What challenges have you encountered in leading a remote workforce?

1.6k views4 Comments

Director Business Technology in Software, 10,001+ employees
I've worked with several high growth companies and hiring and retaining talent is quite a challenge. As part of the onboarding at Shopify, you book a ton of meet and greets. I was trying to explain to someone who just joined that typically you run into someone in the hallway or in the kitchen, and you just get to know them. Maybe you grab lunch with them. But there is more effort required to build those relationships now.

There are a good number of people that have been successful in that because they're very methodical. They book the meeting and you're the same person online. Others feel uncomfortable about just booking that one-on-one and just won't do it, so they don't build relationships. Whereas in person, those same would just run into people and get to know them.

A lot of that has to do with whether you are an introvert or extrovert. I've been able to book those one-on-ones and ironically I'm very much an introvert but all I do is talk to people all day. It's worked for me great but I have talked to some of my leads that aren't building those relationships. I've been very honest and said, “It's very uncomfortable but you just have to book it. And make it a bit more comfortable for you.” It is more challenging but if you can acknowledge it, that’s the first step to sort of overcoming that hurdle.
1 1 Reply
CIO in Education, 1,001 - 5,000 employees

I think if you've figured out where to meet people along the way, you'll get there sooner. At a previous organization we had a reasonably sized team of 50-75 folks and I thought it was a crime that my boss didn't know everybody's name. There's just no excuse.

Senior Executive Advisor in Software, 10,001+ employees
Being in densely populated areas like the Bay Area or New York City, working remotely has a lot of advantages. There will always be a small minority of people who are scared to go 100% remote because there is no familiarity of going back to the office and actually meeting people. We've seen it in a number of places. You're 100% remote and that's okay but as social animals, we always want to meet and interact with people to have that symbol of familiarity that indicates what we are. And just having swag or t-shirts or being on the same Zoom call is not going to help that much.
Advisor | Investor | Former CIO in Services (non-Government), Self-employed
All those little water cooler conversations where a formal meeting takes place but then the hallway conversation is where the decision is made, those are lost. And now it's taking much longer because everybody has an opinion and it's too easy to get everybody involved. So there are pros and cons; we'll have to iron out the kinks.

Content you might like

No plans on undergoing a migration yet34%

Currently deploying SAP S/4HANA27%

Migrating to SAP S/4HANA within the next 1-2 years19%

Migrating to SAP S/4HANA within the next 3-6 years10%

Already have SAP S/4HANA in production9%


31.4k views154 Upvotes32 Comments


It’s being considered40%


Don't know5%



CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
Read More Comments
48.7k views133 Upvotes326 Comments