The Two Most Magical Questions to Ask a Direct Report
The data shows, and my experience affirms, that most leaders aren't doing regular OOO (one-on-one) meetings with their direct reports.
I've discussed in previous articles that it's critical for leaders to meet with each of their direct reports. I believe these meetings should occur at least every couple of weeks, but I actually think the best practice is to do them once a week. Often, I receive pushback from leaders who argue that weekly meetings are too frequent, with comments like, "That's too many meetings. We need to focus on work. Meeting that often is excessive."
However, we are talking about your people. They need the appropriate amount of support and challenge from you, and you need to be intentional about creating a space for that to happen. So let me make this strong, principled statement, and then we will move on to the meat of the article: You should be meeting OOO with your direct reports on a regular basis.
Now, what should the meeting be about?
I want to keep this really simple and straightforward. You should ask your direct report two questions, and then the direct report should ask you the same two questions.
Question #1: How am I loving you so well since we last met? Yes, how am I loving you? The spirit behind this question lies in recognizing what you're doing right as a leader to serve, to support, and to challenge your direct report. It's about clearly understanding how you are fighting for the highest possible good for your direct report. By seeking a 20/20 hindsight into your actions, you aim to identify areas where you excel in supporting your direct report. You don't want to assume anything. You don't want to believe you are "getting it right"; instead, you want to unequivocally know how you are doing it right. Therefore, you ask the question, "How am I loving you so well since we last met?" The objective is not to seek praise or validation but to genuinely comprehend how you can continue to champion their best interests.
If this love language trips you up, insert your own language. Maybe the question is, "How am I serving you well right now over the last couple of weeks that feels like a home run?" But you want specifics. You want to ensure you understand what you're doing right so that you can keep doing more of it. "Loving" is one of RethinkWork's core values, so it's easy for us to ask a probing question with the word love in it. But be yourself and ask it in your own way.
And then you are going to flip the script. Your direct report will ask you the same question, "Hey Boss, how am I loving you so well right now?" And then you tell them. You express gratitude, give them specifics, and tell them how they are serving you so well.
Now let's get to Question #2: How can I be loving you better than I have over the last couple of weeks? Or, if you feel uncomfortable with RethinkWork's wording, you can rephrase the question as, "What's the one thing you could be doing to serve me better?" And when you ask the question, tell them you want the last 10%. As you ask, you are prepping yourself to be openhanded and openhearted, and you will listen to the feedback keenly. Resist the urge to make excuses for the feedback and instead embrace it with gratitude, viewing it as an opportunity to help you be a better leader. The bottom line is that you're asking for feedback so you can redirect your leadership and fully fight for your direct report's highest possible good. You want to be loving them as well as you can. Just like with the first question, it's an exponential multiplier that improves the relationship and the business. And just like before, you will flip the script. You will share with your direct report what they could be doing to serve you better, support you better, and love you better.
If nothing else exists in your OOO meeting, these questions will aid you in being a more unified and fortified team. If you do this on a frequent basis, the answers get more real and they get more authentic. That means the relationship gets more real and more authentic. That means the business gets more real, authentic, and aligned.
Honestly, if I'm left to my innate devices (where I'm more of a reaction-reactionary leader than an intentional leader), I want to skip a lot of this, and I want to go to the meeting with a direct report where I tell them where they need to improve. And there's the rub; it's a general cancer that exists in the corporate world – and it's why many direct reports don't like their OOO meetings with their boss. They feel like their OOO meetings are a "beat-up" session.
But this is a two-way street because relationships are a two-way street – and you want to be a unified team. Therefore, I challenge my natural tendencies and adopt positive learned behaviors, recognizing the immense value that comes out of these two questions. This simple shift is truly a game changer.
I believe in this so much I have carried it over to my family. I take each of my kids on a date once a month. Just me and each kid – alone. Just the two of us. And we go through these two questions. We spend a lot of time on the first question and try not to accelerate it. We spend time there unpacking how we serve, love, support and challenge each other in the best of ways. And then, we move to the second question. Candidly, this is hard for them. Every time, they push back. They usually give me something like, "Oh my stars, Daddy, you're the best daddy in the world. You're loving me so well." But I fight hard, and I push them. I say, "I want the last 10%. This is so I can be the best daddy in the world to you."
Guess what happens next? They start to spill the beans. And I dig in with humble curiosity. Then, the floodgates open up. They unpack with tangible examples of how I have missed the mark on something. I love it. I take it in. Honestly, sometimes it hurts. But I truly do love it because it's almost always a blind spot I didn't know about, and now it's been revealed to me – and I've got something actionable I can do to love them better over the next four weeks. It's magical.
Then, I flip the script, answer the questions for them, and tell them how they can be loving me better. It's not to beat anybody up. It's fighting for the highest possible good for each other and for the relationship.
So here are some questions for you:
How are you engaging your direct reports?
Are you inviting them into a space where they can be affirmed for what they're doing and challenged for how they could be doing better?
Are you flipping the script and allowing yourself to receive this information?
It's normal to feel a little uneasy when you start asking these questions to your direct reports. Change, especially when it involves vulnerability, can be unsettling. As a leader, why wouldn't you strive to know your team members deeply and ensure they understand you, too? You owe this to yourself, you owe this to your direct report, and you owe this to the business.