One on One Meetings

One-on-one meetings are the atomic unit of alignment in an organization. They aren't “check-ins”. They aren't “how ya doing?”. They are highly structured, execution focused meetings to ensure that what a specific person is working on is aligned with the company strategy and fully informed. Not doing them or doing them poorly guarantees misalignment, wasted work, and low momentum. Doing them well serves as a high-bandwidth feedback loop that ensures every direct report is unblocked, coached, and pushing the company forward, together. We encourage you to treat these meetings as non-negotiable, hard blocks rather than placeholders. As a team, employees and their manager should ensure they are not spending time on administrative chores but on productive time that identifies issues early, addresses them, and ensures work is constantly brought into alignment with what the company as a whole is trying to do.

But wait:

"I don't have a lot on my agenda this week, so I'm going to give you your time back."
- Or maybe “I haven't prepared, and I assume you haven't either.”
"I have to move us. [Enterprise Client] is demanding a call during this slot, and we can’t risk the churn."
- Or maybe “I am prioritizing short-term revenue retention over long-term team performance.”
"We talk on Slack all day anyway, so we probably don't need a formal sit-down this week."
- Or maybe the person is confusing high-frequency noise with high-bandwidth alignment.
"We’re in crunch time to ship the Q3 release by Friday; let’s skip the sync so we can just focus on execution."
- Or maybe “I view management as a distraction from work, rather than the work itself.”
"It’s the last week of the quarter and I need to be on sales calls to help close the gap to our target."
- Or maybe “My lack of pipeline planning is now becoming your lack of coaching.”

Companies and people thrive on structure. Remote companies - where employees work from home and are spread our globally - more than the rest. Alignment with norms and objectives doesn’t happen by magic. It requires active, disciplined effort. As you scale—when you start adding layers of management and headcount explodes—it gets even harder and the signal-to-noise ratio drops.

The one-on-one (1:1) is the fundamental way we keep a specific person aligned with what the company as a whole is doing. If you treat it as a recurring calendar invite that can be dragged and dropped whenever a customer sneezes, you are breaking the feedback loop that keeps everyone in the organization pulling in the same direction.

What a 1:1 is

Most managers treat 1:1s as a status update or a venting session. They say stupid shit like “a one on one is my employees chance to talk about whatever they want to talk about.” At best these managers are poorly trained, at worst they’re lazy. In both scenarios they’re running poor one on ones that are a waste of expensive hours.

A 1:1 is a structured conversation about the work a person is doing and how they are performing at it. It is a rigorous synchronization protocol designed to achieve four specific outcomes:

Clarity of Execution: Ensuring the employee knows exactly what they should be working on for the coming period - typically one to two weeks - and why it matters in the broader team and company context.
Cascading Context: Ensuring company and department wide items are communicated directly to the person and any impacts to their job are explored collaboratively.
Feedback: Providing a safe space for their manager to provide feedback to the employee on their performance. Providing a safe space for the employee to provide feedback and ideas that should be communicated "up" in the organization for follow-up.
Growth: Providing coaching and guidance to the employee on their development.

If you leave either a manager or employee leaves a 1:1 and doesn’t have a clear picture of what they are working on, any blockers that need to be resolved to allow that work to complete and clear picture of expectations of what successfully completing the work means you haven’t had a one on one. You’ve had a great coffee break - not a successful meetings. These meetings are the main venue for coaching, goal progression tracking, and removing obstacles. They are the engine maintenance that prevents the car from exploding on the highway.

Inviolate Priority

One on ones are required and must happen. But wait? Customers come first, right? If a big client wants to meet at 2:00 PM on Tuesday, you cancel your internal meetings to accommodate them, right? No. Internal 1:1s are hard blocks. Yes, they take priority over customer meetings. Yes, they take priority over "picking your brain" sessions. Yes, they take priority over random fires.

Why? If you neglect your primary reporting relationship, yes, you might save that account today, but you will start a habit that says “one on ones aren’t important.” That will very quickly devolve into an ad-hoc, optional approach to the health of your primary reporting relationship. I will guarantee - with 100% certainty - that will then show up as misalignment in the most important relationship that team member has. When that alignment breaks, you run the risk of losing many customers and that specific team member.

1:1 Rules of The Roads

Never Cancel

If the building is literally on fire, you reschedule. Absent a legitimate emergency you never cancel. Canceling signals that the employee's development and blockers are optional.

Note: While you never cancel rescheduling from time to time is fine. I strongly recommend starting with a standing, set schedule for these meetings. Life and business happen, though, and if the meeting needs to move on a given week to a more convenient time for both parties rescheduling is fine. What we want to avoid is making rescheduling a habit.

Timing and Cadence

Start with a weekly cadence of one hour. “Ugh, that’s so long, what will we talk about.” I promise in the beginning, or with a new hire, you will have enough stuff to fill that time. As you and your direct report build "shorthand"—that intuitive understanding of how the other thinks—you’ll likely naturally shorten these meetings to either 30 minutes weekly or one hour every other week.

Timing and cadence is also strongly informed by seniority and experience. Senior or more experienced leaders may perform better with every other week half hour 1:1 meetings and more time spent aligning across the team. Staff earlier in their careers or new to the job likely need weekly touchpoints without fail.

The Agenda

One of the things I hate the most is when managers say the following (stupid bullshit): “The one on one - that’s my report’s meeting, I let them run it” or equally annoying “We just talk about whatever comes up.” No. Fuck no. God no. That’s not empowerment — that’s abdication of your job as a manager. If you’re a manager, structuring the 1:1 is part of the job. Refusing to do that is a fundamental failure of the role.

All 1:1 should run on repeatable, well-designed agendas that are mostly about execution and performance: how the person did over the prior period, what they’re planning to do in the coming period, and what needs to change to make that plan real. There should be zero ambiguity about “what are we talking about?” We should know exactly what we’re talking about every single time.

While the agenda is highly detailed the prep is one sided: the employee owns the prep. It’s the employees job to show up with a clear summary of prior work and a thought out forward plan (or the right questions to get answer to in the meeting to create a plan.) If you’re the manager and you’re digging for updates—scrolling Slack, interrogating tickets, trying to piece together what happened—you’re doing it wrong. That turns the 1:1 into a status extraction exercise, and it teaches the employee that clarity is optional and you’ll do the work of synthesis for them. The right model is the opposite: the employee comes in presenting, “Here’s what I got done, here’s what I’m doing next, here’s what’s stuck, and here’s what I need from you.” Your job is to pressure-test, coach, and unblock—not to play detective.

Agenda Item One - Look Back

The employee walks through what they accomplished in the last one to two weeks.

The Dynamic: They present; you listen.
The Goal: Accountability. "Here is what I said I would do, and here is what I did."

Agenda Item Two - Look Forward

The employee presents their plan for the coming period.

The Dynamic: They propose; you ratify or course-correct.
The Goal: Alignment. This is where you catch them working on a "nice-to-have" project when the house is burning down. You align their trajectory before they waste a week on low-leverage work.

Agenda Three - Review Performance

Operational Performance Review

A direct inspection of the metrics the individual owns against their performance to date and their forecast through the end of the quarter. This applies to any role with a target measurable in a system of record—whether that’s sales quotas, marketing MQLs, or engineering sprint velocity.

The key thing here, have the employee present the results out of the relevant system of record: no Excel spreadsheets. If you are discussing a sales forecast, the employee must present the data live, directly out of Salesforce as an example. If you’re looking at support tickets or dev cycles, present out of ServiceNow or Jira. Moving data into a "report" allows for polishing, hiding, and "spreadsheet engineering." By looking at the live system, you see the raw data and have a chance to inspect the rigor with which the person is using the live system.

Milestone Performance

Operational metrics track the "day-to-day" running of the business while Milestone Performance objectives track the "big-picture." This is a check on progress against specific Objectives and Key Results (OKRs) or major project plans. Notably, I tend to treat software or product development activities as milestone based goals.

If we can’t accomplish the objectives or a project is slipping, this is the moment to diagnose whether it’s a resource issue, a priority conflict, or a shift in market reality. This can often lead effectively into the next topic - blockers and support.

Agenda Four - Blockers and Support

A simple exploration of any challenges the employee has such as "Where are you stuck?" "Who isn't emailing you back?" "what resource are you missing?" The job of the manager is to be a snowplow and remove any objectives in the way of the employee.

Agenda Five - Open Discussion

Invariably, big hairy topics come up—compensation, team conflict, a new product idea. We strongly recommend *not* addressing those in this meeting but adding them to your running notes in the form of a "backlog" list. Once the core agenda is done, use the remaining time to tackle the backlog. If you run out of time, schedule a separate ad-hoc session for that specific topic.

Agenda Six - The Engagement Check

Wrap up with a simple, quantitative question: "On a scale of 1 to 10, how engaged are you right now?"

It sounds mechanical. It is. But if someone is an "8" for six months and suddenly drops to a "4," you have an early warning system for burnout or attrition. Ask it every time. Track the number.

Logistics and Systems

We recommend keeping all 1:1 notes in company controlled electronic systems rather than personal notebooks. This ensures they are secure and can be audited by human resources as and if needed. No physical notebooks, no sticky pads.

Keeping good notes ensures that you have a 52-week trail of data. When performance reviews roll around, you won't be relying on your "general vibe" of the last month; you’ll have a year’s worth of objective data showing exactly what they shipped and where they stalled. No surprises, just records.

We generally recommend creating a single, shared Google document for every direct report. Each meeting is added to the top of the document and the meeting continues on indefinitely. This creates an infinite scroll of history that you can search.

Peer One on Ones

A quick warning on a common scaling trap: The "Peer 1:1." As you grow, people get nervous about silos. To fix this, they set up recurring 30-minute meetings with their peers "just to align."

Kill these. They serve to clog up a calendar with redundant meetings and add more sidebar conversation to the mix to manage. It’s also one of the fastest ways to clog a calendar. They usually lack an agenda and fall into the ad-hoc “check-in” category. They devolve into complaining sessions or social hours. That doesn't mean peers shouldn't talk—they absolutely should. But the bar for a recurring meeting must be incredibly high.

If you can’t clearly explain the specific artifact or outcome the meeting produces, and why it can’t happen in an existing cross-functional forum or via async updates, don't schedule it. Use ad-hoc check-ins when specific friction arises. Protect your makers' time.

Meeting Follow-up

If the 1:1 generates Action Items, those need to live where the work lives. If you use a task management system or a specific platform for tracking execution (like the tasks area in Forge), put the items there immediately. If the employee spends most of their time in a specific system of record - like Salesforce - create the task in the system. Have the employee add a section to the agenda to review any open action items from prior meetings. By default for action items the employee is responsible for doing the work and the manager is responsible for unblocking commitments.

As an example, if the employee promised to email the CEO to get approval for a budget, that is now an agenda item to follow-up on in the next meeting. Getting from 1 to 100 is rarely about brilliance, it’s almost always about boring consistency. The 1:1 is the drumbeat of that boring consistency.