Coaching for startup Chiefs of Staff
"A total shift in the way I show up."
I coach Chiefs of Staff inside VC backed, pre-Series B startups who want to embrace the incredible leadership opportunity the role offers, scale as the company scales, and position themselves for the next leadership role after the COS tour ends.
I've been an exec for 15 years inside fast growing companies, including as Chief of Staff for Yelp Restaurants for 2 years, and as a VC-backed Ops Exec from Seed through Series B for 5 years. I know what it feels like to have hard conversations as you manage peers for the first time (all the interpersonal traps), how to hire, fire, and run run layoffs (I once had to lay off my own roommate), and how to scale yourself as the company scales (it's an inside job).
If you're curious, book some time with me. We'll meet over video, you'll share what's going on, I'll answer questions, and we'll vibe check to see if it feels like a good match. Rather email questions first? Hit me up at shaina.e.anderson@gmail.com.
Who I work with
You're a Chief of Staff for a fast growing pre-Series B Startup, and you want to embrace the incredible leadership opportunity the role offers, scale as the company scales, and position themselves for the next leadership role after the COS tour ends.
Other than wanting support in reaching your goals, most people start coaching because they feel stuck, blocked, or frustrated with part of their job — or part of how they're showing up.
Below is a sampling of what I regularly hear from people I coach. If this sounds like you, we may be a good fit:
- This startup is a mess. I was promised growth and development, but I'm actually drowning.
- I’ve always wanted to sit at the exec table, but that I'm here, I'm not totally sure what my role is.
- It's really hard to connect with my CEO.
- I want to develop my own leadership style, but I feel like a total imposter.
- My team's growing, and the things I used to own are now being done by a new VP. Feels really weird.
- I'm supposed to lead companywide planning / build a financial forecast / define our hiring plan / fill-in-project-here, and the internet is filled with a bunch of noise. Where do I start?
- I'm scared to be a generalist. It felt really good to be an expert in my old role, and I'm not unsure what I'm actually great at. Is this a real career path?
"I was holding onto a lot of angst, anxiety, fear, and self-doubt. Now, there's a big change in how I'm showing up for my team, my organization, and most importantly myself. I'm more confident, transparent, vulnerable, and thoughtful because of our work."
— Megan, Chief of Staff at At Present
What we'll do
There's two parts to the work we'll do together.
- Our work starts with a 12 week track on leadership, mindfulness, and self reflection. You'll complete reading and writing work each week, and we'll use the lessons from your homework live together, applying what you worked on to whatever challenges you're facing that week. The reading pulls from a large variety of sources to help you connect the dots: from neurolinguistic studies, to work from the world's great writers, to coursework from Stanford Business School.
- After the 12 weeks, we'll continue to meet weekly, but the agenda becomes loose and open, and there's no more required work — you'll bring whatever challenges you're facing, and we'll work through them together.
Starting with the structured 12 weeks is a requirement to working with me. Beyond that, there's no minimum or maximum time that you need to meet, but most people work with me for an average of 18 months.
There's no hiding it: this work takes effort. Internal, emotional effort, and an ask of your time. Each week, we'll meet live for 50 minutes week, and, during the first 12 weeks, you'll need to set aside at least 1 hour for reading and writing homework. But I promise it's worth it effort — People I work with share that this is meaningful, life changing work, both in and out of their COS role.
Pricing
$175 for each weekly 50 minute session. Most people use professional development benefits, or ask their company to support the cost. I'll give you a template to use if you need help making the budget ask.
What you get:
- 50 minute 1:1 weekly sessions with me on video call
- To start, a 12 week structured program on leadership, mindfulness, and self reflection, that includes journaling prompts and reading pulled from neurolinguistic studies, the world's greatest writers, and coursework from Stanford Business School alike.
- After the 12 weeks, ongoing, unstructured weekly sessions.
- Access to my COS Resource Library: I've brought together the templates, articles, books, interviews, videos and more that I've used over the years to grow VC backed start. It's available to you at any time, and we'll reference it regularly during our work.
"Shaina's positivity and warm approach to coaching makes working with her feel like an actually safe place where you can really explore."
My path to coaching
I started with my first coach for the same reasons many people do: I was stuck, blocked, and frustrated with how I was showing up in my life. I was sick of feeling that way, but didn’t know how to move through it.
Professionally, I was in the midst of launching 4 new markets for VC-backed startup Chewse, and working through wild insecurity and imposter syndrome as we were scaling. Chewse was my first high growth startup, and I joined at the Seed Stage: I was hired as a young leader to lead our even younger team. Over the years, I was regularly promoted, and given new teams to build, but didn’t have the tools to show up as my whole, authentic self. Inside, I was desperate to succeed and trying my hardest. Outside, I could come across as forceful and dismissive. Oh, and did I mention I was also newly out of a bad, longterm relationship? Woof.
Over the course of a year, my coach cracked me wide open. He helped me tap into new vulnerability and openness through radical self inquiry. It wasn’t magic — it was neuroscience. With journaling, meditation, and his help, I learned to listen to my body for cues, and how to quiet the noise so my own truth could emerge. I softened. And I saw the impact ripple through my team at work and my relationships outside of work.
"Shaina's empathy is unmatched and her ability to relate made talking about certain challenges and insecurities much easier."
— Megan, Chief of Staff at At Present
Why I coach Chiefs of Staff
Work with that first coach of mine changed my life. It not only changed the kind of leader I am, but it fundamentally changed how I showed up for myself and others.
To borrow a phrase from Reboot, I think the practice of radical self inquiry is the way to create the brilliant leaders our world so desperately needs: Self inquiry creates better humans, and better humans make better leaders.
The Chief of Staff role is a particularly primed for this. People in the role are often the rising, high potential, future leaders for the company, but typically land in their very first leadership seat as they accept the role. You were the best at what you did before, which is why you were promoted, but now, everything is new: you have to guide leaders who are senior to you, hold this weird, flashy title without directly managing anyone, and take on a huge variety of work you've never done before. It's easy to harden, isolate, or disconnect. Instead, I help leaders go deep.
Chad Herst, my first coach, frames it best. The following is pulled from his writing:
We know that if leaders keep marching to the tune that led us here, we’re in trouble. The Type A approach to living and working is proving to be unsustainable. US business spends an average of $500 billion a year on stress-related illness. Caffeine and sugar are fueling the relentless drive for results. The focus is on short-term gains rather than long-term sustainability.
Burning the candle at both ends, 24/7/365 availability, faking it till we make it, fear of missing out—it’s killing us. On an individual level, our health and sense of well-being are suffering. On a macro level, we are depleting and polluting the planet. We need leaders in all arenas—business, media, the public sector, and NGOs—who can help us forge a better future. In the past, we’ve seen a handful of bright lights in each generation. If we are going to be able to tackle the significant problems ahead of us, we need an entire generation of brilliant leaders.
What makes a brilliant leader? The prevailing image is of a charismatic force of personality, will, and intellect who stands alone and is fueled by an innate and eternal fountain of energy. People follow because one can’t help but be inspired by someone so strong, visionary and infallible. Do you know any leaders like that? Because I don’t. This kind of leader is a fiction and a dangerous one at that because it promotes disconnection.
A leader’s ability to connect is more important than standing alone, seeing the future or being heroic. Charisma only takes you so far, and people don’t trust perfection. Leaders need to be fully human to be able to connect meaningfully with others. This is no easy task, and there are few good models for how to go about it.
Brilliant leaders, regardless of rank or title, serve as a light that attracts, illuminates and brings out the best in others. They bring energy, clarity, meaning, and trust in their endeavors.
Becoming this kind of leader is an inside job, and it’s a full-bodied experience. You need to connect with your own body and mind before you can connect with others. It starts with you.