Is telework/remote the future?

My office recently started regular telework up to two days a week. So far it seems to be a win. You can access everything you need from home with KT Fileshare, CON-IT, Skype for Business video chat, DCS, and VPN. We view it as increasing our capability (with experience) to operate as a distributed team.

The biggest challenge has been figuring out what tools work on the Air Force network and adjusting how our leadership team leads, communicates, and manages our teams (sometimes differently but often for the better.) BTW most of the leadership team teleworks too.

For the skeptics, a good book to see telework from a different perspective is

Basecamp founders Jason Fried and David Heinemeier Hansson explore the “work from home” phenomenon and show precisely how a remote work setup can be accomplished in Remote .

The Industrial Revolution’s “under one roof” model of conducting work is steadily declining as technology creates virtual workspaces that allow employees to provide their vital contribution without physically clustering together. Today, the new paradigm is “move work to the workers, rather than workers to the workplace.”

Remote work increases the talent pool, reduces turnover, lessens the real estate footprint, and improves the ability to conduct business across multiple time zones, to name just a few advantages. As Fried and Hansson explain the challenges and unexpected benefits of this phenomenon, they show why–with a few controversial exceptions such as Yahoo–more businesses will want to promote this model of getting things done.

Here is a blog post with short summary of some key points:

For the telework fans, here is a counterpoint from a startup founder:

What do you think? Is remote work the future? Or is it a fad that will fall out of favor like open office? (Open office is a discussion for another thread)


You’ve presented a lot of good reading on the topic!

From my experience I am PRO telework while in many circumstances I consider it an earned privilege. I’ve found great value in telework for various teams I’ve been part of and/or supervised. Generally it works best with a set of teammates ‘in the local area’ regularly making it to the office for face-to-face meetings as required. While I’ve had some success with 100% remote (other time zone) teammates it is harder and candidly it was a learning experience with failures on my leadership end. I eagerly soaked in every bit of secondhand experience I could gleam off a good friend running ‘the other half of the company in India’ thereby proving out several 100% remote concepts. Even after those talks I’m sticking with 100% remote as a very challenging situation.

What I both foresee and hope for is a future state allowing far more telework as a total % of labor hours delivered over the year. This runs tightly alongside my desired state for far fewer meetings (so often fruitless meetings) and making those meetings that do occur actually count (be they virtual or F2F).

I foresee a plausible future of teams coalescing around what is most productive and they eagerly pursue peek mission effectiveness. I think it will look odd to many compared to how we work now – such as M-W-F in the office and T-T from the home office (don’t let my example limit your creative variations). I will at this point caution how teleworking Mon & Friday can get dubious. 9-80 schedules/ RDOs are NOT to be conflated with telework. I strive to start from a trusting place, trust is foundational to strong team dynamics w/o you’re guaranteed to experience at least some of the “The Five Dysfunctions of a Team”. M&F telework might be best considered an ‘as needed exception’ simply due to a slippery slope effect eroding team trust. Hopefully we all get the pleasure of teams so hot this doesn’t need to be a consideration.

Additionally worth consideration should be chunking the work week into half days increments where by example; after a large team meeting on say Tuesday morning, folks break for lunch and don’t return to the office until Weds afternoon. In this example I’m proposing Tues afternoons & Weds mornings are telework time. Conceptually this gets folks together to really plan and obtain true team commitments about what they’ll execute. Then BREAK (hand clap) we let trust & accountability kick in - let our folks just be great! Go perform the work/mission and we’ll regroup in after 24hrs of uninterrupted time to slay dragons however you best slay dragons. The half day blocks are important because face it you can’t get good work done in those 20min chucks between endless meetings. Most of our best work happens in multi-hours chunks of time.

Anyway I think this needs to stop now – I’ve bleed a lot of Agile teams into my reply here, y’all get it. Happy Teleworking when you can!


@Brent_Reimer awesome overview of your telework experience!! Thanks for sharing!

The key elements of successful telework are trust & accountability!

Here are a couple other blog posts I came across today:

Blog Post: Working remotely, 4 years in

I live in Montreal. 4 years ago, I decided to take a job working remotely for a company based in San Francisco. At the time, I was worried that it wouldn’t work out – I’d never worked remotely before, so it was a pretty big unknown for me. You can see me struggling with it on this blog after 3 months and 8 months. But Avi (one of the people who interviewed me, who works remotely) convinced me that it was a reasonable thing to try, and I could see that it was working for him, and I really liked all the people who interviewed me, so I decided to give it a shot.

It worked out. It obviously hasn’t always been 100% perfect in every way, but working remotely has been a great career move for me. I’ve learned a ton from my coworkers and have been able to do some really cool projects that I’m proud of. So here are some thoughts about what I think has made it work for me.

As usual this isn’t advice, and I’m not saying that you should work remotely. I’ve only done remote work at one company (Stripe) and I am only one person (even other remotes at Stripe will have different experiences than me!).

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SAF-AQ? published a great slide deck on telework and even addressed common myths and benefits.

I know several contract support services contractors that successfully telework in support of government contracts. Makes sense; a performance based contract for contract specialist type services seems ripe for telework, right? Remember FAR 7.108

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I didn’t, so here it is for anyone else.

7.108 - Additional Requirements for Telecommuting.

In accordance with 41 U.S.C. 3306(f), an agency shall generally not discourage a contractor from allowing its employees to telecommute in the performance of Government contracts. Therefore, agencies shall not–

(a) Include in a solicitation a requirement that prohibits an offeror from permitting its employees to telecommute unless the contracting officer first determines that the requirements of the agency, including security requirements, cannot be met if telecommuting is permitted. The contracting officer shall document the basis for the determination in writing and specify the prohibition in the solicitation; or

(b) When telecommuting is not prohibited, unfavorably evaluate an offer because it includes telecommuting, unless the contracting officer first determines that the requirements of the agency, including security requirements, would be adversely impacted if telecommuting is permitted. The contracting officer shall document the basis for the determination in writing and address the evaluation procedures in the solicitation.

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Good stuff. I am definitely a fan of telework. I don’t love doing it so much myself if I’m honest but there is great value in it for many folks. We need to continue to advance Contracting as a professional career. I recently heard a career academic state that the difference in a job and a career is you clock out of the job and you never clock out of the career…you are always thinking. I think that working in a knowledge-based service (which contracting is) we don’t have to follow the industrial age model of come to a location, clock in, produce and leave. We can work from anywhere and we should probably consider carving out time for our folks to work on innovations or to cross work on base with other orgs. For instance, what if you mandated (with coordination) that your folks would spend at least 2-3 hrs a month going over to Finance and supporting them in anyway they could or MX or whatever. It sounds like a waste of time until you realize that we are TRULY force enablers. What does that mean? In our case it means that we have LITERALLY zero to add to the mission if we are not solving other peoples problems. If we create and solve our own myopic problems you will see virtually no payoff for the mission. But when we focus on being NITROUS and not the filter, we can project immense power. Telework encourages that environment and so does cross-work.


A common question is what will you do when there is a meeting with the MSG, Wing, or other mission partner?

  1. Request a call in number
  2. Offer to set up a teleconference, DCS, or Skype Business (which has video conference capability) for the meeting
  3. If face-to-face is important, members can come in for the meeting

Telework is not a barrier to having a meeting. Thousands of companies across the world have meetings everyday without getting together face to face. We may have to change our processes (e.g. add a call in number to meetings), but that is point. We’re building the experience of operating as a distributed organization.

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I’m a big fan of telework. It’s an important COOP element for bad weather or other disasters.

If you don’t use OMB MAX, it’s basically SharePoint for the Federal Gov. They are deploying a new screen sharing technology soon. If it’s good, I’ll post about it.


As promised, my review of MAX…gov’s screen share. Yes, it works but it’s a little difficult. First you register for an account at Then, you go to and start a virtual machine session via a citrix product. This gives you a brand new computer on a virtual machine that has Adobe Connect built in on it. You will need to load windows and install Adobe connect. this is a little weird since your computer will have 2 start buttons, 2 clocks, 2 My Documents; one is your computer and the other is a virtual machine so don’t get confused but it works on AFNET. You can host Adobe Connect sessions and upload PPT files to share but if you screen-share it will only share the virtual machine, not your AF laptop. If you want to get really fancy, you can download the Adobe Connect app on your phone and use the camera to broadcast yourself (I did this last week TDY to Gunter).

Since DCS is awful, this is a little hack to have SOME webcast functionality. Good luck!


Awesome, thanks! The technical approach of running through a virtual machine is an interesting approach. So it’s better than DCS?