For those of you that do not yet know the name you’ll do well to remember it as software marketing expert Kieran Flanagan is one of the world's foremost remote working experts.

His knowledge on the subject is about to become a superpower as the globe’s businesses attempt to run ‘business as normal’ from home!

And while for the vast majority it is fresh ground HubSpot’s VP of Marketing has been perfecting the art for more than a decade, learning how to most effectively run a distributed team.

So, who better to ask than the Dubliner when it comes to expert advice on how to set up, and effectively run a remote business and team?

We spent an hour or so in his company to extract the very best advice he could offer the world’s managers, directors and company owners on how to make remote work…

01 You've long been a proponent of remote working.
When did that start - and why?

When discussing remote work, there are variations of it. For the past 12 years, I've worked for US-based tech companies, so I always worked in distributed teams (across offices).

However, in 2016 I took on a role for HubSpot leading marketing and growth for our freemium business. Near all my hires ended up being outside of Ireland, where I'm based.

Today, from the 70 people across my teams, five are based in Dublin, so I've embraced remote work and rarely work from an office.

02 What would your perfect 'tech stacks' be for remote
working effectiveness?

I think so much depends on the company’s needs, what your team prefers, and your personal preference. There is such a wide variety of tools used across my teams.

The most common tools are - Gsuite, Slack, Zoom, Loom, Airtable, Dropbox, Paper.

03 Does remote work best for small, medium or large businesses?
Does size matter and if so why?

I don't think size matters. 

I do think from the remote first companies I've spent time with, their business and communication processes tend to be a lot more advanced for their size.

It's also easier for smaller companies to adopt remote work policies than larger companies.

However, at HubSpot, we've embraced remote work, and it's been an enormous success, so overall, I think companies of all sizes can both adopt remote work practices and benefit from them.

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04 What 3 thing would you say to focus on as a business
leader when launching an official remote working process?

I think there are a couple of things:

1. Optimize for early success: If you've just launched a remote working process for your company, then you want to ensure there is some initial success.

Think of those people who try it initially as your evangelists. If the experience for them is terrible, it's going to stop others from trying it. 

If it's something you want to build momentum in, then go that extra mile to ensure their experience is a good one. Small things like, ensure they're encouraged to participate in meetings, even if they're the only person on the video chat.

2. Document more: One of the most significant changes when moving to remote work culture is you need to document a lot more of your work vs. relying on conversations that happen in the office.

Time and again, I've seen the problems companies run into when they don't communicate effectively via documentation. People both feel and are left out of critical decisions.

For example, we've become over-reliant on meetings to communicate and ship decisions. Instead, use the memo format, assign them to the people, and ask them to articulate recommendations through those memos along with reasons for decisions. Then share with the relevant group for feedback and use a meeting if you need to ship a decision that people didn't agree on.

I would recommend reading up on how companies like Amazon communicate in this way.

3. Be transparent around policy: If planning to adopt remote work practices, be prepared for questions about what your policy is around things like home office equipment, subsidies towards shared workspaces. Remote employees will want to know how you plan to support them. 

05 How important is culture is hybrid and remote working
- and what would you suggest leaders think about when
getting it right in this area.

It is very important and I’d suggest leaders think deeply around a couple of things:

1. Empathy: One of the things I did early on for my group was ask everyone to work remotely for a week. 

We have a hybrid model, so about 50% of my group works remotely, the other in HubSpot offices. I wanted everyone to experience being remote, so we could be more mindful of the challenges that come from joining meetings remotely or trying to follow along with the status of a project.

It's not as applicable for companies who are fully remote, but I think essential in building a fantastic culture for hybrid teams.

2. Not all work: Something strange happens when you move to work remotely. 100% of your interactions with work colleagues become about work. 

Now, I know that statement is strange, their work colleagues, after all. But in an office, there are a lot more opportunities for catching up about last night's sports game, the latest TV show, or just asking someone how their weekend went.

You need to find ways to include these things in your remote work culture. 

As a leader, ask non-work-related questions to get people participating in meetings. Take the first 10 minutes of a meeting and ask people about their weekends. Create Slack channels where people can talk about non-work subjects.

3. Team building: As a follow on from the above, I think we're going to see online team events become ever more popular. A lot of remote-first companies use retreats to get people together to do fun stuff.

More and more, I think we'll see services offering companies different options to do things online that are non-work related.

For example, last month, I joined a virtual wine tasting night with my team, we did a giant online quiz and played a virtual game online.

06 What should people who aren't accustomed to remote
work do to get psychologically ready for it?

The reality is, remote work isn't for everyone. Some people love it; some people hate it.

That's no different from working in the office.

The biggest thing people miss about working remotely is the personal interaction with the community of friends they've built at their workplace.

For those people, the only solution is to continue working in the office or look for ways to build that community of friends where you live, instead of where you work.

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07 How should those check-ins happen? As a group?
In one-on-ones? Via phone calls? Or video chats?

You could write an entire book on this subject. Here are some things that I do feel work.

1. Don't micromanage. When managers first go remote, every part of them will want to start micro-managing their team. We're programmed to think if we can't see people doing work, they mustn't be doing work.

It's why in most office cultures, we still have a race to be in first and leave last.

Trust your team, and only adjust if it's clear an employee isn't respecting that trust.

2. Clear goals. Make sure you have clear weekly, monthly, quarterly goals for your team documented and shared. The cadence of these goals depends a lot on both company and team size.

3. Clear expectations around communication. Let people know how you want updates. It takes the stress away from remote employees on how they can best communicate progress. 

When it comes to communication, I prefer updates via memo's or video updates using Loom if the person is comfortable, or some kind of document.

08 In your experience what impact does remote working
have on productivity? 

I'm one of those people who enjoy working remotely. I feel more productive and can structure my working day around how I work best.

I like to split my day into half a day for work, half a day of meetings.

I think remote work can be a big adjustment for people at first. It can be challenging to find your routine. But for a lot of us, it's how we work best.

09 Where does hybrid and remote working fall over/go wrong most
frequently? What are the trip hazards to watch out for?

There are some common reasons why hybrid or remote work fails:

a. Leadership isn't supportive. If managers and leaders aren't supporters of remote work, it's not going to be a great experience for either the manager or remote employee. Your leadership/management needs to be supportive of the initiative.

b. Bad communication hygiene. I mentioned above; communication is key to making remote work successful. You need to have clear documentation processes that make it easier to collaborate. I've mentioned some of these above.