Effectively Leading Remote Workers – Part 2: Regular Check-Ins

Last week we talked about setting expectations for your remote workers.

The idea from that article is that everybody is crystal clear on what the work is and when it is due. The bosswoman is clear. The remote worker is clear. The team is clear. Everybody knows what is going on.

This week I want to riff on regular check-ins.

Many of us in the Generation X general membership are micro-managing averse. We hated having our Baby Boomer bosses sniffing around our cubicles and checking on us. Something in our DNA makes us chafe when this happens.

This aversion manifests into us pushing the pendulum way up the other side of not micro-managing. Check-ins sometimes get lost in our good intentions.

If you think about check-ins in this way, you have my permission to change your mind.

I contend that it’s not the check-in by itself that is the problem, rather how the check-in is deployed.

The biggest problem I have found is that check-ins are inconsistent.

Inconsistent check-ins give the person being checked upon a story to tell themselves. When there are no check-ins, the story is that our boss thinks we are doing fine with our work. Then, when the check-ins start, we tell ourselves the story that our boss thinks we are unable to do the work in the way he or she wants it to be done. The boss is doubting us which equals bad.

Unless you are explicitly doubting your employee’s effort during your intermittent check-ins, the employee’s story comes from the inconsistency of the check-in, not necessarily the check-in itself.

Now, the story we all tell ourselves isn’t always correct, but that is beside the point. The point is that the inconsistency creates the storytelling opportunity to begin with.

The second biggest problem I see with check-ins is that the leader just plain sucks at performing them.

Employees see through the hanging-around-the-cubicle-acting-casually-and-asking-questions front no problem. We know what you want when you are calling to have an informal chat. Employees expect that bosses like you have questions, so just be up front about what you want and get it out into the fresh air.

Let’s move on to getting better at the art of check-ins.

First – here’s the overall point of the check-in:

For you, as the leader, to get the data you need to create the larger picture of what’s happening on various projects so you can make adjustments as needed to meet deadlines or other expectations.

When you have the data, you can figure out whether things are on track or off track. Knowing that, you can make course corrections as needed.

This seems reasonable, right?

Here’s what I suggest:

#1 – Set a regular time to check in at least once per week with each of your remotes. Make it a 1-30 minute check in depending on what the work is and how much of it there is. This is a block of time specifically for status updates. You don’t need a conference room, you can do it standing up at a cubicle or over a work table.

“Every Tuesday at 10:00 am for 10 minutes we will do a formal download. Then we can meet more often if the work dictates.”

Set up check-ins as a recurring calendar appointment on your calendar and on their calendar.

#2 – During the check-in, ID what is working well first. Focus first on what is going right. What are the wins? What are the successes?

#3 – Then, ID where any friction is coming from. Identify any pain points in the work. What is missing that needs to be supplemented? What is creating the friction?

#4 – Think about what you are hearing and think between the sentences. Step back in your mind and assess what is really going on here. What is the story all of this data is telling? How does what your hearing fit with the plan? What adjustments may need to be made?

#5 – Ask what resources you can help provide if any, and mean it. Part of being a leader is having the back of your employees. When you are there for them, they will be there for you. When they succeed, you too will succeed. So, how can you help them be successful? What resources do they need? Ask them the question and see what they say. They might say they need nothing which is fine. They might say they need a lot and that is fine too. They are telling you what is required to keep things moving along. The sooner you listen and act on the info, the better.

#6 – Consistently repeat steps 1-5. Leadership is partly about showing up on a consistent basis for your team. Make time for the check-ins and stick to it. People trust actions and are cautious about words. So make your actions consistent over time.

I am convinced that all of us can get better at the art of check-ins if we decide to get better at them.

First comes the thought, then comes the decision, then comes the action.

Next week we will talk about evaluating the work that is being produced by your remote workers.

Stay tuned.

by Jonathan Wilson

Jonathan is the Head Coach at Sandcastle Company, a Seattle-based leadership training organization. His first book, Future Leader: Rebooting Leadership to Win the Millennial and Tech Future [link], is now available. Jonathan regularly writes and speaks about The New Leader Way, leadership resilience, and the future of work. He has years of leadership experience in both the public and private sectors, a master's degree from Seattle University, and professional coach training from the University of Miami.
Published on July 7, 2017

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