Every team is made up of individuals with different needs, abilities, and styles. The “culture” on your team can and should change over time as your team grows. Leadership experts and authors Anne Morriss and Frances Frei say that both “presence” and “absence” leadership are crucial elements of management. This means that the leadership impact you have extends beyond moments where you're actively involved, or even in the room.

You are responsible for building a psychologically safe work environment that enables your team to achieve your collective goals. This includes helping your team learn how to operate independently and as a group.

“We are imperfect humans leading imperfect humans, by definition,” says Morriss. “We are going to build imperfect companies.”

You and others on your team will make mistakes, and the key is to practice repair and learn how to adapt and come back stronger than before.

STEPS TO BUILDING A CULTURE OF SUCCESS

In order to build a culture of success in your team, you'll start with building relationships, as you did with your managers, as well as creating a rhythm around helping your team goals.

CREATING A PERFORMANCE CADENCE WITH YOUR TEAM

Daily

• Daily virtual and/or async standups (depending on the organization)

Weekly

• Weekly 1:1
• Weekly team meeting, which is less of a status update, more where each member of your team can share Wins/Highlights, Challenges, Upcoming Team changes/PTO, and Asks for Help, and you check in around department OKRs. They should fill this out in advance in a Notion or Wiki doc and/or shared slides.

Biweekly/Monthly

• At least biweekly or monthly “Career” 1:1 that's just about individual team members' career goals, personal topics, anything they want to chat with you about.

Quarterly

• Discuss direct reports' OKRs for the upcoming quarter as well as review their wins, challenges, and learnings from the previous quarter.

THE 1:1S WITH YOUR DIRECT REPORTS

Your reports should create 1:1 agendas shared in an ongoing, updated doc in your wiki or docs that follows similar formats to your CEO 1:1. They should highlight what's going on in their department, discuss their progress against OKRs, and get your feedback. They should also have space to bring up concerns or issues before they become larger.

CREATE BETTER 1:1S BY ASKING BETTER QUESTIONS

Great managers ask their direct reports great questions. Asking better, open‐ended questions is crucial to a successful one‐on‐one or any meeting between you and your reports.

Questions like:

• What does success look like?
• What are the obstacles?
• What are the options and next steps?
• What are your thoughts on this so far?

As the department lead, your job is to help your direct reports clarify their thinking, to understand the work they and their department are doing toward department goals and company goals, and to help them get unstuck.

GOAL SETTING AND OKRs

Create a rhythm around individual OKRs that roll up to group OKRs, as you do for your team and its department. Make sure your reports understand the prioritization and weight of goals. For instance, driving pipeline revenue and opportunities may be weighted as the most important goal, while a goal around implementing tools and processes contributes less to their overall goals and bonus compensation.

Communicate with your reports what you expect them to deliver, what success looks like, and what a big win would be. A note: goal setting should be aspirational. If you set goals that are too unrealistic or too easy, neither sets your team up for success. Set goals that push your team to deliver their best work, while rewarding truly outstanding outcomes. If your startup is open to not capping bonuses (it depends on your department and various other stages), giving your reports the chance to earn even more than 100% of their bonus can be highly motivating.

CARVE OUT TIME TO TALK CAREERS AND GIVE FEEDBACK

Schedule a 1:1 for each of your direct reports to talk about their goals and their career aspirations. You may make assumptions about what your reports care about that they don't share. It truly depends on them. For instance, I once asked one of my marketing reports what his vision was for his career, and he told me bluntly that he wanted his current role to be “his last W2” and be in business for himself after accomplishing his mission in his current role. I never would have known that, and if I'd assumed he'd wanted to become a CMO one day, I'd have managed him incorrectly. Never assume. Ask your reports regularly what their goals are and look for ways to help them meet those goals.

SMALL GESTURES ADD UP TO A CARING MANAGEMENT STYLE

Kindness and caring are under‐rated in leadership. If you pay attention to your reports, truly listen to them (stop multi‐tasking during your 1:1s!) and give them the gift of your undivided attention when you can, it'll profoundly impact their ability to be successful on your team. Listen to what they care about and ask them how they want to grow.

If a report of yours wants to learn a specific skill set outside their role, you could look into giving them stretch assignments or helping them tap into company learning and development resources to take a course. Sometimes, small gestures like letting the report know you believe in them in what they hope to accomplish can make the world of difference. Don't underestimate the power of believing in people on your team. You can be that person that helps your reports build their own journeys and you should let them lead the way while offering new ideas if they're open to them.

MEETINGS: HOW MANY DO YOU REALLY NEED TO BE IN?

Often, early‐stage startup leaders will be in too many meetings with their team and cross‐functional peers. While meetings are a crucial part of your role, at a point, you need to delegate and have your leaders take them on your behalf. You can always attend strategically or once every few meetings, but you can't be in every meeting all day. If you go through your calendar and find it filling up with many meetings (particularly cross‐functional ones without your peers), see if you can take yourself out and review the notes. This is great for many reasons, in that it truly empowers your reports and frees you up to do more strategic work.

IS THIS MEETING SET UP TO FAIL? HERE ARE WARNING SIGNS THIS WON'T BE A PRODUCTIVE MEETING

• No agenda.
• You're in attendance but neither contributing nor adding value.
• People aren't prepared prior if there are things to review together (particularly cross‐functional meetings; no one wants to wait while someone tries frantically to create reports on the fly).
• Misalignment between meeting goals and meeting actual. (Is it a meeting designed to get clarity on a topic and people are debating another topic? Focusing on what the meeting is supposed to do is helpful.)
• No clear action items after. (All meetings need some agenda items after so it's clear what's next and who is accountable. For instance, in a cross‐functional meeting between sales and marketing after a field marketing event, it should be clear what marketing will do to follow up with the attendees and no‐shows and how sales will follow up with their named accounts, etc.)

MANAGEMENT TIP: DON'T SEND “CAN WE TALK” MESSAGES TO YOUR TEAM

If you don't give context, a majority of the population will suffer a jolt of anxiety when receiving a vague message out of nowhere from their manager that simply asks “to talk.” No matter how secure a relationship is, this is scary to the human nervous system. Imagine receiving this from your CEO, or from your partner, or a random friend … particularly out of the blue. See? Nerve‐wracking. Our human brains are wired to detect threats in this sudden unknown.

Don't send ambiguous messages to your boss either if you can help it; it works both ways. In the absence of context, humans often assume the worst. Especially in our remote world, even a bit of context can put people at ease. If you have to schedule a last‐minute meeting, try to give context so your report doesn't assume the sky is falling.

BE EMPATHETIC TO WHAT PEOPLE ARE GOING THROUGH WHILE SETTING HEALTHY BOUNDARIES

Everyone going through the pandemic faced unprecedented stresses—some more than others. You never know what someone is going through. If someone slips on performance or an assignment or doesn't communicate, or a typical extrovert is unusually quiet, it could be something in their personal life that's throwing them off and don't jump to conclusions.

You also don't need to be your reports' therapist; it's a balance, but understand when you're feeling depleted and out of your depth. It's okay to say “I'm not the right person to help you through this, but I want to encourage you to get support with the resources our company offers and/or outside of work.”

You can set boundaries around where you can support. It's totally fine to listen and part of being a manager means finding out about people's personal lives (that's not a bad thing). Even if you are a licensed therapist, that's not your role as a startup leader; leave that to professionals to give people the advice, support, and care they need (and deserve).

Some things you can do other than provide “therapy:”

• What kind of support do you need? Do they need help in accessing the company's benefit policies around mental health and/or support in the area they're needing? Maybe they just want people to give them space. Others may want to process (and it's okay if you set a boundary around helping them find other outlets for that support.).
• Do you need to take some time off in accordance with our time off policy? Sometimes people are just burnt out and it can help when managers point them to take their PTO and not let it lapse. You'd be surprised how much can be solved by time to “unplug.”
• How can our team support you better? Sometimes people could use extra support at work around a project or campaign, say if they have a sick family member or something is going on that's distracting them for a short time. While in the long term this would need to be addressed, that's what teamwork is about: supporting each other and helping each other around difficult times and celebrating the wins together.

BUILD FEEDBACK INTO YOUR REGULAR COMMUNICATION AND PROCESSES

In Radical Candor, Kim Scott famously shares the danger of “ruinous empathy,” or being so empathetic and concerned about people's feelings that you fail to give them the honest, compassionate feedback they need to thrive. Often people can miss the feedback that something is awry unless it's given early and often. Make it a habit to carve out time in your 1:1's and team meetings to review progress against goals and share areas to work on. Also, be open to feedback from your direct reports to improve. It'll feel awkward, but it's worth it.

Retrospectives are a great tool for teams. Questions to explore in regular feedback:

• What is going well?
• What is not going well?
• What could we be doing differently?
• What are we going to start doing?
• What are we going to stop doing?
• What should we keep doing based on what we've just learned?

Pauses to truly reflect and learn make the difference.

BEWARE THE PITFALLS OF “SKIP LEVELS”

Katrin Grunwald, coach at The Globe Team, suggests being careful around “skip levels,” aka interactions with your managers' team members, and ensuring that you're not going around a manager to speak with their team members either. “Assuming good intent, you're disempowering your leaders if you're not letting them do the work of managing their own team,” says Grunwald.

It's great to schedule a regular biweekly or monthly 1:1 with your skip levels, and many organizations advocate for this to gain a better understanding of their worlds. It's also a chance to assess how your reports are performing and how their reports are doing. If you do need something from one of your direct report's reports, work with your direct report. The same rules apply if you need something from one of your peer's reports. While this is a startup environment and we're all collaborative, honor the reporting structures put in place at your organization in order to work most effectively and efficiently.

SOLVING CONFLICTS ON YOUR TEAM

Conflicts can fall into various categories. At the highest level, they're about work itself (tasks, etc.), then roles, behavior, values, personality profile, identity. Conflicts at the bottom (identity) are tricky. You may think you're talking about changing the air conditioning, but let's say you've read the study that women tend to prefer and need warmer office temperatures than men. For a woman on your team, your insistence on keeping the office cold becomes an identity and belonging issue. The point is, conflicts can happen at all levels, and resolve them by understanding the level.

ENSURING YOUR TEAM (INCLUDING YOU) TAKES ADEQUATE TIME OFF

Many startups these days offer “unlimited PTO.” This can be a benefit for many reasons, and also can trap people into feeling guilty about taking time off. While it's great that companies are starting to set “suggested minimums,” in reality, if you as a manager don't encourage and model taking time off, your team will struggle to do this. You want your team to take time off and rest; it's good for them, it's good for the overall team. The global pandemic blurred boundaries between the personal and professional, and made it even more crucial for people to invest in time off.

TAKE TIME TO REALLY UNPLUG YOURSELF TO SHOW YOUR TEAM THAT'S THE CULTURE

When you take off, it makes your team relax when they take off. It can be hard in our always‐on economy when there's never really a time that's truly convenient to be out of pocket, but you have to do it. Take time off from work, and you'll return better for it. Managers, team leaders, and individuals have to take responsibility for their own health and the health of their team. It's not just because it's good for you as an individual. It's truly the best thing for the output of the team.

CULTIVATE AS FLEXIBLE A WORK ENVIRONMENT AS POSSIBLE

Studies from LinkedIn show that as offices are opening up, many under‐represented folks are in a worse position than when they were able to work remotely during the pandemic (while dealing with a lot of other trauma and issues, of course). The reason for this is that many modern offices did not create healthy nor supportive environments for everyone. Women of color, in particular, found more discrimination and challenge in office environments that did not cater to their needs.²

From struggling to meet discriminatory dress codes to needing to “code switch,” under‐represented folks can struggle in homogeneous, open office work environments. Parents, people caring for family members, and other groups need flexibility around work hours and how work gets done.

Office environments can be very tricky for people of all backgrounds, particularly for those who studies show benefit from flexible work and flexible work environments. It's not just the commute people dislike. It's what happens in these physical spaces that can prioritize certain people's boundaries and needs over others, and cause some to have to “code switch” and turn off parts of themselves in order to make other people (read: the dominant group) comfortable. I've been in the startup world for more than a decade and have been caught in the crossfire of a nerf pellet, a rubber band, and various startup swag in physical offices at multiple companies. I've never once been hit by anything while working remotely.

We're all dealing with a lot, all the time, whether it's a global event or in our personal lives, in addition to stress at work. Try to be understanding of your people's personal needs and schedules and create a communication culture where people can voice if they need to move a meeting due to a personal obligation. People won't do it unless they have to. If you let people be the leaders of their own lives and schedules, they're more likely to be happier, healthier, and do their best work. But, even if it didn't make them overall more productive (it does), it's just the right thing to do.

EMBRACE FEELINGS WHILE ESTABLISHING HEALTHY BOUNDARIES AROUND HOW YOU DEAL WITH THEM

Feelings are information. Strong emotions can be normal in the startup world, and dealing with them in a healthy way is what differentiates a healthy culture from an unhealthy one. If you hide your feelings, know that your team will notice.

“Vulnerability matters because we're really good at picking up on fakeness, especially in our leaders,” says Liz Fosselien and Mollie West Duffy in their book No Hard Feelings: The Secret Power of Embracing Emotions at Work.³

Fosselien and West Duffy share the view that it's important to “be selectively vulnerable.” This is because, especially for under‐represented leaders, sharing too much can cause stress for reports, whereas not sharing at all can also cause friction, because people can tell you're hiding something.

Coach, investor, and operations leader Julie Penner recommends “red–yellow–green” check‐ins. Teams can talk about how they are doing in a color scheme, without necessarily divulging the ins and outs of how they are doing or “oversharing” details beyond their comfort. This makes it safe to share the context of how individuals are doing in real‐time so that teammates can take into account other factors that might affect the way someone is showing up. It's like a water gauge for how strong the current is underneath the ice.

DEFINING SUCCESS AND TRUE OWNERSHIP

Matt Harada, startup leader, and former startup CEO, drew a chart for me once: it had a large circle with many circles inside.

“As a leader, when everyone owns little pieces, you can see all of the gaps in between,” says Harada. “What you want is to move to a pie ownership model, where everyone on the team owns their slice, and there isn't any space in between. As a leader, that's what will enable you to scale.”

GET YOUR REPORTS TO THINK LIKE OWNERS

To the degree you're able to within your startup's culture, sharing context helps align people to perform at their best and helps them understand decisions. In your 1:1s and team meetings, share the context you have from all of your cross‐functional meetings and board‐level awareness (while being careful not to share things you're unable to).

A NAVY VETERAN SHARES THE CASE AGAINST COMMAND AND CONTROL LEADERSHIP

Dave Cass, Head of Partner Development at Techstars, lecturer at the University of Colorado Boulder—Leeds, and former founder of Uvize, a Techstars company that supports veterans, began his leadership journey while in the Navy. In that environment, leadership could literally mean the difference between life and death. An incorrect move could cost people their lives. That's a lot more pressure than most startup leaders face, but it set the stage for Cass' journey to be a lifelong student, mentor, and mentee of leadership.

Cass' tenure as an officer in the military helped him see that leadership had little to do with title. Title may define authority, but it has almost nothing to do with respect.

Cass says that the “command and control” leadership style, of telling your reports what to do and giving them orders, isn't even best practice in the military, counter to what some may assume.

“In the military, just giving orders is the lowest form of leadership. To lead well, you need to earn people's respect,” says Cass. “When you show respect, regardless of rank, other people respect you.”

Cass says when he's promoting leaders on his teams, he looks for those who are respected by their peers, as well as those who work below them on the hierarchy.

“When peers respect someone, you know, it truly is earned and it's genuine,” says Cass.

HAVE YOUR TEAM'S BACK

We've all worked for leaders who were quick to throw us and our work under the bus when things weren't going well, and who took full credit for our work when things were succeeding. Cass says he coaches his students and teams at Techstars not to do this.

“I see a lot of people with the self‐cover instinct,” says Cass. “Could you imagine a CEO saying ‘that's not my problem?’ Leaders take ownership and don't blame others for what's happening around them.”

LET YOUR TEAM KNOW IT'S SAFE TO MAKE MISTAKES, AS LONG AS THEY LEARN FROM THEM

The psychological safety to make mistakes and learn from them is crucial to a healthy team environment. When you make a mistake, let your team know, and also let them know how you plan to learn from it and not make it again. If you cover up your mistakes, your team will learn that this is the way to do things, even if you tell them not to. Cass says his business students most often do this, and he has to help them see that “spilling the milk” isn't the problem, it's an attempt to cover it up.

“You spilled that milk. Metaphorically just own it and clean it up. I only get upset if you lie about it on my team,” says Cass.

TEACH YOUR TEAM TO PROBLEM‐SOLVE AND LET THEM DO THINGS IN DIFFERENT WAYS THAN YOU WOULD

Agile coach Therese Pocrnick teaches her leaders to help people embrace problem‐solving. She says that this is particularly helpful with “mundane” work that can be less glamorous.

“Problem‐solving is something that a lot of people can get behind, and if you layer on things like emphasizing lifelong learning, creating psychological safety for them to fail and learn, and trying things to run experiments. Those are the things that I think will keep people engaged until the next exciting thing comes along,” says Pocrnick.

Pocrnick suggests that leaders communicate intent and decentralize the decision‐making of the “how” of the work.

“I can't be married to how somebody does things. Just because they don't do it my way doesn't mean that it won't get us to the right conclusion,” says Pocrnick.

IF YOU'RE GOING TO BE A MANAGER, DECIDE TO CARE ABOUT PEOPLE PROBLEMS

At one point in her career, Pocrnick had to decide if she wanted to be an individual contributor or people manager.

“I was deciding whether to be a principal engineer or an architect. As a software engineer, I made a choice that I liked solving people's problems,” says Pocrnick.

Pocrnick's advice to new managers on her teams who aren't sure how to lead is to “put people first.”

“If you put people first, chances are you'll be directionally correct,” says Pocrnick.

INVEST IN LEARNING HOW TO BECOME A MORE INCLUSIVE LEADER

Many rising leaders are so focused on making a good impression or delivering business outcomes, the idea of creating an inclusive team can feel like an afterthought, especially if you're a member of a privileged group. No matter your privilege, we all have biases, and building a more inclusive and diverse team requires effort.

According to diversity and inclusion expert Jennifer Brown, “when you are the one with the power, you have a responsibility to think three steps ahead of the comfort of others, regardless of your own identity.”⁴ Brown suggests that to be inclusive leaders, we all have to take actions that make our teams safer and more inclusive of difference.

HAVE FUN AS A TEAM!

Build fun into your team's success plan. From icebreakers to virtual team building days, you can consciously cultivate an environment where people on your team get to know one another and have fun together to help them become more cohesive.

The fun doesn't have to be elaborate to bring your team together. Try things like:

• A group improv class.
• Virtual icebreaker activities to find out fun facts about each other.
• Playing games together (in real life or online).
• Art activities.
• Making “fun” chat channels where people can geek out on music they like, films they've seen, or favorite recipes.

PRACTICE REPAIR AND BUILD IT INTO YOUR TEAM RHYTHM

Rupture and repair are important for secure relationships. Think about a time you or someone else made a mistake and then made amends in a personal relationship; hopefully, after, your bond was stronger. The process is the same for secure teams. On your team, figure out how you're going to do retrospectives and repair and improve when things go awry. You don't need to be perfect, but you need to ensure that, when things go wrong, everyone feels heard and you're able to grow from your mistakes.

Pocrnick tells people, her teams, and the leaders she coaches that “Sometimes you have to say, ‘Sorry, I didn't show up as my best self today, or at that moment,’ and then focus on asking the question of what did we learn from this?”

DO RETROSPECTIVES TO ENSURE THE TEAM SHARES THEIR VOICES AND GROWS WISER

If someone on your team makes a mistake (including you), if a launch doesn't go well, if a feature bombs, if a cross‐functional meeting turns heated—these things are all okay on a team that practices retrospectives and integrates insights into making the organization perform better.

“After actions” or retrospectives identify what's happened, get everyone involved to weigh in on their experiences, and then work together to figure out how to improve going forward. If you're the one responsible for why things have gone awry, you should own up to it, but the focus here isn't on individual blame‚ it's on the entire organization taking responsibility.

RETROSPECTIVE PROCESS (START–STOP–CONTINUE)

Time: 1–2 hours (team)

Have a member of the team, ideally the person directly responsible for the initiative, launch, or project, run the meeting and take notes in a shared document or wiki for the team to contribute to. In addition to having people potentially contribute asynchronously, do this meeting “in real‐time” to repair the team dynamic and talk through the topics together.

Here's a sample retrospective agenda. Ask all team members to contribute.

• What worked well? (Continue)
• What didn't work well? (Stop)
• What do we want to do differently next time? (Start)
• Are there unresolved topics, requests, or feelings we need to address as a team? (I add this to ensure everyone's voice is heard and to re‐establish psychological safety as a team after a rupture. This may require another meeting.)

After a recent retrospective on a topic that was sensitive to many on the team, several team members shared with me how grateful they were for the process. They seemed lighter and happier after discussing what was on their minds. Doing the retro can seem daunting, but not doing it creates a buildup of unresolved tension in your organization. Let your team make the most of learning and give them a chance to correct and grow, and you'll go far to set the stage for a high‐performing team.