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The Art of Leadership

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The Art of Leadership

Small Things, Done Well


15 min read
7 take-aways
Audio & text

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Great leadership is a series of small steps executed correctly.

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  • Comprehensive
  • Applicable
  • Concrete Examples


“Small things, done well” make a big difference in a leader’s career, says Silicon Valley engineer-turned-executive Michael Lopp. He recounts working his way up at Netscape, Apple and Slack in this three-part – or three “Act” – memoir covering what it means to be a manager, director and executive. He encourages all leaders – from new managers to experienced executives – to sweat the small stuff when hiring, delegating, managing meetings, handling problematic “capital-S” crises, controlling rumors and more. His stories enliven even mundane topics, and he includes a chapter on no-win situations with some fun for Star Trek fans.


  • Managers must listen to employees, prepare well for meetings and handle problems with a cool head.
  • Managers must carry out frequent performance evaluations.
  • Effective time management is crucial for managers.
  • Managers who gain promotion to the director level must manage expectations, delegate and always be recruiting.
  • Directors must run efficient meetings, work well with remote employees and provide constructive feedback.
  • Executives should smooth the gaps among different cultures within the company.
  • Executives benefit from having a mentor.


Managers must listen to employees, prepare well for meetings and handle problems with a cool head.

Many new managers receive no managerial training and must learn by experience. It is hard for managers, even those a year or more into their roles, to work out the most efficient or productive way to run things.

Competence in synthesizing information is an important skill for managers. They tend to sign up for too many things and don’t realize they have overextended themselves, especially if they’re new to management. Then, they have to delegate a previous commitment or maintain all their commitments and perform poorly. Both are bad choices. Managers who don’t deliver on their promises seem incompetent or lazy. That signals to their team that it’s okay to drop assignments. Good managers use self-insight to understand their own capabilities.

They are conscientious about communicating with and meeting with their staff members, both in valuable one-on-one meetings and as a team. However, managers must prepare for these sessions; novice managers who don’t prepare for staff or one-on-one meetings by setting an agenda and considering priorities just waste everyone’s time.

Every manager has to cope with pressure and many face dealing with a high-pressure “Situation.” Whether the crisis is small or large, managers need to use their judgment and experience to help their teams handle difficult issues.

“For capital-S Situations, there’s no easy answer. A Situation is a complicated, never-seen-before-beast, and the reason that everyone in the room is energetically quiet is that they’ve never seen this before, and they’re wondering what the hell is going to happen.” ”

If you are a manager in a complex Situation, you must consider multiple factors. Don’t make decisions until you’ve fully processed all the available information and answered these questions.

  • Are you the right person to handle this unique Situation? If not, who is?
  • Do you have all relevant information surrounding the Situation – all essential facts, opinions and misconceptions? Have you talked to everyone involved?
  • Do your information sources have reliable track records, and are they trustworthy?
  • Are there inconsistencies in the facts you discovered? Do these inconsistencies derive from different perspectives or is someone lying?
  • Can you explain the different perspectives of the Situation to a neutral, third party? Are you aware of your own biases?
  • Are you in an emotional state that might affect your response?
  • Go back to the first question. Are you the right person to handle this Situation?

It’s easy to getting caught up in a dramatic moment and to want to drop everything else to handle the Situation. But, to prevail, you should take a calm and measured approach.

Managers must carry out frequent performance evaluations.

Managers should conduct performance evaluations several times a year. Ask your staff members and yourself questions with diagnostic meaning but no right or wrong answers: What are people’s strengths and weaknesses? What do they need to do to improve? Do they feel their compensation is fair? If not, have they discussed that with their supervisor? Does their direct manager give them useful feedback? What was the last project they enjoyed? What did they learn from their last failure? When was the last time they changed jobs or companies? Why? What is their dream job or company? Why?

Professional growth is a daily process. To stay aware of your own perceptions and progress, review and answer these questions often; don’t wait for an annual performance evaluation. Run this review quarterly to develop specific ideas about your own career trajectory. That will help you become a better mentor for your employees.

“During these hard conversations…you become a better communicator, you learn the value of different perspectives, you build empathy, you become a better coach and you become a better leader.”

Many managers fail at guiding their direct reports because they wait until things are bad, and then have a difficult conversation. Instead, have at least three conversations. Don’t send your employees emails about performance problems and then expect results. Hold one-on-one meetings. Performance management issues can take months to resolve; you and your employee should agree on what needs to be done and set milestones and a deadline to make it happen.

Effective time management is crucial for managers.

Time is a manager’s most important asset. Adopting good habits will increase your efficiency and alleviate stress. One way to save time is to make your internet browser more efficient. Copy your bookmarks to a folder and delete your current bookmarks. Put news sites, blogs or other “daily consumables” in a feed reader, such as Feedly. Use an ad blocker. Put no more than five of your most valuable tools in your browser, such as your email, calendar and feed reader. Try to have only one browser window open at a time. Have no more than 10 tabs open at once. Turn off non-critical notifications.

“These habits will substantially increase your productivity by reducing stress, increasing focus and ultimately improving the quality of the things you build with your hands.”

Find an app that blocks spam calls, texts and emails. Delete any apps you haven’t used for a week. Winnow down your email inbox by reading and “unsubscribing” from unwanted emails, reporting email as “spam” if unsubscribing doesn’t work and turning off automatic notifications.

Managers who gain promotion to the director level must manage expectations, delegate and always be recruiting.

Seasoned managers get promoted into senior management positions, such as department head or director. Starting a new management position is like having contractors at your house. Think of your new job as marking any imperfections with blue tape. Make a note of any needed changes – big or small. Mentally mark them with blue tape and wait a month to see if issues that seem urgent really are. Address everything on your blue tape list.

All new managers must adjust to a shift in leadership responsibilities. Delegation is one of the most difficult, but most necessary, skills that directors or upper-level managers must master.

“A common complaint I hear about managers is the classic, ‘What do they do all day?’ You know what a good manager is doing? They’re giving away just about everything that lands on their plate to members of their team because their job isn’t building the product, their job is building a team that is capable of building the product.”

Managers delegate small, well-defined projects to individuals; executives at the top of the ladder delegate large, complex projects to cross-functional teams or departments, and then exercise limited oversight. In between those two levels are senior managers, directors and senior directors with gradually increasing responsibilities to delegate.

Directors must spend a minimum of an hour a day up to a maximum of 50% of their time recruiting for every open position on their team. Recruiting involves screening resumes and applications, conducting phone and in-person interviews, making an offer and then hiring. This process can take up to six months in some cases. Spending half your time recruiting is worth the effort and ultimately makes your business run more smoothly.

Directors must run efficient meetings, work well with remote employees and provide constructive feedback.

Meetings aren’t popular, but they do offer opportunities to address problems and handle rumors and gossip. Well-run meetings feature healthy discussion and debate about 95% of the time. Allocate someone as a “Meeting Runner” who will organize the session, set the agenda and manage the meeting’s flow. Assign a second person as a “Meeting Historian” to keep the minutes and follow up afterward. The Meeting Historian should capture everything and distribute the minutes to everyone in the company; this helps prevent the spread of gossip.

For meetings that don’t occur on a regular schedule, directors should use a three-point agenda.

  1. A “minimal metrics story” – Minimal metrics are whatever the team measures regularly – revenue, application performance, security incidents, and the like.
  2. “Rolling team-sourced topics” – These are agenda items that team members added ​​​​​​at the end of a previous meeting to be addressed at the next meeting.
  3. “Gossip, rumors and lies” – Give your employees a safe space to discuss issues and find out facts. This is especially important if the team or the company is going through a transition period with the potential for confusion and concern.

Today, many employees work remotely and companies use hi-tech video and audio conferencing equipment to conduct meetings. Many companies use the term “remote” to describe employees who work offsite, that is, from home. However, “distributed” turns out to be a better term, because it means “elsewhere” rather than away from the action, as “remote” implies. Regardless of terminology, realize that offsite employees suffer a professional disadvantage. Never let them feel that their contributions don’t matter.

“There is a communication, culture and context tax applied to folks who are distributed. Your job as a leader is to actively invest in reducing that tax.”

“Distributed meetings” are hard to run compared to meetings when everyone is present, but give your distributed meetings and your distant team members the same attention and care that they would receive in person at an on-site meeting.

Compliments go a long way. Recognize how someone accomplished an achievement, whether it’s large or small. On the flip side, “saying the hard thing” is just as important as giving compliments. Managers often ignore that voice inside their head calling out potential future problems because they want to avoid confrontation.

Constructive feedback falls into three categories: “no big deal,” “slow burn” and “just plain hard” feedback. With the first category, the person accepts the feedback and moves on. Ideally, all feedback would fall into this bucket. “Slow burn” feedback feels like it shouldn’t be a big deal until it hits the person later on that they received important information. Difficult feedback is hard to hear because the human brain is wired to fight it. Listen carefully to hard feedback so you understand it and repeat it back for clarification. Taking that step is calming and helps the guidance sink in.

Executives should smooth the gaps among different cultures within the company.

Many corporate cultures divide into two groups of employees: the “Old Guard” and the “New Guard.” The Old Guard is made up of the first employees hired during a company’s start-up. They’re proud of their products and corporate culture. The Old Guard was so successful the company hired a New Guard. 

“These two populations exist because they have not yet gone through the critical and often painful process of building trust.”

Eventually, the New Guard gets to know the Old Guard, but the New Guard feels less empowered. People in the Old Guard don’t ask people in the New Guard for help because they don’t trust them yet. Executives must understand the dynamics of these groups, leading them through the process of building trust, so they unite and they eventually become “The Guard.”

Executives benefit from having a mentor.

Executives have at least one boss, often a busy CEO who expects them to manage their departments competently without asking for help except when absolutely necessary. Hopefully, if you’re an executive and something blows up in a department under your supervision, you have competent people to help you put out the fires. Just remain aware that the buck stops with you.

“Marty taught me the phrase, ‘Feedback is a gift.’ The phrase is designed to remove the fear of receiving critical feedback, to reinforce the fact that you are about to receive a useful thing.”

Executives need an external “sounding board.”Author Michael Lopp’s mentor was Marty, an external coach he hired when he was first promoted to director. He asked Marty to conduct a 360-degree performance evaluation.Marty held in-depth, 30- to 60-minute interviews with Lopp’s co-workers, his direct reports, his manager and his manager’s peers. Marty answered Lopp’s questions about feedback from his interviews without betraying any confidence, and told Lopp to sleep on what he had learned. They maintained a trusting relationship for years.

Finally, in a world in which leaders can choose to be anything, choose to be “unfailingly kind.”

About the Author

Michael Lopp has worked as an engineer and business leader for Slack, Borland, Netscape, Palantir, Pinterest and Apple. He also wrote Managing Humans, Third Edition and Being Geek.

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