The Messy Middle by Scott Belsky

Chapter: ENDURE

LEADING THROUGH THE ANGUISH AND THE UNKNOWN

Leadership is a journey of embracing uncertainty and learning to control your reward system.
  • Short-circuit your reward system:
    • DO: Redefine what success means to you and take pleasure in small, real achievements.
    • DON'T: Reward yourself prematurely or celebrate progress that isn't backed by substantial results.
  • Don't seek positive feedback or celebrate fake wins at the expense of hard truths:
    • DO: Seek honest and constructive criticism to understand where improvement is needed.
    • DON'T: Surround yourself with 'yes' people who only reinforce your existing views without challenging them.
  • Accept the burden of processing uncertainty:
    • DO: Embrace uncertainty as an inevitable part of leadership and find ways to navigate through it.
    • DON'T: Ignore or downplay uncertainties.
  • Fight resistance with a commitment to suffering:
    • DO: Embrace difficult tasks and situations, realizing that they often lead to growth.
    • DON'T: Avoid challenging situations or tasks simply because they are uncomfortable.
  • Friction brings us closer:
    • DO: Encourage healthy debates and confrontations within your team, they often lead to better results.
    • DON'T: Stifle disagreements or avoid confrontations.
  • Be the steward of perspective:
    • DO: Maintain a balanced perspective and encourage others to see things from different angles.
    • DON'T: Get stuck in a single viewpoint and ignore others' perspectives.
  • Leave every conversation with energy:
    • DO: Be mindful about the energy you bring into and take away from conversations.
    • DON'T: Allow negative discussions to drain your energy and motivation.
  • If you don't like the way government is being run, cross party lines:
    • DO: Be willing to step out of your comfort zone and question the status quo.
    • DON'T: Stick rigidly to your own views without considering alternatives.
  • DYFJ. Do your fucking job:
    • DO: Fulfill your responsibilities, even when the tasks are challenging.
    • DON'T: Avoid tasks or responsibilities that are a part of your role.

STRENGTHENING YOUR RESOLVE

Strengthening resolve requires embracing individuality, questioning perspectives, and pushing beyond comfort zones.
  • The only "sustainable competitive advantage" in business is self-awareness:
    • DO: Regularly reflect on your strengths, weaknesses, and values.
    • DON'T: Neglect the importance of self-awareness in your professional growth.
  • Nobody remembers, or is inspired by, anything that fits in:
    • DO: Be unique and unafraid to stand out.
    • DON'T: Dilute your uniqueness to blend into the crowd.
  • Take a dose of 0BECALP and suspend your disbeliefs in yourself:
    • DO: Believe in your abilities and potential.
    • DON'T: Allow self-doubt to hinder your progress.
  • Attempt a new perspective of it before you quit it:
    • DO: Seek fresh perspectives when facing difficulties instead of giving up.
    • DON'T: Quitwithout exploring all possible solutions and perspectives.
  • To create what will be, you must remove yourself from the constant concern for what already is:
    • DO: Focus on creating the future rather than dwelling on the present or past.
    • DON'T: Let the fear of losing what you have now prevent you from achieving what could be.
  • Prompt clarity with questions:
    • DO: Ask questions to clear up any confusion or uncertainties.
    • DON'T: Assume you have all the answers or avoid asking questions out of fear.
  • Sometimes a reset is the only way forward:
    • DO: Be willing to start anew when necessary for progress.
    • DON'T: Hang on to strategies or ideas that are not working just because of the effort put into them.

EMBRACING THE LONG GAME

Successful execution of long-term strategies requires patience, dedicated effort, and the willingness to tackle tasks irrespective of whose responsibility they traditionally are.
  • Playing the long game requires moves that don't map to traditional measures of productivity:
    • DO: Make decisions that contribute to your long-term goals, even if they may not bring immediate results.
    • DON'T: Focus solely on short-term productivity at the expense of long-term goals.
  • Strategy is nourished by patience:
    • DO: Exercise patience in implementing and seeing the results of your strategy.
    • DON'T: Expect immediate results and abandon strategies too quickly.
  • Break the long game down into chapters:
    • DO: Divide long-term plans into manageable stages or "chapters".
    • DON'T: Get overwhelmed by the totality of your long-term goals.
  • Just stay alive long enough to become an expert:
    • DO: Persevere in your field to gain expertise over time.
    • DON'T: Give up prematurely or jump from one field to another without gaining depth.
  • Do the work regardless of whose work it is:
    • DO: Take responsibility and complete tasks necessary for success, irrespective of job descriptions.
    • DON'T: Limit yourself strictly to your assigned responsibilities and miss opportunities to contribute more.

Chapter: OPTIMIZE

OPTIMIZING YOUR TEAM

Optimizing your team involves careful hiring decisions, cultivation of a conducive culture, and smart structural decisions.

BUILDING, HIRING, AND FIRING

  • Resourcefulness > Resources:
    • DO: Value and seek out resourcefulness in your team members over their available resources.
    • DON'T: Base hiring decisions solely on the resources a candidate can bring to the table.
  • Initiative > Experience:
    • DO: Look for individuals who show initiative, even if they may lack experience.
    • DON'T: Overemphasize past experience at the expense of potential for future growth and initiative.
  • Diversity drives differentiation:
    • DO: Cultivate a diverse team to drive innovation and creativity.
    • DON'T: Stick with a homogenous team and miss out on the benefits of diversity.
  • Hire people who have endured adversity:
    • DO: Value resilience and the ability to handle adversity when making hiring decisions.
    • DON'T: Discount candidates who have faced challenges or adversities in their lives.
  • Seek people with whom discussions evolve by a step function:
    • DO: Look for team members who can bring fresh insights and perspectives that elevate discussions.
    • DON'T: Settle for individuals who don't contribute significantly to discussions or problem-solving sessions.
  • If you avoid folks who are polarizing, you avoid bold outcomes:
    • DO: Be open to hiring individuals who may have polarizing opinions, as they could lead to innovative outcomes.
    • DON'T: Avoid hiring individuals with strong or controversial opinions just to maintain status quo.
  • Cultivate your team's immune system, and occasionally suppress it:
    • DO: Encourage your team to develop resilience but also know when to provide support and protection.
    • DON'T: Overprotect your team from challenges, preventing them from developing resilience.
  • Grafting talent is just as important as recruiting talent:
    • DO: Invest in training and developing the skills of your existing team.
    • DON'T: Rely solely on recruitment to meet your talent needs.
  • Foster apprenticeship:
    • DO: Encourage experienced team members to mentor newer or less experienced ones.
    • DON'T: Ignore the benefits of mentorship and peer learning.
  • Shed the bad to keep the good:
    • DO: Let go of bad practices, strategies, or even team members to maintain the overall health of the team.
    • DON'T: Hold onto bad elements out of habit or fear of change.
  • A steady state is unsustainable; keep people moving:
    • DO: Encourage growth, learning, and movement within your team.
    • DON'T: Allow stagnation to set in within your team.
 

CULTURE, TOOLS, AND SPACE

Creating a supportive environment for your team involves shaping culture, providing tools, and designing conducive spaces.

CULTURE, TOOLS, AND SPACE

  • Culture is created through the stories your team tells:
    • DO: Foster a culture where everyone's story matters and can be heard.
    • DON'T: Ignore the stories that your team members have to tell.
  • Accommodate free radicals:
    • DO: Allow room for innovative and radical ideas to flourish.
    • DON'T: Suppress or discourage out-of-the-box thinking.
  • Be frugal with everything except your bed, your chair, your space, and your team:
    • DO: Invest in a good workspace and team, as these are areas where quality matters.
    • DON'T: Waste resources on non-essential elements.
  • The products you use to create impact the products you create:
    • DO: Choose your tools wisely, as they can significantly affect the outcome of your work.
    • DON'T: Underestimate the impact of your work tools on your final products.
  • Attribute the right amount of credit to the right people:
    • DO: Ensure fair credit distribution among your team members.
    • DON'T: Fail to acknowledge the contributions of each team member.

STRUCTURE AND COMMUNICATION

Effective communication and smart structuring of teams help to optimize work output and team morale.

STRUCTURE AND COMMUNICATION

  • When you have the right people, there are no rules for structure:
    • DO: Trust in the abilities of your team members and allow flexibility in how they organize their work.
    • DON'T: Force rigid structures onto high-performing teams.
  • Process is the excretion of misalignment:
    • DO: Use processes to realign your team when necessary.
    • DON'T: Ignore signs of misalignment within your team.
  • Don't rob people of their process:
    • DO: Respect the individual processes of your team members.
    • DON'T: Disregard or belittle the unique workflows of your team members.
  • Merchandise to capture and keep your team's attention:
    • DO: Use creative means to keep your team engaged.
    • DON'T: Underestimate the value of presentation in maintaining your team's interest.
  • A mock-up > Any other method of sharing your vision:
    • DO: Use mock-ups or prototypes to effectively convey your vision.
    • DON'T: Rely solely on verbal or written communication to share your vision.
  • Present your ideas, don't promote them:
    • DO: Present your ideas in an objective and clear manner.
    • DON'T: Force your ideas onto others.
  • Delegate, entrust, debrief, and repeat:
    • DO: Follow this cycle for effective team management and to foster a sense of ownership among your team members.
    • DON'T: Micromanage or withhold trust from your team.
  • Know how and when to say it:
    • DO: Understand the importance of timing and delivery in communication.
    • DON'T: Overlook the significance of context in communication.
  • Nothing beats explicitness. Aspire to say it like it is:
    • DO: Be clear and explicit in your communication.
    • DON'T: Leave room for assumptions or misunderstandings.
  • There is power in brevity:
    • DO: Communicate your ideas concisely and clearly.
    • DON'T: Overcomplicate your messages with unnecessary details or jargon.
  • Make communication frequent and informal:
    • DO: Encourage regular and casual communication within the team.
    • DON'T: Create an environment where communication is infrequent and overly formal.
  • Use technology as an enabler, not a crutch:
    • DO: Leverage technology to enhance your team's performance and communication.
    • DON'T: Depend on technology to the point where it hinders human interaction and creativity.
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THE FINAL MILE

This section discusses the various aspects one needs to consider and pay attention to when nearing the completion of a project or goal.

APPROACHING THE FINISH LINE

  • The "final mile" is a different sport:
    • DO: Adapt your strategy as you approach the end of a project, as the dynamics often change.
    • DON'T: Assume that what worked at the beginning of the project will work at the end.
  • Stay in the early innings:
    • DO: Maintain the mindset of being in the early stages of a project to ensure continuous improvement and attention to detail.
    • DON'T: Become complacent or lose focus as the project nears its completion.
  • Overcome your resistance to a great outcome:
    • DO: Recognize and address any personal resistance or fear of success.
    • DON'T: Allow fear of success or change to hinder your progress or the project's outcome.
  • Don't underestimate the value of adding a brick:
    • DO: Appreciate the value of every small contribution to the project.
    • DON'T: Overlook the smaller tasks or contributions, as they are essential to building the larger structure.

PASSING THE BATON

  • If you can't end wonderfully, end gracefully:
    • DO: Strive to end a project on a positive note, but if that's not possible, ensure a graceful and respectful conclusion.
    • DON'T: Leave projects or tasks unfinished or concluded in a negative manner.
  • You are not your work:
    • DO: Maintain a healthy separation between your personal identity and your work.
    • DON'T: Define your self-worth or identity solely based on your work or professional success.
  • Aspire to finish on your own terms:
    • DO: Aim to complete projects in a way that aligns with your values and goals.
    • DON'T: Allow external pressures to dictate the terms of your project's completion.

NEVER BEING FINISHED

  • Continuing to learn is an elixir to life:
    • DO: Embrace lifelong learning as a key to personal and professional growth.
    • DON'T: Cease learning or become complacent in your knowledge.
  • You're either part of the living or the dying:
    • DO: Stay active, engaged, and involved in your work and life.
    • DON'T: Become stagnant or disengaged, as this leads to a lack of growth.
  • We are so willing to trade time for money when we are young, and money for time as we age:
    • DO: Recognize and balance the value of time and money at different stages of your life.
    • DON'T: Overvalue money at the expense of time, especially as you grow older.
  • To be done is to die:
    • DO: Stay engaged, active, and always have something that you're working on or towards.
    • DON'T: Allow yourself to fall into a state of inactivity or disengagement.
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