How to Level Up One on Ones with Your Team

This guest post is by Cali Harris, Managing Director of Entrepreneurship, Innovation, and Design at the University of Colorado, and formerly Director of Partnerships at TechStars.

Many organizations struggle with conducting great one on one meetings. As managers, we know we should have regular check-ins with our team, but we may be hesitant to invest the time, or unsure how to make that time valuable. As employees, meanwhile, we crave a consistent opportunity to discuss our work, get feedback, and explore development within our companies and careers, but aren't sure how to ask.

In my role at Techstars, I was on both sides of the equation. Through my experience, and the insight of other managers and employees about what makes good (and lousy) one on ones, I’ve found that better one on ones lead to better results and better relationships, and there are several simple ways to get from “good” to “great” meetings.

Four Ways Managers Can Level Up One on One Meetings

  1. Create a framework for one on ones. Ideally, this time together should beyond a simple status check on current projects. Ask your team member to create the agenda: they should show up prepared with questions, concerns, and ideas. This empowers them to own the meeting as “their” time. Suggest to them that within the agenda, the meeting can be split into two parts:
    1. The first part is tactical and covers project status. Ask questions like, “What big rocks are you facing right now?” or “May I provide some feedback on your client pitch last Tuesday?” This time also allows your team member to discuss obstacles and updates on projects.
    2. The second part is big picture and covers “work well-being.” You might prompt the discussion by asking, “Do you feel like you’re growing in role right now?” or “What can we provide to make you excited to walk into the office each day?” or “What do I do that helps you? What can I do less of?” Make notes during the meeting so you can follow up on concerns or ideas discussed.
  2. Make one on ones a priority. Build trust with your team by treating 1:1s as fixed meetings on your calendar. Only reschedule when it’s absolutely unavoidable. Holding weekly 30- or 60-minute meetings is ideal. If you think you don’t have the time, just try regular one on ones for one month. Schedule an hour-long meeting each week with each of your team members. At the end of that month, discuss with them whether or not the meetings were a valuable use of time, and how you’d like to schedule them going forward. (You might be surprised to learn that the time spent is worth every single moment!)
  3. Hold one on ones outside the office. There’s magic in having conversations in different environments. If your team is used to meeting with you in your office and sitting face-to-face across a desk, switch it up: Go for a walk, meet in a nearby coffee shop, walk through a local art museum, sit at a park bench. By moving from a structured to an unstructured environment, you take the rigidity out of regular meetings. Bring a notepad and pen to make notes on the conversation for follow-up. You’ll likely find that diverse environments inspire deeper, more open conversations.
  4. Track one on one key actions over time. Use a shared document, such as Google Docs, or a project management tool, like Basecamp or Asana, to keep high-level, bullet-point style notes after each meeting. Share it with your employee so they can add notes, too. Rather than detailed meeting notes, this is meant to be a place to track next steps and keep you accountable. Review the notes prior to each meeting to make sure you’re supporting requests and checking off action items.

Takeaway: Great one on one meetings have the power to transform a relationship between an employee and a manager. And by transforming individual relationships, we can evolve our team and organizational cultures as well.

Does your team have a better way to run a meeting, or a unique approach to performance reviews? If you'd like to write a guest post on new ways of working, contact us. 


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