Are you having open and meaningful one on ones?

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You and your employee enter the room. "Hey, how are you?", "Good, and you?", "Great." She's anxious. She doesn't know what she should talk about. An awkward silence ensues. Now you're anxious. You jump to your topics with little thought. You discuss how the projects are going, maybe something about life. The meeting ends, and you both leave the room feeling like that was not what it was supposed to be. She still has many doubts about her career, about the priority changes, about the company's changes, about what's coming next–all things that you didn't even know were making her eager.

We've all had a mediocre one-on-one–and even lousy ones. We've all been on both sides of this table. Failed to share or were unable to make the other person share their priorities. It doesn't have to be like that. One-on-Ones can be great tools for managers, and their directs. They can be one of the best means to push people's careers forward and allow them to grow faster.

Dilbert Cartoon on One on Ones Lousy meetings tend to back-fire in ways we can't even imagine

Meaningful One-on-Ones are one of those things that are simple but aren't easy. So I'll share a few tips I've learned that help me a great deal in avoiding the awkward silence or the time waste.

Before going forward, if life hasn't yet convinced you that you need to do one-on-ones, read these 25 reasons why you do need to and come back understanding just how important these meetings are. It will help.

Have them Frequently and make them Regularly Scheduled

Frequency is crucial. The more time passes without a one-on-one, the more things will happen, more feelings will accumulate, and you'll have the same amount of time to discuss. A small problem that happens can snowball into a huge problem when left unaddressed.

A common pushback here is, "But I want the people who work with me to share problems as soon as they happen, not wait until the next one-on-one." This makes perfect sense. But I've found that, while we can drive people to share blockers with the projects more frequently during the teams' rituals, it's way harder to share about happiness, career, and feedback to their leaders as soon as they happen. Having frequent one-on-one creates a safe space to share these issues before they grow into something we'll have a hard time handling.

When your meetings are far apart, you'll also feel more pressed to jump straight to it. They will be more jam-packed. The hurry will make you miss one of the most incredible benefits of having one-on-ones: Building Rapport. Rapport won't come unless we show a genuine interest in the other person's life and make space to talk about it. And this takes time.

The second most common pushback is the "I don't have the time to schedule them frequently." The truth is that we don't have time for anything. We make time for things. Let me give you some data to help you overcome this pushback when it shows up: 30 minutes is 1% of your time in a week. If you have eight directs, you'll need four hours to meet with all of them, giving them 8% of your time in the week. One-on-Ones are usually the highest leverage activities for managers. Are they really not worth 8% of your time?

Dilbert Cartoon on Meeting Overload We need to be proactive and vigilant with our calendars and clear space for what matters–people are always what matters the most

Being Regularly Scheduled is also crucial. People need to feel and believe that addressing their priorities is essential in our schedules. If we don't regularly make time for that, we send the opposite message. Regularity also gives them time to plan. It's about telling people we value their time and value that meeting. This means you need to avoid as much as possible canceling your one-on-ones, rescheduling them often, and being late.

Dilbert Cartoon on Being Late Value people's time. Being late frequently sends the message that you don't.

Listen first, then listen again.

The employee must own the agenda. The best topics are their priorities, the things that are most important for them–even if they can't put their finger on what are those priorities. There's a straightforward way to pass this message along: Let them start and insist on them bringing what matters the most to them. Say, "Understand this is your One-on-One, and this is your portion of it. It's for brainstorming, asking for help, questions, discussions, sharing–whatever you want to talk about." And if they still don't have anything to share, ask. Some questions that can spark up good discussions:

  1. What are your top priorities until next week?
  2. What's on your mind this week?
  3. How happy were you this past week?
  4. How productive were you this past week?
  5. What is the one thing I could do better to {thing you might need to improve} (e.g., strengthen our relationship)?

One-on-Ones are great moments to develop our listening skills as long as we dedicate ourselves to asking better questions. Questions are not just to learn new information. They bring us closer together by providing psychological safety. They show people we don't believe we always–or even often–have the answers. They build trust and spark new ideas.

What's the difference between a statement and a question? Besides the grammar, a question invites a response. That one little difference can be extremely powerful. To take advantage of this wonderful capability, managers must know what type of question to ask that will solicit a productive response. But that's not all. How you engage in the entire question conversation will determine whether your questions have their intended impact.

The Modern Manager Podcast Episode 142, Ask Better Questions

Having frequent one on ones enables us to vary the questions we use and the discussions we have. So we can use that in our favor. Vary what we ask. Vary how we ask about each subject–what, why, and how lead to different answers. We can ask these questions and be genuinely curious about the answers.

If we aren't curious about the answers, we erode trust. Questions will back-fire. Listening well is critical just as much as it is hard. It's hard because we tend not to be present. Our insecurity triggers us to value being right, being knowledgeable, and receiving validation. It prevents us from showing vulnerability.

"What makes embracing vulnerability feel the most terrifying is how taking off the armor and exposing our hearts can open us up to experiencing shame. Our egos are willing to keep our hearts encased in armor, no matter the cost, if we can avoid feeling "less than" or unworthy of love and belonging. What the ego doesn't understand is that stunting our emotional growth and shutting down our vulnerability doesn't protect us from shame, disconnection, and isolation. It guarantees them."

– Brené Brown on Dare to Lead

When we dedicate ourselves to becoming better listeners, it deepens our relationships with everyone around us. Here are some things I've started trying out and that are helping me:

  1. Be present. Don't check Slack or email, or let your mind drift to other things. If you do, take notice and bring yourself back to the talk with a regenerated commitment to being there.
  2. Do not interrupt. Do not assume you know what the other person will say.
  3. Don't rush to react. Listen. Wait. Think about it and then decide if you'd like to go deeper with other questions.
  4. After listening, try starting by explaining the story you're making up in your head. Use expressions that show this like "The Story I'm making up in my head is {...}" or "What I understood, and please correct me if I'm wrong, is {...}"

One-on-ones are about Trust.

When we already trust the person in front of us, one-on-ones will be way more productive, more profound, and enjoyable. At the same time, having these one-on-ones will make us trust each other even more. They are one of our best tools to develop this trust.

Besides being curious, listening well, valuing peoples' times, there are other things we can do to build trust in our one-on-ones:

  1. Serve: Lead with generosity in the service of the other person. When we learn about their struggles and priorities, we find ways to help and follow through on our promises.
  2. Share more: Show vulnerability, share how we feel, share our experiences.
  3. Care genuinely about the other person. Demonstrate this as often as you can.

🎥 Serving, Sharing, and Caring are healthy ways we earn permission to lead and build connection and commitment, and Keith Ferrazzi has this great video on that.

A graph showing how much emotion we think you should express at work and how that is closer to how you look in drunk pics than it is how to how you look in your passport photo Show emotion. Show vulnerability. Allow yourself to trust and be trusted.

Meaningful One-on-Ones are hard, but they're worth it. We learn so much. more and engage way more deeply. I hope these tips help you as much as they helped me be a better leader.

Thanks for reading this far. If you know someone who wants to have better one-on-ones and if you liked the content here, take a moment to share it and let me know. 🤗