How to Thrive in a New Role and Overcome Self-Doubt

Announcing our Newest Grand Quest ✨

Today's post is written by Jeanette Jordan, Lead Facilitator for our newest Grand Quest - Thriving in a New Role ✨

Even though I have been working since I was 15 years old and have had almost 2 dozen jobs, I still get nervous when taking on a new role and assignment. 

For me, imposter syndrome – doubting myself or feeling like a fraud – is something I battle with on a regular basis, especially as I venture into the unknown. As I am about to start a new job, which I tend to do every few years, I often worry about if I have the knowledge, skills and experience to succeed in my new role. I wonder how well I will get along with my new colleagues, I worry the culture may not be as good as it seems and I obsessively think about how I can make an impact quickly to establish my credibility.

Though it can be scary to start a new job, my amazing colleague and friend Anita Hossain asked me a poignant question, as I was considering a career transition earlier this year,

“If it doesn’t scare you, is it big enough?” 

This question reminded me that growth and learning happen beyond your comfort zone. ​​

The Learning Zone is where you have the opportunity to stretch yourself and develop new skills. If done correctly, learning something new can be a fun adventure where you allow yourself to be curious, creative and take new risks. The goal is to challenge yourself in a positive and healthy way, without pushing you over the edge, into the panic zone. 😱

After decades of managing, coaching and navigating my own job changes, I want to share a few tips to keep you out of the panic zone:

  • Build a support team. It’s so important when you are feeling uncomfortable to have support. Your support team may consist of mentors, friends or old colleagues who you feel comfortable asking “dumb” questions and who can remind you of all the transferrable skills you bring to the table. One of the things I love about The Grand is we design all of our group coaching cohorts to be a safe and supportive environment for our community members.

  • Create a routine. When there are a lot of factors out of your control, creating a routine can help reduce stress and keep you focused. Simple routines like establishing regular 1:1 meetings, dedicating time to clearing your inbox, creating to-do lists and setting weekly goals can help stay positive and productive as you get settled in a new role. At The Grand, we use the S.M.A.R.T. goal framework to help our members set realistic and timely goals to support their transitions. This is a tangible way to help them focus on a few things they’d like to achieve without getting overwhelmed by trying to take on everything at once.

  • Ask a lot of questions. One of the benefits of being new is that people do not expect you to have all of the answers. This is a great opportunity to get to know new people, understanding their roles and responsibilities, and learn how your job fits into the broader organization. Don’t skip an opportunity to ask questions and gain a real understanding of how things work early on in your job change. One of the cornerstones of each group coaching program, which we call Quest, is that we teach and practice empathic listening and asking open and honest questions. These frameworks will help you understand another person's experience and explore new possibilities and outcomes as you start to problem solve challenges you face.

  • Celebrate your wins. Make time on a regular basis to reflect on what you’ve accomplished. I recommend creating a list weekly or bi-weekly of at least 3-5 wins. Recognizing even small wins can help keep you motivated and build your confidence as you establish yourself in a new role or company. One of our rituals at The Grand is to close every cohort by reflecting on the progress and the growth that each member made during their Quest.  We share appreciations for everyone who contributed their unique talents and perspectives to the community. This exercise is one that can be used far beyond your Quest to help you both take stock and celebrate your wins.

As I reflect on some of my proudest accomplishments during my career, I realize they would not have happened without me taking a risk and trying something new. Early on in my tech career, I had a rare opportunity to work at Millennial Media, a mobile advertising startup, when they went public on the NYSE and to participate in that process by contributing to the S-1 filing. As exciting as the moment was, and it’s a memory I will always cherish, the reality is I only had that experience because I was willing to accept a loosely defined role, at a company I had never heard of before.

More recently, after almost a decade of working in Product Marketing, I was asked to move into a newly created role as the Head of Corporate Marketing and rebrand the company AdRoll Inc. to NextRoll Inc. While I initially had no idea what I was doing or where to start, after months of research, learning and building a support system, I was able to define both my new role and a strategy for rebranding the organization. Though I was terrified at the outset, successfully launching a global rebrand (with a small team and scant budget) is truly one of my proudest accomplishments, mainly because it helped push past the limiting beliefs I had about myself.  

Often imposter syndrome is rooted in our fear of failure and/or rejections and the lessons I learned about overcoming it can be summarized by my favorite Adam Grant quote:

The most meaningful way to succeed is to help others succeed.”

If you are able to shift the focus from your own fear of failure to the unique gifts you can contribute to your team and organization, it will feel a lot less scary to venture into something new.

Our Newest Quest: Thriving In a New Role

Coaching and peer support groups have been key to my success throughout my career. They have given me perspective, support and a safe space to workshop my challenges. For that reason, I am excited to launch a new Quest for The Grand called Thriving in a New Role. This Quest is designed for our members to learn and understand the stages of team development, how to build trust and rapport, and how to effectively communicate with different personality types. The goal is to give you, our community members, a safe environment to build upon your strengths and gain confidence as you navigate a new role and/or team.  

If you’ve recently joined a new company or started a new role within your company, and you are looking for additional support, consider joining The Grand.

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We also love drawing on the collective knowledge and diverse experience of our community members, so we want to hear from you! What are your best tip and tricks for overcoming new job jitters? Please reply to this tweet and let us know.



Returning to Work After Becoming a Parent

My 6 month reflection on being a mother

"Constantly conflicted"

Those were the words that one mom at The Grand shared when I asked a group of parents to choose one word that described how they feel as a working parent.

It resonated deeply.

Yesterday was my daughter's 6 month birthday. This half-year has been filled with some of my deepest moments of joy and also my most challenging moments as well. Becoming a mother has been the greatest transition of my life and this week I learned that there is a term for it: matrescence.

Like adolescence, matrescence is a hard and sometimes awkward transitionary period of becoming a mother. Aurélie Athan, a reproductive psychologist at Columbia University, describes it as:

“A holistic change in multiple domains of your life. You're going to feel it perhaps bodily, psychologically. You're going to feel it with your peer groups. You're going to feel it at your job. You're going to feel it in terms of the big philosophical questions.”

The hardest part about this transition is adapting to all of these changes while maintaining a sense of self.

There was a moment when I found out that I was pregnant and I wondered if I'd be able to be a mom and a founder at the same time. I questioned my ability to lead and stay focused while bringing a tiny human into the world. I wondered if I’d be good enough or if I’d let both my work side and my family side down. I was scared and unsure about it all.

Then through conversations with my family, I realized that I shouldn’t limit myself and who I am at the core, just because my identity was going to shift. In fact, I tried to think of it as my identity and sense of self both expanding. It was going to be hard, but I was up for the challenge.

And it has been challenging. There are so many sleepless nights, anxiety around if I’m making the right parenting decisions, feelings of wanting to be in two places at once, guilt from not being able to be there for my colleagues, friends, and family the way I want to be. But it’s also been so meaningful and allowed me to be the fullest version of myself.

Though I still wrestle with feelings of being constantly conflicted, I also learned some things along the way that help me feel a little lighter:

  • Take the risk. I now realize that it's a greater risk to not take the risk, to not change and grow. Yes, though it's hard to do both (in my case, be a founder and a mother), I've noticed that time spent away from my daughter to do the thing that aligns with my purpose allows me to bring more joy and energy when I'm with her.

  • Be flexible. You never know how you're going to feel when you become a parent until you’ve gone through the transition. So yes, make all the plans, but be flexible and know that those plans may change. And give your family, friends, and co-workers a heads up on being flexible too.

  • Enjoy the little moments. I love this Japanese saying, mono no aware that translates to "the ahhness of things" and speaks to the awareness of impermanence. It helps me realize that everything in life is fleeting and encourages me to create a deeper connection with it as a result. So in the middle of the night when I'm exhausted and trying to rock my baby girl to sleep, I try to remember that she will only fit in the nook of my arm for so long and I squeeze her just a little tighter.

  • Find a peer group. The more we get out of our heads and share our journeys with one another, the less alone this transition feels. I'm fortunate to have friends and family that have been there before, and a peer group through The Grand.

At the end of our session with moms at The Grand, the tone shifted. We listened intently to each other’s stories and we talked about how being a mom can be a revolutionary game-changing experience, that it's awe-inspiring, and that there is incredible power and energy in it. And most importantly, we walked away knowing that we are not alone and that we have a peer group that we can turn to when we need it.

If you're a parent who wants to learn more about our future quest, Returning to Work After Becoming a Parent, please let us know by joining our waitlist. Both moms and dads are welcome.

Join the Waitlist

I'd also love to hear your matrescence and patrescence stories, so please reply and tell me what you've learned throughout your journey.



It has never felt more lonely to be

A call for more support systems

Yesterday I found a bird nest with a single pearl colored egg above my power box. I paused, and pictured a mama bird foraging our hillside to gather a bundle of twigs to create a support structure for her baby bird to develop and grow. It made me smile, and think of Invitation, one my favorite Mary Oliver poems.

Later on, I read a research report by January Ventures, and this chart stopped me in my tracks.

“More money than ever is flowing into startups, yet our data revealed that it has never felt more lonely to be a founder, especially for founders who don't fit the traditional mold, such as Black founders and older founders.”

Loneliness is real — the majority of founders do not feel supported, and I’d argue the same is true for the majority of working professionals.

Simply stated, it has never felt more lonely to be.

Support structures are critical. An egg needs a support structure to enable it to hatch and become a bird. As humans, we need to feel supported by our community in order to achieve our personal and professional ambitions.

Loneliness isn’t just a sad feeling, it results in greater disparity. Women-founded teams received nearly 30% less funding in 2020 than they did in 2019. (Crunchbase) Why are we regressing? My hunch? Because it has never felt more lonely to be a female founder.

So, what do we do?

Keep investing in founders and people outside of the Bay Area, who are women, who are Black, who are over 50, but also create support structures.

What types of support structures?

To find the answers to that, I have a creative suggestion inspired by Candy Chang.

  1. Put up a poster board in your common area, or an anonymous Google doc with rows that says,

    “It has never felt more lonely to be __________.”

  2. Observe what your team writes.

  3. Share the results with your team publicly.

  4. Identify the themes that emerge.

  5. Form small discussion groups around the most prevalent themes.

I guarantee you supportive ideas will emerge.

At The Grand, we recognize it’s never felt more lonely to be making a career change or a first-time parent, or a new manager. Feel free to browse our topics or add your own. I’d love to hear how we can be your support system.

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What Giannis Antetokounmpo taught me about leadership

Two things that I never thought would happen:

  1. I'd move back to my hometown Milwaukee, Wisconsin

  2. The Bucks would win the NBA Championship

This past year, against all odds, both of these things came true. And last Tuesday, after The Bucks won Game 6 where Giannis scored a record-high of 50 points, the energy in Milwaukee was palpable. It felt good to be back to our Midwestern roots.

By watching The Bucks through the years, and in particular this season, one thing became very evident: Giannis Antetokounmpo is a servant leader that we can all learn from.

Robert K. Greenleaf coined the term and defines a servant leader as someone who focuses primarily on the growth and well-being of people and the communities to which they belong. They share power, put the needs of others first, and help people develop and perform as highly as possible.

How he served his family

Right after Giannis won the championship, he found a corner of the stadium, took a seat and was brought to tears. When asked what was going through his mind,

"The whole journey," he said. "In order for me to be in this position, how much my parents sacrificed. I saw that every day."

As Nigerian immigrants living in Greece, his parents did whatever they could to put food on the table. When they were growing up, Giannis saw how much his parents struggled and wanted to find ways to serve the family. That's how he ultimately started playing basketball — as a way to potentially get them out of their daily challenges with poverty. There were days when he didn’t have enough food and he still went to basketball practice on an empty stomach. Oftentimes, he slept at the gym, to make it in time for the two-a-day practices. 

He was the lottery ticket for Milwaukee when they drafted him in 2013 – a skinny, tall, 18-year-old from Greece with raw talent. No one knew if he would actually grow into the two-time MVP that he is today. Now, whenever he talks about his journey, he says that he owes it to his mom, his dad, his brothers, and his partner.

How he served his team

Over the past 8 years, even as the best player on the team, his work ethic is unparalleled. After games, he would go back and practice for hours. Like his teammate, Pat Connaughton noted,

"He works as if he's a second-round role player, but his talent is that of an MVP."

He served his team by being a bar-raiser helping build the team culture of working hard together. He also did it in a way that was human first – by building relationships and friendships with everyone on the team and inspiring them to work harder.

How he served his city

One of the most profound moments after Giannis won Game 6 was when he said "we did it, we're champions, my city is a champion". This was an indication of how loyal he is and how he serves his city. In December 2020, he signed a 5-year supermax extension with the Milwaukee Bucks, knowing that he could have transferred to a more prominent team that's won a championship title before. This was going to be the hard way, but he stayed resilient. As he said, "there was a job that had to be finished" and last week he saw it through and then some.

Giannis is the ultimate servant leader, existing to serve his family, his team, his city, his country. And doing so all while being himself - a humble, bright-eyed, silly, down-to-earth person.

This interview really sums it all up. So much wisdom.

When you focus on your past, that's ego.

When you focus on your future, that's pride.

I try to focus on the present, that's humility.

Servant leadership is just one style of leadership that we talk about at The Grand. And we acknowledge that with all leadership styles, there are pros and cons:

  • The pro is that servant leadership helps create happier, more effective, and productive teams by making sure everyone on the team is looked after.

  • The con is that as a servant leader, it’s challenging to constantly put your needs on the back burner; you need to focus on self-care too.

Come explore yourself and your leadership style with The Grand.

Explore The Grand Experience

And feel free to drop me a line and tell me about the leaders you admire.



When The Golden Rule Doesn't Apply

How to adapt our communication styles to meet others' preferred styles

I wrote a post about feedback last month that sparked some spicy 🌶 discussion on Twitter.

Some folks replied saying they actually dislike tactful, long-winded feedback because it can be too obtuse, and prefer direct, to-the-point feedback.

Great! You’ve done the hard work of identifying your preferred communication style. While it’s important to know your preferred communication style, you can’t assume your default working style applies universally to the other members of your team.

One of the fallacies new managers often make is they assume The Golden Rule applies to all scenarios. They ask themselves, “How would I like to be managed?” or “How would I like to receive feedback?”, and then they communicate using their default style.

Being an effective leader is all about learning to how to influence. To influence, we need to understand how others prefer to be communicated and worked with, and adapt our communication styles to meet others' preferred styles. This enables us to build stronger partnerships and resolve tensions.

My co-founder Anita wrote a great post about DISC recently, check it out and identify your team members’ DISC type.

After you’ve identified if they’re Dominance, Influence, Steadiness, or Compliance then use this cheat sheet in conjunction with The Grand’s Feedback Tool for communicating with them.

Check Out The Grand’s Feedback Method

  • If they’re a D — Keep the Situation and Behavior short and to the point. Get to the Impact ASAP.

  • If they’re an I — Be sure to invite them to brainstorm with you when it comes to the Opportunity.

  • If they’re an S — Provide a full picture when describing the Situation, and make sure to deliver the feedback in a context where the recipient feels psychologically safe.

  • If they’re a C — Share specific details and examples when it comes to the Behavior. When discussing the Opportunity present 2-3 options they can respond to.

I hope this cheat sheet helps you communicate and influence more effectively. If you use it, let me how it goes!



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