Time Management
How to supercharge your next one-on-one

How to supercharge your next one-on-one

November 26, 2022

How to supercharge your next one-on-one
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Whether you’re a manager or an IC, the one-on-one meeting is a must. This guide offers tips on how to get the most value out of your time and how to streamline the scheduling process.

The purpose of a one-on-one meeting

Regularly scheduled one-on-one meetings between a manager and their reports require a lot of time. But we think they’re worth the investment. Here’s why. 

First, legendary CEO and investor Ben Horowitz considers regular one-on-ones so important that he nearly fired a senior leader for failing to regularly hold one-on-ones with his direct reports. 

Another data point: Our research showed workers are spending 24% more time in one-on-ones after we began working from home during the pandemic. 

So why do people value one-on-ones so highly? This meeting serves three important functions. It’s the primary place for managers and their reports to:

  1. Build mutual trust and understanding
  2. Prioritize tasks effectively
  3. Keep the lines of communication open

Research shows that workers who have mutual trust with their managers are more engaged and perform better on the job. 

“The key is to build a relationship with your team so that they can trust you,” Engineering Manager and Coach Ling Abson wrote to managers. “A trusting relationship is important as it allows your team to surface any issues that may be preventing them from delivering and trusting that there’s safety in bringing those issues to you.”

A regular one-on-one helps workers feel confident that they’re prioritizing their workload correctly and accomplishing enough to meet or exceed expectations. It’s also a place for workers and managers to exchange feedback so that each can change course quickly. Lastly, a well-utilized one-on-one helps ensure there are no surprises when it comes time for performance reviews. 

Since communication failures cost companies $37 billion per year it’s worth putting in some upfront work to improve communication going forward. 

With so much potential upside, why do so many managers push out or skip their one-on-ones? Often it’s because they’re not getting enough value out of them. The rest of this guide will cover how to ensure your one-on-ones do the most work possible for you and your team. First up, let’s talk about how to set a meeting agenda that ensures you cover all the important bases. 

The ideal one-on-one meeting agenda 

So how do you ensure your one-on-ones effectively build mutual trust, help managers and reports work better together, and exchange vital info? It’s helpful to go into each one-on-one with a pre-set agenda which addresses each goal. 

The agenda should be aimed at getting each person to share and solicit the following:

  1. Workload
  2. Feedback
  3. Blockers
  4. Requests

By the end of the meeting, each party should know what the other is working on and towards. It’s a good idea for each person to summarize their tasks and projects. A manager listing their tasks gives the report useful insight into the company’s goals and priorities. It also helps ensure ongoing alignment. When a manager knows what their report is working on they have a better understanding of capacity and the chance to offer feedback on priorities. That way both can be sure there’s agreement on which tasks are most important/urgent and which are more “if you have time.” 

It’s also a good idea for each person to ask the other for feedback on their work product, working style, communication habits, etc. The goal is threefold: To learn and grow, make it easier to work together, and avoid surprises. The last thing a manager wants is to learn a worker is unhappy as they walk out the door. And the last thing a worker wants is to learn their manager is unhappy at review time.  

Be sure to build an opportunity to address any blockers into the meeting agenda. Missing a deadline or failing to deliver a promised resource without warning or explanation erodes trust. Build trust by disclosing and explaining disappointments or blockers as soon as possible.

Lastly, a one-on-one is a good time to bring up any requests you might have of your manager or report. This is especially true of requests that might require some discussion.

One way to build an agenda is to write down some questions to ask during the meeting. Here are some to consider.

5 great questions for one-on-one meetings

Here are five questions managers can use to help ensure a successful one-on-one:

1. What’s been on your mind recently?

2. How are you? How’s life outside of work?

3. What are you struggling with lately?

4. If you had to pick one skill you want to level up -- be it technical skills, leadership skills, speaking skills, soft skills — what would it be?

5. What would make you not just willing but excited to stay with us for the next two years?

Here are five questions reports can use to help ensure a successful one-on-one: 

1. What are you working on lately?

2. Here are my tasks and priorities. Does that sound right to you?

3. Do you have any feedback for me?

4. Have there been any changes to our priorities I should know about?

5. Is there anything I can do to make your life easier?

Tips for a better one-on-one

Now that you know how to optimize your actual one-on-one meeting, let’s talk about optimizing the scheduling and rescheduling process. Many managers skip or push out their one-on-ones (even knowing how valuable they can be) because they cut into so much focused work time and are such a pain to schedule and reschedule manually every week. 

Luckily, you can keep your one-on-ones while also preserving your Focus Time. And you can automate the scheduling and rescheduling process. Here’s how.  

Scheduling 30-minute meetings whenever there’s availability destroys your productivity. It takes an average of 25 minutes to get back on track after a distraction. The key is to stack your one-on-ones. When you schedule with Clockwise we automatically suggest the time to meet that preserves the most Focus Time for you and your boss or reports. And if something comes up, we’ll automatically reschedule to the next best time with no manual effort on your part. Schedule each one-on-one with Clockwise once and you’ll never have to worry about it again. 

In addition, Clockwise’s 1:1 dashboard shows you how many one-on-ones you have right now and their cadence. This makes it easy for you to remove any duplicative or unnecessary meetings. The ones you want to keep, you can make flexible with just one click. 

Go forth and meet

One-on-one meetings offer a ton of value. They help build trust and streamline communication, which research shows makes companies more effective. The key is to build the right structure into your one-on-ones to ensure they cover all the important points. Creating an agenda ahead of time and writing down good questions is key. To streamline the scheduling and rescheduling process, and ensure you preserve Focus Time, try Clockwise free today. Happy meeting!

About the author

Cathy Reisenwitz

Cathy Reisenwitz is the former Head of Content at Clockwise. She has covered business software for six years and has been published in Newsweek, Forbes, the Daily Beast, VICE Motherboard, Reason magazine, Talking Points Memo and other publications.

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