How to approach your boss about telework

Anywhere workers do it daily. Corporate workers do it once or twice a week. Flex workers do it when appropriate. What is it? Teleworking. The US government is working to get the Telework Enhancement Act passed. Though I have not read the act, I have experienced resistance to telework from many employers and clients. The hard truth is that if you want a telework arrangement, it is your responsibility to make it work, not management’s.

NEWS UPDATE: President Obama signs The Telework Enhancement Act into Law December 9, 2010

It’s a start – now do your part! Let’s make the movement into the anywhere worker world – one person at a time! Here are some tips to get you started.

do your homework

If you are serious about making the move to anywhere / telework, you’ll most likely have to develop a campaign and make a proposal to your manager. There are four prerequisites that must be met before having a conversation with your manager about telework. Any one of these items may indicate an obstacle, but it is important to know this information before having the conversation. First you will have more knowledge than you do already, and second it will indicate to your manager that you are serious enough about telework to take the extra effort to do the research.


1.  Make sure you are a good producer. If you are not a valued worker to begin with, you will have little leverage with your manager. Make sure your manager is happy with your contributions and that you deliver on your promises. If there is any question of your value, take time now to make a change. You need to make sure your manager believes you can manage yourself and don’t need step by step guidance. Although many teleworkers are entry level, they are usually stepping into an existing telework organization.

2. Make sure your work can be done remotely. Is your job compatible with telework arrangements? If you must interact face to face with co-workers and/or clients, chances are you can not telework. Some examples: Healthcare workers, Retail workers at brick & mortar shops, confidential and secure work, or manufacturing. Take a realistic look at your responsibilities and assess their telework capabilities. If you are not sure, do some research to see if a comparable role in another company allows telework.

3. Research your company’s policies on telework. If the company or organization already has a specific policy, you need to read and understand it. If telework is not allowed, find out why. The policy may have been written in a different environment and you may be able to petition for it’s revision.

4. Research precedence in your organization / department. Are others in your organization teleworking? If so, find out as much as you can about their situation. What is their role and responsibilities. Who is their manager? How often do they telework? Understanding the situations in which your organization allows telework will help you build your case to present to your manager.

have a conversation

Once you have analysed the research / homework, it is time to approach your manager. Caution: do not expect to get a ‘yes’ on your first try (hurray if you do, but don’t expect it). Many managers resist telework. The reasons vary, but often it is due to a lack of skills / experience managing teleworkers. Another possibility is that your manager has allowed telework in the past with unsuccessful results. Whatever the reason, take the telework proposal one step at a time.

1. Have a conversation with your immediate manager with the single intent of understanding her perspective point of view on telework. Notice her mindset and openness to the discussion. Do not assume that she does or does not support telework and most importantly do not judge her for her position. This is a fact finding mission. You want to get to know her thoughts on telework and understand her concerns. Here are a few questions to get you started, but you should write your own based on your relationship:

  • Have you ever managed a teleworker in this or a previous job?
  • Have you ever been a teleworker?
  • What do you think are the benefits of telework for the employee? for the manager?
  • What do you think are the obstacles of telework for the employee? for the manager?
  • Have you ever considered offering telework opportunities in our department? If so, what happened? If not, why not?

Remember: Do you judge or challenge your boss’s answers. Truly listen with the intent to understand her position and motivation. At the end of the conversation let her know that you value her opinion and that you want to investigate the possibility of telework for yourself. The information she provided will help you to assess telework for your current role. Make a follow-up appointment to revisit telework in a couple of weeks so you can discuss your findings.

2. Remove the obstacles. Your manager most likely identified the obstacles (from her perspective) to telework. Now your real work begins. It is your mission now to remove those obstacles that are within your power. Three of the main obstacles identified by organizations implementing telework programs are:

obstacles to telework

  • Management skills – many managers are never trained on how to manage remote workers. Motivation, communication, work assignments – all differ for an anywhere worker than for an in house worker. The good news: skills can be learned!
  • Employee skills – let’s face it if you aren’t self motivated or have trouble with procrastination, time management, and meeting deadlines then you need to work on those skills before you can be successful in telework arrangements. Again, skills that can be learned!
  • Technology – staying connected, having access to the information, people, and technology necessary to be successful is a foundation for telework. Usually a computer, high speed internet, phone, and teleconferencing or web conferencing services is all that is necessary. Make sure you know what you’ll need to do you job anywhere.

And to give you a few things to consider as benefits:

benefits of telework

  • Continuity of operations for many organizations (including the federal government)
  • Reduction in commuting costs (not to mention reduction in accidents!)
  • Reduction in pollution from automobile emissions
  • Reduction in sick leave
  • Improved work / life balance
  • Improved morale
  • Improved performance / productivity
  • Improved human capital retention
  • More attractive to valuable talent

If telework is a must have for you and you are not able to negotiate a telework agreement in your current role, you may need to consider changing roles. Be patient in either negotiate telework in your current role or in making the decision to move on.  One final caution: Telework is not for everyone. If you have trouble with self management and self motivation, you may not be an ideal candidate for telework. In a future post we’ll look at the consideration in making the decision to telework. Until then, do your part!


Hey, thanks for reading. If you enjoy this post, please consider forwarding to friends or coworkers. If you need help in making changes to your life of business, consider hiring a coach – I’m here to help – contact me for a consultation!