What to Do When Your Smartest People Hate Each Other

Let me describe a scene and you tell me if it hits too close to home:

You’ve got two brilliant people.

One owns the product vision like their life depends on it. The other? Ops genius. Gets things done at warp speed.

Both are respected. Both are valuable. Both… can’t stand each other.

And you?

You’re stuck in the middle, praying one of them takes a sabbatical before Slack becomes a battlefield.

Let’s call it what it is: the brilliant co-worker clash. The kind no training video prepared you for.

Smart people, sharp edges

People with high cognitive horsepower often come with… let’s say… strong opinions delivered at volume.

They want control. They hate inefficiency. And most of all? They deeply resent having to explain themselves to someone they don’t respect.

It’s all about power, identity, and perceived value.

Here’s what I know:

• Threat to status or competence → amygdala lights up

• Amygdala lights up → prefrontal cortex goes dark

• Prefrontal cortex goes dark → no logic, no empathy, just ego warfare in a Google Doc

So when two A-players start side-eyeing each other on Zoom and “cc”-ing you into oblivion, don’t expect it to fix itself.

This is a leadership-level system failure, and it’s on you to intervene.

What won’t work

1. Telling them to “talk it out” over coffee

2. Mediation sessions without structural change

3. Hoping it dies down (it won’t, it metastasizes)

4. Forcing one to “be the bigger person” (congrats, now you’ve lost both)

What does work

This isn’t about making people like each other about making collaboration functional, even if feelings are…less than warm.

Here’s a proven (by me and teams I worked with) 4-part protocol I’ve used in toxic-simmering-into-full-boil teams:

1. Name the dynamic out loud (with neutrality)

Example:

“I’ve noticed consistent friction between you two that’s slowing down execution.”

You’re not asking for emotion. You’re naming a system behavior.

Think: surgeon, not therapist.

2. Map the collisions

Use a simple diagnostic:

• Where do their responsibilities overlap?

• Where are their definitions of “success” in conflict?

• Where are decisions delayed because no one trusts the other’s judgment?

Put it on paper. Literally. Visual tension is easier to defuse than invisible resentment.

3. Redraw ownership with surgical clarity

Conflict thrives in ambiguity. Fix it by redefining who owns what and how disagreement is escalated.

Use this template: X owns the decision. Y has input. If they disagree, Z is the tie-breaker.

4. Install new interaction rituals

Don’t just say “communicate better.” Build new rules:

• Weekly alignment call with a fixed structure

• “Request → Response → Record” feedback loops

• A third-party (you or ops) to moderate high-stakes convos for 30 days

People behave better when systems make misbehavior obvious.

If the tension continues despite the structure?

You have a prioritization decision to make:

• Who is mission-critical and collaboration-capable?

• Who might be brilliant but is burning down the village to prove a point?

Sometimes, the smartest person in the room isn’t the one you need long-term. They’re the one teaching you where your values stop being real.

Feedback Culture Is a Lie (And Everyone Knows It)

Let’s not waste time. You don’t have a feedback culture.

You have a “don’t get fired” culture.

You have a “smile during the Zoom call and then vent in Slack” culture.

You have a “we put Radical Candor in our onboarding doc but we actually punish people for speaking up” culture.

Feedback culture? Cute.

Your team doesn’t need another values slide. They need a system that doesn’t make their nervous systems short-circuit every time someone says, ‘Can I give you some feedback?’

Let me guess:

You say “We welcome open, honest dialogue.” But people still spend 30 minutes rehearsing a 2-sentence opinion.

And your highest-paid person in the room never gets challenged.

And the person who did speak up in last quarter’s retro now looks like they’ve been sent to the shadow realm.

Here’s why it happens

Let’s talk biology, because trust falls aren’t going to fix this.

Humans are wired to avoid social pain. Your brain treats psychological threat the same way it treats physical threat.

You think your team is being “quiet” because they’re disengaged? No. They’re just protecting themselves.

Fight, flight, freeze.

Except in the workplace it looks like:

• Smiling while silently panicking

• Not replying to that “please share your thoughts” thread

• Watering down every comment until it’s basically soup

So what do we do? Burn it all down? (Tempting, but no.)

No. You rebuild feedback as a system.

1. Stop asking for “feedback.” It’s a cursed word.

Instead, ask:

• “What’s one thing I did this week that made your job harder?”

• “What’s something I keep doing that you think is actually hurting the team?”

Train your people to give DATA, not drama. Let feedback be small, frequent, and boring until it becomes normal.

2. Ritualize it or forget it

You want feedback to be a habit?

Cool. Then make it a part of your calendar. Literally.

• End every team sync with “1 up, 1 tweak”

• Run “Feedback Fridays” where people anonymously write what’s helping/hurting execution

• Add “Give one piece of feedback” as a recurring line in your OKRs. (No, I’m not kidding.)

3. Change what happens after the feedback

This is the killer. If someone gives honest input and then:

• Nothing changes

• Or they get left out of the next project

• Or you say “Thanks, noted” and ghost them

…then it’s over. Game’s done. No one will ever speak up again.

Reward the risk. Even if the feedback is messy. Especially if it is.

If you’ve made it this far: you probably already know you’ve got a problem

Good. Admitting it is the first step. Now here’s your 3-step homework (of course it is):

1. Identify one place in your team where truth is hiding

2. Design a repeatable ritual to bring it out

3. Make damn sure no one gets punished for telling it

Feedback culture isn’t “being nice.” It’s being operationally brave. And if your team isn’t telling you the truth, they’re telling someone else.

Their friends. Or Glassdoor.

Time-to-Productivity: Why It’s Slower Than You Think (and What to Do About It)

In your head, it’s 90 days.

That’s how long you expect a new hire to ramp. Three months, give or take. Enough time to learn the tools, meet the team, and start delivering. It sounds reasonable. Feels reasonable. It’s also wrong.

Because in practice, especially in hybrid or remote teams, time-to-productivity stretches like a rubber band.

According to research across fast-growing tech companies (50–500 employees), real ramp time ranges from 3 to 9 months for most roles. For engineers and product teams? Closer to 6-12 months. Even sales reps, supposedly fast to onboard, often take 90+ days just to hit quota for the first time. And that’s with support.

A Gallup report reflects that a new employee takes around 12 months to meet productivity standards. Human Panel is a little more optimistic, estimating it to be about 8-10 months.

So, why the lag?

Because scale-ups don’t hire in a vacuum. They hire into chaos.

Let’s look at the systems.

The Welcome That Never Lands

Startups with 50-100 employees often pride themselves on “personal onboarding.” But what that actually means is:

“We haven’t documented anything, so John will Slack you stuff as you go.”

That works... until it doesn’t.

When new hires are remote, you lose all the ambient learning. No desk neighbor. No “just overheard” clarity. And when no one owns onboarding end-to-end, time-to-productivity slows not because the hire is incompetent, but because nobody told them what ‘productive’ even means here.

100–500 Employees? Now You’re Formalizing… Sort Of

Mid-sized tech companies tend to have a People team. Maybe even a full-time L&D hire. Great.

Except now onboarding gets split across HR, IT, compliance, managers, and culture committees, and the new hire is stuck assembling meaning like a jigsaw puzzle.

You get welcome emails, Day 1 Zooms, and a Notion page called “Start Here,” last updated eight months ago. The result? Activity without clarity. High effort, low signal. And your new hire might be logging hours, but they’re not accelerating output.

So, What Works?

Structured 30-60-90 Plans

“Learn as you go” sounds scrappy... until it turns into “float until you sink.”

The fastest-growing teams don’t guess their way through onboarding. They build 30-60-90 day plans with actual deliverables tied to role-specific outcomes. Not vague goals like “get familiar with the product,” but concrete milestones like:

• Day 30: Complete onboarding modules + shadow 3 customer calls

• Day 60: Lead internal project update + push first feature to staging

• Day 90: Own key accounts or launch a feature end-to-end

One VP I worked with called it “training wheels for ambiguity.” It gives new hires direction without suffocating initiative and gives managers a way to measure progress that’s more meaningful than “they seem busy.”

These plans also clarify when a hire is truly ramped, so you’re not sitting in month five asking, “Are they…doing okay?”

Self-Service Is Speed: Remove the Middleman

Every time a new hire has to ping their manager for a password, a policy doc, or “that one deck from last quarter,” you slow them down.

High-functioning teams design for self-service from Day 1:

• Wikis and internal handbooks (e.g. Notion, Confluence, GitLab’s open handbook) that act as onboarding GPS

• Onboarding portals like WorkRamp or BambooHR that guide employees through setup, training, and expectations

• Role-specific “starter kits” - curated folders with everything a new engineer, PM, or CSM needs to survive their first 30 days

• AI assistants or chatbots (e.g. Paradox.ai, custom GPTs) that answer FAQs like “Where do I submit expenses?” or “What’s our API rate limit?” - 24/7, no manager required

At one company I advised, we built a Notion-based “First 10 Days” board with embedded Loom videos, SOP links, team intros, and a running FAQ. It cut manager time spent onboarding by 40% - and gave new hires a sense of ownership from hour one.

When a system makes the right thing easy to find, productivity isn’t just faster, it’s inevitable.

If your onboarding depends on heroic managers or Slack archeology, you’re not onboarding - you’re hoping.

And hope is a bad operating model.

At one scale-up I worked with (~50 employees, mostly remote), we realized time-to-productivity was dragging, especially for ops and customer-facing hires. Onboarding was a Slack thread here, a Notion link there. No path, no milestones, no clarity.

Here’s what we did:

• Documented reality. We mapped what successful team members actually did in their first 30, 60, and 90 days. Not what we thought they should do. This helped us create role-specific onboarding tracks.

• Gave managers a playbook. Instead of winging it, managers got templates for welcome messages, Day 1 checklists, and weekly check-ins. They loved it. So did new hires.

• Used async rituals. We created onboarding videos for key tools, short “how we work” Looms, and a weekly async “get to know your team” board in Notion. It scaled without Zoom fatigue.

• Set a definition of done. For each role, we defined what “fully ramped” looked like. For example: for a Customer Success Manager, it was owning X accounts and leading Y calls independently by Day 60.

RESULT: New hires hit autonomy weeks faster. Managers stopped dreading onboarding. And leadership had visibility into whether onboarding was actually working, not just “feeling okay.”

TL;DR: If You’re Scaling, Fix This First:

1. Define what “fully ramped” means per role. Not just “feels productive” - measurable outputs.

2. Build onboarding for reality, not fantasy. That means cross-functional coordination, not just a Day 1 deck.

3. Give hires access to what they need without gatekeeping: clear expectations, internal tools, social context.

4. Shorten the distance between starting and contributing — with structure, support, and simplicity.

Because the real risk isn’t that your new hires take too long to ramp. It’s that nobody knows when, or if, they ever did.

Stretch Goals, Stretched Teams, and the Science of Giving Up

OKRs are supposed to be simple. Set a goal. Track it. Celebrate.

Except that’s not what happens, is it?

What happens is: you launch a shiny OKR framework at the all-hands. Everyone nods. Slack emojis fly. Then Q2 hits, and… nothing.

No one updates their progress. Objectives go stale. “Stretch goals” become inside jokes. And by the time the exec team does a retro, you’re asking: “Did we even use OKRs this quarter?”

The Brain Science of Why OKRs Fail

1. Cognitive Overload: Humans can’t juggle 10 priorities. We think we can, but our prefrontal cortex taps out after 3 or 4. Pile on more, and people either shut down or default to old habits. (Usually email. Or doomscrolling.)

2. Reward Prediction Error: If the gap between effort and reward is too big, the brain stops caring. That “10x moonshot”? It sounds ambitious. But to the brain, it’s demotivating. Your team needs micro-wins, not just one big parade in December.

3. Unclear Cues = No Action: Behavioral science 101: No clear trigger, no behavior. If the OKR isn’t tied to a weekly workflow, it’s just a sentence in a doc nobody opens.

So how do you make OKRs actually work?

Let’s make it tactical. Here’s how I build OKRs that survive Q2:

1. Fewer. Clearer. Tied to behavior.

Set no more than 3 Objectives per team. And make every Key Result observable. Not “Improve product-market fit.” Say:

• “Conduct 10 user interviews/month”

• “Launch V2 onboarding flow by July 15”

2. Link to weekly rituals

• Every Monday = status check.

• Every Friday = KR review.

No extra meetings. Just slot them into existing standups or team check-ins. The brain loves rhythm. Use it.

3. Make them visual, not invisible

Goals hidden in dashboards don’t exist. Use posters. Whiteboards. Miro. Widgets. Whatever keeps the goal in visual working memory.

4. Tie incentives to progress, not perfection

Celebrate progress early and often. The dopamine hit of “moving closer” is what keeps people trying. Not a quarterly scorecard.

OKRs are not just strategy tools. They’re behavior-shaping tools.

And if you want your team to follow through, you need to design them like behavior-change systems, not wish lists.

So. Next time you roll out OKRs, ask not just: “What’s the goal?”

Ask: “What does this objective look like in someone’s calendar?”

If you can’t answer that, it’s not an OKR. It’s a fantasy.

How Emotional Systems Shape Operational Ones

The Monday stand-up started on time. Everyone showed up. Cameras on. Smiles in place. A few people took notes. A few nodded along. There was laughter at the right moment.

By all appearances, the team was fine. But by Wednesday, the project mentioned in the meeting still hadn’t moved forward. No one had followed up on the decision that was “definitely clear.” And one person had quietly started doing the thing they thought was safer, not what had been agreed.

No crisis. No obvious conflict. Just a subtle, accumulating drag.

This is how teams slow down. Not with one major blow-up, but with dozens of quiet hesitations, misunderstandings, and unspoken assumptions.

And while founders and leaders often look to process, resourcing, or urgency to fix it, the real problem is harder to name:

The soft stuff. The invisible system underneath the visible one.

A Different Kind of Breakdown

Most fast-growing teams eventually experience a moment when speed slips. The tools are in place. The goals are set. People are still working hard.

And yet, things feel heavier.

Decisions take longer. People check in more, but say less. Initiative shrinks. Meetings get longer, and more crowded.

From the outside, nothing looks broken. But inside the team, something is misaligned. Not in the task list - in the emotional atmosphere that governs how people operate.

The Gap Between What’s Said and What’s Felt

It is common, particularly in remote-first tech companies, for leaders to declare that feedback is encouraged, that conflict is healthy, that ownership is expected.

It’s also common for no one to test whether people believe it.

In one team I worked with, globally distributed, lean, high-functioning, senior leadership was surprised by what surfaced in 1:1s and retrospectives.

“I didn’t want to seem difficult.”

“I wasn’t sure if I was supposed to make that call.”

“I thought we agreed in the meeting, but I wasn’t confident enough to move forward.”

The systems were in place: Quarterly OKRs. Async updates. Slack threads for decisions.

But the behavior suggested a different truth. People were complying, not engaging. They were protecting themselves, not pushing the work forward.

Not Culture. Structure.

It’s tempting to call this a culture issue but that implies it’s informal, fuzzy, or hard to change.

It isn’t.

What most companies call culture is actually an informal system of emotional norms - who speaks first, who gets interrupted, what happens when someone disagrees, whether silence means consensus or fear.

And like any system, it produces outputs. Here’s what tends to show up:

• Decisions revisited multiple times

• “Checking in” before every small move

• Feedback replaced by triangulated side conversations

• Rising burnout, even when workloads are stable

All of which costs time, trust, and energy. Not in dramatic ways. In slow, invisible ones.

What Safety Actually Sounds Like

The science behind this isn’t new. Threat perception, cognitive load, and psychological safety all play a role in how people interpret signals, especially under pressure.

When safety is high, people take risks. They share dissent. They surface problems early. They lean into ambiguity.

When it’s low, they seek control. They delay action. They double-check. They nod when they disagree.

You can hear the difference in team conversations, if you’re listening for it.

A Case in Point

In a leadership debrief last year, I was brought in to review decision-making across a 40-person product team. The team was moving slowly, despite having clear documentation, strong individual contributors, and seemingly healthy team dynamics.

But week after week, their roadmap execution slipped. We didn’t change the team structure. We didn’t change the tools. We looked at how people were interpreting leadership signals.

• Who was speaking first in meetings, and whose ideas followed theirs?

• How often were people naming risks directly?

• Were the same three voices giving updates every week?

What we saw wasn’t dysfunction. It was fear of misstepping, cloaked in politeness. The system didn’t punish mistakes. But it didn’t reward dissent, either.

So we shifted three things:

• Every decision tracked with what was said, who said it, and what happened next

• Regular prompts in team reviews: What’s unclear? What’s unspoken?

• Explicit modeling of disagreement, from the top down

Six weeks later, momentum returned. Same people. Same goals. Different signals.

The Real System Is Always the Human One

What this work reminded me, and continues to remind me, is that organizational performance is not built on willpower or dashboards.

It’s built on signals.

And those signals, of safety, of permission, of clarity - live in the soft stuff.

They’re hard to track and easy to overlook. And absolutely essential if you want your team to keep moving.

The Execution Triangle: Three Words That Fix Most Team Slowdowns

There’s a moment in every fast-growing company where things stop moving the way they used to. The energy’s still there. The people are still smart. The work is getting done.

But the weight of the day starts to shift. People aren’t sure which priority is the priority. Decisions stretch out longer than they should. Everyone’s calendars are full, but no one’s quite sure what moved forward.

There are a lot of ways to describe what’s going wrong: misalignment, inefficiency, growing pains.

But when I’m inside a company, sitting in on exec meetings, watching how decisions move, how people update each other, I’m looking for just three things.

Not five values. Not seventeen KPIs. Three.

Clarity. Structure. Momentum.

And usually, one of them is missing.

Clarity

This is the most common gap.

Ask ten people in the company what matters most this quarter. You’ll get ten answers. All reasonable. All different.

Clarity isn’t a mission statement. It’s being able to say:

• Here’s what we’re focused on.

• Here’s how we’ll know it’s working.

• Here’s what’s not a priority right now.

When this breaks, teams do what they think is best — in ten different directions. Leaders end up reviewing work that’s perfectly done and completely off-track. And nobody sees it coming until they’re halfway through the quarter.

Structure

Every team says they value autonomy. Few have the systems to support it.

Structure doesn’t mean more process. It means having enough rhythm, visibility, and shared norms that people don’t have to invent the wheel every Monday.

Without it:

• Prioritization happens in DMs.

• Updates come too late.

• Ownership is vague enough that no one wants to take the risk of making the wrong call.

This is when you hear things like “Wait, who’s driving this?” or “Wasn’t that decided already?”

And suddenly every decision needs a meeting.

Momentum

If clarity is the compass and structure is the map, momentum is the pace. You don’t need a dashboard to feel when it’s gone. It shows up in silence. Delay.

That awkward space where everyone is “still waiting on X” and no one’s quite sure who’s supposed to move first.

Momentum is what happens when the path is clear, and the system isn’t in the way. It’s also fragile. It doesn’t fix itself. It’s either designed for or it disappears.

What this looked like inside a real team

A few months ago, I worked with a startup — 40 people, just past Series A.

Sharp founders. Fast early growth. But somewhere between doubling the team and launching a new product, things got quiet.

Not in the good, focused way. In the “are we all still aligned?” way. They didn’t need new hires. They needed to see what had quietly broken.

So we sat down and mapped what was actually happening week to week. Not the strategy decks — the real rhythms, tools, decisions.

Here’s what surfaced:

• No shared priorities beyond “ASAP”

• Two different teams building toward slightly different goals

• Meetings that filled the calendar but didn’t move decisions forward

We didn’t launch a big initiative. We fixed one layer at a time:

1. Named what mattered

2. Built a simple weekly review system

3. Clarified who decides what, and how

It took three weeks to feel the shift. Not in slides, in how people talked to each other. What they stopped apologizing for. What they stopped waiting for.

That’s how momentum returns.

A final note…

When things slow down, most leaders look at their people. I look at their system.

Clarity, structure, momentum. That’s the triangle. You don’t need to fix all three at once. Just notice which one’s wobbling.

And start there.

This Is Why Your Smartest People Keep Misunderstanding Each Other

When capability is high but alignment is low, communication is the first place to look.

It’s a pattern I’ve seen across high-growth startups, global tech teams, and executive leadership cohorts: a room full of smart people working hard — and yet, projects stall, tension builds, and no one’s quite sure where the misstep happened.

It’s not dysfunction.

It’s not politics.

It’s communication drift... subtle, persistent, and costly.

These teams aren’t broken. But their communication systems often are. And when pressure builds, the cracks widen. High performers start second-guessing each other. Execution slows down. Meetings multiply. Energy gets spent on clarification instead of creation.

Why Communication Breaks Down in Smart Teams

Communication challenges don’t disappear with IQ points or credentials. In fact, high-functioning teams often fall into four predictable traps:

1. Assumed Context

In teams where people move fast and trust each other, there’s often an unspoken assumption:

“We all know what we mean.”

But context lives in people’s heads, not in the message itself. Without explicitly naming background, priorities, or constraints, people will fill in the gaps with their own assumptions. But good intentions lead to diverging decisions.

2. Information Compression

Leaders who process quickly often communicate quickly. They summarize, skip steps, and distill decisions into short bursts: emails, Slack messages, or a few words at the end of a meeting.

But what feels “clear enough” to them may feel ambiguous to others. And in an environment where no one wants to look slow or out of the loop, they may not speak up.

3. Cognitive Load

When teams are overwhelmed (tight deadlines, multiple stakeholders, constant change...) the brain prioritizes short-term survival.

Under stress, people hear selectively. They process less. They interpret messages through a lens of urgency or risk. Even neutral updates can sound like criticism. Even silence can feel like rejection.

4. Remote and Asynchronous Work

Without tone of voice, facial expression, or immediate clarification, messages can easily be misread. Slack messages sent in a rush can feel abrupt. Emails written late at night can be interpreted as pressure.

In remote-first cultures, the margin for misunderstanding is wider — unless communication is structured to prevent it.

Four Systems That Improve Clarity and Reduce Misalignment

Here are a few repeatable practices that make clarity part of the system, not the personality of one person.

1. The “Context Sandwich”

Start every major message, project kickoff, or update with a clear structure:

• What got us here? (background, previous decisions, why now)

• Where are we now? (current status, what we know, what’s unknown)

• What’s next? (specific action, timeline, who’s doing what)

This reduces ambiguity and ensures that everyone starts from the same page — especially across functions and time zones.

2. Make Understanding Explicit

Instead of ending conversations with “Any questions?”, shift the burden away from passive clarification. Ask:

“Can you talk me through how you’re planning to move forward?”

“How would you explain this to your team?”

This small shift surfaces confusion early — without implying failure. It creates space for alignment without putting anyone on the defensive.

3. Write It Down

Oral communication is fast but fleeting. If something matters (a decision, a shift in direction, a scope clarification) document it.

• Use clear, structured bullets.

• Keep it visible (Notion, a shared doc, a pinned message).

• Make it searchable.

This helps avoid version control issues and provides a single source of truth. It also reduces the need to repeat yourself, and protects clarity when someone new joins the team.

4. Repeat Key Messages Frequently

In leadership, repetition is a discipline.

Most people don’t retain important information after hearing it once, especially when they’re multitasking or under pressure. That’s not a failure of attention. It’s how human memory works.

Say it in writing. Say it in 1:1s. Say it in all-hands.

If your team can quote you, you’re doing it right.

Miscommunication is a signal that your environment needs more clarity, not more hustle.

When performance slows, start by reviewing the communication systems. Often, a few targeted shifts in how information is shared and checked can realign even the most overloaded team.

This Kills 80% of Pointless Meetings: My System for Async Ops in Scaleups

If you’re a founder or exec at a growth-stage startup, your week probably looks like a Zoom-induced fever dream: back-to-back status meetings, 1:1s with no agenda, and a calendar that screams "no thinking allowed." You’re exhausted, reactive, and have zero time for actual strategy.

It doesn’t have to be this way.

The most effective companies don't run on meetings. They run on systems. Async systems.

Here’s a bit long, science-backed, founder-tested playbook I use to build async ops in chaos-loving companies. Steal it, tweak it, or tattoo it on your project manager’s arm. Just stop pretending your calendar is going to fix itself.

The Case for Async Ops (AKA Stop the Meeting Madness)

Meetings are not collaboration. They’re often the absence of a system.

Research shows:

• Cutting meetings by 40% boosts productivity by 71%

• The average knowledge worker spends 392 hours a year in meetings (yes, that’s 10 full work weeks)

• Async work protects deep focus and supports better decision-making.

Translation? More Loom. Less Zoom.

What Async Ops Actually Means

Async isn’t just sending Slack messages at odd hours. It’s a deliberate operating system. It means replacing real-time conversations with structured, documented workflows that don’t require everyone to be in the same room (or timezone, or mood).

It’s:

• Loom videos instead of live demos

• Notion docs instead of status meetings

• Slack threads instead of verbal check-ins

• AI assistants instead of 10-person brainstorming sessions

The result: more clarity, fewer interruptions, and time for leaders to actually lead.

Tools That Will Actually Help You

(warning: do not try all of them at once)

• Notion (Docs/Wiki): Central knowledge base and project hub. Used for product roadmaps, handbooks, and async brainstorming.

• Slack/Threads/Twist (Chat): Threaded discussions (often with AI summaries) let teams collaborate without real-time chat.  Buffer, for example, uses Slack threads as an async backbone and encourages no @-mention pressure.

• Loom (Video): Quick screen-and-cam recordings replace many standups or demos.  Loom offers AI transcripts and summaries, making it easy to “record your screen and face” and share updates asynchronously.

• Email Triage (e.g. SaneBox): Filters and snooze rules to prioritize async email.

• Linear (Issue Tracker): Modern issue/PM tool that keeps “discussions around work, not endless meetings”.  Product teams log specs and tickets in Linear and comment asynchronously on requirements.

• Almanac (Docs/Decisions): Asana-like docs with approvals and version control .  Good for formalizing processes (e.g. weekly OKR reviews) and keeping approvals async.

• Motion (AI Calendar): Auto-schedules tasks around existing events, carving out deep-work windows.  Ensures async tasks get time without manual planning.

• AI Assistants – Generative models (ChatGPT, Notebook LM, Notion AI, etc.) help write docs, summarize threads, and generate action items.

Build a company wiki (Notion/Almanac) for strategy and reference. Use Loom for project updates instead of status meetings. Train teams on writing clear, link-rich messages (even practice writing intros and context).

The Async Workflow, Department by Department

(Examples You Can Steal)

Product & Engineering

Replace daily standups with a weekly update doc or short Loom.

e.g. each PM/team writes a Notion doc with “Accomplishments, Roadblocks, Next Steps”.  Designers post FigJam mockups and gather async feedback via comments.  Bug triage lives in Linear tickets. The Linear team itself uses Slack for casual chat and notes that “issues and discussions happen around work”, minimizing status calls.

Complex decisions (e.g. new feature spec) start as shared Google/Notion docs (async brainstorming) before any live discussion.

People/HR

Onboarding uses Notion handbooks and screen-recorded tours (Loom) instead of in-person tours. 1:1s can be replaced by quick asynchronous check-ins (e.g. a Slack thread or form where employees post wins/blocks ahead of time), freeing time and letting introverts respond thoughtfully.

Performance and hiring updates live in shared spreadsheets or Slack channels (so any executive can review when they have bandwidth).

HR announcements (policy changes, hiring updates) go out as Loom or video newsletters, ensuring remote staff worldwide see the same content without a big live meeting.

Finance/Ops

Monthly budgets and forecasts are compiled in cloud sheets with live comments, not PowerPoint reviews. The CFO might record a Loom recap of key metrics, linking to financial dashboards, rather than calling an hour-long meeting.

Financial approvals (expenses, hiring) follow pre-agreed async workflows via forms or Slack integrations.  For example, teams update a shared Notion “quarterly plan & spend” page, and execs review/comment on their own schedule.

Sales & Marketing (GTM)

Sales pipeline reviews happen in CRM boards with written notes; weekly “how was your week” emails let reps share status without huddles.

New product feature demos are captured on Loom or as shareable videos for the Sales team to watch on demand.

Marketing operates from a shared content calendar (Notion/Asana) where creatives post drafts and feedback asynchronously (comments, tracked changes) instead of meetings.  Campaign metrics are shared in dashboards that any stakeholder can check anytime.

“Work is typically done asynchronously,” says Basecamp’s Jason Fried – letting people read and respond “when they have a chance”.

Likewise, GitLab (1,000+ remote employees) credits “extensively asynchronous” communication for its success.

Other scale-ups like Doist (makers of Todoist/Twist) and Zapier also adopt async norms, favoring written updates and Loom recaps.  For example, Doist’s “Art of Async” guide documents how they set response-time expectations and use async standups and docs to coordinate teams across time zones.

How to Roll This Out Without a Revolt

Define Norms & Channels

Explicitly decide what belongs in which medium. For example, designate one channel for urgent items (e.g. #emergency on Slack) so people know where to ping if a real-time response is needed. Otherwise assume non-urgent requests can wait for an async reply.

Replace (Don’t Just Cancel) Meetings

Audit recurring meetings and ask: “Can this be an async update instead?”

Most status/update meetings can be reimagined as a Loom video or a Notion doc. Convert information-sharing meetings into a quick video or written update. For collaboration meetings, use shared Google Docs or Miro boards: team members leave comments or edits on their own time.

Invest in Writing & Training

Async work depends on clear writing.  Managers should coach teams on crafting concise but thorough messages.  Encourage linking to relevant docs/files so nothing is lost.  Share examples of good async communication (such as templates).

You can even offer micro-training (e.g. an internal guide on effective async emails, Slack etiquette, or Loom usage).

Leadership Buy-In

Executives must model async behavior.  Leaders should prioritize documentation and patiently wait for responses.  If leaders drop into meetings or expect instant replies, teams will follow suit. Instead, leaders can start meetings with a public writeup (e.g. a Notion post) and gather questions asynchronously.

Set Cadence & Transparency

Establish async rituals: e.g. a weekly company newsletter or Loom roundup from the CEO, shared project dashboards, and fixed “response windows” (e.g. everyone checks Slack at certain hours).

For example, you might set a rule that all weekly updates are due by end-of-day Friday via Notion, and any replies can happen on Monday.

“Over-Communicate”

Encourage thoroughness. When asking someone to “write a draft” or similar, include all context (links, deadlines, examples) in one message. This reduces back-and-forth and gets work done faster.

Continuously Improve

Collect feedback on what’s working. Periodically survey the team on what sync interactions still add value. Use retrospectives (which can themselves be async) to refine norms. The goal is a learning async system that evolves.

Bonus: Templates & Prompts for Quick Start

• Notion Weekly Update Template: Notion’s template gallery offers Weekly Team Update pages. These include sections like Key Wins, Project Updates, Roadblocks, and Metrics.  Teams can duplicate and fill these out every week.

• Loom Script Outline: Start with your video objective (e.g. “Project X status”), then share your screen and talk through updates. A simple structure: (1) Context: brief recap of goals, (2) Progress: show numbers/demos, (3) Next steps: what’s coming and who’s responsible. Close by inviting questions (e.g. “Leave comments on this video or Slack post”).  Keep it under 5 minutes if possible.

• Executive Decision Tracker with NotebookLM: “Summarize this leadership meeting transcript into key decisions, owner assignments, and deadlines.” You can upload meeting transcripts, strategy decks, or past decisions into NotebookLM’s notebook. It will cross-reference and generate consistent summaries while flagging decisions that deviate from previous direction.

• Async One-on-One Template: Instead of an hour meeting, try an asynchronous check-in doc.  Create a shared doc with prompts like “What have you achieved since our last check-in? Any blockers or support needed? Feedback for me?”. Both manager and direct report fill it out on their own time, then review together in a short follow-up (or resolve via Slack).

• Company Asks Board: Use a public board (Trello/Notion database) for team-wide requests.  For example, a “Help Needed” board where anyone can post requests (with due dates and context). Others can grab tasks asynchronously. This keeps requests visible rather than buried in chat.

• Context-Rich Recaps for Absent Stakeholders with Notebook LM: “Turn this meeting into a digestible update for stakeholders who missed it, grouped by topic and with links to referenced docs.” It references uploaded materials (project plans, Notion pages) and adds inline citations. Great for teams spread across time zones - everyone gets the same reliable recap.

• Action Item Extraction with Accountability with Notebook LM or ChatGPT: “Extract all action items from this transcript/audio file and list them by assignee, due date (if mentioned), and priority.” It doesn’t just pull to-do’s, it maps them against previous notes if stored. If someone is repeatedly assigned the same task across meetings, AI will catch that pattern.

Next time someone asks for a quick sync, send them this article. Then send them a Loom.

This 4-Step Framework Turns Feedback Into a Superpower

Let’s play a game.

Think of the last time someone gave you real feedback. Not a compliment. Not a vague “you’re doing great.” Actual, useful, behavior-based feedback.

Now think of the last time you gave it to someone else. Not in a panic. Not as an afterthought. As part of a repeatable, safe, and structured system.

If both of those examples feel rare or awkward, you don’t need more training.

You need a feedback system that fits how real teams operate: fast, remote, under pressure, and allergic to fluff.

Because the best leaders aren’t the ones who avoid conflict. They’re the ones who design feedback loops that catch problems before they spiral into politics, turnover, or six Slack threads debating tone.

The 4-Part Feedback Framework That Actually Works

This isn’t a feelings circle. It’s a system: designed with neuroscience, behavioral science, and operational clarity baked in.

1. Normalize It (Before It’s Needed)

Humans are wired to avoid threat. Surprise feedback? Feels like threat.

According to David Rock’s SCARF model, unexpected social evaluation activates the same brain regions as physical pain.

Fix it:

• Build cadence into your workflow. Weekly retros. Monthly 1:1s. Quarterly growth check-ins.

• Make it boring. Like brushing teeth. The more predictable, the less threatening.

• Teach people what feedback means in your culture.

“We use feedback to grow, not to punish.”

2. Format It (So It Doesn’t Spiral)

Unstructured feedback is a professional jump scare. Your brain panics, your ego flares, and suddenly you’re Googling jobs in Portugal.

Use this formula:

SBI + SIFT = Constructive Feedback Without Drama

• SBI (Situation – Behavior – Impact):

• SIFT (Sensations – Images – Feelings – Thoughts):

💡 Why it works: This dual-layer approach combines observable facts (SBI) with subjective awareness (SIFT) to prevent blame spirals. It also taps into interpersonal neurobiology, we co-regulate through empathy.

3. Make It Mutual (Feedback is a Two-Way Street or It’s a Trap)

If your team can only “receive” feedback but never give it to you, that’s not leadership. That’s a dictatorship in Asana.

Build mutuality:

• Ask: “What feedback do you have for me?”

• Model: Share something you’re working on.

• Protect: When they tell you the hard thing, thank them. Do not explain. Do not defend. Just… sit.

Why it matters: Power dynamics mess with our perception of psychological safety. Leaders who give and receive feedback create trust loops. According to Harvard’s Center for the Developing Child, safety = learning.

4. Close the Loop (Or Nothing Changes)

Feedback without follow-up is like sending a postcard into the void.

Do this:

• Log feedback themes.

• Revisit them in future check-ins: “Last month you mentioned I tend to rush decisions. Have you noticed a shift?”

• Celebrate progress. Even small wins. Brains love closure—it reduces cognitive load and increases motivation.

Cognitive Science Bonus: This step triggers the Zeigarnik Effect: our brains crave resolution. You close the loop, you reduce tension. Everyone sleeps better.

TL;DR Cheat Sheet: The Feedback Flywheel

A repeatable, science-backed flow to build resilient teams:

Normalize ➜ Format ➜ Mutualize ➜ Close the Loop

This isn’t about being “nice.” It’s about designing the kind of environment where performance isn’t killed by avoidance. Where problems are caught early, not buried under “we’ll talk about it in QBR.”

Where feedback is fuel, not fire.

Try This Today:

Start your next team meeting with this:

“This month, I’m working on interrupting less and asking better questions. I’d love your feedback - DM me or drop it in our feedback thread.”

Watch what happens when you go first.

The 3 Invisible Systems Every Team Needs Before 100 People

Because scaling isn’t what breaks companies. The lack of structure does.

At 30 people, you still know everyone’s coffee order.

At 50, Slack starts getting weird.

At 75, half your team is asking, “Who owns this?”

By 100, you’re losing good people and wondering when everything got so… blurry.

This is the moment most founders realize: Hiring is easy. Scaling operations without losing your mind (or your team)? Not so much.

If you’re leading, or working in, a company headed toward the triple digits, these are the three invisible systems you need before things break.

Let’s make them visible.

1. The Decision-Making System

“Who’s making the call?” should not be a daily mystery.

When you’re small, decisions happen in hallways, DMs, and adrenaline. When you’re scaling? That turns into confusion, duplication, and silent bottlenecks.

Here’s what happens without a system:

• Two teams are building the same thing.

• Everyone’s waiting on the founder.

• Nobody’s quite sure if a decision was made… or just talked about in Slack.

What to install: A Decision Log

It’s not fancy. It’s just effective.

1. One shared doc.

2. Anyone can log a decision they need from leadership.

3. Decisions are tagged by urgency (🔵 Urgent / 🟡 This Week / ⚪ Later).

4. CEO or execs review twice a week.

5. No random Slack pings allowed.

Why it works: You remove 30% of interruptions and 100% of “Sorry, forgot we talked about that.”

2. The Priority Alignment System

If everything’s important, nothing is. Especially at 100 people.

Companies in growth-phase die by distraction.

Not because people aren’t working, but because they’re working on ten different versions of what they think matters.

Without a clear alignment system:

• Product is building what sales didn’t sell.

• Marketing is launching what ops can’t support.

• The founder says “go faster,” but nobody knows where.

What to install: The 3x3 Priority Framework

It’s simple:

• 3 company-level priorities per quarter.

• Each team identifies 3 of their own, tied to the company’s.

• Public. Visible. Tracked.

Put it in Notion. Or a whiteboard. Or tattoo it on someone’s forearm. Just don’t let it live in a Google Doc nobody opens after the all-hands.

3. The Leadership Feedback Loop

High-trust teams don’t guess. They talk. And they write stuff down.

At 20 people, you “just know” when something’s off.

At 100, gut checks aren’t enough, you need real systems for keeping leaders aligned and honest.

Without it:

1. You over-meet and under-communicate.

2. People smile through meetings and vent in private.

3. Problems grow in silence, then explode in Q4.

What to install: The Weekly Leadership Loop

• 1 shared weekly update (written, async, 5–7 bullets per leader)

• 1 leadership check-in (30 mins max) to unblock and align

• 1 monthly “trust pulse” — a short survey or 1:1s to catch what metrics don’t show

Why it works: It gives you just enough structure to stay on the same page - without turning into a bureaucracy.

You don’t need these systems to be perfect. You just need them to exist. Because what breaks companies at scale isn’t people.

It’s the absence of systems that protect your people’s brains, time, and trust.

Start now. Before you hit 100 and wonder when things started falling apart.

Pick one system from this list and start small.

You don’t need to roll out some 47-slide Notion doc.

You just need to install something real before the wheels come off at 80 people.

If you’re the one holding it all together, founder, operator, head of people, unofficial Chief of Calm, this newsletter’s for you.

Your Team Is Not Fine. The 5-Point Safety Check

“We’re like a family here.” — a company seconds before everyone rage-quits

Let’s get this out of the way: your team is not fine.

They’re not “just tired.” They’re checked out, treading water, or secretly updating their Notion resume during your all-hands.

And the worst part?

They’re probably smiling through it, hitting “👍” in Slack, and telling you everything’s okay while their brains are in full flight mode.

So what’s really happening?

Let’s talk psychological safety.

Not the warm, fuzzy kind. The actual brain-based kind. The kind Google studied. The kind Amy Edmondson publishes papers on. The kind your team doesn’t feel if they:

• Say “yes” to everything but offer zero ideas

• Don’t push back in meetings

• Nod a lot, but act laterally or not at all

• Treat 1:1s like parole hearings

Why? Because their SCARF is on fire.

What’s SCARF and why should you care?

David Rock’s SCARF Model explains the 5 brain-based needs that govern how we respond to social threats:

• Status (Am I respected?)

• Certainty (Do I know what’s coming?)

• Autonomy (Do I have any control?)

• Relatedness (Do I belong here?)

• Fairness (Is this even remotely just?)

If you’re running a high-growth org and your communication is chaotic, your team structure changed 4 times this quarter, and you still haven’t defined decision rights - you’re hitting every single SCARF trigger.

Congratulations, you’ve created a workplace where everyone is smiling and silently panicking.

Run the 5-Point Safety Check

Ask your leadership team these 5 questions this week (and listen to their tone, not just their answers):

1. Where do you feel least clear about expectations right now?

2. When was the last time you felt hesitant to speak up?

3. What part of your role feels ambiguous or out of control?

4. Who do you lean on when things get messy?

5. What’s one thing happening that feels unfair?

If they fumble, deflect, or laugh it off?

You’ve got a trust problem, not a motivation one.

Red Flag Radar

🚩 People who used to challenge decisions are now nodding.

🚩 Cameras off, mics muted, no questions asked.

🚩 Everyone’s “too busy” for retros, reflection, or feedback loops.

Spoiler: That’s not “focus.” That’s shutdown.

What I Told a Leader Last Week

“You don’t need a culture deck. You need to stop calling your team a family and start making them feel safe enough to be honest with you.”

He laughed. Then asked for help redoing his leadership rituals.

This Week’s Brain Nugget

Threat shuts down learning.

If someone’s brain detects danger, social, emotional, performance... they literally lose access to prefrontal cortex resources like reasoning, planning, and memory.

Translation: If your leadership culture feels unsafe, your smartest people are getting dumber by the day.

Try the 5-Point Safety Check. Seriously.

Pick one team, one 1:1, one meeting. Run it. See what surfaces.

Then ask yourself: Am I leading a culture where people speak the truth? Or just trying to survive it?

👉 If this hit a nerve - good. That’s your signal.