I made a direct report cry at work once. In fact, it’s the only time I’ve ever made someone cry at work. As Head of Sales, I sat this person down during our 1:1 with the intention of getting the most out of her. I wanted to challenge her. I wanted to us to find out what she was truly capable of and in that process, I made her cry.

As I reflect on this experience, I don’t regret the intention I had with this person. I saw the best in her. I saw the truth of her potential. I knew what she could be and it was my job to draw that out. I do regret the way in which I executed on it though.

In Kim Scott’s book, Radical Candor, she submits that in order to participate in a healthy feedback relationship, you must care about them personally and challenge them directly. In essence, this is what radical candor is about. You must actively and intentionally be doing both.

I believe in this framework. It’s powerful when it’s employed properly and with integrity. I teach this framework to leaders all the time. It’s my go-to. But there’s an important step before it that all leaders must do before stepping into a radical candor relationship. They must create powerful agreements.

You see, I believe that I was being radically candid with my direct report. I cared for her deeply. I cared about her growth and her success. I knew about her personally too. I knew how much she loved her dog, her partner and Drake. And I wasn’t afraid to challenge her directly. I knew it was necessary to tell her hard truths in order for her to grow.

What I failed to do was co-create powerful agreements with her.

Thriving Under Powerful Agreements

We thrive under structure and we generally understand the reason why hierarchies exist in the workplace. However, nobody likes to be told what to do. I have a 2 year old and she hates being told what to do. It’s in our DNA. With that said, we do thrive under clear expectations and the freedom to create within well understood boundaries.

This is what agreements can do. They can create a field in which your team can flourish.

Here are some powerful agreements I’ve created with teams and 1:1 clients:

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Coaching is a 200% relationship

With clients, we agree to bring our whole selves. We hide nothing and hold nothing back. We make the coaching space safe enough so we can make powerful requests of one another. If something feels uncomfortable to say or do, we agree to lean into it.

Fun is Freedom

We take the work seriously but we don’t take ourselves too seriously. One way in which we do this is by allowing one weekly meeting to spend the first 5 minutes settling in. In this meeting, we don’t jump straight into work mode. We keep the first part of the meeting light. We agree to create room for laughter and water cooler talk. We bring in silly questions like “Is a hotdog a sandwich?” and spend a few minutes laughing as we debate on them.

Permission for Feedback

Hearing hard truths is a challenge. Both parties need to be in a good mind space to participate in tough conversations. So before we do, we agree to ask for permission.

Here’s how I asked recently: “Hi! I had some thoughts (positive and constructive) regarding that meeting we just had. Is now a good time to talk through it? All good if we need to wait, let me know when you’re okay to hear it.”

I’ve found that asking for permission is a respectful way to honor someone’s boundary and wellbeing. It’s an effective way to show that you care about someone personally while being committed to their growth.

To Serve, Not to Please

This is hard for me. I want everyone to like me. I want them to think I’m awesome to work with and I can’t stand the feeling of pissing someone off. But I remember that I’m not here to please my clients. I’m here to serve them.

To that end, we know that problems arise because we created it with a standard of thinking that needs to evolve. In order for our thinking to continue to grow, we must be willing to step into service by challenging our thinking. We must be willing to piss each other off. We must be willing to allow the discomfort.

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How I wish I could have co-created agreements like these with my direct reports back when I became Head of Sales. It might have been different if we all agreed that hard truths were necessary for us to grow together. Leaning into challenging conversations would have been a norm. It would have lifted the field we were playing in. We would have come to the table with a clear understanding of the mindset we must operate with to be successful together.

How about you? What agreements could you co-create with your co-founder, partner, direct reports or children?How would that change the arena you’re playing in?

Fiercely loving you,

Jomar

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