Part 4: Tackling the tough stuff

October 13, 2020 • 11am – 2pm EDT • EMEA and APAC replays


Sarah Milstein

Senior Director of Engineering


Sarah Milstein


Frantz Joseph

Director of Engineering


Frantz Joseph

Session summary

Alongside all of the positive experiences of being a manager, there will also be times when you have to navigate difficult situations. Managing underperformance, addressing bad behaviour, and even letting people go are possible, and likely inevitable parts of your job.

They can be uncomfortable to tackle, but as a good manager it’s your job to develop these skills so that if the time comes you can do right by your employees. These conversations will also be the ones that shape and define who you are as a leader.

So how do you handle tough conversations with empathy, but also the feeling that you’re doing the right thing.

You’ll leave this session with:

  • An understanding of what your role is as a leader in tough situations
  • A toolkit for avoiding mindsets that can hinder your interactions in these settings
  • A framework to support you in these conversations and processes
  • Strategies for preparation and advice on planning follow-ups and aftercare

Talks and panels

David Yee

Difficult listening and having difficult conversations

Difficult conversations as a manager can be tough. In this session we’ll take a look at some guiding principles for these conversations including resilience building; empathy, transparency, candor; and how to support people before, during, and after a conversation has taken place.

Racine Harris + Speaker TBC

Perspectives on difficult conversations

In this session, two speakers will give their perspectives on a situation involving a difficult conversation. One perspective will be from the manager, and the other from the person being managed. After these talks, both speakers will join Sarah and Frantz for a discussion of the two talks, speaking about what they learnt from hearing the perspective of the other speaker, how it changed their own understanding of the situation, and how it would affect how they took part in these conversations in the future.

Gordon Radlein, Lisa Van Gelder, Dheerja Kaur

[Panel] Dealing with times when change isn’t happening

There are times when someone on your team will approach you saying that something needs to change, maybe it’s a piece of company culture or a practice. And you agree with them, it should be changed - but you also know that that change is not going to happen. In this session, we’ll take a look at how to navigate these circumstances.

Timings around the world

Live show October, 13

Daytime in North America, early evening in Europe and Africa.

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EMEA friendly replay October, 14

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APAC friendly replay October, 14

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About Sarah Milstein

Sarah Milstein is a Senior Director of Engineering at Mailchimp. Previous roles include Head of Sales & Marketing for; VP of Programs for; CEO and co-founder of Lean Startup Productions; and co-author of The Twitter Book. She's also held senior management positions at O’Reilly Media, UBM TechWeb, and several startups.

Earlier, she was a freelance journalist writing regularly for The New York Times, she co-founded a record label with children’s musician Laurie Berkner, and she started Just Food's CSA program. She holds an MBA from UC Berkeley and a BA from Rutgers University. Bonus fact: She was the 21st user of Twitter.

About Frantz Joseph

Frantz Joseph is a Director of Engineering working remotely at Mailchimp. He manages multiple, distributed teams from his home in Los Angeles. Over his 16 year career, he has worked as an engineer and manager in various parts of tech including video games, streaming radio, e-commerce, marketing, and a social network. He has a passion for building inclusive communities, extending opportunity to often overlooked groups, and leading with empathy.

When not talking about leadership in tech you can find Frantz consuming classic film or in the kitchen experimenting with cuisine from his native Haiti.

Got questions?

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