The 3 lessons on leadership I’ve learned from 1,000+ managers in the past few months
By: Mandy Moore
Tags: Entrepreneurship, Startup, Management, Leadership, Business

The 3 lessons on leadership I’ve learned from 1,000+ managers in the past few months

From our 1,000+ managers all over the world in our Watercooler community, here are the 3 most helpful lessons on leadership that I’ve personally learned recently.

Lessons on leadership are typically learned the hard way. You make the mistake of hiring the wrong person, you wait too long to let someone go, or don’t give helpful, actionable feedback. This is why we at Know Your Team 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 your challenges in the workplace, and support one another through wins and losses.

When I started here at Know Your Team as Operations Manager, I had no formal leadership training whatsoever. What I did have was a plethora of uncracked leadership books that I bought impulsively and intended to read over my beloved fiction books (at some unknown point 😉) . When Claire, our CEO, introduced me to The Watercooler community, it was a game-changer. Now I have access to thousands of conversations 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 been having in The Watercooler lately…

Lesson #1: What do you do when people aren’t pulling their weight?

One of the hardest leadership lessons to learn is when someone on our team is floundering. Perhaps they accidentally fell into a role within your team, or they recently started contributing to an area outside their domain and are struggling — what do you do?

Evaluate if the person has got the potential of what it will take to succeed in the position. If so, keep them and give them extra attention. If not, see if they could be better in another position and move them over. If that’s not possible or desirable, let them go — the sooner the better.

of what it will take to succeed in the position. If so, keep them and give them extra attention. If not, see if they could be better in another position and move them over. If that’s not possible or desirable, let them go — the sooner the better. Get the input of others: Ask your teammates for their opinions and add your own. Write down in one column the “must abilities” for the job and in another column what the employee has been doing. See how much of the list overlaps. I could just be a question of building confidence in this person and giving them a bit of extra training. If the overlap doesn’t exist, let them go. You need to find someone to fulfill their duties within the organization.

Ask your teammates for their opinions and add your own. Write down in one column the “must abilities” for the job and in another column what the employee has been doing. See how much of the list overlaps. I could just be a question of building confidence in this person and giving them a bit of extra training. If the overlap doesn’t exist, let them go. You need to find someone to fulfill their duties within the organization. Use SMART goals : They should be written down so it’s extremely clear what their role is, and how their success is measured.

They should be written down so it’s extremely clear what their role is, and how their success is measured. Make sure you are asking them to do what you hired them to do: If they have been given additional responsibility incrementally as they’ve ramped up in her role, were they aware that was the plan? Did they know they were going to take on more and more responsibility over time? It’s best if this is documented in an onboarding plan.

If they have been given additional responsibility incrementally as they’ve ramped up in her role, were they aware that was the plan? Did they know they were going to take on more and more responsibility over time? It’s best if this is documented in an onboarding plan. Evaluate the workload: Is it reasonable? Have other people been able to successfully handle it before? If you compared the role to a similar role at a competitor company, would the responsibilities align?

Is it reasonable? Have other people been able to successfully handle it before? If you compared the role to a similar role at a competitor company, would the responsibilities align? Is it a case of growth resistance? If the person is saying, “I don’t know” or “I’m not confident” — that’s one thing. Responding with offering training and coaching is appropriate. On the other hand, them saying flat-out “no” to a job responsibility is another situation entirely. Confronting that in the moment is effective by saying something like, “It sounds like you think this request is optional, and I want to be clear that it is not optional. This is part of your job duty here, and part of why you were hired.”

If the person is saying, “I don’t know” or “I’m not confident” — that’s one thing. Responding with offering training and coaching is appropriate. On the other hand, them saying flat-out “no” to a job responsibility is another situation entirely. Confronting that in the moment is effective by saying something like, “It sounds like you think this request is optional, and I want to be clear that it is not optional. This is part of your job duty here, and part of why you were hired.” Ask for their thoughts on their own performance: Information surfaces when we ask the people to share how they think they’re performing.

Wondering what else you can do when a direct report is underperforming? You may find these resources on our blog additionally useful:

Lesson #2: How often should you have team gatherings?

Team gatherings are an essential way to help everyone in team feel connected. But how often should you exactly have them? What ensures that they are in fact beneficial? Should you work with external folks (trainers, facilitators)? Here are some tips from our Watercooler community members…

Have an event once every month: While team events should be optional, it’s pretty easy for people to feel like they’re obligated to be there. (And if they’re fun, people will want to be there too!) (See below for ideas!)

While team events should be optional, it’s pretty easy for people to feel like they’re obligated to be there. (And if they’re fun, people will want to be there too!) (See below for ideas!) Schedule some events during work hours: If people feel they’re missing out on time with their family, they might not want to go.

If people feel they’re missing out on time with their family, they might not want to go. Be respectful of introverted employees: Organize a gathering, but don’t pressure people to come. Mandatory is not fun.

Organize a gathering, but don’t pressure people to come. Mandatory is not fun. Avoid the bar: Some people don’t like to drink and feel awkward by being there.

Some people don’t like to drink and feel awkward by being there. Hold in-person meetings for remote teams: These are invaluable for team cohesion and motivation. If you are small enough that you can avoid clashing with occasions (like birthdays or anniversaries), that is recommended. Give a minimum of 5 months notice.

These are invaluable for team cohesion and motivation. If you are small enough that you can avoid clashing with occasions (like birthdays or anniversaries), that is recommended. Give a minimum of 5 months notice. Get opinions: When everyone has a say on topics and schedule, it’s more enjoyable for everyone.

When everyone has a say on topics and schedule, it’s more enjoyable for everyone. Be mindful of travel: Structure Monday and Friday as travel days. Use Tuesday as a fun/flex day as some people are still tired from travel. Use Wednesday and Thursday to have meetings and team planning time.

Structure Monday and Friday as travel days. Use Tuesday as a fun/flex day as some people are still tired from travel. Use Wednesday and Thursday to have meetings and team planning time. Use your webcam: If you can’t make in-person gatherings often, schedule some fun time on Zoom, Skype, or your preferred video chat tool. Have a weekly “Wins & Miseries” Call. Make it last no more than 30 minutes and not mandatory for large companies — just encourage them. Use the popcorn method to share one win, misery or both. They can be personal or professional.

If you can’t make in-person gatherings often, schedule some fun time on Zoom, Skype, or your preferred video chat tool. Have a weekly “Wins & Miseries” Call. Make it last no more than 30 minutes and not mandatory for large companies — just encourage them. Use the popcorn method to share one win, misery or both. They can be personal or professional. Hold gatherings in an inclusive environment: Taking a class allows for voluntary participation. Some folks will be active and some are happy to sit on the side and watch. It still makes for a shared experience to look back on.

Taking a class allows for voluntary participation. Some folks will be active and some are happy to sit on the side and watch. It still makes for a shared experience to look back on. Use a facilitator: It takes pressure off leaders to be “the person” that needs to make sure everything goes smoothly and then they can participate too as a teammate and get to actually sit back, listen, ponder, reflect, etc.

💡 Ideas for gatherings:

Caffeine Crawl — Hit up your local caffeinated beverages shops and have a drink in each!

Day of Wander — Get out and just explore your city. Visit places you’ve never been before!

Dinner and a movie

No Return Lunch

Team Bonfire

Symphony on the Prairie

Video Game Party

5-day Team Retreat in a cool location

Day of Learning

Karaoke

Do a class together — i.e.: Glass blowing, cooking, painting, crafting

Art and Museum Tours

Looking for more ideas on how to precisely plan an all-team retreat? You might want to check out a relevant blog post our CEO, Claire, wrote that outlines the exact 3-day team retreat agenda we held in Point Reyes, California.

Lesson #3: How should we get feedback on our team: Anonymously, or non-anonymously?

When we want honest feedback within our team, we’re often faced with whether we should ask for it anonymously or not. Of all the lessons on leadership, it’s one where the answer feels a bit more ambiguous. A Watercooler member recently faced this exact issue, as they’d been asked by employees for a way to submit anonymous feedback on an ongoing basis rather than just once a year. While we here at Know Your Team tend to discourage this type of feedback, a great conversation took place within the community.

✅ Pro Anonymous feedback

The feedback might more honest and direct, since employees know their names won’t be attached. Employees are given a space to speak up where reprisal is not at play. It might allow both outspoken and more passive employees to be heard equally.

🚫 Against Anonymous feedback

Anonymity can reinforce the idea that it’s risky to speak up. It’s difficult to action anonymous feedback without context or a conversation. You can create mistrust. If feedback is negative and about an individual, that person is likely to be less trusting of colleagues if they don’t know who gave the feedback. Anonymous feedback will be intentionally vague as the person giving the feedback won’t want to identify themselves with too many details. Anonymous feedback is more likely to be used as a vehicle for office politics and personal attacks rather than constructive feedback.

💬 Some members suggested the following:

Address the request for anonymous feedback: During an all-hands/leadership meeting, set an expectation that all anonymous feedback will be reviewed and taken into consideration. However, because anonymity breeds no path for further details or follow-up with the person raising the feedback, there is little to no chance for any action to be taken to address it.

During an all-hands/leadership meeting, set an expectation that all anonymous feedback will be reviewed and taken into consideration. However, because anonymity breeds no path for further details or follow-up with the person raising the feedback, there is little to no chance for any action to be taken to address it. Gather feedback once a quarter: This will give your organization more chances to address trends and settle issues faster — especially if more than one person is saying the same things.

This will give your organization more chances to address trends and settle issues faster — especially if more than one person is saying the same things. Actively seek feedback using retrospectives meetings: Feedback without action following it is just complaining. Put your team in a position where they have to provide feedback, design a path to improvement, and lastly make them responsible for implementing it. This accomplishes more than just improvement, and you will empower your team to make necessary changes. Start small and work your way up.

Feedback without action following it is just complaining. Put your team in a position where they have to provide feedback, design a path to improvement, and lastly make them responsible for implementing it. This accomplishes more than just improvement, and you will empower your team to make necessary changes. Start small and work your way up. Go first: If you want employees to be brave and put their name to things then you have to go first. Give them your own opinion on something that you think you or the CEO could do better. (In fact, we have a post on the Know Your Team blog here on this exact topic of why it’s important for you to go first as a manager.)

Curious for how you can deliberately create an open, honest culture of feedback? You’ll want to peek at these pieces we’ve written:

In just a few months’ time, I’ve personally learn a myriad of lessons on leadership from participating in The Watercooler every day. I hope you’ll consider joining me in doing the same.