How to Meet One-On-One With a Chief of Staff

Meeting with the top individuals at your company can feel intimidating. However, if you’re a leader within your team or organization, meeting one-on-one with executives will provide you with an opportunity to connect your work to the overall company vision. 

Let’s explore the chief of staff (COS) role, why meeting one-on-one with an individual in this role can be beneficial for you, and some tips for hosting a productive meeting with your company’s COS. 

• What is the role of a chief of staff? 
• What is the purpose of one-on-one meetings with a chief of staff? 
• Why are one-on-ones essential between CEOs and chiefs of staff?
• How to host a productive one-on-one meeting with a COS
• Free 1:1 meeting agenda template

What is the role of a chief of staff? 

The COS at an organization is a workplace leader who works closely with the chief executive officer (CEO), president, and vice president on high-level, day-to-day decision-making. These individuals are usually jacks of all trades. They can close the gap between strategy and reality within a company, turning lofty goals into actionable results. 

A COS’s knowledge is second only to the CEO of the company. The COS has broad content knowledge across departments and can connect the dots across people, projects, and teams to make the organization run smoothly. Their daily tasks may include creating pitch decks, presenting investor updates, and preparing speeches and presentations on behalf of the CEO, among many other things!

What is the purpose of one-on-one meetings with a chief of staff? 

Given leaders in this position focus on high-level company initiatives, meetings with a COS will often revolve around company projects, management, or post-project accountability reporting. The purpose of a one-on-one meeting is to discuss diverse topics ranging from management to stakeholder relations to leading top-to-bottom consensus to company policies. 

A COS is responsible for making sure company policies are implemented and company-wide goals are achieved. You may be meeting with your COS to give insight into how something is working at the team or departmental level, provide important updates, or develop a plan of action for implementing a major project or campaign.

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Why are one-on-ones essential between CEOs and chiefs of staff?

The CEO and COS at a company will meet regularly to discuss business matters. As the second in command to the CEO, the COS will use this time to update the CEO on the intel they gathered when functioning as an extra set of ears and eyes for the CEO within the company. For these reasons, a COS needs to be strategic, adaptable, reliable, and an excellent communicator. 

The relationship between a CEO and COS can set the tone for the entire organization; that’s why these two individuals need to keep each other updated. When the CEO and COS are aligned, the COS can help a company achieve large gains in impact and productivity!

How to host a productive one-on-one meeting with a COS

• Create a collaborative meeting agenda 
• Share communication materials 
• Plan ahead
• Guide the conversation
• Have questions ready
• Dedicate time to feedback 
• Align on CEO priorities 
• Discuss board meetings
• Schedule the next meeting 

1Create a collaborative meeting agenda 

You don’t want to waste a COS’s time with mundane status updates. Instead, create a collaborative meeting agenda that you can both add to in the days leading up to your one-on-one. Include the meeting objectives, specific meeting topics, a work plan, deadlines for any upcoming projects, and documents you would like the COS to review in advance of the meeting. 

Use Fellow’s collaborative meeting agenda to transform meetings with your COS into productive work sessions. Show up to your next one-on-one with prepared talking points and a full history of archived meeting notes right in Fellow. During your meeting, use the provided tool to record action items, apply one of our prebuilt templates, and send meeting notes by email or in Slack with the click of a button.

2Share communication materials 

Before the meeting begins, send along any communications materials that will guide your decision-making during the meeting. By sharing materials like fact sheets, consumer summaries, and sales reports, you can help your business refine its approach to many challenges by using data and facts to inform your strategies and decisions. 

Did you know that Fellow can integrate your workflow with some of the most popular digital communications tools like Slack, Microsoft Teams, and Jira? Connect Fellow to the tools you already love to make management, meeting, and productivity workflows even better! 

3Plan ahead

Your COS is busy, so use your meeting time effectively. Plan by defining your desired results before the meeting begins. Take note of the results that you and the COS are striving to achieve by the end of the scheduled one-on-one. Then, identify how much meeting time will be needed to achieve the meeting’s purpose. Match the amount of time to your needs and those of the COS. Lastly, create your collaborative meeting agenda in Fellow and share it with your colleague at least 24 hours before the meeting. 

4Guide the conversation

It’s just as much your one-on-one meeting as it is the COS’s. Guide the conversation to ensure that the topics you’ve outlined in the meeting agenda are addressed during the meeting. Begin the meeting with a check-in; share how your week has been and ask the COS how they’re feeling. Then, jump into the talking points outlined in the agenda. Keep it moving by using technology wisely, staying on topic, and starting and ending the meeting on time. 

5Have questions ready

Have prepared questions to ask throughout the meeting. Some examples of questions to ask a COS are:

• What is the budget for project X so I can assign my department’s resources accordingly? 
• Members of my marketing team are having a difficult time understanding one part of the overall business strategy the CEO recently announced. Can you please explain it in simpler terms so I can report back to my team and we can use parts of it in our next campaign?
• Now that we’ve hit our targets for Q2, how would you like to continue to see the team improve in the remainder of the quarter?

6Dedicate time to feedback 

One of the most important parts of any one-on-one meeting is feedback. Meeting with a COS is no different. During this time, you have an opportunity to give your COS feedback about the company’s strategic direction and overall vision. Your COS can also use this time to give you feedback regarding your team or department’s day-to-day operations. Additionally, COS may use their sublime planning skills to give you meaningful feedback that helps identify ineffective work practices, underperforming groups, and other roadblocks that hinder productivity at work.

7Align on CEO priorities 

Most CEOs have a list of strategic priorities that are communicated to other executives and trickle down to the rest of the company. Take time during your meeting with the COS to ensure that your team or department’s objectives are well aligned with those of the CEO. Additionally, ask for suggestions on where you can use the CEO’s vision to motivate your team members and improve their work so the entire company is cross-functional and collaborative! 

8Discuss board meetings

A COS is one of the few individuals within a company who has direct access to the board of directors. As the group that represents the company’s shareholders and provides guidance to the CEO and executive team, the board’s input matters! If there was a recent board meeting, discuss topics like company structure, vision, strategy, and accountability during your one-on-one with the COS. 

9Schedule the next meeting 

Recurring meetings keep everyone on the same page. Once the meeting has ended, schedule another to discuss future priorities and goals. Ask the COS how often they would like to meet and establish whether weekly, bi-weekly, monthly, or quarterly meetings are necessary. Don’t forget to ask what time of day works for the meetings. In the meantime, share status updates on matters you discussed with the COS via email or Slack. 

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Parting advice

Your COS may be occupied managing high-level company affairs alongside the CEO, but that doesn’t mean they’re inaccessible. If anything, the COS is the bridge between the C-suite and the rest of the company, so good ones will prioritize meetings with other leaders within the company. 

Whether you have a meeting coming up or are planning on asking for one, use our 9 tips to make the most out of your meeting with the COS!