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How to check in with remote employees – CEO Reflections #10

Updated August 20, 2022 by Carl Lindberg

Do you have direct reports or team members working in a remote location? Do you meet one on one once a month, every two months, or even less? Even if you meet on a weekly basis, it can be important to create good communication channels to stay connected with each other.

Since I have worked with global teams for more than a decade, I know it can be a struggle to stay in tight contact with everybody to the extent that you need it and they need it. Here are some ways I have handled this successfully over the years, applicable both for single direct reports as well as whole management teams.

In a nutshell:
How to check-in with remote employees?
Have frequent catch-up meetings where the employee owns the agenda. This is the employee’s
time with their leader and it should preferably be used to help or coach the direct report rather than controlling and monitoring. Be a leader, not a manager!

Oh, and here is an obvious tip: Use proper equipment so you can hear each other properly.

Frequent catch-up sessions with remote employees

Pre-book 30-60-minute slots with everybody on a regular basis, be it every week or every other week. In my experience, the more senior the people, the lower the frequency needed. For example: you need to talk more often to a service technician than a country director due to skill, experience, and the type of work they do. During my career, these meetings have almost always been via phone, online conferencing tools, or similarly. Use Video if you can, it helps with transmitting body language and ensuring focus on the other person.

Having a pre-booked slot means there is no risk that people forget to book meetings or forget to reach out because of other things taking their time. It takes a lot more to actively cancel a pre-booked meeting than to actually book the meeting.

Furthermore, if you don’t have anything of importance, you will be reluctant to schedule an appointment – having pre-agreed slots takes care of that since you don’t know whether the other party still needs the meeting or not.

If you always end up not having anything to talk about, then the frequency is too high, you essentially meet too often. Just move the meetings apart further in time and you will most likely notice a change.

If you need advice on how to run group meetings across time zones, then check out this article: 6 tips on hosting team meetings across time zones.

Who is this meeting intended for?

I go out of my way to make this the time of the remote employee, not the time for me. If I need to talk, I can easily book a meeting with any of my reports, after all, I am the boss. It might be more difficult for them to get into my schedule; hence, they should be free to use the catch-up time however they want. If you are the leader, you can of course bring up smaller items, but make sure that most of the time is “owned” by the employee.

Topics to discuss with remote employees

The topics will depend a lot on the remote employee and what he or she is doing. Again, speaking to a service technician or a country manager will mean very different topics. In general, leave the agenda fluid. I try to cover the following items when possible and if appropriate

How are things in general for your remote employee?

Health, family, what did you do last weekend, etc. All the small stuff that you don’t get exposed to when you do not meet daily or even weekly in the same location. It is even more important to use empathy in your leadership.

How is the workload for the remote worker?

Sometimes this does not have to be addressed as a question, often you can judge this from the rest of the meeting. Essentially, I want to make sure my direct reports have the right number of things to do. Not too much, not too little.

Any problems or challenges currently?

Let the other party decide which things fit into this section as much as you can, then coach the employee on those items as required. Refer to this article for additional tips: Coaching Leadership Style.

“How can I help?”

How can I help? Can I do something to assist? Free up resources? Resolve conflicts? Communicate? Adjust plans? This can be anything. Ask the employee what he or she needs from you – you might be surprised to hear what they need in terms of assistance. Just be cautious – the purpose is not to give the team member an opportunity to delegate upwards. Also, it should not be an opportunity to go into a complaint rant. These should be constructive and sensible requests from the employee. If you tell them what you will do to help them without asking what they need – you might appear as taking over control or micromanaging the area. This will not help you since you can expect to stay away from the topic until the next time you meet, which could be weeks down the road. If you want to help your employee as much as possible, check out this article on the Servant Leadership Style.

What you should not do in this meeting with remote employees..

Do not turn this into a long line of controlling questions

Don’t use this as a follow-up meeting and demand updates on each ongoing topic. Are you a manager or a leader? Since you do not have daily access to this individual, the person must be able to manage him or herself somehow, and that requires creativity, responsibility, empowerment, and many other things. Turning this into a “teacher checking that the homework has been done” type meeting will not fly with remote reports.

Do not talk about yourself, visions, company strategy, etc. the whole meeting

Remember, this meeting is primarily about the employee, not about you. If you have things to communicate, you can do that in a better and more structured way, most likely with the whole team attending at the same time. It might actually be a good idea to read my 17 tips on improving communication as a leader.

Do not automatically follow up on the items from the previous meeting

Perhaps other items are now more important or perhaps the previous ones are no longer relevant. Let the employee set the pace and the topic, so you do not spend time on irrelevant items or items that the employee already has under control. There are exceptions, of course, sometimes your SHOULD in fact follow up on one or two items from the previous meeting

Make some rough notes during or after the meeting. Try to have them available for the next meeting and connect back to the previous meeting somehow so the team member understands you remember. There is a lot of value in giving the right perception here. If you have numerous direct reports, each of them deserves to feel important. Simply asking if the sick dog is feeling better or stating that “last time we spoke about project progress I recall, what would you like for us to discuss today?” or similar signals that the employee and the tasks are important and that you value your time together. This can be very motivating if done correctly and very demotivating when done incorrectly.

Cancelling or rescheduling catch-up meetings with remote employees

I see a lot of articles online underlining that it is absolutely crucial to never cancel or reschedule this type of meetings since it gives the wrong perception. I disagree. I would say this depends a lot on what you do for a living and what level you are working at. If it is obvious to the team member that you as a leader have reasons to cancel or reschedule, you will be fine. They will understand this. What if you go through with the meeting anyway and multitask or feign interest because you are working on something else – wouldn’t that be even more disrespectful and way worse?

Re-evaluate the setup every now and then..

Last but not least, evaluate your setup with your team members. Ask them regularly if you speak often enough and if you have the required level of accessibility. If you get feedback that a change is needed, then simply change things around a bit.

The more you know your team members and the more relaxed and comfortable you are with each other, the less of the above you will need according to my experience. It is not easy to be approachable if you are sitting on the other side of the world, and employees can very easily think that they shouldn’t “bother” the boss with this thing, or that “the boss is probably busy” or “it’s the wrong time of day over in that location” etc. The more you instill in your team members that they can and should contact you when needed, the less you will need the above set-up.

As mentioned above, make sure you use good equipment. You save a lot of time and misunderstandings if you can hear each other properly and not be disturbed by noise and other sound issues.

Have you tried something similar? Did you do it differently? What was your experience? Please comment below, it would be very interesting to hear about your story.

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