Name: Phil Montero
Headquarters: Florida, USA
Superpower: Thoughtfully applying the right technology
Operations: Cloud Computing and Mobile Work Expert,

“It’s not just the right technology but the right technology thoughtfully applied”

Phil Montero is a mobile work and virtual office expert. His interest in telework started when he was a child watching his Dad commute back and forth between New Jersey and New York City. Even as a child he thought “There’s got to be a better way.”

When Phil entered the work world, he found he enjoyed working with technology. And after seeing what his Dad sacrificed to have the job that he did, Phil felt passionate about enabling companies and the people he worked with to be able to work remotely and have more work-life balance.

Phil has been keeping up with the collaboration tools and various technologies to make remote work happen. He has developed impressive processes for both teams who are working remotely as well as a specific training for managers who are working with remote teams. In this interview we discuss management, trust, tools (of course), leadership, and more.

AnywhereOfficeWhat does your “Anywhere Office” look like?

My anywhere office is mainly my home. I’m a stay-at-home dad with two kids. So the beauty of my work anywhere situation is that I get to spend a lot of time with my kids. But I can also work from almost anywhere so I just work from wherever I want to or wherever I need to.

What do you like about working remotely?

For me, it’s work-life integration. I love that I don’t have to compartmentalize my life. There are so many options for how to get work done because technology is ubiquitous and can be everywhere. And of course, the other side of that is that sometimes it’s not easy to draw a line in the sand.

I’m certainly not a fan of working all the time. And while I may have to answer some emails and do a few things while I’m on vacation, that’s a vacation that, in the past, I wouldn’t have been able to take because I had to be in the office to be able to handle that work.

What is the main resistance?

I find that the biggest resistance to remote work is management.

It’s the fear of trusting your employees. Managers still think they need to micromanage. There are so many old school managers in the world that think that because they can’t see you, how do they know you’re working? And it’s ridiculous because it should all be based on deliverables and clear objectives, and doing what you say you’re going to do. That’s how you build trust.

When you go to a college, nobody micromanages you. You have a report that’s due. You have class work that’s due, and you’re told what’s expected of you (“Here’s how you get an A”). There are certain milestones along the way. You work in the library, you pull an all nighter, you do whatever you want – as long as the work gets done. Then you leave college and go into an office and are told, “You can’t possibly work without me watching you. I need you at this desk from 9 to 5 because clearly that’s the only way work is going to get done”.  And it’s ridiculous, backwards thinking. I understand that it’s the way we’ve always done it, but that mentality doesn’t work for me.

Eventually, those dinosaurs are going to sink into the tar pit like all dinosaurs do, and the smart companies, the ones that are embracing remote work (because it’s unavoidable) are going to excel. We’re already working this way so they might as well admit that, and learn how to do it well, rather than trying to decide whether it’s something you should do – because that’s really not the question here.

Every day, people on Facebook are communicating and collaborating with people that many have never seen or met. The same goes for Twitter and LinkedIn. People are getting used to working on their Smartphones, and they’re getting used to working in multiple locations. Everybody’s becoming more entrepreneurial. And as the workforce gets infused with the younger generations that are accustomed to that, the less remote work is going to be an issue.

Unfortunately, a lot of managers don’t know how to manage remote employees so there’s fear there. There’s fear that they’re going to lose control. There’s fear that deadlines are going to be missed or that your product or deliverable is going to suffer.

Managers need to overcome that fear and learn that in today’s world, you can trust people remotely. People are generally not looking to scam the system. Most people just want to be able to have a life and work. And if they want to take an hour off in the middle of the day and go have lunch with a friend or run some errands… who cares? As long as the work gets done and the client is happy.

“I think you have to become more of a leader and less of a manager.”

ArtOfVirtualLeadership_webinarI recommend that managers be trained for working with remote staff. It’s not a whole new way of managing, but there are important shifts that are involved. My on demand workshop called The Art of Virtual Leadership walks managers through the shifts that are important to becoming more of a leader.

How do you know what technology to use?

If you’re working in larger teams, I’m a big believer in online shared workspaces. There are a number of tools, but things like Basecamp or Teamwork are great tools because within them they have shared calendars, task lists, files and collaboration spaces. And I’d be remiss if I didn’t mention Google and all of their tools: Gmail and Google calendar, and Hangouts. All of those tools together are invaluable for me in allowing myself and the clients that I work with to be able to really work from anywhere.

If you’re a solo professional or a small group, then plugging together a bunch of tools like Evernote or Dropbox is a great option. Wunderlist is another tool that I love.  It’s a list sharing app for to-do lists and tasks

My personal favorite tool is my Smartphone: talk about the anywhere office all the time! I can respond to emails, I can have video chats, I can get access to documents, even update websites.

After working with a number of different sized clients across various industries, I realized that there were some common denominators when it came to working outside the office. You have to look at your work style and the kind of projects you do and break it down into three categories: information, communication, and collaboration. I call it the “ICC Workflow Audit”. Think of it as a lens you can look at your work through to help you narrow down the technology choices.


Whether you’re a solo professional or you’re a team of some sort, ask yourself “What kind of information do you need to have with you to do the projects you do?” Are there certain kind of documents? Sales flyers, reports, databases that you need access to?


What kinds of communication do you need to engage in for your projects and to get your work done? Do you need to fax or make phone calls? When you communicate with people, is it usually one on one, or do you need multiple people?  Do you need video?  Do you need to see people?


Do you mostly collaborate asynchronously? Do you need to edit a document at the same time?  Do you need to see each other?  Are there time zone differences?

There are a number of questions I have people work their way through. And then we have the information needed to choose the best technology. One thing that’s extremely important to remember is “It’s not just the right technology, but the right technology thoughtfully applied.”

A lot of technology is unfortunately implemented with a sink or swim mentality. Employees get the tools thrown on them and managers say, “Okay, now work and collaborate remotely.” If there’s no training involved and people don’t have time to play with the tool, then adoption is really going to suffer.

One of the things I suggest is what I call “sandbox time”: find a way to use the tool for a non-work related task. So if it’s a collaboration space, maybe you have everybody go in and write a story together. Something fun they can do where it’s building the team unity and it’s bringing the team together. The idea is to use the technology without the pressure of a work project being there.  And teams are more likely to explore and play with it if it’s more like playing in the sandbox.

Remember, there’s a learning curve for the team: some people will take to working remotely quicker than others. That learning curve is an important part of the process. The technology needs to be embraced. If people don’t see the value in it for themselves or how it’s going to make what they do easier, then they’re going to ignore it.

Another thing I’m seeing becoming more prevalent these days is that employees are finding technology that they’re excited about and bringing it to the company and saying, “Hey look, I’m using this already. Is there some way we can use it as a team?” The great thing about that is that not only are people already coming in excited about it, but you’ve also got a champion on the team that will help teach other people.

What personality traits are important for working remotely?

“Not every job and not every personality type is right for remote work.”

If you can’t manage yourself, if you don’t have the basic grasp of your technology, if you’re not a good communicator, if you can’t communicate well in the office, you’re not going to communicate well when you’re out of the office. So anything that is an issue when you’re co-located gets magnified when you’re not.

From the personal standpoint, it’s always good to turn off distractions or change perspective: go to a coffee shop, go to the library, travel somewhere.

From the management standpoint, it’s important to create a culture where people are not afraid to admit mistakes and let you know where they are struggling. This can be done by regularly asking about what’s working and not working, and why. In addition, set up communication guidelines. You’ve got a bunch of people and they’re all using different communication styles and that can get very confusing, so I think you need to set up some ground rules. Things like ‘how often should I be checking email?’ or ‘what’s an expected response time for phone call or email?’, or ‘what is our hierarchy?’  Some people might send text messages. Others are checking email all day.

From the team standpoint, look at the ICC needs in your own situation. Start slowly and experiment with what works and what doesn’t. Start with one project and as you get more comfortable expand it from there.

Do you want to know more about Phil?

The Art of Virtual Leadership training course



Article: Thoughtfully applying the right technology


Watch the full interview

Please note: there were some sound issues half way through the video.

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