94 Actionable Ideas From 7 Books That Made Me a Better Leader.

Jake Wilder
Feb 12 · 9 min read

The mark of a great book, at least to me, is whether it changes how we see the world and how we act within it. And while there’s no shortage of great books out there, when I think about those that helped define my own leadership practices, the following seven stand out.

I highly encourage you to read them yourself, because the below points don’t do them justice. But if you’re pressed for time, or want a quick teaser as to the material, I hope that the below points can help you as much as they’ve helped me.

  1. Share your work early and share it often. Great ideas, and great work, are forged through feedback and iteration.
  2. Strive to be authentic, consistent, and empathetic with people. There’s no better way to develop trust.
  3. The most important part of any failure is your reaction to it. All failures offer the chance to learn and grow. You ignore that opportunity at your own peril.
  4. When hiring people, focus more on their potential to grow than their current experience or skills. What they’ll contribute in the future is more important than the short cut they bring today.
  5. Being open to the ideas of others isn’t enough. As a leader, engaging people and encouraging them to share their perspectives is a never-ending process.
  6. If someone disagrees with you, there is a reason. Your job is to understand that reason and the logic behind their conclusions.
  7. Downplaying problems or parroting the company line undermines trust. If you’re unwilling to be honest and transparent with people, don’t expect them to offer you that courtesy.
  8. Too much emphasis on planning leads to repeating what’s worked before. It’s always easier to plan derivative work and merely copy someone else’s success.
  9. When leaders talk about their mistakes, they make it safe for others to do so. Before people can learn from their problems, they need to be open about them.
  10. When everyone feels ownership and responsibility for the product, they’ll take pride in making sure it’s a success. Make sure those executing a plan are free to adapt and change direction when things go wrong.
  11. Look for the opportunity in every crisis. Every issue offers the chance to reinforce your values demonstrate your decision-making process, and bond people together.
  12. A focus on smooth operations will prioritize a lack of mistakes over the ability to move the company forward in new, exciting ways.
  13. People hesitate to say things that will rock the boat. To soften the process, have people make two lists: five positive things to keep and five things they think you should change.
  14. Change and uncertainty are a part of life. Your goal is not to fight that, but to build the agility to respond when the unexpected happens.
  15. Don’t confuse the process with the goal. Improving a process to save time and money is important, but it’s not the goal. Making a great product is the goal.
  16. The future is a direction, not a destination. The path to success is full of uncertainty, change, and frequent corrections to adjust our course. And that’s what makes it so much fun.
  1. In order to manage your time, you first need to know where it goes.
  2. Develop the habit of asking, “What would happen if I stopped doing this?” And if the answer is nothing, then the obvious next step is to stop doing it.
  3. Similarly, ask yourself, “If I wasn’t already doing this, would I start doing it today?” And if not, then it’s probably not worth continuing.
  4. The only thing worth measuring is performance. It doesn’t matter how hard someone works if it doesn’t bring results.
  5. Put your best people on your opportunities rather than problems. Opportunities build your future. Problems only preserve yesterday’s status.
  6. Candid discussion and dissenting opinions lead to effective decisions much more often than consensus.
  7. Running quality meetings is both a critical and an unfortunately rare skill. Know why you’re meeting, develop a focused agenda, and then maintain the discipline to stick to it.
  8. Great leaders don’t think or say “I.” They think and say “we.” Your authority as a leader is fully dependent on the trust and support of your team.
  9. Every success and every failure creates new opportunities. If your plan is too rigid, you’ll miss these as they come up.
  10. A lack of creativity is rarely a lack of good ideas. The problem is that everyone’s still busy doing tasks of yesterday. Challenging legacy projects and cutting old programs will do more for innovation than any new idea.
  11. If you celebrate problem solvers and neglect problem preventers, you’ll encourage people to unnecessarily create drama.
  12. Unique events are rare. Whenever one seems to appear, ask yourself, “Is this a true exception or simply the first instance of a new trend?”
  13. The temporary quickly becomes the permanent. Before implementing any decision, ask yourself, “If I had to live with this solution for a long time, would I be willing to?”
  14. All decisions become obsolete eventually. Whenever you make a decision, build in feedback mechanisms to assess whether it’s giving you the results that you want.
  1. Live by design, not by default.
  2. Relentlessly pursuing success can distract you from the activities that actually lead to success.
  3. View trade-offs not by what you need to give up, but by deciding where you truly want to go big.
  4. If you’re too busy to think, then you’re too busy.
  5. When evaluating an option, think about the most important criterion and then give it a score between 0 and 100. If you rate it lower than 90, change the rating to 0 and reject it.
  6. We commit to too many options when our selection criteria are too broad.
  7. The best protection from distractions is a strong internal sense of purpose.
  8. The more you can think about what you’re giving up by saying yes to someone, the easier it is to say no.
  9. Admitting to a mistake is merely saying that you’re now wiser than you once were.
  10. If you don’t set your own boundaries, someone else will happily set them for you.
  11. The most effective form of human motivation is progress.
  12. As you face major decisions or crossroads in life, ask yourself one simple question: “What is essential?”
  1. Plans aren’t enough to win. A detailed plan doesn’t prove that all of the tasks will add up to a sustainable competitive advantage.
  2. Strategy is a coordinated and integrated set of five choices: a winning aspiration, where to play, how to win, core capabilities, and management systems.
  3. It’s natural to want to keep your options open. But you can only win by making decisions and acting on them.
  4. No company can be everything to everyone and still win. Deciding where to play is deciding where you’ll have the best opportunity to win.
  5. Setting too-modest aspirations is much more dangerous than setting too-aggressive ones.
  6. When deciding on your core capabilities, don’t simply focus on your strengths. Focus on areas that will bring you a competitive advantage.
  7. Clear, simple strategies have the best chance of winning. They are more easily understood and internalized, and help the organization align on execution.
  8. All maps have edges and limitations. It’s only in exploring the edges that you can see things differently.
  9. Don’t attempt to convince people which choice is best. Run a process that enables them to convince themselves.
  10. A good strategy discussion isn’t about pitching a perfect plan to management. It’s about coming out of the meeting with a better strategy than you began it with.
  1. The fundamental activity of a startup is to turn ideas into products, obtain customer feedback, and then decide whether to pivot or persevere.
  2. Accelerating this build-measure-learn cycle is the key to developing a sustainable business model quickly.
  3. Use minimum viable products to test hypotheses as quickly as possible and validate learning.
  4. Reduce the emotional factors by scheduling regular “pivot or persevere” meetings.
  5. Every technical problem is includes a human component. Failing to address the human problem sets you up to repeat the technical problem.
  6. Quality is relative. If you don’t understand your customer, you can’t define your quality.
  7. That which optimizes one part of a system undermines the system as a whole.
  8. Effective metrics have three A’s: actionable, accessible, and auditable.
  9. The core work of a business is the boring stuff: setting priorities, developing milestones, measuring progress, and holding people accountable.
  10. Every vision must be broken down into critical assumptions
  11. If someone can break your system with one mistake, you have a poorly designed system.
  12. Your value hypothesis assumes early adopters will accept a product.
  13. Your growth hypothesis assumes your product will appeal to a larger group of people later.
  14. The earlier you can validate these assumptions, the better off your business will be.
  1. As a manager, you need to plan similar to a fire department. They don’t know where the next fire will occur. So they position their team to quickly respond to the unanticipated.
  2. The earlier you can find your problems, the easier they’ll be to fix.
  3. In order for your indicators to be effective, you need to focus them on a specific operational goal.
  4. Indicators are like riding a bicycle — they’ll steer you where you’re looking. Guard against overreaction.
  5. You increase productivity by emphasizing the output. If you do the opposite, you only increase activity.
  6. Formal reports and recommendations can be useful in driving the discipline behind the decisions.
  7. Delegation without follow-through is abdication.
  8. One-on-ones are the employee’s meetings. They set the agenda and the tone.
  9. Grove’s Principle of Didactic Management: Ask one more question! Whenever you think someone’s said all they want to, ask another question.
  10. Decision-making is not a spectator sport.
  11. As you develop plans, ask yourself: “What do I have to do today to solve — or better, avoid — tomorrow’s problem?”
  12. Useful key results contain specific wording and dates. When the deadline arrives, don’t leave room for ambiguity.
  13. A manager needs to see the work as it is seen by the people who do it every day.
  14. A manager can raise an individual’s performance in two ways: training and motivation.
  15. Look at your calendar for last week and classify activities as low, medium or high-leverage. Then generate a plan to do more high-leverage activities going forward.
  1. Company profit and shareholder value don’t inspire people. In order to drive commitment, you need to connect the work people do each day to the mission.
  2. Stories are critical to selling the vision. If you can’t tell it, you can’t sell it.
  3. Don’t blame external events for your limitations. The biggest problem is always internal.
  4. Don’t focus on total market, focus on total problem. When you make this shift, you stop looking for a percentage of the marketplace and want it all.
  5. Try to make one new connection every day. You build a newtork one day, and one person, at a time.
  6. Create a monthly “I Can Do This” list to hold yourself accountable for getting out of your comfort zone.
  7. Bin investments in three boxes — Core, Adjacent, and New — to protect your established business lines while innovating at the edges.
  8. Two questions can drive agility and speed-to-market: What problem are we trying to solve? And, what’s the simplest, fastest way to test a solution?
  9. The biggest threat to new products is existing products. Challenge entitlement funding every chance you can get.
  10. Challenge yourself to ask one question or make one comment during each meeting. Develop the habit of sharing your perspective.
  11. Encourage everyone to have one part of their job that they’re working to improve.
  12. When someone says, “It’s an outlier, don’t worry about it,” ask, “What if it’s not? How would we know if this is the beginning of something new?” It’s easy to write off these as anomalies, but remember that the center always gets its innovations from the edge.
  13. If you see a better way, it’s your job to pursue it.

If you think this is helpful, let me know. I try to read around 50 books a year and I’d be happy to post takeaways and actions from others if you think it’s worthwhile. Cheers!

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Jake Wilder

Written by

Enemy of the Status Quo.

The Startup

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Jake Wilder

Written by

Enemy of the Status Quo.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +785K followers.

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