The Awkward Adolescence of Growing Companies

Companies do not go from “scrappy startup” to “well-oiled machine.”

They go from “scrappy startup” to “a stressed-out teenager wearing their parent’s suit jacket,” and then they stay there for years.

This is the awkward adolescence of growing companies, the phase where you keep the chaos of a startup and add the bureaucracy of a corporate org. You get the worst of both worlds, and everyone acts like it is progress because now the meeting has a deck.

I have a name for it: mid-growth dysfunction. It is what happens when a company tries to “grow up” without actually learning the skills of adulthood, like making decisions, setting priorities, or saying no to things.

Most companies treat this stage like a temporary inconvenience. “We are scaling, it is normal.” “Growing pains.” “Just hang in there.”

Cool story. Now explain why we have a weekly prioritization meeting for the prioritization meeting, but nobody can tell you what the actual priorities are.

This stage does not resolve itself. You do not “get through it” by working harder or by hiring a VP of Something Important who adds more layers and calls it operating model maturity. You resolve it by changing how the company makes decisions and how it communicates them, which is harder than pretending you are still a startup.

In a small startup, the chaos is at least honest. Decisions happen fast. Someone says “we are doing this,” and you do it. It might be a bad decision, but it is a decision.

In the awkward adolescence, the company introduces process, but it is not the kind of process that creates clarity. It is the kind that creates visibility theatre and plausible deniability.

You start seeing:

• approvals without clear criteria

• meetings without outcomes

• documents that exist to prove the document exists

• “alignment” as a substitute for leadership

• stakeholders who do not own anything, but can block everything

The company is not more disciplined. It is just louder.

The biggest shift in this stage is that decisions stop being made. Not because people are lazy. Because decisions create accountability, and accountability makes people uncomfortable.

So instead of deciding, the company:

• discusses

• explores

• aligns

• socializes

• revisits

• circles back

The goal becomes avoiding blame rather than creating outcomes. When the safest move is “let’s get more input,” you get infinite input and zero action.

You end up with two kinds of meetings:

1. Meetings where everyone agrees but nothing changes

2. Meetings where nobody agrees and also nothing changes

Either way, your calendar is full and your product is still on fire.

Early startups usually have one priority: survive. Ship. Keep the lights on.

In mid-growth dysfunction, the priorities become abstract and contradictory, like a horoscope for strategy:

• “Move fast, but be careful”

• “Be customer-obsessed, but hit the quarter”

• “Build quality, but ship yesterday”

• “Innovate, but do not take risks”

Every leader has a different interpretation, and the interpretation changes based on which exec had the last conversation with the CEO.

So teams do what humans do in ambiguous environments. They hedge. They build decks. They keep options open. They avoid committing to anything that could later be called a mistake.

This is how you end up with a roadmap that is technically a roadmap, in the same way a pile of spaghetti is technically a structure.

This stage is where burnout becomes a feature, not a bug.

The company is bigger, the scope is bigger, customers are louder, and the expectations are higher. The resourcing, however, is still “startup lean,” because leadership read a book about efficiency and decided headcount is a moral failing.

So you get:

• teams carrying multiple roles with no backfill

• constant “just one more thing” scope creep

• heroic efforts treated as baseline performance

• missed deadlines blamed on execution instead of capacity

The company keeps demanding “senior level output” while refusing to fund “senior level systems.”

People burn out, and then leadership says things like “we need to focus on wellness,” as if wellness is a mindset problem and not a math problem.

This is one of the more insulting parts.

The company starts adding gates, committees, and approvals. Everything takes longer. The feedback loop gets slower. The cost of being wrong increases, so people take fewer swings.

Then leadership gets on stage and says, “We need to be more innovative.”

No, you need to stop punishing innovation. You cannot build a system that rewards caution and then act surprised when everyone becomes cautious.

Mid-growth dysfunction is when bold ideas die in meetings, not because they are bad, but because nobody wants to be the person who took the risk.

Middle managers in this phase get hit from both sides.

From above: “Why is delivery slow. Why are we behind. Why are we not executing.”

From below: “What are we doing. Why are we doing it. Who decided this.”

If leadership does not provide clarity, managers start manufacturing control. That turns into:

• constant status reporting

• excessive tracking

• intrusive check-ins

• decisions being escalated because nobody feels safe making them

It is not because managers love micromanagement. It is because the system makes control feel like the only lever available, and fear is a hell of a motivator.

At a certain size, you cannot run a company by shouting across the room. That part is real.

The problem is that many companies respond by increasing communication volume, not communication clarity. You get:

• announcements that say nothing

• updates that are all framing and no decisions

• threads where nobody answers the question

• meetings that exist to restate the meeting that happened last week

This is where “transparency” becomes a performance. Leadership shares more words, but fewer facts. People feel informed, but they cannot act, because nothing has actually been decided.

Startups are often chaotic, but they can be good for growth because you can take on real scope fast.

In the awkward adolescence, you get the opposite. The company is too big to hand you scope without coordination, and too immature to provide clear career paths.

So growth becomes:

• dependent on who advocates for you

• tied to visibility instead of impact

• based on whatever the current leadership narrative values this quarter

People who are great at the work get stuck. People who are great at self-promotion get rewarded. Everyone learns the lesson, and the company slowly becomes a stage production of competent-sounding people.

This dysfunction is not inevitable. It is common, but it is a choice.

A company can grow and still operate like adults. The difference is whether leadership is willing to:

• set clear priorities and stick to them

• define decision rights so teams can actually move

• fund the systems that scaling requires

• remove rituals that do not create outcomes

• tell the truth about tradeoffs

If leadership will not do those things, the company becomes a place where everyone is busy, nobody is sure what matters, and the product moves slower every quarter.

If any of these feel familiar, congratulations. You are living in mid-growth dysfunction:

• You do more reporting than building

• “Alignment” is a recurring deliverable

• Everyone complains about too many meetings, and then schedules more meetings

• Priorities change, but the old priorities never get cancelled

• Decisions get delayed until they become emergencies

• People are rewarded for looking busy, not for finishing

If you are thinking “yes, all of that,” you are not alone. Many companies park here and build a whole life in the messy middle.

The awkward adolescence of growing companies is what happens when a business scales its headcount and revenue, but not its decision-making.

You cannot out-hustle this stage. You cannot fix it with another meeting. You cannot solve it with a new template.

You fix it when leadership stops being scared of making calls and starts building a real operating system, one that creates clarity instead of noise.

Until then, enjoy the teenage phase. The acne is metaphorical, but the frustration is very real, and yes, it is a lot of bullshit.