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Single topic deep dives. Bite-sized episodes. Expert advice to help you work smarter and manage better — remotely. For distributed team leaders and remote professionals. Podcast FKA "Outside the Valley."
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Mastering Remote
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Employees vs Contractors: How to Stay Compliant When Remote – Dee Coakley of Boundless | S2E5
27:40
27:40
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27:40
What you’ll learn in this episode: Know when to hire a remote team member as an employee versus contractor How compliance can be actually help you recruit and retain great talent How to evaluate an employer of record before selecting one Resources mentioned: Boundless Gavin Sheridan’s Twitter list of experts on COVID Morning Brew Coda Asana Present…
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Mastering Remote
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How a Strong Employer Brand Helps Recruit Top Talent – Diane Tate of Mozilla | S2E4
20:56
20:56
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20:56
What you’ll learn in this episode: Why a strong employer brand can help attract hard-to-hire candidates How to research and build your employer value propositions from scratch The metrics to help measure the effectiveness of your employer brand story Resources mentioned: Mozilla’s employer value propositions Job Portraits agency Anand Giridharadas …
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Mastering Remote
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How to Lead Through Uncertainty – Dominic Price of Atlassian | S2E3
31:59
31:59
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31:59
What you’ll learn in this episode Several exercises to help you be a more effective leader, especially now How to keep your old habits from holding you and your team back How to turn experimentation into a core part of your organization’s DNA Bonus: Why and how Atlassian decided to embrace being a hybrid organization. Resources mentioned Atlassian …
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Mastering Remote
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How to Raise Funds Remotely – Joe Blair of Cota Capital | S2E2
22:31
22:31
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22:31
What you’ll learn in this episode: How to ace your next VC interview and get funded How to overcome the trust deficit when raising capital remotely What unexpected challenges founders will face and how to overcome them Resources mentioned: Distributed Valley Cota Capital Remote Startup Expo 3.0 Remo virtual events platform Del Johnson on Twitter “L…
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Mastering Remote
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How to Transition to 100% Remote – Chris Winn, Creative Market CEO | S2E1
24:13
24:13
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24:13
What you’ll learn in this episode: How to transition from an office-based to fully distributed company (and culture) How to get team buy-in and handle people leaving as change occurs Why meaningful work is the secret to strong remote team connections Resources mentioned: Creative Market “Hiring Your Dream Team,” video of Chris speaking at Calibrate…
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Mastering Remote
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Chris Ruder (Spikeball): Shaping Up Your Company's Culture and Values - S1E30
50:16
50:16
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50:16
Topics also covered on the podcast episode: The history of SpikeBall Why playfulness and kindness is essential to SpikeBall’s company culture Identifying traits that makes someone suitable for remote work during the interview process SpikeBall’s onboarding process for new employees Mentioned resources: Chris Ruder Spikeball Ken Weary of Hotjar: How…
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Mastering Remote
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Recruiting and Remote Work in a Post-COVID World - S1E29
58:15
58:15
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58:15
Topics also covered in this episode: How recruiting teams can adapt to shifts in the talent market. Creating a job description that attracts the right candidate. Purposefully building infrastructure so your remote team can be sustainable and succeed. The importance of culture when bringing new hires together in remote teams. Practices or processes …
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Mastering Remote
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Jennifer Aldrich (InVision) - Why Remote Work is More Than a Job Perk - S1E28
44:05
44:05
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44:05
Topics also covered on the podcast episode: How culture and onboarding evolved at InVision as they experienced rapid growth What companies should know about building a community Challenges Jennifer faced as a community builder Why remote work is a life-changer for disabled individuals Advice for remote job-seekers Mentioned resources: InVision Clar…
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Mastering Remote
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Remote Engineering Team Best Practices: AMA with TaxJar and Help Scout - S1E27
49:38
49:38
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49:38
Topics also covered in this episode: How COVID-19 pandemic has affected Matt and Megan’s working routines How Matt and Megan kept the morale and culture of their engineering teams intact during this challenging time How they go about figuring out meetings and setting goals for their teams The hiring processes and interview questions at TaxJar and H…
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Mastering Remote
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Brooke Hurford (Workfrom) - Building a Community of Remote Workers - S1E26
38:38
38:38
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38:38
Topics also covered in this episode: Why Brooke was initially attracted to remote work Brooke’s experiences with isolation while working remotely How Workfrom helps remote workers to interact with each other How Brooke thinks COVID-19 will impact the dynamics of remote work in the future Why remote work is a big benefit to local communities Mention…
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Mastering Remote
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All About Pair Programming: AMA with Ben Orenstein of Tuple - S1E25
55:15
55:15
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55:15
Mentioned resources: Tuple Ben’s Twitter How to pair with a junior developer Basecamp Shape Up The Manager’s Handbook Clearbit Alex MacCaw Extreme Programming Learntopair.comBy Jovian Gautama
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Mastering Remote
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Remote Work FAQs - Live with the Arc Team - S1E24
53:59
53:59
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53:59
Topics also covered on the podcast episode: How our communication style and processes have evolved How we designed our workspaces at home Handling criticism and feedback in remote teams How remote work affected our routines and daily life Mentioned resources: Zoom Notion Airtable Kap Loom Liam Martin: How to Be a Remote Executive Workstation Popcor…
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Mastering Remote
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Darren Murph (GitLab) - Why Companies Should Go All-Remote - S1E23
53:34
53:34
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53:34
Topics also covered on the podcast episode: How Darren got the rare title of “Head of Remote” Why GitLab choose “all-remote” as their company identity Why hybrid remote teams can lead to guilt and burnout Why “storytelling ability” is important in GitLab GitLab’s “handbook-first” approach Darren answering questions from Twitter Mentioned resources:…
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Mastering Remote
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Steph Smith (Integral Labs) - The Main Qualities of Effective Leadership - S1E22
52:51
52:51
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52:51
Topics also covered on the podcast episode: What attracted Steph to remote work The “give and take” approach in remote hiring How Steph learned to be a better communicator Can you deliberately train communication skills? How to encourage top-down empathy in an organization Why humility should be at the core of leadership The three must-have qualiti…
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Mastering Remote
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Laurel Farrer (Distribute Consulting) - Re-skilling Via Remote Work - S1E21
51:19
51:19
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51:19
Topics also covered on the podcast episode: How Laurel persuaded the executives of his previous company to experiment with remote work Why Laurel thinks compliance is the number one thing companies should figure out before going remote How Laurel measures the cost of transitioning to remote work (as well as the metrics for measuring whether this tr…
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Mastering Remote
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Ken Weary (Hotjar) - How to Regain Productivity in Your Remote Team - S1E20
48:23
48:23
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48:23
Topics also covered on the podcast episode: How Ken and his spouse manage their children’s education while being digital nomads Why Hotjar decided to always default to asynchronous communication whenever possible How Hotjar realized that productivity was going down Hotjar’s meeting culture and requirements How Hotjar’s utilizes the “Tribes” system …
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Mastering Remote
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Fred Perrotta (Tortuga Backpacks) - Encourage Remote Team Risk-Taking - S1E19
51:04
51:04
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51:04
Topics also covered on the podcast episode: The challenges of developing a physical product as a 100% remote company How you can create an “epic place to work” How Fred applies the principle of “gentle guidance” as a remote leader Tortuga’s hiring process Signals to find out if someone can work remotely well Fred’s one million dollar mistake The im…
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Mastering Remote
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Jesse Mecham (YNAB) - Building a Helpful & Kind Remote Team Culture - S1E18
43:48
43:48
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43:48
Topics also covered on the podcast episode: How Jesse started YNAB back in 2004 and found his CTO remotely How Jesse delivers feedback and criticism as a remote CEO YNAB’s unique ritual for all-hands meetings YNAB’s hiring and onboarding process The growing pains experienced while scaling a remote company The unique interview questions that YNAB as…
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Mastering Remote
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Max Makeev (Owl Labs) - Making Remote Meetings Better - S1E17
58:33
58:33
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58:33
Topics also covered on the podcast episode: How Max started in the world of robotics and helped created Roomba The very first prototype of Meeting Owl How Max and his co-founder found early adopters and gathered feedback How can a hardware startup vet their suppliers? Does a 100% distributed team need a Meeting Owl? Unique use-cases of Meeting Owl …
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Mastering Remote
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Laura Roeder (MeetEdgar) - How to Build a Company That Doesn't Need You - S1E16
54:30
54:30
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54:30
Topics also covered on the podcast episode: Laura’s current role and why MeetEdgar has a “President” Why Laura decided to create a company that can run without her Mistakes and challenges Laura made while growing MeetEdgar The importance of transparency Why you should not put criticism on Slack Why meetings are essential for remote teams Is MeetEdg…
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Mastering Remote
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Kieran Flanagan (HubSpot) - Remote Work as a Growth Lever - S1E15
46:20
46:20
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46:20
Topics also covered on the podcast episode: How remote work helped Kieran in his career and personal life Why geographical boundaries shouldn't limit career opportunities The hardest part of remote leadership Why remote hiring is one of the best things you can do for company growth. Using "squads" in distributed teams Avoiding too many processes in…
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Mastering Remote
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Tammy Bjelland (Workplaceless) - Leveling Up Your Company with Remote Work - S1E14
49:38
49:38
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49:38
Topics also covered on the podcast episode: 04:12 — How Tammy realized that working in an office is not really for her 07:00 — What fascinates Tammy the most about remote work 08:27 — How remote work can improve the education sector 13:30 — How Workplaceless started 16:46 — Why companies and managers need training to successfully become “remote” 21…
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Mastering Remote
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Liam Martin (Time Doctor) - How to Be a "Remote Executive" - S1E13
1:08:55
1:08:55
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1:08:55
Topics also covered on the podcast episode: 04:10 — How Liam realized that overworking and hustle culture is dangerous 09:00 — The main difference between “entrepreneur” and “executive” 14:15 — The top two things that Liam needed to re-teach himself to be a better remote executive 24:14 — The million-dollar mistakes that Liam and his co-founder mad…
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Mastering Remote
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Eddie Zaneski (Digital Ocean) - Fostering Remote Developer Communities - S1E12
39:57
39:57
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39:57
Topics also covered on the podcast episode: 03:31 — What makes DigitalOcean’s hybrid team model successful 06:42 — Examples of the “remote-first mindset” at DigitalOcean 08:03 — Early resource investments by DigitalOcean to make remote work run smoothly 09:16 — The growing pains of DigitalOcean’s remote processes 13:49 — Eddie’s most surprising fin…
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Mastering Remote
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Megan Chinburg (Help Scout) - Help Scout's Remote Hiring Process - S1E11
52:49
52:49
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52:49
We covered: 02:31 — How Megan started her engineering leadership career 08:40 — The differences between managing a remote vs co-located engineering team 18:06 — How Help Scout screens for value alignment and technical competence 35:38 — Help Scout’s onboarding process for new hire 40:10 — Why documentation is important when onboarding new engineer …
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Mastering Remote
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Hailley Griffis (Buffer) - A Peek Into Buffer's Open Culture - S1E10
56:26
56:26
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56:26
We covered: 04:25 — How Hailley convinced her previous company to allow remote work 06:33 — Advantages of remote work for Hailley’s productivity 11:30 — Why Buffer has a super transparent culture (and how this affects Buffer) 13:55 — Why Buffer gives internal team members opportunities to apply for new job openings 20:03 — Do you need to have exper…
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Mastering Remote
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John Doherty (Credo) - Communicating Expectations Well - S1E9
40:56
40:56
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40:56
We covered: 4:30 — How John keeps in touch with the Credo community. 7:00 — Has John's mindset about remote work changed over the years? 11:05 — The difference between managing a client vs managing a product. 14:30 — How a leader can be better at writing expectations, especially in a remote organization. 20:00 — What soft skills John looks for when…
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Mastering Remote
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Peldi (Balsamiq) - Continuous Learning as Remote Company DNA - S1E8
49:21
49:21
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49:21
We covered: 02:31 — Why Peldi moved back to Italy to build Balsamiq 07:26 — What Balsamiq does to maintain a self-aware and continuous learning culture 10:16 — Why “experiment culture” is important in Balsamiq 13:35 — Why Peldi prefers not placing too much weight on his own “voice” within the company 21:15 — The un-sexy part of remote hiring (legal…
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Mastering Remote
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Hiten Shah (FYI) - Figuring Out Your Remote Work Structure - S1E7
35:26
35:26
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35:26
We covered: 2:27 — How Hiten Shah started his very early internet business 4:00 — Why Hiten and his co-founder Marie Prokopets wrote the Remote Work Report 6:10 — The most surprising finding from the Remote Work Report 8:10 — How a remote manager can help remote team members figure out their ideal daily structure 10:10 — What exactly is “overcommun…
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Mastering Remote
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Ho Yin Cheung (Remo) - Challenges of a Remote Startup Leader - S1E6
55:46
55:46
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55:46
We covered 05:54 — What fascinates Ho Yin the most about remote work 08:41 — Challenges and lessons Ho Yin faced while transforming to be a remote startup leader 13:08 — How Ho Yin’s hiring process changed 19:38 — Ho Yin’s “superpower” that helps him manage his remote team better 21:35 — Why recording is a powerful tool for creating processes in re…
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Mastering Remote
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Andreas Klinger (Angel List) - Don't Build Your Eng Team in Silicon Valley - S1E5
56:33
56:33
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56:33
We covered: 01:02 — What is “Head of Remote” actually? 02:00 — Why remote work came naturally to Andreas 04:37 — How investors’ perceptions about remote work have changed over the years 06:24 — Why building an engineering team inside Silicon Valley is now questionable 11:08 — Is there such a thing as a “network effect” in remote work? 15:45 — Why A…
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Mastering Remote
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Justin Mitchell (YAC) - High-Res Communication in Remote Teams - S1E4
52:55
52:55
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52:55
We covered: 01:28 — How Justin got his first startup gig in high school 06:06 — What is YAC? 07:46 — Why voice communications are better than written documents 12:44 — Using voice for async communication and clarity 26:33 — How YAC launched via Product Hunt Maker’s Festival 33:29 — Why Silicon Valley companies are doing themselves a disservice by n…
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Mastering Remote
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Krister Haav (Toggl) - Creating a Playful Remote Culture - S1E3
44:29
44:29
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44:29
We covered: 07:23 — Why “playfulness” is important to Toggl’s culture 11:51 — Does brand authenticity = a higher employee retention rate for Toggl? 13:51 — How Toggl “transfers the vibe” of team culture within the organization 20:45 — The hiring and onboarding process at Toggl 35:45 — Is it possible for remote teams to hire for potential? 40:13 — K…
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Mastering Remote
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Mark Faggiano (TaxJar) - Prioritizing Employee Experience - S1E1
48:55
48:55
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48:55
We covered: 03:00 — Why Mark is passionate about remote work 06:30 — The point during company scaling when it started to become harder to convey the company’s core values 06:30 10:40 — The importance of employee onboarding, and why Mark decided to personally onboard new employees until the company grew to a team of 20 16:00 — The importance of the …
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Mastering Remote
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Claire Lew (Know Your Team) - How To Build Trust In Remote Teams - S1E2
43:10
43:10
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43:10
We covered: 03:00 — The 3 pillars of good leadership and how Claire codified these 08:40 — Attributes of a good remote team leader 10:05 — The importance of “affective trust” in a team 16:10 — Can empathy be trained? 19:40 — Asking the right questions as a leader 29:50 — Claire’s thoughts on hybrid teams (half remote, half co-located) 34:11 — How c…
