A Deep Dive into 1:1s
One of the podcast episodes I send most frequently to my clients as I’m coaching them is my old episode #171 – “How to Have a Successful 1:1 With Your Boss.”
I want to bring that episode into 2026. I also want to frame this as how you, as the boss, can improve your relationship with, and productivity from, your team – as well as how you can improve your 1:1’s with your boss.
For most bosses, 1:1 meetings are little more than status updates. What are you working on? What do you need from me, as your boss?
I propose that you, as the boss, establish a reporting system for status updates. What tech does your company currently utilize that is meant for this purpose – or could be adapted to that purpose?
The question then becomes, if my 1:1s with my boss or my direct reports isn’t to communication project updates and challenges – what are they for?
Ideally, these meetings are for feedback, coaching, relationship-building, and goal-setting.
The goal: Emphasize the “Them” agenda and reserve 2/3 of the time for the direct report’s topics.
Here’s a recommended structure for a weekly or bi-weekly 1:1:
10 minutes – Personal check-in and wins – focusing on the person not the project
30 minutes – Direct report’s agenda, with coaching and unblocking from the boss. The manager asks open-ended questions and avoids giving immediate solutions.
10 minutes – Development & future for growth and goal alignment. Connect the daily work to their long-term career path and skill-building.
5 minutes – Manager feedback for guidance and clarity. This is the manager’s time to provide constructive feedback, recognition, or key policy updates.
5 minutes – Review & next steps for accountability & closure. Quickly summarize action items and confirm next meeting.
Mindset & Tactical Shifts
There are critical procedural and mindset shifts for this agenda to work.
-Use of a shared document for agendas, notes, action items, etc.
-5-minute status rule: Status updates should be in the shared document before the meeting. If something needs to be discussed, limit to the first 5 minutes.
-If the direct report brings a problem to you and asks “What should I do?” immediately respond with “What are your thoughts on how to handle it?” or “What have you considered so far?”
Here are 6 tips to improve the quality of your 1:1’s, as both a boss and as someone with a boss.
1. Don’t let cancellations become the norm.
Having the kind of focused, strategic meetings I am recommending should help this issue tremendously.
If however, cancellations become frequent – this is probably the boss’s fault.
If that’s you – are you cancelling with everyone, or just that person? Tell yourself the truth about why a cancellation happens. Emergencies happen – poor planning or misguided priorities shouldn’t.
If you’re being cancelled on – you can’t change your boss, his schedule, or his priorities. What you CAN do is plan ahead, come prepared, and have honest conversations with your boss.
In either case, reschedule cancelled meetings right away.
2. This shouldn’t be your boss’s meeting – it should be yours.
Bring things you want to talk about – this will show your preparation, your meeting will be more productive, and you will avoid the dread that comes from having nothing to talk about.
Bosses: It’s their meeting. Let it be their meeting.
3. Make an agenda for your meeting.
As you go through your week, jot down things you want to discuss as they come to you. By your next 1:1 meeting, you’ll have a healthy list of topics to discuss.
If you are the boss, send an email out to your direct reports to explain the new structure, and offer suitable topics they may choose from – with the understanding that your list is not all-inclusive.
Here are some possible topics:
-Your career/growth goals (don’t assume your manager knows your career aspirations – bring them up. And not just one time.)
-Team improvement ideas (what ideas do you have to help the team work better?)
-Self-improvement needs (ask for coaching, feedback, help — and be specific)
-Interpersonal issues (ask your boss to help mediate or coach you through difficulties with a coworker)
-Personal topics (let your boss know of a family death, serious illness, particular stressors at home – this opens the door for potential reasonable accommodations)
4. Leverage an AI note taker.
Whether you are the boss or the direct report, use the “Action Items” section of the notes to set up a structure for accomplishing those items in your calendar.
5. Set up the next meeting.
You want to close the meeting by talking about steps for next time. You could ask something like “What do you think we can both do for next time based on what we talked about?”
By presenting it as a question, both parties should feel like part of the solution, which makes both more likely to do whatever they said they would do.
This essentially creates a social contract: if you deliver on your action items, your boss or direct report will be more likely to keep their end of the agreement, too.
Taking five minutes at the end of your 1:1 to set next steps can make all the difference.
6. Think about your manager’s view.
Ask about how you can help and support your boss. Here are a few ways you can better manage up and make work life better for your boss:
-Find out if there’s anything you are doing that your boss feels out-of-the-loop about.
-Offer to take the lead on one part of a project your boss is responsible for; this is also a great way to build leadership skills.
-Adapt some of your deliverables to fit your boss’s style and preferences, such as a summary page, a certain template they prefer, or timing of when to request feedback.
I thought I would leave you with some great coaching questions for your 1:1s.
For checking in:
“How are you doing this week – not just with work, but overall?”
“What was your biggest win or learning since we last spoke?”
For the direct report’s agenda section:
“What’s the #1 thing on your mind for this meeting?”
“What’s been the hardest part about that challenge?”
“What have you tried so far, and what has happened?”
“If you had total freedom, what are three options you could try to solve this?”
“What’s one concrete next step you will take?
For the development & future section:
“What progress have you made on the long-term development goal we set?”
“Is there a skill you want to develop that we could find a project for?”
“What’s a stretch assignment you’d be excited about taking on?”
For guidance & clarity:
“Is there anything you need clarity from me on regarding the team’s goals?”
For review and next steps:
“What are the two or three action items you’re walking away with?”