6 Books All Remote Team Leaders Should Read

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Here are six books that offer thought-provoking and practical advice for leaders, whether they are just laying down the foundations for a newly distributed team or have been running one for years.

ReWork: Change the Way You Work Forever

Jason Fried and David Heinemeier Hanson are the co-founders of Basecamp and pioneers in distributed team-building. In 2010, they published ReWork, which describes the principles they relied on to run Basecamp (formerly 37signals).

“Workaholics don’t actually accomplish more than nonworkaholics. They may claim to be perfectionists, but that just means they’re wasting time fixating on inconsequential details instead of moving on to the next task.”

The book offers a revolutionary take on work, with a minimalist approach that is practical and effective. 

“Find a judo solution, one that delivers maximum efficiency with minimum effort. When good enough gets the job done, go for it.”

The explanations for managers to succeed on their own terms are concise and easy to read, and beautiful black-and-white illustrations drive home the points covered by each topic.

The book advocates taking immediate action and striving for results, instead of overplanning.

“Don’t make up problems you don’t have yet. It’s not a problem until it’s a real problem. Most of the things you worry about never happen anyway.”

Key insights:

  • Interruption is the enemy of productivity — When you are at work, you need to work. If you’re not getting the work done during working hours, you need to think about the interruptions that might be causing this.
  • Throw less at the problem — The book suggests a back-to-basics approach that cuts out complications and encourages doing more with less. This will lead to greater efficiency and better focus. 
  • Culture is the byproduct of consistent behaviour — the culture of a business comes from demonstrating consistent behaviour. If a manager encourages sharing, sharing will be built into the culture. If you reward trust, that will become part of the company culture.
  • Nurture a culture of open communication and trust — highly-successful remote teams are the ones that are trusted to make their own decisions and voice their opinions. These team members are there to work to produce instead of fulfilling a certain quota of hours worked.

Traction: Get a Grip on Your Business 

Gino Hackman’s Traction introduces the Entrepreneurial Operating System® (EOS®).

While Traction is targeted at business owners, the 6 key components of the EOS® can also be used by remote managers to gain clarity and run their teams more successfully.

“There are three stages in documenting your Way. First, identify your core processes. Then break down what happens in each one and document it. Finally, compile the information into a single package for everyone in your company.”

This system was designed to overcome common entrepreneurial hurdles, which include a lack of control, people problems, insufficient profit, hitting growth ceiling or lack of effective strategies.

“When everyone follows their process, it’s much easier for managers to manage, troubleshoot, identify and solve issues, and therefore grow the business. The clear lines of process enable you to let go and gain more control. Your business now becomes more scalable, which means that you can add more customers, transactions, revenue, and employees while reducing complexity.”

Managers often assume that their team view their vision and objectives as clearly as they do, and so they don’t communicate it enough.

“What you need to show is how the new system will create efficiencies to make their lives easier and the company more successful. They need to understand how the processes tie together into a complete system.”

Traction suggests that by keeping up-to-date on certain metrics, business owners are able to keep a finger on the pulse of the business. These metrics can also be applied to gauging team performance.

“A vital first step is creating a workplace where people feel comfortable calling out the issues that stand in the way of your vision. To do this, your leadership team must be comfortable with this type of environment.”

A key element to the EOS® is setting long-term goals with realistic milestones along the way, and finding the right people to move a company forward towards those goals.

“Numbers create teamwork. When a team composed of the the right people in the right seats agree to a number to hit, they ask themselves “how can we hit it,” creating camaraderie and peer pressure.”

The EOS® framework provides managers a structure clear communication with key team members. This will ensure problems are prioritized and tasks are solved efficiently. Confusion is eliminated and team members are guided towards working cohesively.

Key insights:

  • Develop and communicate a strong vision  —  Develop a compelling vision for the team and help members to see it. When everyone is aligned in the same direction, it creates a focus that propels the entire team forward.
  • Build a real leadership team — delegate specific areas to team members who can do certain tasks better. Gino Wickman highlights the compelling need to get the right people in the right seats.
  • Be open-minded — Traction encourages leaders to be open and honest about vulnerabilities and be willing to adopt new ideas.

Never Split the Difference: Negotiating As If Your Life Depended On It

“The fastest and most efficient means of establishing a quick working relationship is to acknowledge the negative and diffuse it.”

Running a team means often dealing with issues and conflicts, but conflicts can lead to growth, as long as there are good resolutions to problems.

Chris Voss’s book calls on skills acquired his previous career as a hostage negotiator for FBI to equip readers with the negotiating skills needed to run a remote team effectively.

Never Split the Difference advocates the use of tactical empathy, described as “emotional intelligence on steroids”, as a powerful tool to successful negotiations.

“… when individuals feel listened to, they tend to listen to themselves more carefully and to openly evaluate and clarify their own thoughts and feelings.”

The book teaches communication skills crucial for effectively managing any team. Tools such as empathy and active listening skills improve cooperation and problem-solving between team members.

Key insights:

  • Negotiation begins with listening — validating other people’s emotions create trust and safety for a real conversation to begin, which leads to more effective problem-solving.
  • Empathy brings attention to the emotional obstacles — which leads to finding potential pathways to getting to an agreement
  • “No” provides a great opportunity — it allows both parties to clarify what they want by eliminating what the don’t want

Extreme Ownership: How U.S. Navy SEALs Lead and Win

Jocko Willink and Leif Babin paired up to write a book offering useful leadership advice gleaned from their career in the military. 

“The most fundamental and important truths at the heart of Extreme Ownership: there are no bad teams, only bad leaders.”

Running a remote team often means swift decision-making in high-stakes situations. This can feel as stressful as navigating a military operation. Extreme Ownership applies the management lessons learnt on the battlefield to the workplace.

The two Navy SEALs apply leadership lessons they have learned from their combat experiences.

“As SEALs, we operate as a team of high-caliber, multitalented individuals who have been through perhaps the toughest military training and most rigorous screening process anywhere. But in the SEAL program, it is all about the Team. The sum is far greater than the parts.”

Leaders make mistakes too, and Leif and Babin state that good leaders should show accountability when their teams encounter failure.

“Implementing Extreme Ownership requires checking your ego and operating with a high degree of humility. Admitting mistakes, taking ownership, and developing a plan to overcome challenges are integral to any successful team.”

Extreme Ownership is highly applicable to remote managers. The advice book equips all leaders with a sense of self-awareness and accountability — crucial to running a successful distributed team.

Key insights:

  • A leader who takes responsibility for failure is vital to team success — a manager should take responsibility for mistakes in order to set a good example for their teams. All members become more efficient when they own their mistakes. This leads to the next step of developing plans to overcome them.
  • When pressure mounts, remain calm and effective — identify priorities and take action to deal with them one at a time to remain efficient.
  • Anticipate risks before they pop up — a good manager plans for potential issues ahead of time, and has contingencies in place to deal with the inevitable inconveniences that will occur.

Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.

Brené Brown believes true leadership requires vulnerability, values, trust, and resilience. Dare to Lead is a guide for leading from the heart, instead of letting fear get in the way of developing good working relationships.

“I define a leader as anyone who takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential.”

Daring to Lead combines principles in Brown’s earlier works with actionable advice for managers and leaders.

“People are opting out of vital conversations about diversity and inclusivity because they fear looking wrong, saying something wrong, or being wrong. Choosing our own comfort over hard conversations is the epitome of privilege, and it corrodes trust and moves us away from meaningful and lasting change.”

Leaders who engage with their team by viewing them as individuals “with real lives and real problems” are more likely to be able to forge stronger connections with team members.

“If we want people to fully show up, to bring their whole selves including their unarmored, whole hearts—so that we can innovate, solve problems, and serve people — we have to be vigilant about creating a culture in which people feel safe, seen, heard, and respected.”

Dare to Lead offers a brand of leadership that empowers managers to proactively acknowledge and address their fears and uncomfortable emotions. By doing so they will form the connections that will lead their team to success 

Key insights:

  • Connect with your team — for wholehearted and productive working relationships, leaders should have courage to build authentic connections. These connections encourage team members to fully apply themselves at work. An atmosphere in which people feel validated and respected leads to more productive and innovative results.
  • Embrace vulnerability — courage and fear are not mutually exclusive, and even leaders often experience both emotions simultaneously. Having conversations on these emotions can help with identifying problems and finding solutions to issues.
  • Be clear —  expectations that are not well-defined are unproductive in the workplace. The author states that being clear is being kind. Half-truths and avoidant behaviour from managers will eventually lead to team members failing to deliver. Leaders can also solicit clearer feedback from the team by really listening to their team.

Measure What Matters: OKRs: The Simple Idea that Drives 10x Growth

John Doerr’s Measure What Matters is about using Objectives and Key Results (OKRs). This is a goal-setting system to make tough choices in business, and while not strictly targeted at remote managers, it provides useful tools for managers to align team members towards common goals.

“An effective goal-setting system starts with disciplined thinking at the top, with leaders who invest the time and energy to choose what counts.”

Measure what matters states that ideas are useless without good execution. OKRs help to create clarity, focus, accountability, alignment and momentum to deliver results for managers.

“Leaders must get across the why as well as the what. Their people need more than milestones for motivation. They are thirsting for meaning, to understand how their goals relate to the mission.”

Key insights:

  • Less is more — limit of only 3-5 OKRs each cycle helps managers prioritise what matters most.
  • Set goals from the bottom up — to promote engagement, managers should consult with team members and encouraged them to create half of their own OKRs
  • Tracking OKRs is crucial — OKR management software packages allow managers and team members to create and track their OKRs. Doing so promotes internal networking, increases drive engagement and clarifies goals.

Knowledge of how to excel at remote businesses and managing distributed teams is still in the early stages. However, there are many resources out there that offer relevant and useful advice for remote managers. These six books above offer different perspectives and actionable advice that can easily be applied to running distributed teams.

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