“In the future, there will be no female leaders. There will just be leaders.” 
― Sheryl Sandberg

Making Meaningful 1:1s With Your Manager

Making Meaningful 1:1s With Your Manager

Caitland Conley


Whether you’ve had dozens of bosses or this is your first full-time corporate gig, the value of the one-on-one (1:1) meeting with your manager can’t be understated. A good one-one-one checks off several boxes in just one weekly meeting—it’s a pulse check on your performance, a way to establish and maintain a strong relationship with your manager, a guiding light when you run into questions or issues in a project, a safe space to express your hopes and disappointments and, in time, a place for personal life updates or things you share in common.

Setting expectations for these meetings with your manager is crucial. If they’re not used to having direct reports or they don’t typically hold one-on-one meetings, you may need to broach the topic and take charge to make a regular check-in happen. Once you get the OK, keep these five tips in mind to ensure the one-on-one with your boss is playing its part to push forward your career:

1. Be proactive, not reactive

A meeting with a new boss can be intimidating, especially if you’re still feeling out your job responsibilities, figuring out how your role ties into other departments, or if you’re anxious about doing a good job. The key to an effective one-on-one meeting is being proactive about the help you require from your manager. You should be the one “managing up” and guiding conversations about how things are going with your own work, not waiting for them to ask questions.

Don’t wait for your manager to assign work or ask you how XYZ project is going. Come prepared with a notebook, a bullet point list of your priorities, and questions only your boss can answer. That way, you’ll appear prepared and you won’t have to ask for a million clarifications on your priorities over Slack or email later. It’s also a good idea to send a weekly update on your projects before your meeting, or type up your takeaways from the meeting afterward.

2. Outline your projects for the next six months

You can only really succeed in a new job (or as you take on additional work) if you know the vision for your role and the long-term projects you may be expected to absorb once you’ve acclimated to the company. Unclear expectations occur when you’re unsure of the value you bring, and your one-on-one meetings can reflect that lack of insight or vision. Instead, you’ll start giving a laundry list of updates about what you’re currently working on, but won’t be able to see how those projects fit into the bigger picture. A map of your three- to six-month career trajectory will put everyone involved on the same page about your responsibilities.

If your company doesn’t have an idea of what the next six months holds for your position, bring suggestions in areas where you’d like to grow or take on additional responsibility. Then, as time passes, a good boss will advocate for you taking on projects as they arise.

3. Leave room for professional development

“What do you think about XYZ’s marketing e-course?”

“Have you heard about this industry trade show happening in a few months?”

“I’d love to represent the company at next year’s conference.”

Your one-on-one is the perfect time for addressing professional development opportunities. Keep a running list of workshops, conferences or trainings you might be interested in attending. The earlier you approach this topic with your boss, the more likely she’ll be able to follow through on making it happen—plus, it shows you’re proactive about continued learning and improvement.

4. Ask strategic questions

Even if your role expects you to execute day-to-day operations, understanding the larger strategy of your company will help you create better work. If you create content, there should be a content strategy that drives how you write blog posts, create marketing materials and interact with customers. If you’re in sales, you may have a yearly revenue goal your company is targeting. Asking your boss questions like, “What does success look like for our team after we launch this product?” or “What do you project for revenue next quarter?” show you’re invested in the long-term progress of your team.

5. Prioritize your needs

Ultimately, the one-on-one meeting is a vehicle for expressing your skill set and the ways you can benefit your team. It’s also a time during which you get to talk to your boss in a private environment for a specific purpose. Make the most of it. If you’ve run into an unexpected road block with a product launch, or you’re stumped on how to approach a conflict with a coworker, one-on-one with your manager can alleviate stress and make you feel heard.

Rescheduling your one-on-one meeting occasionally is to be expected from time to time. Busy people and packed schedules mean other meetings take priority, sometimes. But if you find yourself getting rescheduled or pushed back again and again, it may be time to point it out to your manager. Your time and professional growth is valuable, and a good manager will recognize and meet your effort to discuss your projects and performance.

Once, I was struggling to get an important project off the ground. At the same time, I was put on a new team with a new boss, who was a senior executive at the company. Her days were jam-packed with meetings, so we started scheduling our one-on-ones at the very end of the day to accommodate her schedule. She was trying to figure out who would do what, and the best way to play to everyone’s strengths. She often asked my take on how to structure the team, which made me feel seen and heard during our meetings.

I was working to implement policy and content strategy, but I didn’t have the seniority to pitch them to our editors. I didn’t want to appear disrespectful to my higher-ups as a junior employee, but I told her how important I thought having documentation and policy was to our overarching goals. Luckily, she agreed with me, and during our one-on-ones, we made a plan where I would create the policies and she would make sure the appropriate stakeholders adopted it. She stood behind my ideas at every meeting and demonstrated that she found my work valuable, all while encouraging other members of the team to buy in.

When done the right way, the one-on-one is an opportunity to prove you’re a driven, results-oriented team member who is hungry for growth. Ultimately, it’s your time to shine. Don’t have a regularly scheduled meeting with your boss on the calendar? Make the one-on-one a career must-have for 2019.


Caitland is a writer and editor based in New York by way of Tallahassee, Florida. She recently traded in her 9 to 5—and the ability to sing the Dolly Parton song—to freelance. In her free time, she runs Prospect Park, and stops to get coffee on the way to get coffee.

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