Permission to Speak Freely

Sean K. Gabriel
5 min readJul 21, 2021

Most of us dread giving individual feedback in the workplace. It’s awkward, cumbersome, and risky. Doubly so with your boss. Triply so if they were previously your peer.

But it’s not impossible to have a candid, collaborative dialogue about how you work with your manager. While you might feel more comfortable avoiding manager feedback altogether, a little structure can go a long way towards making it easier — by setting the right tone and balancing the conversation.

Here’s the story of how a member of my team, Megan, and I discovered a format to do just that, and what happened when we put it to the test.

As a result of working in the same area of the business, I was fortunate enough to cross paths with Meg, a UX Designer at Red Badger. Meg and I spent a good 6 months as friends before I became her line manager. After four months I raised the question of “how am I doing as a line manager?”, knowing that if this new dynamic had created tension we couldn’t resolve, it would mean the loss of a friendship as well as a working relationship.

In some ways, getting to know each other beforehand made the transition easier, but it had also raised the stakes.

We had some options, but they seemed too formal.

We considered the written feedback tools at Red Badger, but this sort of feedback often comes across as a performance assessment. We were more interested in jointly understanding, in real-time:

  • Has our dynamic changed as a result of my becoming Meg’s line manager?
  • If so, do either of us need to change anything about how we’re working together?

An in-person conversation felt like the best way to explore this collaboratively, but it’s difficult to navigate such open-ended questions without a structure.

Luckily, we realised we could adapt a structure from our project team work. For anyone who’s worked in an agile environment, the retrospective (retro) will be a familiar sight. It’s that regular time where teams get together to discuss what’s working well and what isn’t, in order to facilitate their continuous improvement as a team.

We figured that by adopting this structure for a 1:1 conversation, we would each have room to share our views, unpack them together and then collaborate on appropriate next steps.

We ran our first retro using the format, “Loved, Learned, Would like to know, Even better if”. This format was great because it allowed us to reflect on our working relationship from a number of angles by following those four prompts.

Importantly, it also gave us permission to share our anxieties about what we thought we each weren’t doing well enough (for the “Would like to know” prompt, two examples raised were “Do I advocate for you enough?” and “Am I meeting your expectations?”).

It felt so cathartic to have these questions answered and rewarding to hear what we were doing well that we agreed to continue to hold a retro every 3–6 months.

Retrospectives work best once you’ve agreed on what’s most important as a team. We hadn’t.

We noticed similar themes kept cropping up each time. During our second retro, I raised the question of “Am I wearing both ‘hats’ of project director & line manager well?” and Meg asked “What are the behaviours we want to demonstrate?” As a result, despite the initial calmness after each retro, the original anxiety kept creeping back in that we might each be unwittingly impacting the quality of our relationship somehow.

Eventually Meg realised this was because we hadn’t yet aligned on our shared values and expectations, to determine what we both wanted to improve. When planning the next retro, she designed an activity to first elicit our shared values before reviewing what we could both do to maintain the quality of our relationship.

To elicit these values, we started by individually brainstorming what is most important to us in our working relationship, then grouped the items into themes. Some themes that emerged for us were maintaining a balanced/two-way relationship, being able to challenge one another effectively, having shared side projects and working things out collaboratively.

We then rated how we felt we were doing with each of these shared values on a scale of 1 to 10, before discussing why we rated each item the way we did, and what opportunities existed to bump up our ratings going forward. (In fact, one outcome was deciding to write this blog as a shared side project.)

We learned that retrospectives can be just as useful for relationship building as for reviewing project work.

Ultimately for me, it wasn’t just about experimenting with new feedback formats, but being an effective manager for Meg without the hierarchy of the org chart creeping into the relationship we had previously established. Perhaps given its heritage in agile ways of working, I found something quite democratising about the retro format — it gave both our voices an equal footing and allowed us to align in real-time, as our conversation was a bidirectional exchange by design.

Having started out as friends who were invested in each other’s development, it was important to Meg to maintain a sense of contributing to my growth and happiness at work. Our latest retrospective was a great way to reestablish an awareness and understanding of how to balance the needs of our friendship with the needs of our individual roles. The strongest relationships in life are those where you can navigate the stickier conversations constructively in order to learn from them and grow together, and this retro format enabled that for us.

Try adding retrospectives to your line management toolkit. You might be surprised by what you uncover.

Whether you’ve recently had a peer become your line manager or started managing a former peer yourself, it’s worth establishing what’s important to you both. As time progresses, if you feel like something’s not right or you want to know how you’re doing, don’t shy away from having a conversation about it.

We found the retro structure made these conversations easier for us. If we’ve piqued your interest, why not give our retrospective format a try? We’ve made a template in Miro to get you started — and we’d love to hear your experiences putting it into practice.

Written by Megan Trotter, UX Designer at Red Badger and Sean Gabriel, Delivery Director at Red Badger.



Sean K. Gabriel

Aloha (🤙。◕‿‿◕。)🤙 big on team building & lean product dev. Author @ Thinking aloud with #weeknotes. Works best when caffeinated ☕️