How to Negotiate Flexible In-Office Return Arrangements

8 Sep 2026 · 11 min · 5 chapters

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In short

Negotiating flexible in-office return arrangements (especially extending work-from-home during COVID-era risk) using solution-focused language, manager empathy, and trial periods.

Guest backgrounds

Karen Madison, UK flexible working consultant and co-founder of TimeWise; advises workplaces on valuing flexible work beyond “what you can’t do.”

Key claims

Avoid starting with “why” or personal limitations; focus on “how” your proposal helps the business and delivers outcomes. Don’t frame requests as inability; frame as what you can deliver safely. Use a trial period (e.g., 1–2 months) with a review to reduce employer fear of permanent commitments.

Notable examples

A mock negotiation script asking to work from home longer due to discomfort and public-transport risk; a revised approach emphasizing WFH successes and proposing early/partial in-office schedules to avoid rush-hour travel.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Flexible Work Options

0:30 to 1:24

Expert Karen Madison shares insights on flexible work arrangements.

“It could be chronic migraine, 15 or more headache days a month, each lasting four hours or more.”

Understanding Flexible Work Options

2:26 to 3:02

Expert Karen Madison shares insights on flexible work arrangements.

“She helps workplaces think differently about the value of flexible working.”

Strategies for Negotiating Work-from-Home

3:02 to 4:49

Learn practical language to negotiate extended work-from-home arrangements.

“So I should mention that even before I had my conversation with Karen, I did a little exercise.”

Advancing Negotiation Techniques

4:49 to 6:22

Karen shares advice on approaching flexible work negotiations effectively.

“I've been thinking about how we could design work maybe for this next phase of COVID-19 and how we could design the roles so people will feel safe but also the business gets what the business needs.”

Role-Playing Negotiation Scenarios

7:01 to 10:31

A role-play demonstration showcases effective negotiation tactics.

“If you take anything from this video, Karen has an ace in the hole for if and when negotiations seem to be going in the wrong direction.”
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Transcript

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0:00When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications, and more. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. I get so many headaches every month. It could be chronic migraine, 15 or more headache days a month, each lasting four hours or more.

1:02allergic reactions, neck and injection site pain, fatigue, and headache. Allergic reactions can include rash, welts, asthma symptoms, and dizziness. Don't receive Botox if there's a skin infection. Tell your doctor your medical history, muscle or nerve conditions, including ALS Lou Gehrig's disease, myasthenia gravis or Lambert-Eaton syndrome, and medications, including botulinum toxins, as these may increase the risk of serious side effects. Why wait? Ask your doctor. Visit BotoxChronicMigraine.com or call 1-800-44-BOTOX to learn more. It's official. The American economy is reopening and I'm having a lot of complicated feelings about that.

1:37I'll be real with you. I'm too scared to go back to the office right now. And I know I'm not alone. To do my job well and equitably, I want to be out in the community. But at the same time, I'm put more at risk. I am not in a rush to get back. I can work from home very effectively. Similar to a lot of people where I think it's a bad idea, The risk of COVID-19 hasn't disappeared. So for the moment, I'm really, really lucky. I can continue working from home. But, you know, in the not-so-distant future, I can assume one day I'm going to be asked to go back to the office, and I have to think to myself, how am I going to talk to my manager if I'm not ready?

2:16What if I want to just continue working from home? What if that's better? I found an expert, and she's going to help me answer these questions. Karen Madison is a flexible working consultant and co-founder of TimeWise, based in the UK. She helps workplaces think differently about the value of flexible working. When people talk about flexible working until now, it's always about what you can't do. So it's been a very limiting kind of conversation. Oh, you can't do that. I can't see you. How will I trust my team if I can't see them? How will I know they've done their job? And I think actually there's so much about the possibility in terms of how can people combine caring responsibilities, reduce travel, do better things for the environment, work in a different way.

2:56And I think we just haven't had our eyes and ears open to what's possible. And I think now we really have. So I should mention that even before I had my conversation with Karen, I did a little exercise. I was curious, what would I even say if I tried to negotiate working from home a little bit more and postponing re-entry? So I did a little mock interview. And here's kind of the language that I ended up using. My request for you is, is it possible to work from home for just a little bit longer? I don't quite feel comfortable going back in yet. I think if the company truly cared about its staff, you know, on top of all these safety precautions, I think it would stand that you guys might listen and consider us as people and humans and maybe understand that we may not necessarily feel comfortable coming back.

3:48I increase my risk because I take public transportation to work. And that is my only option, really. So I would hate to take, you know, sick days or worse. So thoughts, how'd I do? Well, I think you did good, but I would probably go to a negotiation like that. less I think you put yourself in a down position in the beginning by just talking about your needs try and take solutions as well as the problems and I think when you started you just said I'm just not ready to come back now I think while that might be true you could put it in a different way so what you could have done is said to him there's been some amazing things about working from home that I think we've all taken I've spoken to colleagues and it's been an incredible experiment about what we can achieve what do you think and sort of get him to talk about what's worked well and then maybe think for yourself what's your deal breaker are you saying you never want to go or you don't want to travel every day or you don't want to go in rush hour and then say I've been thinking about how we could design work maybe for this next phase of COVID-19 and how we could design the roles so people will feel safe but also the business gets what the business needs.

5:06Essentially, you just want to try to put yourself in your manager's shoes. I know. Easier said than done, right? But Karen had some great advice. Try to steer away from the why. Like, why you're negotiating for this or why you need a flexible work schedule. Instead, you want to focus on the how. You want to explain how your solution is going to help them and When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more. Spend less time searching and more time actually interviewing candidates who check all your boxes.

5:47Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. I get so many headaches every month. It could be chronic migraine, 15 or more headache days a month, each lasting four hours or more. Botox, on a botulinum toxin A, prevents headaches in adults with chronic migraine. It's not for those who have 14 or fewer headache days a month. Prescription Botox is injected by your doctor. Effects of Botox may spread hours to weeks after injection, causing serious symptoms.

6:22Alert your doctor right away as difficulty swallowing, speaking, breathing, eye problems, or muscle weakness can be signs of a life-threatening condition. Patients with these conditions before injection are at highest risk. Side effects may include allergic reactions, neck and injection site pain, fatigue, and headache. Allergic reactions can include rash, welts, asthma symptoms, and dizziness. Don't receive Botox if there's a skin infection. Tell your doctor your medical history, muscle or nerve conditions, including ALS Lou Gehrig's disease, myasthenia gravis or Lambert-Eaton syndrome, and medications, including botulinum toxins, as these may increase the risk of serious side effects.

6:53Why wait? Ask your doctor. Visit BotoxChronicMigraine.com or call 1-800-44-BOTOX to learn more.

7:24upfront as you said a solution like here is the vision what are what are other common ways that people might um you know naturally go in as a down position that you've seen people start with an apology or people start talking about their complex so in a you know people might say well I need to work flexibly because my children's nursery finishes at four and that means I've got to leave at three and you know sometimes I might miss the train or I can't find parking and then it's like hang on a sec I'm dealing with your chaos I've got my own chaos and it's like no so I think generally people put themselves in a down position by telling you what they can't do rather than talking about what they think they could deliver.

8:06Look doing this kind of thing is really tricky and it can be especially daunting if you've never done it before but like anything else in life it just gets easier with practice and Karen suggests doing some role play maybe with a friend or with someone in your network who happens to be a manager. If you take anything from this video, Karen has an ace in the hole for if and when negotiations seem to be going in the wrong direction. If it's not going well and you feel yourself being backed into a corner, the one thing that I would try that's actually really underutilized is the trial period. Could we try it for a month and review on both sides how it goes?

8:47And I think when people use that, it generally ends up pretty well. And people use that for when they come back for maternity leave or in these times as well. Can we try it for a month? Can we try it for two months? I understand you don't want to commit to it because I think one of the things that will back an employer into the corner is if they think they agree to something now and that's there forever. So try that. So to recap, one, negotiating this kind of thing takes a lot of practice. And two, it's critical to see it from your manager's point of view. But just to be safe, I wanted to see Karen do it.

9:18I feel nervous now. It's showtime. I understand that there's a huge number of people now coming through to ask for flexible working. So I understand that you don't have a policy for that at the moment. But I'm wondering if we could work together and see if we could come up with one that worked for the business and worked for the employees. I don't feel completely comfortable on my journey to work. so I'm just wondering whether for example you can give some flexibility on when I can come to work so I'd be really happy to come very early in the morning and leave mid-afternoon so that I avoid traveling on busy commuter trains is that something you'd be able to offer?

9:58If we can meet each other halfway in transitioning back to a way that's good for the business but where I feel safe in how I get to work and when I am work and also feel trusted to work from home for part of the week I think that sounds like an amazing thing for us both to be doing. Wow so that is how an expert does it. I am truly inspired by Karen and I'm very appreciative of the advice and the tips that she gave and it seems to me at the end of the day success in a negotiation about your flexible working arrangement, it really hinges on the core relationship and trust that you have with your manager and your company.

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From the publisher

How to Negotiate a Flexible Return to the Office

28 May 2020

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𝙎𝙪𝙗𝙨𝙘𝙧𝙞𝙗𝙚 𝙩𝙤 𝘼𝙨𝙘𝙚𝙣𝙙 𝙩𝙤𝙙𝙖𝙮! ✨ https://www.youtube.com/c/HBRAscend ✨

Many of those working from home during quarantine are now being asked to return to the office. But how do you talk to your manager if you don’t want to go back in?

The pandemic forced physical coworking spaces to temporarily shutter, and for many employees the transition from working in an office to working from home was abrupt. However, many of us have adapted to working from home—and what may have seemed unfamiliar at first now feels more routine. And until a Covid-19 vaccine is widely available, office re-entry carries both measured and unknown risks.

Karen Mattison, a flexible working consultant and co-founder of Timewise, offers advice on how to enter a negotiation with your manager for an alternative working arrangement during this crisis.

Tips for negotiating flexible work:
1. See things from your manager’s perspective. They’re most likely under a lot of stress during this time, so your goal is to make this difficult transition smoother for them as well as for yourself.
2. Take the time to practice. Role-play with a friend or someone in your network who’s a manager. You can even record your sessions so you can replay them later and workshop what you could have said differently during the scenarios.
3. Avoid going into the negotiation with an apology, a wishlist of your needs, or all the reasons why you need a different work arrangement. These approaches instantly put you in a “down position” and weakens your leverage. Instead, go into the conversation with a proposed solution and explain how it’s beneficial to your manager and to your company.
4. Know before going into the negotiation where you are willing to compromise and where your dealbreakers lie.
5. Trust is paramount. Success lies in the strength of your core relationship with your manager. Use it to your advantage.

Learn more about Karen Mattison: https://timewise.co.uk

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How to Negotiate Flexible In-Office Return ArrangementsHarvard Business Review · 11 min
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