The ultimate one-on-one meeting:

Before you start: Icebreaker

Building rapport can take time and is often hard to do during designated meetings or video calls. Icebreakers can take away some of the awkwardness by offloading the creative curiosity to a lighter question that gets the conversation juices flowing. Adding variability to these questions keeps things easy and fun and you're likely to learn new and interesting things about your team that you otherwise might not have.

Pick a topic of the week and design questions around it, or choose from a list of questions to ask in a 1:1 meeting online. Hypercontext has an enormous list of conversation starters built in to each meeting's workspace—Try picking one of those at random.

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Things to discuss every week

1. OKR & Goals Check in (Quick 🟢🟡🔴 Rating)

In our 2022 State of High Performing Teams report, the evidence is clear that frequent and productive conversations about individual and team goals need to happen on a weekly basis. Goal check-ins don't have to be an in-depth review, but they do need to happen very often. The frequency increases attention, information retention, and accountability for all.

A quick green/yellow/red scoring or check-in on your work OKRs/goals should give you the proper framing for the rest of your week.

Read more about the importance of talking about goals weekly. If you're looking for inspiration on goals, check out the largest library of goal examples on the internet. Finally, if you haven't already, you should see how Hypercontext's built-in goal check in functionality ties all of this together.

2. On a scale of 1-10, how are you feeling this week?

As we've previously said, we're fans of this question. But, the power of it comes from the follow-up.

Let's pretend the answer to this question is "7/10". The context of why anyone said 7 is helpful, but it's not always actionable. Following this discussion with "What do you think would make you an 8/10?" gives you a more actionable road map of what we need to do first to positively impact this person at work.

Often you'll find a bunch of little quick wins that can add up in big ways to impact the morale of your team.

3. Your feedback to me from last week...

As our State of High Performing Teams Report has mentions: "consistent feedback allows teams to continuously course-correct and rely on one another. One-on-ones are a recurring touch point that allow employees and their managers to share feedback with one another habitually.". However, before feedback is a habit, it's often awkward and painful for everyone.

We've found creating an explicit expectation and time for it enables more feedback to happen. We're breaking the ice with their feedback for you. This will help you model how to recieve feedback and turn it into something positive.

If you're not getting any great feedback, we'd recommend sharing the lettuce pact story with your team.

If you find feedback waning with time, we'd recommend learning about creating a culture of High Safety, Low Effort, and High Benefit in these meetings.

4. My feedback to you from last week...

While the previous question is about gathering data on yourself, and modeling how to receive feedback productively. You should not gloss over the fact that you're now modeling how to give high quality feedback.

When the time comes, if you don't have a PhD in cognitive psychology, we recommend following this 4 step guide on giving constructive feedback.

5. Let's review any next steps from this meeting together before we leave

Spend the last 1-5mins reviewing any next steps. Document these somewhere (or in a meeting tool built to track next steps.)

Each next step should have a clear due date and a directly responsible person assigned to it. The extra clarity documented now helps foster a culture of accountability later as you should review all outstanding next steps at the start of your next meeting.

Setting the frequency of this meeting to weekly means you'll always have natural time to sync up on these outstanding topics without feeling the need to nudge, pester, and micromanage 😱.

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Things to discuss periodically

What should we do next quarter to get more traction towards company goals?

About 1/4 of managers find developing a clear vision and strategy to be their largest challenge.

Often managers find immense value in sharing that burden (or opportunity) with their team. Visions, strategies, and goals should change with new data and ideas. Your team should be the source of the majority of that new information. By turning this conversation into a monthly discussion with each report you'll be generating themes and ideas as you prepare for that next quarterly planning session.

Take notes, ask why, and set aside time at the end of the quarter for the entire group to bring the vision together.

What professional goals would you like to accomplish in the next 6 to 12 months, and what makes you say that?

When it comes to supporting career development and performance, 14% of people agree it’s where their manager needs to improve. Similarly, 15% of managers find it to be their single biggest challenge; and after seeing the reasons why your team is quitting, the cost of that, and the impact a great 1:1 can have towards retention, it should be a no-brainer why bringing up this topic monthly/quarterly can lead to increased retention on your team.

The goal of having this conversation is to build and evolve a roadmap for this person's career at your company. Find and develop projects that they'd be great at and allow them to unleash more of their passion during their day-to-day.

What's blocking you from achieving your goals this month? Anything I can do to help?

While you might feel you have goals covered with the weekly questions, this question is more about coaching. By requesting an area of focus for the upcoming month you get an invitation to narrow the feedback you'll share in the following meetings to a specifically identified area of improvement.

You should think about helping identify potential areas for improvement by looking at historical performance or projects that you can use for learning. You'll find a great breakdown of how the former CRO of hubspot was able to accomplish exactly this with his his sales team on our podcast.

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Things to discuss once (and probably rarely again)

Why we're doing one-on-ones?

We cover everything you'd need to know in our 1:1 guide. Often people can have the wrong idea about 1:1s from their previous workplace or manager — For some, they consider it to be an annual review, while for others it’s the weekly, bi-weekly or monthly meeting that employees have with their manager.

Use your first one-on-one to reset expectations on these meetings and how they should be run. Some messages to consider sharing include:

• One-on-ones are a type of meeting held between a manager and their employee, often on a routine cadence that involves discussing growth, performance, development and motivation.
• Both people have a responsibility for the agenda, however it's the direct report who should eventually take it over.
• A dependable, weekly routine cadence is the consensus on the most valuable frequency.

How to use Hypercontext for one-on-ones

Hypercontext is a simple yet powerful tool for your one on one meetings. A full list of features and a series of videos on how to use the application are available on hypercontext.com.

We've written a full guide on how to introduce a tool like hypercontext to your team. You should borrow any tips that you think will work well for your team from that article.

One common thing we've found managers forget to do is to share expectations of use with their team. Something as simple as the following could help:

Hi team. You’ll all be receiving an invite from Hypercontext shortly. I think it’ll help us stay more organized by combining our goals, meeting agendas, and notes all in one place. Please make sure you sign up and download the chrome extension before the next meeting. My expectation is that we'll use this to gather our thoughts ahead of our 1:1 meeting from now on. Please add items you'd like to discuss to the list in app so I can better prepare for you. Thanks!

What are each-others communication preferences during work?

Understanding both party's communication styles and preferences can sometimes take time. It might be helpful to be upfront about any desires or patterns you've noticed about yourself — and ask for the same from the other person. Do you prefer email? phone calls? chat messages? Do you send email after hours or schedule it for the next day?

See a huge list of over 40 manager readmes for inspiration on what you might want to prepare for your team.

What's the best way for sharing feedback with each other?

It turns out people have very different preferences when it comes to feedback. While this question can help you get at the ideal form of feedback to give in a 1:1 the main benefit is setting the expectation that it's going to happen.

If you haven't already, this could be a fun time to form a Lettuce Pact.

Use this meeting agenda template as a starting point for your 1:1s. Both people own this meeting and are expected to add content to it.

Default topics are recommendations based on data published by Hypercontext found to build a high performing teams. Read more about this template: https://hypercontext.com/agenda-templates/ultimate-one-on-one-meeting