HR & Leadership

Teach, Be Curious, and Challenge Them to Rise: Tips for Better 1:1s

August 11, 2021

Arguably a manager’s most important meetings of the week, 1:1s are ideally a time to ask employees strategic questions, problem solve, collaborate, and discuss the future. The only problem is that without structure and planning, these regular check-ins can feel like a waste of time.

So to help you improve your 1:1s, we asked leaders in the OpenView network to share their best advice for making these meetings both enjoyable and productive. Here’s what they had to say:

“Don’t tell. Teach, be curious, and challenge them to rise. If you simply tell people what to do, you get *one* behavior. When you teach them how to do something and/or help them through personal obstacles or blocks to performance, you open the gate for them to run hard with far more confidence. Not everyone explores *why* their direct reports are stuck or not meeting their performance goals—sometimes those reasons can feel more personal—but those ‘whys’ can unlock problematic areas and help people to rise.”
–Dr. Julie Gurner, Managing Partner and Executive Performance Coach at Gurner LLC


“Listen, listen, listen. And then talk, advise, assist. 1:1s are primarily for the individuals, not for the managers (i.e., helping them is the priority, not having them provide ‘updates’).”
–Saeed Khan, Founder of Transformation Labs


“I focus 1:1s to make sure they’re filling the void for each team member as best supports them in the organization. There is always a basic piece of ‘What things should both of us be focused on?’ in order to be doing a better job of getting the outcomes we want as individuals and as a business.

Most team members are great, and actually need little motivation to work hard and drive themselves through an improvement process (this will get harder as we scale hiring). So questions or comments or nudges from a performance perspective are minimal. So for these members I focus on feeding their other motivational reserves. We dig into longer term business objectives and strategies, technical ideas they want to present, and even into their personal life plans/strategy if that’s where they take the conversation. Life at a startup is a lot of hard work, and I strive to ensure that my team is full to the brim with work and home life needs as motivation.”
–Chris Raethke, CEO at Notiv


“1:1s are more effective with a defined agenda and a cadence to discuss specific topics. For my direct reports, I have them set the agenda and I set the cadence for development conversations outside of the normal day-to-day. For 1:1s with colleagues, I focus more on relationship development in addition to the weekly or monthly topics we need to address to drive effectiveness between our teams.”
–Anne Hollander, Senior Director of Product Marketing and Growth at Trimble


“There are three tips for increasing the value of 1:1s that I always share with new managers:

  1. Share the 1:1 agenda well in advance so team members come prepared and are not surprised by what you (and they!) want to discuss
  1. Set aside time at the end of the 1:1 specifically for reflection. If the 1:1 is an hour, then ensure that the last 5-10 minutes are all about talking action items, next steps, or just processing feelings.
  1. From time to time, ask direct reports point blank if the 1:1s are providing value to them. If the answer is anything other than a resounding ‘Yes!’, then ask how it could be made better for them. It could be anything from making the 1:1 a walking meeting, to setting a quarterly ‘theme’ for 1:1s.”

–Chris de Jong, Director of Marketing at 7shifts


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Header image by #WOCinTechChat.

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.