Leadership Meditations — Thoughts on Mentoring, Interviewing, Hiring, Firing, and Style

The following are thoughts and advice on people management and leadership that I’ve learned so far in my career as a manager. These topics were learned mostly through mistakes I have made. While I’m sure many of them will seem obvious, I hope that the musings help someone out there.

On Style

• Each team has their personality and dynamics based on the individuals that comprise it. The art of a good manager is to understand people and the fact that no two teams are alike.
• Be genuine and honest with your team. Loyalty and trust are hard to earn and easy to lose. There is never be a reason to lie to a team member.
• Admit when you make mistakes. So many managers I’ve interacted with have this problem. The ability to admit mistakes is a powerful one with multiple benefits. Simply, admitting mistakes allows you to change to decisions to better ones. The action also encourages the group to admit their own mistakes and course-correct too.
• You lead a team — not a family. You don’t have the ability to fire family members, nor are you (typically) with a company for longer than a few years. As a leader, you have a responsibility to make tough decisions in the interest of the company. Teams that treat each other as professionals rather than siblings have the best chemistry.
• When something goes wrong, and there is a crisis, don’t focus on who is to blame. Blaming doesn’t help. While a house is on fire, it doesn’t help asking why or how the fire started. Your first question should be how the fire can be put out. After the fire is put out, then ask how can the fire be prevented from happening in the future.
• Tangentially, encourage the team to report when there is smoke, not fire. Address issues prophylactically; fix problems before they become incidents.
• You don’t have to be the most skilled or knowledgeable member of your team to be a good manager or leader. Don’t pretend to be or assume that your team expects you to be. Good managers understand the nature of what team members strengths are, and know how to delegate different types of work to the right person.
• A manager should aspire for a team’s output to be as predictable as possible. Predictability provides more accurate estimates of work to stakeholders and makes planning worthwhile.

On Mentorship

• Don’t assume that someone who is older or even more experienced can’t learn something from you. Likewise, don’t assume that someone who is younger and less experienced can’t teach you something.
• Delegation is a major part of your job. Entrusting team members to own a project can lead to surprisingly positive results.
• However, be careful of isolated pockets of knowledge on your team. Often only one (and only one) team member has the mastery of a complex component or external relationship. Proper documentation may seem like a solution, but internal documentation is rarely assumed complete, up to date, or read. What is better is to work to replicate the knowledge to other team members. Instead of always assigning tasks to the same person, assign to others and ask for the team to work together to complete it.
• Identify and train your replacement. Have this person occasionally run your meetings and delegate tasks to other team members. While helping the company in case you left, this benefits you in three ways. One, it builds rapport and loyalty with that team member. Two, if done right, you will be freer to tackle larger company projects and vision. Three, having a self-sustaining team makes it easier for you to leave the team when it is beneficial for you to do so.
• Don’t treat your team the way you would want to be treated. Learn how to treat team members the way they want to be treated. Some employees are introverted while others are extroverted. Some learn better through email while others via conversation. In the long run, you will have superior success in communicating with your team by adjusting your method to the individual.
• Schedule a one-on-one meeting cadence every 1–2 weeks with each of your direct reports to check in on how things are going. While these meetings sometimes last just a few minutes, they provide a proper place for team members to discuss their career growth, performance issues, or anything else on their mind.
• I’ve met many managers who believe that job titles don’t matter. I have found that titles can matter a great deal. One, job titles help customers, vendors, and potential job candidates navigate the organization. Two, most employees want to know their career progression within the company. Third, job titles are often used by to value and compare employee compensation.
• Employees should have one and only one boss. Having more than one manager creates prioritization confusion and conflict.

On Hiring

• Hiring is mostly instinctive; over time, you will make hiring mistakes no matter how rigorous your methods and process.
• A company should make it as easy as possible for qualified applicants to apply. If your team is requiring an applicant to sign up on some hiring portal or go through pages of paperwork before even a phone screening, your hiring process is broken.
• Avoid, whenever possible, hiring negative attitudes. You and your team most likely interact with each other more than most people in your lives. Life is short, why spend so much time with negativity?
• Avoid hiring stubborn people who chastise conflicting points of view. These attitudes create an unhealthy culture of conflict where decisions are made loud voices rather than by rationals ones.
• There is never enough information to precisely predict how a candidate will perform if hired on your team. Even if a manager has previously worked with a candidate, the dynamics, culture, and the stage of life of the candidate was different at that experience than this one.
• Hiring is usually easier than firing. Everyone is happy when there is a new hire; the opposite is true when firing. Beware the trap of thinking that hiring someone won’t be risky since you can always fire that person. Breaking up is much harder to do and is the worst outcome on both sides.
• For new open positions, avoid super specific job descriptions. I’ve found it is better to have more candidates to choose from than less. Refine your job description after having initial candidate screenings. Often you will end up hiring someone who is very different than what you originally thought you wanted. Someone who isn’t qualified for a particular job may qualify for a new role or with a position on another team.
• Too often, companies view conducting interviews as a high cost. However, there are other values that the interview process brings to teams. The exercise builds the team’s interview experience, giving a chance for team members to better understand one another’s values. It also gives a chance to confirm or refine job requirements and the interview process itself.
• Indecisiveness in hiring is a plague infecting many small companies. Surprisingly, a common reason why some candidates don’t get hired is due to a team never making up their mind.
• Keep candidates informed of the decision making progress. It goes a long way in improving the reputation of you, your group, and the company.
• Salary is only one component in a candidate’s decision. Role, title, stock options, team dynamic, commute to work, retirement benefits, health plan, perks, vacation policy, work from home policy, and career growth opportunities also matter.
• Many companies don’t share feedback with declined candidates, but this is a mistake. Writing feedback does two positive things. One, feedback can provide a candidate with a guide on how to improve. Two, the exercise helps train a manager’s ability to justify their hiring decisions.

On Interviewing

• Interviewing is an inexact science. The total amount of exposure a candidate has with a company during the interview process is usually only a few hours. There is simply not enough data to perfectly predict.
• The worst interview questions are ones that have little relevance to the day to day aspects of a job. Asking a politician a gotcha​ question such as “Who is the President of the Zimbabwe?” is worse than “What is your philosophy on foreign aid?”
• No one single interview question will qualify or disqualify a candidate.
• Almost always, the image in your mind of what and how the candidate will work and function on your team will change in ways you never expect. Consider how a candidate will react when that change inevitably happens.
• It can be a mistake to have your entire team interview a candidate. Not everyone on a team is necessarily qualified or trained on how to interview candidates. Some team members don’t know how to conduct themselves in an interview which can negatively represent the team and company. Inexperienced interviewers will tend to ask questions that are too difficult or irrelevant. Think carefully about who you want representing your team and company in interviews.
• Here are three important attributes I have found in my best hires. The ability to communicate technical concepts clearly and honestly, a tenacious desire to learn and improve, and they give a shit.
• The best hires I have ever made ironically did not go through an extensive interview process. The candidates met with relevant team members and me to discuss the job, their experiences and aspirations, and their competency for the role. I‘ve had more success with conversations than interviews.
• Avoid converting candidates to numbers. It is impossible given the limited amount of interaction that happens between interviewers and interviewees. Grading a candidate a “75%” in “Culture Fit” is a mostly useless, meaningless measure that may make hiring feel easier (candidates below an arbitrary threshold don’t get hired). Taking emotion out of decision-making may seem logical; however, teams comprise of emotional human beings. Candidates who score 100% on a multiple-choice technical assessment could be awful to work with in ways that numbers won’t show. Instead of making decisions based solely on a syllabus, have a post-interview discussion with the interviewers.
• A candidate who is well experienced and skilled is a poor hire if they exhibits the antithesis of the culture your team strives for.

On Firing

• Be quantitative. While the ultimate decision is up to a manager, metrics should ideally be the driving force for the decision. With little exception, firing should be a data-driven decision. Any other reason may be ambiguous and open to interpretation. Unlike hiring, which is a decision typically made with limited information, firing should be done with copious amounts of data.
• While firing someone, if you have nothing nice to say, don’t say anything at all. Burning bridges does not help anyone. Express specific facts if possible and avoid using hearsay.

On Discipline

• You lead people, not machines, to do work. These people have mostly encapsulated their personal lives from their work; recognize and respect that privacy. Realize that work is most likely not the top priority in their lives.
• Young leaders are unlikely able to identify with the trials and tribulations of unexpected life events that an older team member may experience. Be mindful of this truth. Compassion during those times goes a long way in building loyalty.
• It is not always advantageous to have a team member work long hours and weekends. Here are two reasons to dissuade this behavior. One, overworking can lead people to burnout. Second, excessive work creates a sense of competition and expectation with other team members to do the same.
• The larger the team, the more likely there is a conflict between two team members (birthday paradox). It is normal, expected, and unavoidable at scale.
• So often will someone on a team say, “We should do X” or “Someone should do Y”; discourage the team from using the word “we should” since usually nobody will end up doing anything. Hold someone accountable for the work.

On Measuring Performance

• The most common mistake I have seen teams make is simply working on things that don’t need to be worked on. There are two reasons this usually happens. One, teams don’t spend enough time thinking about the ROI of their tasks. Two, teams don’t prioterize their work effectively. Reflect often on whether your team is working on the most important items right now.
• Another common performance problem I have seen is team members not finishing their commitments. Not finishing is usually due to misunderstood requirements and over-engineering. Here are two strategies that help employees complete work. One, work with the employee to break down their work into smaller tasks and then track the progress of each of those tasks. Two, set deadlines. Deadlines help dissuade over-engineering of solutions to problems.
• Describe two or three quantifiable outputs of work each team member has recently accomplished. If you have trouble naming things for a particular team member, then you probably have a performance problem. Here are two ways to encourage output. One, require your team track their work using software and demand regular updates. With the data, evaluating an individual’s performance becomes easier. And with continuous updates, mistakes can be corrected sooner. Two, have a demo day, or meetings where team members present their recent work to the team. Demo days can be very valuable. They don’t just encourage team members to produce demonstrable work, but they help transform a team to value finishing. Demo days also have a bonus of showing teams what everyone else is doing.
• The quality of time worked is a better to measure than the quantity of time worked. Don’t confuse an employee that works long hours as always a good thing. Hard work is a valuable personal trait of an employee that should, over time, result in an improvement in their quality of work. Hard work alone is not a virtue.