Leading with Heart - Part 1: Weekly Team Check-in

Reflecting back on my most recent role, I was very privileged to lead a large and diverse team to help make leadership development more accessible, ongoing, and differentiated across all levels of the organization. As many teams do, the six leads on my team and I would meet both 1:1 and with others throughout the week to ensure we were accomplishing what we needed to achieve together. These were the meetings for us to focus on WHAT we were doing, HOW we were doing it, and WHY what we were doing was important to the organization.

Our weekly leadership team check-in, though, was a very different type of conversation. It focused on WHO we were as humans and the HOW of our partnership together as a team. It had a simple agenda that included three questions that all of us, including myself, took turns speaking to on every weekly call:

  1. How are you feeling, really?
    (Invitation to answer with Green, Yellow, or Red, with an option to add context. The goal is not to be Green, but to share how you truly feel.)

  2. How is your team doing?
    (Not with their work, but as human beings.)

  3. What support do you need from this group this week?
    (Could be anything from an open ear to a specific action.)

We made it a point to always have this check-in meeting each week. Sure, there were some weeks when someone had a conflict they couldn’t avoid, but whoever was available always met. Sometimes we connected for just 20-30 minutes and other times we used the entire hour… to take care of each other. During these conversations, there was space for any and every emotion. We held space for each other to express what was on our hearts, minds, and souls. Together, we discussed and supported each other through everything from birthdays, weddings, babies, graduations, and promotions to aging parents, deaths of loved ones, racism, the pandemic, and mass shootings. Our conversation was sincere, nurturing, compassionate, and sometimes direct and even uncomfortable. It was special, and I miss it.

Oh, and we successfully did this VIRTUALLY, on video, across three continents and five time zones.

So, what did this do for us?

The vulnerability we each demonstrated and the presence we offered to listen to each other without judgment and without trying to solve each other’s problems created a sense of trust and bond that permeated throughout our seven-person leadership team. Were we a flawless team? No. Was I a perfect leader? Absolutely not. However, this trust in each other - to hold space for our most precious personal achievements, challenges, and fears - allowed us to:

  • Partner better professionally through both the good and the not-so-good.

  • Engage in respectful and courageous conversations with one another when misunderstandings or conflicts arose.

  • Have each other’s backs and collaborate at an exceptionally high level when things did not go as planned or when we were challenged to operate in a new way.

  • Set an example as a leadership team and extend this way of partnering together with the rest of our team.

  • Ultimately create an environment where “heart” became one of our documented team values.

For this opportunity and experience, I will be eternally grateful. I learned so much about myself as a leader and I am grateful to each member of this leadership team for their willingness to work, lead, learn, and collaborate in this manner. We have a lot to be proud of.

Curious how to try out this type of conversation with your team?

I hope so! This is definitely more of an art rooted in science, so you’ll have to experiment and figure out how to make this your own. While it may take some time, when you are brave enough to demonstrate vulnerability in the workplace, be open to input from others, and be willing to admit when you’re wrong, the trust and bond you form with your coworkers is well worth the effort.

Here are some tips to help you get started:

  • Schedule and prioritize. Block time on everyone’s calendar, including your own. Don’t schedule over it. Never dive into business unless everyone has had a chance to check in first.

  • Lead by example. This means attending every meeting and showing up on time. It also means showing your own vulnerability as the team leader to offer up what you’re personally dealing with beyond the deliverables at hand so the people on your team can trust you and do the same.

  • Invite, don’t mandate. Especially at the beginning, people may have varying levels of comfort opening up to their colleagues. If someone isn’t comfortable sharing, don’t pressure them to do so. When taking turns sharing, ASK for volunteers to speak vs. telling people they’re next to share.

  • Ensure everyone’s voice has a chance to be heard. Set expectations at the beginning. Use your best judgment to facilitate space for everyone without running out of time.

  • Get personal and interpersonal. Allow space for strong emotions to surface and be felt, and also for silence where needed. Be present for each other without trying to fix or solve for the other person (unless they ask you to).

  • Show gratitude. Sincerely thank each person for sharing, regardless of what or how it was shared, before moving on to the next person.

  • Transition carefully. If there is time left in the meeting after check-ins have finished, consider what was shared before diving into other business. It may help to give people a short break or even do a mindful breathing exercise as a group to help people transition. At other times, it may be more appropriate to give the remaining time back to everyone instead of using every scheduled minute.

  • Ask for feedback. Invite your team to let you know what they think of the conversation, the structure, etc. What did they appreciate about it? What would make it even better?

  • Finally, keep at it. It may feel clunky at first, but don’t let that stop you. The more you all give in this way the more you’ll get out of it.

I hope you found something useful here. Still skeptical about vulnerability and leadership? That's OK. I invite you to check out this Forbes article that references some of today’s leading voices on leadership and teaming, including Brené Brown and Simon Sinek.

Please reach out - I’d love to hear from you. As always, thank you for reading. Please take care of yourself and each other.