How to be a Remote Leader with Nicholas Holland.

Posted on July 23, 2019

Remote work is the future. Companies of all sizes need to be prepared for more of their employees to be working remotely from each other.

That begs the question, how difficult is it to be a remote leader in a high growth company?

We talk to Nicholas Holland, who is a GM and VP of Product at HubSpot. He manages an entire product group from his house in Nashville.

We talk to Nicholas about:

– What it’s like being a remote leader in a fast-growth company
– The four components to being a successful leader and how they change when you’re remote
– How can people be successful as remote employees
– Can you replicate those ‘water cooler’ moments between employees when teams are distributed?

Happy Growing!


Time Stamped Notes

[2:30] Nicholas gives us the best reasons to spend a weekend in Nashville.

[4:25] When Nicholas ran his last agency, one of the issues he ran into was all decisions went through him. It meant the agency couldn’t run without him. To solve this, Nicholas started another company and moved into co-working space, so he was remote to everyone who worked at his agency.

It helped give his team more autonomy to make decisions and also forced Nicholas to be more deliberate in his conversations with other team members.

[9:00] There are four crucial components to being a successful leader at a high growth company – learning the organization, learning your actual job, learning your team, and learning how to communicate differently.

When making the transition to remote, if you’re already in the company, you only need to learn how to communicate differently. If you’re starting as a remote worker for a new company, you need to learn all four, and that’s hard.

[16:45] A lot of managers will look for people who enjoy autonomy, are proactive and self-starters when hiring people for remote roles. Nicholas doesn’t think these traits are any more crucial for remote workers as they are for office workers.

What a remote worker does need to excel at is fog clearing. If a remote worker is unclear about any part of their role, they’re not able to lean over to someone and clear things up. Instead, they need to find people who can answer their questions.

[23:45] How can you possibly replicate the ‘water cooler’ chats when you’re working remotely? We talk about some possible things you can do to mimic them, including:

– Setting up slack channels that allow people to talk about things that interest them outside of work e.g., Game of Thrones.

– Have other channels where people can join and have fun together. For example, we talk about a slack group in HubSpot that posts funny memes about other departments.

[29:30] Two great tips Nicholas has for better connecting with his team are:

– One question Nicholas will always ask is, ‘how was that decision made.’ When you’re remote, often you miss some context on how decisions were made, this is a great way to get details you can miss when working remotely.

– Nicholas invests time in making small talk with his team. He doesn’t try to interview them, he asks for little details – what they were up to at the weekend, what’s happening in their lives.


– Nicholas on Twitter / LinkedIn
– Kieran on Twitter / LinkedIn / Medium
– Scott on Twitter / Linked / Medium