Scaling teams breaks down when clarity slips. Learn the three leadership mistakes that create confusion and how experienced operators prevent them.
This piece is adapted from an Operators Guild Focus Session on Managing up, down, and sideways, featuring insights from seasoned operators in our community. Focus Sessions are small-group, member-only deep dives where operators pressure-test decisions, share lived experience, and get into the practical realities that don’t make it into blog posts or conference talks. If you want access to conversations like this — the recordings, the decks, and the community behind them — you can apply to join OG.
Most teams don’t fall apart because of bad intent, low effort, or weak talent. They stall because small leadership missteps compound over time — usually around clarity, communication, and expectations.
What makes these mistakes dangerous is that they rarely look dramatic in the moment. They feel reasonable. Even responsible. But at scale, they create confusion, resentment, and preventable failure.
Here are three mistakes leaders make again and again as organizations grow — and the operating habits that actually work instead.
Mistake one: waiting to communicate until the story is “ready”
When priorities change, many leaders pause.
They want to understand the full context. They want alignment. They want to anticipate questions. They want to be precise. So they wait — a day, sometimes two — before saying anything.
By then, the damage is already done.
Teams do not pause while leaders are thinking. Other functions reprioritize. Dependencies shift. People continue working under assumptions that are no longer true. By the time the update lands, the team feels behind, confused, or blindsided.
This is how churn starts — not through chaos, but through silence.
What strong leaders do instead
They separate signaling from explaining.
If something changes that affects the team’s work, they send a fast signal immediately, even if the details are incomplete. The goal is not resolution. The goal is alignment.
A simple structure works:
- What changed
- What to do right now
- When more context is coming
That early message stabilizes the system. It prevents other teams from getting ahead of you. It tells people you’re paying attention.
Precision can come later. Speed cannot.
Mistake two: assuming expectations are “obvious”
Many performance problems get misdiagnosed as motivation or capability issues when they are actually expectation failures.
Leaders assume people know:
- What good looks like
- How success will be evaluated
- Which tradeoffs matter most
- Where the role’s boundaries are now, not six months ago
But roles evolve faster than expectations get updated — especially in growing companies. What started as “we’ll figure it out together” quietly turns into unspoken benchmarks that only surface during reviews.
That is where trust breaks.
No one should learn the rules of the game at the moment they are being judged.
What strong leaders do instead
They make expectations explicit before they matter.
That means:
- Defining current success, not historical role definitions
- Sharing how performance will be assessed well ahead of review cycles
- Giving feedback continuously, in small, specific doses
Strong feedback is not dramatic or infrequent. It is calm, frequent, and boring. It removes ambiguity long before stakes are high.
The standard they operate by is simple: no surprises.
If someone is going to miss the mark, they should know early. If expectations shift, they should hear it in real time.
Mistake three: letting critical work stay invisible
Some work naturally gets credit. Some work disappears into the background.
Revenue closes are visible. Product launches are visible. Infrastructure, finance, risk mitigation, and operational discipline often are not — until something breaks.
When essential work stays invisible, it gets undervalued. When it’s undervalued, teams struggle to get resources, credibility, or trust. Over time, that invisibility turns into disengagement or quiet resentment.
This is not a personality problem. It’s a systems problem.
What strong leaders do instead
They treat visibility as part of the job — without turning it into self-promotion.
The goal is not to impress. It is to make work legible.
That often looks like:
- Translating work into outcomes others care about — time saved, dollars protected, decisions accelerated
- Sharing short, consistent updates that explain what changed and why it matters
- Creating simple artifacts — dashboards, commentary, recurring summaries — that tell the story over time
For teams like finance or operations, this can be especially powerful. A clean close, clear forecasting, or strong risk framing directly improves executive and board decision-making. When leaders can move faster and with confidence, the value becomes obvious.
Visibility does not need theatrics. It needs consistency.
The throughline: reducing surprise is leadership leverage
Across all three mistakes, the same pattern shows up.
Problems emerge when leaders:
- Delay communication
- Leave expectations implicit
- Assume impact will be understood without translation
Strong operators do the opposite. They communicate early. They repeat themselves. They clarify ownership. They make work understandable to the people who depend on it.
They are not perfect. They are predictable.
And that predictability is what allows teams to move quickly, trust decisions, and adapt as the company grows.
Scaling is not about having the cleanest org chart or the most elegant framework. It is about reducing surprise — in priorities, in performance, and in how work is valued.
That is how teams stay aligned when everything else is changing.
If you want, I can:
- sharpen this further for SEO,
- add a stronger opening hook,
- or adapt it into a shorter, more opinionated LinkedIn-style essay without losing substance.
Where operators actually compare notes
These conversations are happening inside OG every week in Focus Sessions, small groups, and ongoing threads where operators bring real problems and real context. OG is where senior operators go to pressure-test decisions, learn from lived experience, and build judgment alongside peers who’ve been there before.
If you want access to discussions like this, consider applying to join OG.