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Lessons on leadership: The 10 most impactful lessons I’ve learned from 1,000+ managers in 2019

From 1,000+ managers all over the world in our Watercooler community, here are the 10 most impactful lessons on leadership that I’ve learned in 2019.

Lessons on leadership

When it comes to lessons on leadership, always be learning. This is my motto as Operations Manager here at Know Your Team. Prior to joining the KYT Team in June of this past year, our CEO, Claire Lew, created The Watercooler: A unique, and highly-moderated community for 1000+ managers, leaders, executives, (and you!) to share and discuss lessons on leadership, talk about challenges in the workplace, and support one another through wins and losses.

As I’ve said before, having access to this community has been a game-changer. I have complete access to thousands of conversations on lessons on leadership that I can take five or ten minutes a day to learn from and participate in if I choose to. 

Here are some of the best conversations and top lessons on leadership, I’ve learned from and that we’ve had in The Watercooler in 2019. I hope you’ll consider joining us in 2020!

Lesson #1: How do I ensure psychological safety is present in the workplace?

Watercooler members shared steps they’ve taken to ensure people feel safe in their job, on their teams, and in their company. But what exactly does psychological safety mean at an individual level? As perhaps one of the most important lessons on leadership we could all learn from, Watercooler member and Know Your Team customer, Tim Burgess, co-founder of Shield GEO, wrote the following list:

  • My job is safe for reasons outside of my control.
  • My job is safe for reasons within my control.
  • I know the consequences of making mistakes. And I am ok with those consequences.
  • I am confident in facing the challenges at work. Which might require I know and have confidence in the support available.
  • Nobody is going to harm me at work physically.
  • Nobody is going to harm me at work mentally.
  • I feel comfortable expressing myself to anyone at work.
  • I feel accepted at work.

To accomplish 👆🏻members discussed:

  • Talking about psychological safety at an organizational level. It is the first step in ensuring you are fostering a safe environment by letting your employees know it is a company-wide priority. 
  • Listening actively during all-hands meetings, annual evaluation conversations, and one-on-ones to sense how safe it is to tell the truth, be vulnerable, and share failures.
  • Measuring how safe your employees feel by looking for signs and when people allow emotion. Laughing wholeheartedly, crying without shame, getting angry, and then repairing relationships are all good signs that people feel psychologically safe.
  • Examining whether people have “best work friends.” If so, this is usually a sign that teammates feel safe with each other and are open to socialization. People often feel safer when they have at least one person that they trust and feel connected to.
  • Ensuring that employees have a solid understanding of what is expected of them in their day-to-day work. Set expectations and check-in during one-on-ones when you feel there is misalignment. 

💫 Harvard professor and author of The Fearless Organization, Amy Edmondson, talks more about how psychological safety can be measured within a team in this re:Work with Google tool guide.

Lesson #2: What should I be asking old employers of potential new employees during reference calls? 

Watercooler member Michael Nachbar, Executive Director at Global Online Academy, added these great questions as a follow-on to KYT CEO, Claire Lew’s comprehensive list:

  • Describe the context in which you’ve worked with XX. How long have you known them?
  • What are your overall impressions of XX?
  • What are XX’s three most significant strengths, and why?
  • What are XX’s most significant professional accomplishments?
  • What about areas where they can continue to grow and develop? How have these areas changed over time?
  • In what type of organizational setting/culture would XX do their best work? Why?
  • How would you describe XX’s working style?
    • What about their experience helping other team members develop over time?
      Where have you seen XX be most effective in building relationships, internally and externally? What is their approach? How do they adjust their style to various stakeholder needs and preferences?
    • What relationship-focused challenges have you observed XX encounter? Did they overcome them? If so, how? Do you have an example of when XX provided constructive feedback to you (and vice versa, if applicable)? Are they receptive to feedback?
  • Often we learn most from our mistakes or missteps. Can you give me an example of an error or failure that XX learned and grew from?
  • What advice would you give to our leadership team about how best to work with them?
  • Would you like to work with / hire XX again?
  • Is there anything else you’d like to share?

Lesson #3: How can I master my own listening habits?

Let’s be real. We all need to get better at listening, myself included. I love this thread from Watercooler member and leadership and development coach, Ali Merchant who says his “lifelong practice,” is to get better at listening. He’s been working on it for a long time and has improved over the years, but will always remain a student of this art. Here’s something he wrote on Forbes. Bottom line: one of the most important lessons on leadership you can learn is actually listening 👂🏻.

Ali says these are the three listening habits holding you back:

  • Constantly jumping in: I think we’re all guilty of interrupting – and not to be rude. Some people get excited during conversations and want to add their two cents before they a) forget or b) it’s not relevant to the discussion anymore. Make a concerted effort to wait until someone is done speaking before you take your turn.
  • Being distracted: In the world of technology we live in, it’s often difficult to completely unplug. You get a text message; your watch gives you some notification, or your email dings for attention again. But if you’re having a conversation with somebody, it’s vital that you aren’t giving in to the temptations of checking what’s going on right away. 99% of things can wait a few minutes and don’t require your immediate attention. Give the people you are talking about your respect and full attention.
  • Controlling outcomes: You can’t control what you can’t control, and sometimes you’ll have to have difficult conversations that make you uncomfortable. Hear the person out, and in the end, maybe you’ll learn something new, or you will be able to agree to disagree. Let go of the hypothetical wheel, and don’t try to steer conversations.

Other members suggested the following listening habits:

  • Be genuinely “curious” during a conversation. If the goal is to understand what someone is communicating, it usually turns out well. If you have an agenda that you are trying to get across, just the opposite outcome often happens.
  • Observe people who you think are great listeners.
  • Be in a good mood. You need to have a reasonable energy level to hear the right message: not the words themselves but how they are revealed.
  • Stop everything you are doing. It’s more about them and less about you.
  • Look with your eyes and body facing them. Facial gestures should sync with a person’s feelings.
  • Listen with nods and smiles. Give short affirmative phrases while they’re talking, so they still know they have your attention. If appropriate, share your own experiences and give support.

💫 In the November-December 2019 issue of Harvard Business Review, there is an article that touches on the topic of sustaining collaboration in organizations. One of the aspects it mentions to improve collaboration is to “Teach People to Listen, Not Talk.”

Lesson #4: Are organization charts within a company a good or bad thing to have?

According to Investopedia, “an organizational chart is a diagram that visually conveys a company’s internal structure by detailing the roles, responsibilities, and relationships between individuals within an entity. Organizational charts either broadly depict an enterprise company-wide or drill down to a specific department or unit.” Here are the pros and cons of creating organizational charts within a company.

  • Pros:
    • People like to know where they stand, what is expected of them, and where others stand + what their responsibilities are. 
    • Once your company is beyond ~ 7-10 people, an org chart may be necessary to scale.
    • Some sort of basic formality can be helpful so it’s clear on who reports to who and where people should go to get basic directions. 
    • They make everyone feel like they are a part of the organization.
    • Humans don’t desire structure, we require it. What is not clear to us, we either make it clear in our mind, or we become anxious about it. Org charts help people understand how to get things done. 
    • In large companies when there is a lot of turnover, they help new people learn how the organization works.
  • Cons:
    • They can create silos and prevent people from collaborating across teams. 
    • The benefits could only be there to make managing people easier. For instance: who gets the final say to say a project is done? If you ask three different people questions, most likely you’ll get in three different answers in return.
    • Use an accountability chart instead: It lists the accountabilities rather than just titles/people. It’s a great way – even for small organizations – to give ownership and autonomy to people and let everyone know who to go to for what.
    • They can make people feel “graded”. 
    • They can change all the time, especially in big companies, so they are hard to keep correct. 

Lesson #5: How I support parental leave policies to the best of my company’s ability?

Natalie Gould, CFO of Balsamiq, (who we also happened to have an awesome #AMA with where she shared some A+ lessons on leadership) shared this amazing and well-thought-out plan on supporting parents who need to take time off due to welcoming a new family member:

  • HR + admin: Ensure legal and company policies are clear to all.
    • What are the local employment laws that impact this work coverage? 
    • What are the policies that impact work coverage?
    • What are the benefit rules involved?
    • Are there any risks involved the employee is taking on? (i.e.: Working while traveling for personal reasons.)
    • Are there any elements of this work coverage plan that would be against local laws or put the company or employee at risk? (i.e.: An insurance denial of claim if someone is using an incorrect or false address.)
  • Create a coverage plan: Ensure how an employee’s work will be covered during a period of time. Employees should help create a plan to define:
    • What is the time period for this plan?
    • What work needs to be done?
    • What work doesn’t need to get done?
    • Who is in charge of covering the work?
    • Who can make decisions in place of the absentee?
    • How should the work get done? (SOPs, etc.)
  • Address concerns and align expectations: Before the plan is finalized, an HR facilitator should help make sure concerns are heard openly by all individuals involved and that expectations are clear. Examples of questions that would be discussed in this process:
    • For the person leaving: 
      • What are your concerns about leaving for so long? 
      • Are you worried about decisions that could be made in your absence that would impact your role or your area of work?
      • Are you worried about being overwhelmed or behind when you return?
    • For the team: 
      • What are your concerns with this plan?
      • Are you worried you won’t be able to move projects forward that impact your work?
      • Are you worried this absence will impact your workload negatively?
      • Are you worried any roles aren’t clear?
    • For everyone:
      • What are the known decisions and projects coming up that people might be concerned about? What is the plan for dealing with those things?
      • What are the goals everyone wants to accomplish during this absence?
      • What kinds of situations, would-be areas of work, or decisions that concern anyone if they went forward without the right input? (if they couldn’t go forward at all?)
  • Have a check-in plan. Challenges and needed modifications to the plan can be addressed in a check-in process.
    • What is the schedule you all want for checking in on the plan and how people can share their feelings about how things are going?
    • How will concerns get addressed if something comes up before a scheduled check-in?

Lesson #6: How do you get and keep employees engaged in the workplace?

One of the most effective lessons on leadership that I learned this year is that even if you offer many at-work events like lunch and learns, catered lunches, and give plenty of conference and learning opportunities to your staff, it can still be hard to get people excited and/or truly engaged. How do we improve employee engagement while at work if some teammates seem to only want to be engaged in actual work?

  • Help employees understand how learnings directly apply to their day-to-day: If people are faced with the decision between having an hour to do a lunch and learn and getting ahead on a support ticket, they’ll choose the option that gets them closer to a raise or promotion, or what will make them look better in general. To counter this, work with your frontline managers and tightly incorporate learning opportunities into career progression conversations they are having with their directs. Rather than saying, “These things will be good for you,” directly convey, “Event X will help you achieve Goal Y, which is an important step in your journey to Position Z.”
  • Engage in constant communication around the importance of continuous improvement: People only really start to believe it’s important after hearing it consistently over time.
  • Give Google’s 20 Percent Rule a try: Each team member has one day nearly every week (20% of their time) to work on a side project or study a new skill.
  • Give employees ways to improve their connections with their peers: In the book, Peak, Anders Ericsson concluded that in order for people to be motivated about learning, they must be able to tie what they’re learning in with the people around them. There has to be a connection between a person’s learning tasks and their social community.
  • Understand the current level of engagement of employees by utilizing surveys and asking company culture questions. Determine where your gaps are and prioritize initiatives based on team feedback.
  • Realize that every person has a different mix of things that are important to them, motivate them, and will help them be engaged. Some people mostly care about salary. Others care more about purpose. Ask and they’ll most likely tell you. Keep in mind: the ratio will change for every person over time and under different circumstances. Folks might be motivated by salary until their salary reaches a point where they are financially comfortable, and then other things will become more important to them. Check-in regularly.
  • Other often-stated motivators: 
    • Paid week-long hackathons where you work on new ideas.
    • Professional development budgets for each employee (usually around $2K).
    • Generous time-off policies.

Lesson #7: What do I do when someone on my team is constantly caught up in having the last word?

This phenomenon is frequently referred to as “Last Word Syndrome.” When a team member is always set on having the final say, meetings take longer, decisions are tabled, and other people aren’t heard as loudly.

  • Get to the bottom of, “Where does it come from?  Hold multiple 1:1 meetings with the person who has “last word syndrome” to understand the underlying root cause. Often times, it comes from a strong need to control. During the conversation, assure your coworker that you are there to help them and together you can find the best solutions.
  • Examine: How exactly does it manifest? For example, if there is an agreement reached, does someone feel the need to talk again and re-state what everyone’s already agreed? (Oftentimes this is a power/control issue). Looking at the behavior closely will help you determine where it’s ultimately coming from.
  • Have an agreed phrase or sign that this topic is over and time to move on. One example would be to use colored cards that say ELMO (“Enough, Let’s Move On”) – and to have any meeting members raise the cards when they feel the topic should change.
  • If an agreement isn’t reached in a meeting, record what the team didn’t agree on. This helps everyone feel heard, even if only one path is chosen forward. For example, you can document that “Principal 1, 2 and 3 wanted X. Director and Principal 4 wanted Y. We didn’t agree.”
  • Create a shared agenda where only things on it can be brought up. One Watercooler member shared how they have a Slack Channel for every meeting. If you haven’t added your topic to that Slack channel 18 hours before the meeting, you cannot raise it. This enables folks who are quieter to weigh in, reduces wasted time, and even helps resolve issues before a meeting.

Lesson #8: What are your company’s values, vision, and mission?

This is perhaps one of my absolute favorite lessons in leadership. Having these defined for me within Know Your Team has been so helpful for me as a new employee. I feel like our CEO, Claire, and our CTO, Daniel, defined everything so thoroughly during our company retreat, and therefore I know what my own role within the company is to help us achieve success.

💫 Claire’s blog post, “How to share your company vision as a leader” defines the following:

  • Mission (What we’re doing): To help people become better leaders.
  • Vision (Picture of a better place): A world where bad bosses are the exception, not the norm.
  • Values (How we do our work): Clear communication, Hustle, Humility, Heart, Curiosity.

Several members their favorite values, vision, and mission statements that make for happy and fulfilling careers:

  • “A world without Alzheimer’s Disease.”
  • “To put a man on the moon and return him safely to earth by the end of the decade.”
  • “International Employment Made Simple.”
  • “A software house where there is a healthy balance between people, technology and business.”
  • “A human-oriented culture, best software engineering practices, and win-win relationships with customers.”
  • “An organization that is not afraid to reinvent itself, embracing new projects, new ideas, and new people.”
  • “A company where you feel like going to work when you wake up, day after day, for the rest of our lives.”

Lesson #9: Should I be consulting leadership or business coaches?

Members shared their personal experiences with hiring coaches.

  • It can be a worthwhile investment if you find the right coach and develop the mindset to improve. Your coaching engagement will only be as effective as what you put in it. Good coaches help navigate you through challenges and will guide you to find your own solutions. Every engagement or meeting should revolve around your agenda (not the coach’s).
  • Good coaches help you recognize your blind spots and will help you advance to the next level.
  • There should be some chemistry: someone you can work with, but who you aren’t best friends with. Having a person you can relate to and that you want to work with is key. Maybe it’s someone who intimidates you a bit – someone who is a level or two up from where you would like to be.
  • Be careful that you don’t become lazy and make decisions until talking with your coach. You still need to think for yourself.
  • Find someone who challenges you directly, aggressively holds you accountable, and calls you on your BS. A coach should work well with you and your weaknesses.
  • Talk to several different coaches before making a decision on who to use. Find someone you are excited to work with and learn from.
  • Work with a SCORE coach. For over 50 years, SCORE has served as America’s premier source of free business mentoring and education. Find your local SCORE chapter here.

What to look for in a good coach:

  1. Superior listening skills.
  2. Challenges you appropriately.
  3. Holds you accountable to your commitments.
  4. Investment in you and the belief that your success is their success.
  5. A sounding board for your ideas.

💫 Did you know that Know Your Team is now offering 1:1 leadership coaching with our CEO, Claire Lew? If you’re a first-time manager who is feeling overwhelmed, if you are looking for 1:1 coaching on lessons on leadership, if you’re an executive who feels like they need to “level up” in their role, if you’re a founder or CEO who is worried about your blindspots or plateauing – Claire would love to lend a hand.

👉 You can apply for one-on-one leadership coaching with our CEO, Claire Lew, here.

Lesson #10: Favorite Leadership/Business Podcasts of 2019

Continue your own learning and education on lessons on leadership in 2020 with a compiled list of our members’ personal favorites.

💫 Speaking of podcasts, have you checked out our last two Heartbeat podcasts of the year yet? If not, I urge you to do so because they are 🔥.

In just a few months’ time, I’ve personally learned so many lessons on leadership from participating in The Watercooler every day in 2019. I hope you’ll consider investing in yourself and joining me in doing the same in 2020. Happy New Year!

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