The one-on-one is your most important meeting as a leader with direct reports. They are the focal point of your team's relationship with you, and they are your best point of leverage to enact any changes you want to make.

When we talk to leaders outside of Straddle, one of the first questions we ask is how they run one-on-ones. Surprisingly, most have no system; instead, they run ad hoc, unstructured one-on-one meetings (often with hand-wavy justifications).

In our experience, this is a mistake. A one-on-one should be prepared for and highly structured to make the most use of the time available. This might seem onerous at first, but over time you will realize that the opposite is true; the structure is freeing. It lets you get the mundane topics quickly out of the way, and then focus on more blue-sky thinking.

Note: At Straddle, you have a biweekly one-on-one with the CEO (keith). If you have direct reports, you'll also run one-on-ones with them using this general structure, adapted to your own touches. These principles apply whether you're leading a one-on-or participating in one

The purpose of a one-on-one

A one-on-one serves a few purposes:

• Relationship building, creating an atmosphere of trust between you and your team (or between you and your manager), where it's clear that you care personally about each other

• Feedback giving and receiving, so people understand how they're performing and their areas of growth. This goes both ways - if you're not getting feedback, then elicit it!

• Information sharing, especially highlighting the status of immediate goals. Most of this can be pre-written (and even pre-read) to save time.

• Top tasks accountability, ensuring that people do what they have committed to doing by being an accountability partner (rather than a micro-manager).

• Career growth, talking through aspirations and helping people get there

Effective one-on-ones are like immune systems for companies. They're critical for bubbling up and resolving issues that could otherwise spiral out of control. They're also crucial in giving feedback to people so everyone is clear on how they're performing.

Asking questions

Remember, one-on-ones aren't there for you to micromanage you or your team. Instead, you should be a sounding board that your team can use to bounce ideas off and come up with their own solutions. Ask questions rather than make statements. Help people come to their own conclusions; it's the only way they'll truly become independent.

"When the supervisor thinks the subordinate has said all he wants to about a subject, he should ask another question. He should try to keep the flow of thoughts coming by prompting the subordinate with queries until both feel satisfied they have gotten to the bottom of the problem."

• Andy Grove, High Output Management

The Coaching Habit suggests six questions you can ask to help stimulate the conversation:

1. The kick-start question: "What's on your mind?"

2. The AWE question: "And what else?"

3. The focus question: "What's the real challenge here for you?"

4. The foundation question: "And what do YOU want?"

5. The lazy question: "How can I help?"

6. The strategic question: "If you're saying YES to this, what are you saying NO to?"

7. The learning question: "What was most useful for you?"

Accountability

When people commit to doing something, it's very important that you hold them accountable to that. Ensure that any commitment is written down in Linear with an owner and a due date to remove all disambiguation. We call these “"impeccable agreements.”

You are your team's accountability partner. Make it clear that broken commitments are not acceptable.

Since they are now committed to keeping all of their agreements, it's very important for them to be careful about the things they say "yes" to. If they agree to too many things, they will stretch themselves in a way that will result in broken agreements.

Organizing one-on-ones

The first one-on-one meeting should occur soon after the onboarding process is complete. We recommend starting with a recurring 30-minute meeting every week; you can always make it longer down the road, if required.

We recommend doing all of your one-on-ones back to back on a single day. This is efficient, requires less context switching, and allows you to spot patterns you might otherwise miss.

Setup

We use Notion to track one-on-ones. Create a recurring document or project and give access to both parties. We recommend using the naming convention [Employer] / [Manager].

Preparation

The key to running an effective one-on-one is preparation. This lets you run your one-on-ones in <60 minutes, whizz through procedural work, and get to the more meaty topics (where the fun happens).

The four parts of preparing a one-on-one are:

1. Update

2. Issues & proposed solutions

3. Topics

4. Feedback

Let's talk about each of them.

Update

Your report will pre-write an update detailing what has happened since the last one-on-one. Updates should be added as comments or in a shared doc. Create a commitment with your report to do this every week prior to the one-on-one. Ideally, the update should include "what went well" and "what could improve," grouped around your report's OKRs or key priorities.

• Track progress toward KPIs. Any KPI that's lagging should be turned into an issue below.

• Bubble up any pertinent information about how your goals have gone (e.g., What new information did you gather about the customer? The product?).

Here's a sample update from a Growth team:

This update will be read in silence at the beginning of the one-on-one (or even better, pre-read) so that everyone is synchronized on the state of things. Once you get in the habit of pre-written work, you can even read updates prior to the meeting (and comment on them) to save time.

Issues and proposed solutions

Issues are typically things that are blocking your reports' work and need your assistance or insight.

Any issues that crop up should be written up in the issue style and created under the “issue inventory” in Notion. Ideally, they also have a proposed solution that you can quickly approve. For example:

Topics

Topics are open-ended points of discussion that your report wants to cover. This is usually where the magic happens, where blue-sky thinking flows, and where creativity is unleashed.

Prompt your report to create topics prior to the meeting. This will encourage some prep work and time to think from both parties.

Topics should have a good description that you can quickly read to gain context, but not necessarily contain a conclusion.

Feedback

Ideally, feedback should be prepared beforehand by both parties. This allows for more considered feedback rather than off-the-cuff ideas. But, even if you haven't prepared anything, still make sure you do it at the end of the one-on-one.

Feedback should be in the Like that / Wish that format:

• Like that… Say what you liked about the team member's actions since the previous meeting? Be specific. During the week, actively look for actions to compliment.

• Wish that… What do you wish would change? Be as specific and vulnerable as possible.

• It's required that... behavior that needs to change/improve, otherwise the next step is Performance improvement plans (PIP).

We separated out 'wish that' feedback and critical PIP level feedback because we were finding that some people were constantly afraid they were going to be put on a PIP.

It is important to also elicit negative feedback about your or the company's actions. Do this any way you can, be very thankful for it, and then act to resolve the stated issues quickly. This is the key to making a team member feel heard and valued.

While we have a culture of feedback, it can be difficult to elicit feedback from reports back to their managers. When asking for feedback, be sure to leave several seconds so the other person has time to think and respond, versus feeling the urge to close the awkward silence too soon.

Format

Run one-on-one meetings according to the following template.

1. Kick off the meeting by asking your team member about the highlight of their week. This doesn't need to be restricted to work; anything will do. This gets everyone in a great headspace and builds on your relationship.

2. Then read your team member's prepared update in silence. Read the entire thing before asking any questions. This update should be grouped around their goals, OKRs, or similar milestones for the quarter, and be split into "what went well" and "what could improve" sections around each objective.

3. Next, go through your team member's issues (and proposed solutions). Try to keep to a few minutes for each issue and not get bogged down in minutiae. For clear asks, give an immediate response or create a follow-up task. Otherwise, we recommend helping people come to their own conclusions, which will foster a sense of healthy independence.

4. Next, talk about topics. These are more open-ended discussions and time for blue-sky thinking.

5. Now ask, "What are the three most important things you want to get done by this time next week?" Remember, ideally you are not telling people what to do; they should get used to figuring this out for themselves. Jot down the three tasks in Linear, and set the owner and due date for the next one-on-one. Hold people accountable. If tasks are not completed, ask why, and then ask for a "habit" so that this never happens again. This ensures that your team is working to a regular accountability cadence, and it encourages their minds to be focused on their top priorities.

6. Lastly comes feedback. We have written a whole chapter on this (Feedback), but the key aspect is that if there is any critical feedback, there is mutual trust that it will be shared.

7. Then high-five. This seals any commitments and leaves the meeting on a good note.