How to Gain More Flexibility at Work

I was coaching a client of mine earlier this week and the topic of flexibility came up and I thought it'd be helpful to share with. My client is a CMO at a startup and she is looking to gain more flexibility in her life. Flexibility is so important, especially to me. Working on your own terms allows you to do better work and life a fuller life. If you’re looking to gain more control over your schedule, feel free to use this framework that I used with my client.

The tl;dr:

  1. Define specifically what flexibility means to you. It could be as extreme as a 4-day work week or popping out to a yoga class during lunch.

  2. Timing is everything. Either ask when negotiating a job offer or after 9-12 months after you’ve proven value.

  3. Start with a 3-month trial period.

  4. For your flexible schedule to work in the long run you will need to have more communication with your team since they won’t be seeing you as much.

Define Flexibility

First, you need to answer what is flexibility to you? Is Flexibility just popping into a quick yoga class at lunchtime or is it working on a non traditional schedule, like a four day work week or working from home? Understanding what the ask is going to be is so important. Within the ask there is also context. What are the parameters that you’re working with? Are you in sales and expected to be making calls in the office from eight to five? That's going to be really hard… Or are you a developer and you can really work from anywhere as long as you have your computer? That might be an easier ask. Understanding the context will then help you to make your ask more compelling.


Timing is so important. There is a right time to ask and there's a wrong time to ask. You really only have one shot to ask so make sure you’re cognizant of the timing. A good time to ask could be when you’re negotiating a job offer before you even start. It can be part of the terms of your package. Another good time to ask is after you've proven value to the company, this usually doesn't happen before eight months in a job. When you wait until after you’ve had proven success in your role, you’re able to say, “look at all I’ve achieved and I’m so excited for my continued success with the company but I wanted to talk about how I can further adapt my role to fit my needs.”

Trial period

The ask is easier to swallow when suggested with a trial period. A good rule of thumb is to spend a quarter assessing the new set up. Make a date to reassess the new schedule within three months to see if it’s working for both parties.


With greater levels of flexibility come more responsibility with communication. If you’re not physically in the office or you’re working a reduced schedule, it’s going to be up to you to continue to communicate the value that you’re adding. You need to remain your advocate and ensure you’ve amped up your communication. This can look like weekly reports or weekly check-ins.

I believe over time the traditional work schedule will disappear and this will become more of the norm. I’m already seeing it tons with the execs who I coach.

Nikki Goldman