Not because of the experience itself (which sucks, but must pale in comparison to getting fired) but because it shows they took a risk and faced the consequences when it didn’t work out. Those are the people you truly need on your bench to navigate interdepartmental dynamics and cut through the tension.

Regardless of where your company might fall on this spectrum, it’s never going to eliminate tension between roles. Tension is healthy. Agitation creates momentum and energy from stasis. Constraints breed creative thinking and 10x solutions. Instead, the goal should be to monitor tension and tilt it intentionally to reach a happy medium.