Lead Dev Async AMA Recap: beyond status report

Welcome back to the Lead Dev Async AMA recap, where I’m recapping the conversation we had over on the Lead Dev Slack to kick-off their newest community series. In each post, I share a question that was asked in the series, and how I answered.

Today I’m responding to a question I’ve been asked a lot: how do you get direct reports to go beyond status reports and share how they really feel? This question is great because it was asked by both an engineer and a manager. I’ll start with the question from the manager and my response, and finish with the question from the engineer.

This is my last post in this series.


Going beyond status report: for the manager

I know it’s important to use 1:1 to get ahead of issues before they become real problems, and to make sure I’m hearing what’s really going on. But I also know it can be hard to get my direct reports to open up and go beyond the kind of day-to-day “status updates” that are really better suited for other meetings. Do you have any prompts you’d suggest I use to encourage my direct reports to open up?

I like to open 1:1s with open-ended questions: how are you? How are things going? What was hard this week?

By design, open-ended questions allow your report to lead you. I tend to listen carefully to what they choose to share, and ask follow-up questions that show I’m engaged and I care.

If your direct report is quiet or reluctant, I find it’s worth saying aloud: this is your time. I really care about you and your success here. 1:1s are a time for us to talk about what matters… even if that means you have feedback for me, or have to discuss something that’s uncomfortable or hard. Know that I’ve got your back and that I’m committed to you, even it’s hard. We’ve got this.

You can demonstrate your commitment to this kind of open sharing by routinely and proactively soliciting feedback. Recently in a 1:1 I asked one of my senior directs: “What is missing on our team right now? If you could snap your fingers and change our team for the better in some way, what would you do?”

But not only did I ask the question, I immediately followed by saying: “I really want to know: even if means you have some difficult feedback for me about the way I’ve been leading. I’m ready, open, and need to hear it! And if it’s hard, I promise I can take it—we’ll work through it together. And the team will benefit for it.”

We ended up having a pretty amazing conversation, and he shared deep, descriptive feedback about how we could improve the way we were working together—on the team. His feedback wasn’t even about me, but knowing that I was open to truly hearing what he had to say made him feel safe to share and take us where we needed to go.

Opening up: advice for a developer

I’m currently working as a developer. Do you have any advice for me on how to get out of the “status report” habit and be more open to sharing the tougher stuff? With the power dynamic and my own tendency to please, I can find it really hard to dive beyond the surface and talk about what’s bothering me, or how that project really went. I know my manager needs to hear that stuff to help the team, so I want to be able to open up. How do you raise the safety and comfort level with your manager and break through the awkwardness?

Your question about how to be more open sharing the dark side really touched my heart. I can tell that it’s important for you to be known by your boss and share what matters to you. What a huge opportunity they have there. My mind immediately goes to wondering, what kind of relationship do you have with your manager, and what have they done to make you feel safe to share?

If your manager is already in the habit of saying things like I’ve mentioned above and in the talk—this is your time, I want to hear it even if it’s hard to say, we’ll work through this together—then I implore you to take them seriously and try. I know it can be hard to trust, so take small steps as you grow your confidence. I once worked with a wonderful person who was tremendously shy. The first couple of months we worked together, I worked hard to get them to open up to me about their challenges at work, and it took a while, but eventually they did. It was entirely worth the wait.

On the other hand, if your manager hasn’t already taken actions to try establish trust with you, consider if there are company values or norms that you could bring up when approaching them. For example, if your company says they value transparency, you can lean on that when you bring up your concern with your boss: “I’m sharing this with you today because our organization values transparency, and the way that manifests for me is in sharing foobar with you today.” Or if your company says they value teamwork, you could say, “I love working for a company that values teamwork. Recently I’ve noticed baz about the way we work together, and wanted to see if we could talk through an experience I had, or some feedback I want to share.” Using stated company values or norms is usually a safe and productive jumping off point for hard conversations.

Your question about breaking through the awkwardness made me smile. I will say, it really helps to have a manager/CTO, as I did, who is committed to creating a psychologically safe environment. I absolutely had that at Juice Analytics, where my boss, CTO Chris Gemignani, was 100% willing to hear feedback even when it was hard. We were able to have awkward conversations where I felt awkward and he felt awkward too because more than feeling awkward, we felt SAFE. Above anything else, I hope everyone in the Lead Dev community gets to work in a psychologically safe environment. It’s transformative.

Finally, I am one to embrace, or make friends with, awkwardness. Have you ever heard the phrase, “get comfortable with being uncomfortable”? There’s some real value there! When I feel awkward, I try to notice how it makes me feel, acknowledge it, and let it pass without internalizing it or judging myself. It’s tough, but it’s worth a try.

What do you think? How do you go beyond “status report” to have conversations that count and meetings that matter? Do you embrace the awkwardness, even though it’s hard? I’d love to hear your thoughts.

This concludes the AMA recap series! I hope it has been helpful. Please let me know on Twitter if you have other questions or want to keep the conversation going. I’m here for you!