Amy Kean on Grief

Why do we struggle to talk about grief? Why that matters and what we can do about it, is the subject of this episode.

Summary
Grief is something almost all of us will experience, and yet something we still struggle to talk about openly. Not because it’s rare, but because it makes us uncomfortable. We lack a shared language for it, feel uneasy about how long it lasts, and often don’t know how to sit with people who don’t simply “move on”.

On this episode, I'm joined by Amy Kean, founder of Good Shout, for a deeply human conversation about grief, work, identity, and what it really means to give people space to be themselves.

Amy has been on the podcast before. Since first encountering her work, I have been consistently inspired by her willingness to be unashamedly herself: thoughtful, curious, and open about experiences many of us keep hidden. When she recently shared reflections on grief on LinkedIn, it sparked a desire to invite her back; not for a tightly structured discussion, but for a conversation that could explore the wider dynamics around loss.

What follows is an unusual episode. It begins with grief, but moves into related territory: compassionate leave versus compassionate return, what actually helps when someone is struggling, why workplaces are often so bad at dealing with loss, and why talking about difficult things might be one of the most important human skills we have.

Rather than offering neat frameworks or tidy conclusions, this conversation creates space; for reflection, for discomfort, and for honesty.

If you’ve experienced loss, this episode may offer comfort or recognition. If you haven’t, it may give you insight into how to show up better for others when the time comes. And above all, it helps normalise the idea that grief is not something to be hidden or hurried past, but something we should be able to talk about.

The episode is dedicated to Amy’s dad, Lord Terence Kean.

Relevant Links
Good Shout, Amy's company — https://goodshoutcommunity.com/

Amy on LinkedIn — https://www.linkedin.com/in/amycharlottekean/

Amy’s previous appearance on the show talking aboiut Communicating Effectively —
https://www.humanriskpodcast.com/amy-kean-on-communicating-effectively/

Death of an Ordinary Man by Sarah Perry —
https://www.goodreads.com/book/show/60324067-death-of-an-ordinary-man

AI-Generated Timestamp Summary
01:05 – Why Amy, why now
03:40 – Remembering Amy’s dad
08:30 – Double grief and anticipatory loss
10:40 – Stroke, hope, and uncertainty
14:40 – Grief, work, and performance
17:35 – Naming emotions out loud
22:05 – Talking about grief on LinkedIn
27:40 – Compassionate return
30:05 – The cognitive cost of grief
33:05 – Why we don’t talk about death
35:05 – How to help someone who’s grieving
41:05 – Creativity, curiosity, and grief
49:05 – AI, voice, and being human
53:05 – Shameless and deathbed economics
01:02:00 – Final reflections and dedication