I’m lucky to be running a small team of 20+ people that I get to know very well. I don’t know how it’s going to be with a team of 30 or 40 or 50 folks but I’m going to find out in the years to come, since we’ll eventually have to get to these levels to be able to spread Nozbe’s “good message of productivity” to as many people as we’d like. I guess we’ll see. Now while I can, I still try to get to know my team as much as possible and be approachable to them. That’s why I hold individual one-on-one talks with each company member every three months and this is how I do it:

Originally posted on my personal blog

One-on-one meetings are important!

Again, I’m writing this from the perspective of a 20+ person company, not a 100+ one… so my opinion on this might change with time, but for now I think it’s essential to meet with everyone one on one at least every three months. I schedule a 30- to 60-minute window for this conversation to make sure we give each other full, undivided attention. And it’s important to be prepared for it, to actually have notes and topics to discuss.

Why are these meetings so important? Because in a longer, personal, individual chat people open up and you get feedback that you’d never receive via Slack or Nozbe… and you understand your people better. You get a better feel for people on your team and for the team as a whole.

OK, now that we know that this is super important, let’s dive into some practical aspects. How do I do these meetings?

In person - at Nozbe Reunion

We all work from home but we meet twice a year at “Nozbe Reunions” when we spend a week working and playing together in a hotel somewhere. On Monday, I usually confirm the schedule of my chats with everyone and I spend each morning (Tuesday to Friday) from breakfast til lunch chatting with people one by one.

We either go to a cafe together or find another quiet place to chat… or play pool (which is my favorite activity… and as I’m a very average pool player, people tend to beat me :-))

Each meeting is usually around 45 minutes and I take five-minute breaks in between. It’s a real marathon to do it every day like this but I love it and I do it for my team, so it’s totally worth it :-)

Via Skype, when we can’t be together

As we have our reunions only twice a year, the other two times I do individual chats I run them over a video call on Skype or FaceTime. I schedule them over a few days, always after noon. This way I can get some of my other tasks done before the calls. We just had our reunion this March, so I’ll probably chat with my team around June or July.

Before the meetings - get feedback, be prepared

Something we really practice at Nozbe now is being prepared for a meeting. When we’re not prepared, we cancel our meetings. We just don’t want to waste people’s time. That’s why I want to be prepared for each and every individual chat. Here’s what I do to get prepared:

• I create a project for “individual chats” in Nozbe. I add each person as a task. I create a new comment in the form of a checklist for each person. The checklist consists of the topics I want to discuss with them, ideas, and feedback I got from other team members about them.
• Yes, before I make this checklist I actually ask for feedback. Especially if the person I’m going to talk to is not one of my direct reports. Recently, I asked my two managers, Iwona and Chris, to give me feedback on their team so that I knew more about each person’s individual situation.
• When chatting with each person, I have my iPhone in my hand with their task open and the checklist available. I want the conversation to feel as casual as possible, so I don’t have my iPhone in front of me all the time, but I look at it from time to time to review my checklist and make sure we touched on all the issues and I haven’t forgotten anything.

After the meetings - review

The following week, after I’m done with all the individual chats, I go through all the “tasks” and check my notes to see what we talked about. I then write a short summary in a note in Evernote.

… and action!

Apart from connecting on a more personal level with each individual on my team and getting to know them better, there are always some actionable items at the end of my “chatting marathon.” We often come up with great improvement ideas. Sometimes we’ve even decided to re-organize the company after all this as we saw some people willing to step into additional roles or take on some new projects inside the company. That’s why we make sure to act on these ideas right away because we don’t want to lose momentum.

… and rest…

Don’t tell anyone on my team, but after such a marathon of chatting with everyone, even a social creature like me gets tired. Especially because I really want to give everyone my best and my 100% undivided attention. I do this for them.

That’s why after all these individual sessions I get very tired and I try to have some slower days the following week.

At around 20 people I’m still able to have these chats every quarter. I wonder if it’ll scale with 30, 40 and 50 people. I’m not sure, but we’ll see. We’ll cross that bridge when we get there.

And how often do you chat with your team?

Ask yourself this question. Or if you’re an employee, make sure to schedule a chat with your boss every now and then. It’s totally worth it!

These individual chats help us stay aligned with our goals and make our journey of building the best productivity tool on the Internet so much more enjoyable.