Chief of Staff Stories: Teresa Basich

Formerly of Microsoft, Autodesk, Aetna, & more + community updates

Greetings from the second floor of Jones coffee in South Pasadena, where I’m about to hop over to the Thursday Farmers Market and snag all my vegetables and green juice for the next week. Spring in SoCal is always a dream! 🌸

If you’re ever in East LA / Pasadena, please let me know and I’d love to get coffee with you! (Always looking for an excuse to go to Serj’s new coffee shop tbh)

Announcements

1. Nova

   1. I get a lot of DMs asking how to level up to be a CoS, and I am once again recommending the Nova Chief of Staff certification — I’m biased because I’ve seen a lot of solid graduates come out of the program, created a module on market analysis / updates, and have seen the curriculum. It’s solid.

      • Because I love you and Maggie, CEO of Nova/friend of YCoS, rocks, Nova gives $100 to YCoS subscribers using this link.

      

      2. YCoS Community

      1. We’re working through applications for the YCoS Community and will soon close off the applications for the Founding Membership before we increase prices. You can find the application here.

         • Here’s what we’ve done the past 2 weeks: writing circles, coworking, vent sessions, workshops on Adaptive Leadership (AKA Delegate or Die) from our own Sean, Project Managing your Principal (me), and Mental Fitness from the MIT-trained folks at MYNDY. We’re also gearing up to do some SQL courses. It’s an honor to learn alongside you all.

Chief of Staff Stories 📖

First, welcome to the new series: Chief of Staff stories, where I interview Chiefs past and present.

Being a Chief can be very taxing, lonely, and rewarding work, so I hope these stories help you feel more connected and in solidarity with those also in the arena.

About Today’s Chief: Teresa

Today’s post features an interview with Teresa Basich. Teresa’s a powerhouse OG Chief of Staff – she’s one of those rare leaders that combines both data-driven leadership with a magical knack of deeply understanding people.

Teresa’s resume is a storied and impressive one: her previous companies include Microsoft, Autodesk, Aetna, and Radian6 (acquired by Salesforce) – her career focused on marketing and community strategy before switching to a Chief of Staff role, the first of which saw her supporting her leader and company through an acquisition, merger, and global pandemic, but what makes her exceptional is her self-awareness and passion for values-based leadership.

She now runs her own consultancy doing fractional Chief of Staff work with small business leaders, one of whom is Carrie Melissa Jones, founder of The CMJ Group and owner of the CMJ Community, where I’m a member and how we originally met! She’s also an active member of the Your Chief of Staff community.

They say great art leaves you with more questions than answers, and this conversation made me challenge assumptions, think about the role and the future, and the high rate of burnout Chiefs are all feeling.

Let’s get started!

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Chief of Staff Stories: Teresa Basich

Elise: Tell me your story. You obviously have a lot of really interesting experiences, so walk me through it!

Teresa: I was a vocal performance major in college. For a short period of time, I was going to be a professional singer, then I lost my voice and had to switch majors and so went a totally different direction. I went into political science.

I got out of school, but didn't want to go to law school, the natural next step. So I became a writer in a trade publication company. I did that for a handful of years and then started transitioning into marketing. and then the recession hit, the 2009 recession. I was working in a commercial real estate brokerage firm, so you can imagine that they were hit really hard by the recession. I was laid off and had to kind of reconfigure the way that I was thinking about my career and networking and finding my next job.

I got into the social media / community space and basically got my job via Twitter. I became a community manager & content marketer at the time for a platform company called Radian6 (acquired by Salesforce) – they were a big social media measurement platform.

I lived in that world for quite a while in both the content world and in community management + community strategy, and I ended up at Microsoft doing big content work for them. I oversaw all of the blogs related to their cloud products at the time, and at that point, I was starting to think about what's next.

I was getting more and more curious just around business processes – how all the cogs in the background of a business work. I started exploring that, and then I got an opportunity to shift over to an agency that supported Microsoft and support their CEO.

It was kind of this long game of stepping into a Chief of Staff role. I took on a lightweight marketing role for my first couple months, then I took the Chief of Staff role.

Six weeks after I took the role, we were acquired. I oversaw the communications and run-of-show for announcement day both internally and externally. Two weeks after that, COVID hit and everything shut down. And it was my first CoS role, with a leader who had never had a Chief of Staff either.

Elise: That’s like, three times hard mode.

Teresa: Yeah, definitely hard mode. And with a leadership team that hadn't really experienced working with a Chief of Staff either.

We had to go through a merger and acquisition and then go through the global pandemic. So it was a lot.

I mean, I spent time asking myself: Do I really have the chops to do this Chief of Staff thing longer term?

I've only been doing it for a handful of years, but I really got run through the mill on my first go. So, I was like, we're just going to give it a shot. I did that for about two years. After an additional merger and seeing upcoming leadership changes, I decided to just take some time off and really reset around what I wanted.

Predictably, I think our role can be really heavy. We carry a lot with us and it can burn us out pretty quickly. And so I was like, I don't want to do this again in this capacity. I don't want to burn myself out this way. And I don't think that it's reasonable for this type of role to continue operating in this capacity where we burn ourselves to the ground in service of leaders in our businesses. It just isn't viable long term.

So, it took me a while, but I decided to start my own fractional business, and I positioned it around helping leaders really find more time and space in their days to do deeper strategic thinking.

My platform is now putting in place decision frameworks that allow leaders to really make different decisions around how they spend their time and prioritize the way they're thinking about their business. We can't be in all the meetings! We can't work all of the hours! And so, how do we get to a values-based decision framework that allows leaders to really do their best work? And hopefully find time back in their days to be whole humans.

I'm now working with small businesses in this capacity while still doing some supplementary bigger kind of business management, traditional business management work with larger tech organizations.

Elise: Your background is really interesting to me because you have the writer's background, more analytical-type thinking, which is opposite from many consultant / math types looking to get into the Chief of Staff role and then later honing their writing.

I’m curious, how has that affected your career in becoming and then being a Chief of Staff? Because there are so many people wanting to make that jump, but they’re thinking, I’m not a consultant / MBA-type. How am I right for this?

Teresa: We might not show it to everyone, but we're all in our own brains. All of it shapes every little thing that we do, right? Writing for me was always a way to process and make sense of what was in my head and how I was working through things, and it felt like a very natural part of it.

I have a really strong communications background and comms is where I tend to do best – in the middle of a merger and acquisition, in the middle of a pandemic, I wrote my leader's communications in partnership with her. She would tell me what worked and what didn't, and would review and lightly edit, but it was mostly me writing for her – trying to infuse the stuff that I felt made the most sense.

I think when we look at people trying to come into the role now, I just think it's going to be a really hard wall that they're going to run into.

I worry about the role itself and what people think of it. I don't want the role to erode in the mindset of people. It breaks my heart to think that the wrong types of people may walk into this and…and make the rest of us look like assholes.

I worry about the role itself and what people think of it. I don't want the role to erode in the mindset of people. It breaks my heart to think that the wrong types of people may walk into this…and make the rest of us look like assholes.

Elise: It is clear the demarcation between people who have been in the role versus people who are looking into it for status.

Teresa: Yeah. It's stark. I just don't think you can know what you're getting into until you're in it.

I'm so glad that you have created this community and we're starting to talk through things, because I am like, did all of us have that moment when we got started in the Chief of Staff role where we were like, what did I just get myself into? What is this?

Elise: That’s so real.

Teresa: So many times, I said, I don't know if this is it for me. It took me two years to put a stake in the ground and say this is what I'm doing now, because I just wasn't sure. And I just can't imagine that people who have done this before haven't faced that same reality. Turns out that this is not as Chief-y as I thought it was going to be. It’s rough.

Elise Graham Kennedy: For real.

Teresa: I absolutely pursued the role initially because I wanted the status. It felt very important for me, but I was like, I know that I'm capable of this.

I wanted to learn about the inner workings of the business. There's so much that I want to know. And I loved the idea, which I may be too candid, but I think a lot of us see: a Chief title is a Chief title. And when you get into it, you're like, it is a status role, but it is such an odd status role. It’s a status role that comes with a lot of baggage.

Elise: To me, it almost feels like just a status role externally…because internally to build that status, the amount of trust, there’s a lot of work to build that with every single person and team.

Teresa: There are absolutely instances where people are like, "You're the CEO's little spy. I don't want to tell you things. I don't want to tell you. Are you on my side or what?"

I mean, I had to have really hard conversations where I would not toe the company line and not toe the leadership line because it felt important for my personal and working integrity to be transparent about certain things. It's really difficult and I think it's part of the learning curve that comes with becoming a Chief of Staff.

At some point you're kind of like, I have to do this. I have to build trust in the ways that I know I can, and it is complex.

To your point, I also think there aren't that many leaders who want to bolster their Chiefs of Staff the way that I think the role could really be lifted up. I think it's super important for leaders to set the tone and help employees and their teams understand what the Chief of Staff is for.

And a lot of leaders don't do it. They're just like, “I don't have time for this. You go figure out how to make yourself relevant to everybody else and make yourself most relevant to me.”

I think that externally the role feels very fancy and so many people are like, “Ooh, fancy title. What do you even do?” I was like, I run the company without the money or the glory.

Elise: That's exactly it.

Teresa: I used to say it jokingly to kind of reduce the sting of it. But I was like, that's what it is. You help your leader run the company, but you don't get the glory. You often don't get gratitude, and you don't get the salary that they do. But you understand the power of the role and you understand the effectiveness.

And you believe enough in your leader and in the people and the organization to be like, "Hey, this is what I'm here for."

It's also why I've been so thoughtful about the types of leaders I want to work with moving forward and the types of businesses that I want to work with because I'm really bad at not showing my colors.

If I don't believe in your work, I'm going to be hard pressed to do a good job at this.

Elise It's true. And those leaders where there's not a good fit, they kind of expect unwavering loyalty.

Teresa: Exactly. Yeah.

I hope whoever is coming into this role now, because it seems like it's becoming very popular, there will be a portion of people who are willing to sit through it – and be like, “This isn't what I thought. But I'm willing to figure out how to make sense of it for myself. Because I do really like the work.”

I hope whoever is coming into this role now…there will be a portion of people who are willing to sit through it – and be like, “This isn't what I thought. But I'm willing to figure out how to make sense of it for myself. Because I do really like the work.” And I’m glad I did that.

And I'm glad I did that. But it's hard work and I don't have it mastered. I never will. But I'll do my best and hopefully I just help some people along the journey because it's a hard journey.

Elise: That's all you can do. At the end of the day, we're just humans helping humans.

Rapid-Fire Questions ☄️

Elise: What do you wish you knew before you became a Chief of Staff?

Teresa: It’s work steeped in deep emotion and thinking. It is much more than business.

Elise: That's really good. On that note, what do you think is the number one skill someone needs to be a Chief of Staff?

Teresa: Man, I just think you need to be really good at deep listening. I just feel like deep listening is so critical to every other part of the job.

Elise: Deep listening. I like that term. I like that a lot. Finally, what do you think is the most important thing for the future of the role?

Teresa: I think we have to figure out how to make this role sustainable in the long term. It’s an unsustainable role in its current structure.

Elise: That's real.

Teresa: It is taxing. If we're going to be doing this, and it feels like more people are opting into this role as a true career path, not a stepping stone, how do we do this over the long term?

Which to me also means: How do we reshape leadership so everybody's not burning themselves to the ground?

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Current Chiefs: I’d love to hear your thoughts. Did we nail it? Are you feeling the burnout, too?

Future Chiefs: Did this demystify any of the role for you, for better or worse?

Teresa has obviously thought deeply about this — I so admire her wisdom and willingness to share her experience. I hope current Chiefs feel less alone, and those considering the role understand the struggles we all talk about behind closed doors. Thank you Teresa! 💓

Until next week,

Elise