30 Remote Leadership Lessons in 30 Editions
The Future of Work

30 Remote Leadership Lessons in 30 Editions

by Carla Dewing
30 Remote Leadership Lessons in 30 Editions
Contents
  • Lesson #1: Toss the resume – hire smart, hire fast
  • Lesson #2: Cheap labor costs more - invest in talent for true value
  • Lesson #3: Contract work is real freedom - which fuels real success
  • Lesson #4: Asynchronous work is mastery of autonomous time
  • Lesson #5: Hybrid work can be disruptive – focus on clarity and flexibility
  • Lesson #6: Cognitive aptitude + AI mastery = an unbeatable team advantage
  • Lesson #7: Customize workflows - async collaboration isn't one-size-fits-all
  • Lesson #8: Speed up your hiring - reduce time-to-fill with AI
  • Lesson #9: Recognize remote trailblazers - amplify those redefining remote work
  • Lesson #10: Build community - radical remote success lies in connections
  • Lesson #11: Cognitive aptitude reveals true top talent
  • Lesson #12: Remote work is a DEI game-changer
  • Lesson #13: Pay secrecy undermines fairness – be transparent instead
  • Lesson #14: Redefine connection - cultivate new social and cultural capital
  • Lesson #15: Soft skills aren’t optional – they’re the key to remote leadership
  • Lesson #16: Unreachable means unstoppable - adopt a closed-door policy
  • Lesson #17: SMART goals are dead - embrace more/less lists for true flexibility
  • Lesson #18: AI is the future of hiring - adapt or fall behind
  • Lesson #19: Job security is a myth - equip your team with adaptability
  • Lesson #20: AI skills are essential for remote career advancement
  • Lesson #21: Hybrid work is the illusion of flexibility – only remote is true freedom
  • Lesson #22: Quality beats quantity when applying for jobs – be selective, be strategic
  • Lesson #23: Neurodiversity + AI = Unleashing your team's hidden superpowers
  • Lesson #24: Demand pay that matches your worth – not your location
  • Lesson #25: To unlock wealth and break currency barriers – earn in USD
  • Lesson #26: RTO mandates signal a growing career opportunity
  • Lesson #27: Degrees are outdated - skills are the real currency
  • Lesson #28: Outsourcing is modern exploitation- fight back for fair pay and equal treatment
  • Lesson #29: Remote work isn't just convenient - it's a happiness revolution
  • Lesson #30: Culture eats strategy for breakfast - build a remote workforce that succeeds

Who says you can’t change the world when you’re remote? It’s been over a year since we launched Radically Remote, and it’s fitting that on our 30th edition, we’ve cracked the top 10 LinkedIn Newsletter Charts.

So along with...

  • Being read by nearly 11 million global remote workers this year
  • And more than doubling in size since launch (STILL the largest community of remote workers of all time at 2.3 million)
  • …Now we’re also the #10th largest newsletter on LinkedIn…ever

If this isn’t irrefutable proof that remote work is a human right – we don’t know what is! It’s all thanks to you – our rebel remote leaders.

Without you fighting the good fight every day – against forced return-to-office mandates, tech layoffs, hybrid inflexibility and challenging management styles - the remote revolution would stagnate and end.

From the bottom of our hearts, thank you.

And we didn’t do it alone. A lot of influential experts, academics and thought leaders joined us to bring you the latest remote work news, insights and stories.

A huge shoutout goes to Laurel Farrer, David Burkus, Chase Warrington, Kaleem Clarkson, Nick Bloom and of course our latest expert guest, Iwo Szapar.

These remote leaders are doing more for the revolution than you could imagine.

Every day, they’re working to:

  • Normalize WFH and remote environments in tech today
  • Build the processes that will help you thrive from anywhere
  • Showcase the research that inspires more companies to go remote
  • Create the technology that streamlines and accelerates the way you work
  • Exponentially improve your remote career with AI

If you haven’t already, follow them for outstanding leadership insights.

That brings me to this article. I want to honor the remote leaders that blaze trails for us, by helping you on your journey to becoming a formidable FORCE (pun intended) for remote good.  

It’s time we all returned to what matters: work-life balance. I recently wrote about how that doesn’t exist at the office. But for remote leaders it’s not in a galaxy far, far away. It’s in your hands.

So here are thirty remote leadership lessons from thirty editions of the world’s largest (and *ahem greatest) remote work newsletter.

30 remote leadership lessons infographic

Lesson #1: Toss the resume – hire smart, hire fast

Resumes are ancient history! They miss people’s true potential and encourage bias. Instead, use cognitive tests, structured interviews, and work samples to find the real players in the remote work game.

This approach guarantees that you're not just filling a seat, you’re actually choosing the best fit for your remote team. Break free from outdated norms and revolutionize your hiring process for a stronger, more dynamic workforce.

Read more in edition #1.

Lesson #2: Cheap labor costs more - invest in talent for true value

Picking the cheapest option when outsourcing is a rookie mistake. It might save you money upfront, but it also leads to decreased productivity, low engagement, high turnover, and poor-quality work.

Remote leaders should prioritize fair pay to attract and retain top talent, for long-term success and sustained innovation. Don’t ever forget that you get what you pay for, and investing in quality talent always pays off in the long run.

Read more in edition #2.

Lesson #3: Contract work is real freedom - which fuels real success

Contract work demands resilience, ownership and adaptability. Remote leaders should recognize that while the freedom to choose clients and projects leads to unparalleled growth and satisfaction, it comes with high pressure and occasional financial instability.

Successful contractors thrive by setting clear boundaries, continuously upskilling, and managing their own stability. This path isn’t for everyone, but for those who embrace its challenges, it offers unmatched professional and personal rewards.

Read more in edition #3.

Lesson #4: Asynchronous work is mastery of autonomous time

Asynchronous work revolutionizes productivity by allowing employees to work when they are most effective, rather than sticking to rigid schedules. Remote leaders should champion this approach to unlock creativity, enhance time management, and fuel innovation.

By letting team members control their own time, you not only reduce stress, you also boost their overall performance. Embrace asynchronous work to create a dynamic, efficient, and high impact workforce.

Read more in edition #4.

Lesson #5: Hybrid work can be disruptive – focus on clarity and flexibility

Hybrid work models often muddle the benefits of both remote and in-office setups, leading to mass confusion and inefficiency. Remote leaders should aim for clear, flexible policies that prioritize the pillars of autonomy and productivity.

Avoid the pitfalls of half-measures by committing to either fully remote or well-defined hybrid models that actually serve your team’s core needs. Empower your workforce with the stability and freedom they crave, to maximize their potential and happiness.

Read more in edition #5.

Lesson #6: Cognitive aptitude + AI mastery = an unbeatable team advantage

The future of work hinges on cognitive ability finely paired with AI proficiency. Remote leaders should prioritize hiring individuals with high cognitive aptitude, because they’re best equipped to leverage AI for authentically groundbreaking results.

This combination leads to superior problem-solving, creative innovation, and productivity. Embrace this dynamic duo to propel your team into the next era of unmatched performance and competitive edge.

Read more in edition #6.

Lesson #7: Customize workflows - async collaboration isn't one-size-fits-all

Asynchronous collaboration often falters without a more tailored approach. Remote leaders should identify and respect each team member's optimal work style, creating a balanced 'Goldilocks environment' that’s just right for the individual.

This involves setting clear communication norms, managing preferences, and avoiding both under- and over-engagement. By fine-tuning these dynamics, you’re making sure that your team works harmoniously and efficiently, for max productivity and wellbeing.

Don't settle for a one-size-fits-all solution, rather customize your approach for exceptional results.

Read more in edition #7.

Lesson #8: Speed up your hiring - reduce time-to-fill with AI

Lengthy hiring processes drain resources and exhaust talent. Remote leaders should create warp zones by leveraging skills-based hiring and pre-vetted global talent pools. It works!

This approach slashes time-to-fill by up to 80%, allowing you to focus on final-stage interviews with top-tier candidates. Streamlining your hiring process not only speeds up recruitment, it also guarantees that you're selecting the best fit, boosting overall team production and morale.

Read more in edition #8.

Lesson #9: Recognize remote trailblazers - amplify those redefining remote work

Highlighting and rewarding remote work leaders who are setting new standards and pushing boundaries is important! Remote leaders should actively recognize innovators who challenge the status quo and inspire others in this space.

Celebrating these pioneers acknowledges their contributions and also motivates your entire team to push for excellence. By shining a spotlight on those who lead with creativity and vision, you create a culture of continuous improvement and inspired innovation in your remote workforce.

Read more in edition #9.

Lesson #10: Build community - radical remote success lies in connections

Creating a solid remote work environment requires more than just policies. It demands a strong community. Remote leaders must nurture connections and facilitate knowledge-sharing to elevate our collective experience.

By engaging with platforms like the Radically Remote Newsletter, leaders can stay informed, inspired, and connected with a global network of remote work advocates. This collaborative approach encourages new ideas and solidifies the remote work movement as a sustainable and powerful force in the modern workforce.

Read more in edition #10.

Lesson #11: Cognitive aptitude reveals true top talent

Relying solely on traditional resumes and interviews is a great way to miss hidden candidate potential. Remote leaders should embrace cognitive aptitude tests like the CCAT, which predict long-term job performance and uncover genuine abilities.

This method champions diversity, eliminates human biases, and sees that you select candidates with the right skills for motivated, high-performing teams. Redefine your hiring strategy by focusing on cognitive strengths, leading to workforce that can handle it all.

Read more in edition #11.

Lesson #12: Remote work is a DEI game-changer

Embrace remote work to unlock unparalleled diversity and inclusion. When you let employees work from anywhere, you eliminate geographical, physical, and societal barriers, which creates a truly inclusive environment.

This approach attracts a diverse talent pool and enhances creativity, job satisfaction, and job retention. Remote work isn’t just a policy, it’s a powerful tool to drive DEI and create a more equitable and forward-thinking workforce.

Read more in edition #12.

Lesson #13: Pay secrecy undermines fairness – be transparent instead

Hiding pay details perpetuates inequality and distrust. Remote leaders must champion pay transparency to effectively promote fairness and equity. By making compensation clear and equitable, you dismantle discriminatory practices and empower your team.

This way, you build trust but also attract top talent, enhance satisfaction, and skyrocket productivity in teams. Lead the charge for open conversations about pay to create a more inclusive and high-performing remote team.

Read more in edition #13.

Lesson #14: Redefine connection - cultivate new social and cultural capital

Remote work isn't the social killer it's made out to be. It actually transforms how we build relationships and cultural value. To make it work, remote leaders should inspire intentional connections and leverage virtual platforms to grow social and cultural capital.

This means creating opportunities for meaningful interactions, mentoring, and skill development. By redefining connection, leaders will create a happy, inclusive, and socially well-connected workforce that excels in the digital age.

Read more in edition #14.

Lesson #15: Soft skills aren’t optional – they’re the key to remote leadership

Success in remote leadership is deeply reliant on unconventional soft skills. Beyond technical expertise, remote leaders need emotional agility to navigate complex feelings and team dynamics, team support to foster interdependence, and a strong asynchronous work ethic for global collaboration.

These soft skills are key for building trust, inspiring your team, and promoting exceptional performance. Focus on developing these unique abilities to lead effectively in a remote environment, transforming how you manage and model your team.

Read more in edition #15.

Lesson #16: Unreachable means unstoppable - adopt a closed-door policy

The myth that constant availability is a productivity booster is shattered by the benefits of a closed-door policy. Remote leaders should set dedicated times for deep work, totally free from interruptions.

Doing this will enhance your focus, make your more creative, and amplify your overall output. By intentionally limiting access, leaders protect their mental bandwidth and ensure high-impact work gets done (on time). Seize the power of being selectively unreachable to unlock your team’s true potential for sustained success.

Read more in edition #16.

Lesson #17: SMART goals are dead - embrace more/less lists for true flexibility

SMART goals are too rigid for today’s fast-paced, remote work environment. Instead, adopt more/less lists, which offer better flexibility and adaptability for the modern leader on-the-go.

More/less lists allow your team to focus on broad intentions, promoting creativity and reducing admin stress. By setting goals that are inspiring and easily achievable, you encourage more solutions and maintain morale. Ditch the rigidity of SMART goals and lead with a more dynamic approach to goal-setting for your remote team.

Read more in edition #17.

Lesson #18: AI is the future of hiring - adapt or fall behind

AI is transforming recruitment, and remote leaders need to harness its power to stay competitive. From AI-powered sourcing and resume screening to precise candidate matching, these technologies streamline hiring and efficiently uncover top talent.

To succeed, remote leaders must embrace AI, optimize job applications for AI systems, and continuously upskill their teams (a lot). Ignoring AI is not an option - it's the key to securing the best candidates and driving future success in your virtual team.

Read more in edition #18.

Lesson #19: Job security is a myth - equip your team with adaptability

The illusion of job security is stifling to innovation. As a remote leader, it pays to reject the outdated promise of permanence. Instead, empower your team with continuous learning and flexibility.

That’s how you prepare them for inevitable industry shifts, and build a culture of resilience and proactive growth. Encourage your team to embrace uncertainty and turn it into a fantastic strategic advantage. By focusing on adaptability, you'll build a future-proof workforce ready to tackle any challenge.

Read more in edition #19. 

Lesson #20: AI skills are essential for remote career advancement

In technology today, standing still means falling way…way behind. Remote leaders should champion AI proficiency within their teams to stay fresh and competitive. This means prioritizing continuous learning, practical application, and strategic integration of key AI tools.

Those who master AI will enhance productivity and new innovation, and they’ll secure their place at the forefront of their industry. Don't just adapt to AI - use it to drive your team’s success and set new benchmarks for excellence.

Read more in edition #20. 

Lesson #21: Hybrid work is the illusion of flexibility – only remote is true freedom

Hybrid work often masquerades as flexible but can disrupt your team dynamics with rigid schedules and invisible workload increases (ouch!). Remote leaders like you should recognize these traps and consider fully remote models to authentically enhance flexibility and productivity.

By eliminating the pitfalls of hybrid work, you empower your team with genuine autonomy, which always leads to higher satisfaction and greater performance. Challenge the hybrid norm and opt for a structure that delivers real benefits to your remote teams.

Read more in edition #21.

Lesson #22: Quality beats quantity when applying for jobs – be selective, be strategic

Bombarding companies with applications is a fast track to frustration. Remote leaders should focus on the Red Velvet Rope strategy - targeting only those roles that align with your values and skills.

This approach saves time, reduces burnout, and increases your chances of landing the right job. Build a standout portfolio, highlight your unique strengths, and be super discerning. It’s a way to attract the right opportunities and ensure a more fulfilling and successful career path.

Read more in edition #22.

Lesson #23: Neurodiversity + AI = Unleashing your team's hidden superpowers

Harnessing the unique strengths of neurodiverse team members will significantly enhance AI integration and innovation. Remote leaders must create an inclusive environment where neurodivergent individuals feel safe to disclose their status and contribute fully and authentically.

This involves promoting psychological safety, educating teams about neurodiversity, and providing necessary accommodations. By leveraging the exceptional pattern recognition, problem-solving, and hyperfocus abilities of neurodiverse workers, you will create superior AI performance and unlock your team's full potential.

Read more in edition #23.

Lesson #24: Demand pay that matches your worth – not your location

Accepting lower pay based on geography perpetuates exploitation and undervalues your skills. Boom. All remote leaders must advocate for fair, location-independent compensation so that talent is appropriately rewarded.

This mindset shift not only combats systemic inequity it also boosts morale, engagement, and facilitates job retention. Reject the status quo of location-based pay -demand what you're truly worth, and lead your team to do the same. That’s how you create a fairer and more motivating work environment.

Read more in edition #24.

Lesson #25: To unlock wealth and break currency barriers – earn in USD

Tying earnings to local currencies in developing nations propagates financial instability and limits wealth-building. Remote leaders should champion the power of earning in USD, which offers stability and shields themselves and team members from local economic fluctuations.

It enhances purchasing power and provides a sustainable path to financial growth. So, encourage your team to seek remote opportunities that pay in USD, so that their hard work translates into real financial freedom and security. (And do the same for yourself!)

Read more in edition #25.

Lesson #26: RTO mandates signal a growing career opportunity

Return-to-office mandates may seem restrictive, but they actually signal a shift in power for tech professionals – surprise! Remote leaders should view these mandates as a chance to break free from outdated corporate structures and join innovative, remote-first startups.

This transition offers you more autonomy and places you at the forefront of technological growth and innovation. What’s not to love? Embrace this upheaval to align your career with flexibility, growth, and the future of work.

Read more in edition #26.

Lesson #27: Degrees are outdated - skills are the real currency

The tech industry's obsession with degrees over skills and experience is suffocating innovation. Remote leaders must prioritize practical expertise and continuous learning to identify true talent.

Reject the flawed system that values a piece of paper over proven capabilities. Instead focus on skills-based hiring to unlock potential and drive progress. It's time to break free from antiquated norms and build a workforce that thrives on real-world experience and skills.

Read more in edition #27.

Lesson #28: Outsourcing is modern exploitation- fight back for fair pay and equal treatment

Outsourcing often disguises exploitation, offering low wages and poor working conditions to remote workers. Remote leaders should educate their virtual teams to recognize these tactics and advocate for fair compensation and respectful treatment.

This involves understanding global wage dynamics, identifying signs of exploitation, and refusing jobs that undervalue their skills. By standing firm against these practices, leaders can empower their teams to demand what they deserve. Fair is fair!

Read more in edition #28.

Lesson #29: Remote work isn't just convenient - it's a happiness revolution

Working remotely fundamentally enhances happiness by providing autonomy, flexibility, and actual work-life balance. Remote leaders should support these benefits, so that their teams are aware of the profound impact it has on their well-being.

By prioritizing remote work, you create a more satisfied, productive, and loyal workforce. Challenge the outdated notion that office work is superior (it’s not) and embrace the reality that remote work is the key to a happier, more fulfilled professional life.

Read more in edition #29.

Lesson #30: Culture eats strategy for breakfast - build a remote workforce that succeeds

In remote work, a strong, inclusive culture is EVERYTHING. Remote leaders must intentionally nurture a sense of belonging, shared values, and trust among team members – but no-one can really tell you how to do that.

Try different kinds of virtual meetups, transparent async communication, and celebrating team achievements together, to start off. 

By prioritizing culture, you create a cohesive and motivated workforce that outperforms others, regardless of physical distance. And when you build a vibrant remote culture, nothing can stand in the way of your team. Nothing. The right people connections create the best results.

For us - a remote leader is a disruptor of traditional office bureaucracy, harnessing technology and autonomy to build unstoppable, globally connected teams that thrive on flexibility and innovation.

These individuals don’t live to work, they work to thrive.

Use these remote leadership lessons to inform your own leadership philosophy, and spread the gospel of WFA. Here’s to the next 30 editions, and the inevitable, radical growth of global remote work.

May the remote workforce be with you, rebels.


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