Before coming to TCEA, I was the director of instructional technology in Dallas ISD, with a staff of 17. Like many district department leaders, I found that one leadership challenge was making time for one-on-one meetings amid staff meetings, district meetings, campus visits, and everything else competing for attention. I often wished I’d had more guidance on making those conversations useful for both the employee and me.
You may find yourself in a similar situation. You want to build a team you can count on, but a curriculum rollout, staffing issue, or request from the superintendent can push individual conversations off the calendar. Keeping up with everyone’s priorities and remembering what you promised can feel like another job. And if you’re unsure how to lead the conversation, it’s easy to put it off until there’s a problem.
A little preparation and a consistent way to follow up can help you use these meetings to clarify priorities and address barriers before they require more of your attention. The suggestions below give you a place to start. I’ve also created One-on-One Manager, a Google Sheets-based app that helps you keep meeting notes, goals, and commitments from both people together. You’ll find the demo and download information below.
Establish a Purpose You Both Understand
Before starting regular one-on-ones, explain what you hope the time will accomplish. Some employees may associate a closed-door meeting with being in trouble. Let them know you want time to talk about their priorities, challenges, support needs, and professional growth. Ask what would make the meetings helpful to them, too.
You might say, “I’d like us to have regular time to talk about how your work is going and where you need support. We can both bring topics and decide what needs attention first. What would you like these conversations to include?”
That invitation gives the employee a say in how you spend the time. You don’t have to arrive with every answer or a perfect set of coaching questions. You do need to be willing to listen and act when they need something from you.
Explain how these conversations fit with project updates and formal performance reviews. Feedback can be part of a one-on-one, but employees should know when a meeting has a formal evaluative purpose. Let them decide how much personal information to share.
Start Monthly and Adjust Together
A monthly meeting gives you a starting point. From there, talk with each employee about whether the schedule provides enough support. Someone learning district procedures may need more frequent conversations. An experienced employee may find that monthly meetings work well.
Pay attention to the work, too. A curriculum rollout, staffing change, or difficult project may call for more frequent meetings for a while. Meeting less often can make sense when you both agree that other communication is working. Just be careful about assuming that someone who does their job well doesn’t need your attention.
MIT’s guidance for remote and hybrid workplaces recommends regular, short check-ins and deciding together how often and in what form employees provide updates. Whatever schedule you choose, a problem that needs your attention today shouldn’t have to wait until next month.
Choose a schedule you can sustain during employees’ work hours. With my team of 17, I brought a few questions and reviewed notes from previous meetings so I could follow up on their work. I also wanted staff to feel comfortable bringing their own topics. Many meetings lasted about 15 minutes. Others needed more time, and we gave them that time.
When you need to cancel, offer another time. If you’re repeatedly postponing meetings, revisit the arrangement so you can give employees time you’re able to protect.
Prepare a Few Questions and Leave Room for Theirs
A shared agenda can be a simple document where either person adds topics. Before meeting, review your previous agreements and anything the employee has added. Choose two or three questions that fit their current work. Give them the option to prepare without making a written report another task to complete.
The companion question bank can help you choose where to begin. You might select a workload question for someone juggling deadlines or a growth question for someone interested in a new responsibility. You don’t need to get through every question.
These four questions can help you get started:
- Ask about barriers: “What is getting in your way that I could help address?”
- Invite concerns: “Is there a frustration you’d like to share, even if we can’t resolve it today?”
- Explore priorities: “What do you hope to accomplish before our next meeting?”
- Identify postponed work: “What would you like to work on that keeps getting pushed aside by day-to-day demands?”
Begin by asking what they’d like to spend time on today. If they prefer time to think before answering, share a possible question beforehand. Then let what they tell you guide your follow-up. You may learn more by staying with one concern than by finishing everything you prepared.
Listen for What the Employee Needs from You
Put away unrelated work, allow a pause, and ask about something the employee mentioned before moving to your next question. Google’s management guidance recommends regular one-on-ones, open-ended questions, and coaching that adjusts to the person’s needs.
Suppose a staff member wants to finish a resource collection for teachers, but urgent requests keep interrupting the work. You could ask when they expect to finish. A more helpful question might be, “Which requests are taking the most time, and who is setting those deadlines?” You may discover that two departments expect work to be completed at the same time.
That employee may need a decision from you. If you control the priorities, clarify which work comes first. If another department is involved, help negotiate a deadline. Asking the employee to work more efficiently won’t resolve competing expectations. Before adding another goal, consider what you can pause, simplify, or take off their list.
At other times, an employee may need to share a frustration without immediately looking for a solution. Ask, “Would you like me to listen, help you think this through, or see what I can do?” Acknowledge what you heard without promising something you can’t deliver.
Some concerns require you to act even when the employee mainly wants to be heard. Explain what you need to do and what they can expect next. When they need information or a decision, provide it rather than continuing to ask coaching questions.
If feedback is part of the conversation, my article on giving great feedback to employees offers additional suggestions for keeping it specific, timely, and useful.
Make Your Commitments Clear, Too
Before finishing, briefly summarize what you heard and ask whether you understood correctly. Agree on what happens next, who will take care of it, and when you’ll check back. Some conversations lead to a task or decision. Others help you understand a concern. You don’t need to create an assignment to fill in a section of the conversation guide.
In the resource collection example, the employee might agree to list the remaining work by Tuesday. You agree to confirm priorities with the other department by Thursday and report back that afternoon. Write down both commitments so you can each see what you agreed to do.
An employee shouldn’t leave responsible for resolving a conflict that needs your authority. Keep your notes brief, focused on the work, and consistent with your district’s practices. Make the agreements available to both of you. Then follow up when you said you would, even if your update is that you’re still waiting on a decision.
Keep Follow-Up in One Place
I created One-on-One Manager to help you keep meeting notes and follow-up in one place, instead of piecing them together from email, documents, and memory. The app lets you record meetings, track goals and successes, and see commitments assigned to you or the employee. Its dashboard helps you find upcoming meetings and actions that need attention, including the people waiting on you.
You can try the demo with fictional records before deciding whether it fits your work. NOTE: You will need to log in to your Google account to access it. Please use sample information rather than real employee details in the shared demo. The One-on-One Meeting App Features guide explains what each feature does, with examples and tips. For this demo version, data will reset each night so any info you add will be scrubbed.
To generate this app in your own Google Drive, go to the 1on1-Meeting-Files folder and open START-HERE Google Doc. The package walks you through creating your own Google spreadsheet and installing the app, with directions for people who haven’t used Google Apps Script before. Allow time for the initial setup, and use your district-approved Google account and recordkeeping practices. I used AI to help build the app; the download includes the code so you can keep your own copy.
Ask Whether the Meetings Are Helping
Every so often, ask, “What could we do differently to make this time more useful to you?” Be willing to hear that you talk too much, reschedule too often, or offer solutions before they’ve finished explaining the problem. Thank them, choose an adjustment, and follow through.
Look at what happens between meetings, too. Are you responding to concerns and following through on decisions? If the same obstacle keeps coming up, check whether the response you agreed on has helped. Revisit the schedule as responsibilities change, and use the companion conversation guide and question bank when they’re useful.
You don’t have to redesign every one-on-one this month. Before your next conversation, I encourage you to review the last commitment you made to that employee and be ready to share what happened. Then ask what would make today’s conversation useful to them. Their answer can help you decide where your attention is needed most.
What question has helped you have a more useful one-on-one conversation with a staff member? Share it in the comments so other district department leaders can try it.
