How do you prefer to stay connected with your direct reports? Do you have specific methods for checking in with your IT staff and gauging morale?

I prefer a very personal and approachable style when staying connected with my direct reports. For me, it’s not just about work, it’s about the person behind the role.

Here’s how I approach it:
- Face-to-face whenever possible: I don’t always stay in the office. In summer, I’ll invite someone for a short walk in a nearby park. With others, I’ll grab a coffee outside the work environment. A change of scenery and fresh air often make conversations easier, especially for more reserved team members.
- Adapt to individual preferences: Some colleagues prefer quick chats at the office, while others like to drop by regularly for an informal talk. I try to respect what works best for each person.
- Personal notes for meaningful connections: I keep a OneNote with bullet points for all 90 team members, things like family situation, hobbies, or interests. This helps me find conversation starters when times are tough. I never pry, but if I know someone’s child is studying or a partner has been ill, I’ll check in respectfully.
- Be visible and approachable: I don’t have a fixed desk. I sit wherever there’s space, right on the floor with the team. It makes me easy to reach and part of the daily flow.
- Create informal virtual spaces: Each team has a “virtual office” Teams chat where we share lighthearted moments, like a joke or a fundraiser for a kid’s sports club, always within a professional context.

In short, I focus on the human side, not just the work. Respecting privacy is key, but showing genuine interest builds trust and morale.

We are remote first so scheduled interactions are essential. I have weekly 1 on 1 meetings with my direct reports for 30 minutes. We always talk about the morale of their teams in the conversation and I do random 15 minute check in meetings with staff throughout IT to take my own pulse. We have bi-weekly team meetings of Directors and up which consists of my 6 direct reports and some of their direct reports who are at Director level. I have another bi-weekly meeting with just my directs. On a yearly basis HR conducts the "Great Place to Work" survey which provides another set of data points on team morale. And we bring the whole IT team into the office quarterly where we have an all hands meeting with lunch. I always take this opportunity to talk with as many staff as possible to take another pulse. Bottom line, you need to be intentional and pay attention!

(1) Weekly or bi-weekly 1:1 meetings with each direct report. (2) Bi-weekly meetings with the full leadership team. (3) Informal bi-weekly optional "Coffee Connect" 30-minute meetings with all team members (direct and indirect reports) where we typically chat about non-work related items. (4) Ad-hoc coffee-chat meetings (approximately quarterly) with indirect reports. We work primarily remotely so these virtual meetings are critical to staying connected with one another.