Generalist Speaking… with Alicia Diamond, Chief of Staff
When I started this blog, I did not realize how many folks shared my thoughts on the subject. I am heartened and consoled by the fact that I am not alone, but also intrigued by others’ stories. Starting this month, I will be sharing conversations I am having with other self-proclaimed generalists to get to the bottom of why it is a good club to be in!
This month: Alicia Diamond
Alicia Diamond is a lifelong generalist and passionate business builder. She is a two-time Chief of Staff, most recently at a venture-backed data company in Chicago. Before that, she worked at a startup incubator/family office as a Chief of Staff and later as COO. She’s been glued to leadership throughout her career and loves projects that help to reduce friction and build alignment across the entire organization. She’s a recent transplant to NYC, where she enjoys spending as much time as possible outside, soaking up the city’s energy and exploring new restaurants. She blogs about her “winding path to running a business” on her blog: www.aliciadiamond.com
GS: Do you consider yourself to be a generalist? Why or why not?
AD: Yes! And it took me a long time to embrace it. The world encourages specialization, but I’ve found that my value is in being the glue between specialists. Even a liberal arts focused education encourages you to specialize in a major.
I perceived my inability to stay in my own lane as a weakness for the longest time. Once I finally embraced it as a strength, I found that there are a lot of opportunities for generalists in the world. I encourage anyone who feels curious about many functional areas or subject matters to embrace that curiosity. Don’t specialize just because everyone around you is doing it.
GS: How do you define generalist?
AD: Coming from the perspective of a generalist, I believe we’re people who not only work well with diverse topics, functional areas, or formats of information, but that we thrive in an environment full of variety. I often describe myself as good at the 30,000 foot level and good in the weeds, but great if you give me access to both.
Generalists, in my experience, tend to be incredibly curious about the world. Even when we’re studying one area, we’re aware of what’s going on next to us and curious about how it might be impacting our area. Because we’re comfortable and fluent in a variety of areas, we can be deployed almost anywhere in the organization to do a variety of roles.
GS: What do you think is the biggest strength or asset of a generalist?
AD: Our comfort with the unfamiliar and our ability to make connections between disparate specialties are what make generalists so valuable within an organization. We’re highly adaptive because we’re constantly putting new information within the context of the broader picture. I’m a big analogy person — perhaps other generalists are as well? — so I think of my role as a generalist as being comfortable with the entire map. I may not know all of the territory on the map like the back of my hand, but I’m comfortable enough with it to engage with specialists who know specific areas incredibly well.
I firmly believe that as a generalist one of my biggest roles is to help specialists to be the best they can be. I help to make connections between specialists so that they can focus on their area. Generalists are the glue between the specialized individual parts of the organization.
GS: What is a Chief of Staff?
AD: We are the ultimate generalists! A Chief of Staff’s role is to make their principal (often a CEO, a senior level leader, or perhaps the President of the United States) superhuman. I often use a Wizard of Oz analogy when describing my role: my principal moves effortlessly through the day, fully briefed ahead of every meeting, walking into rooms of people that are well prepared and ready for his attention. Meanwhile, I’m behind the curtain sweating, flipping levers, cranking things, and whatever else the Wizard was doing. What I’m actually doing is running around behind the scenes helping teams to prepare to run really effective meetings, I’m researching, synthesizing, and always preparing for what comes next on my CEO’s schedule. I stay days ahead of my CEO, so that things run smoothly.
One of my favorite parts of the role is the thought partnership component. As a Chief of Staff, you’re living the same day-to-day as your principal. You’re there to help them make the best decisions possible, to help them think through thorny issues, and to nudge them when needed. Sometimes this means being the resident contrarian and disagreeing with everything (this can drive your principal crazy, but it’s a healthy exercise) and sometimes this means reminding them about how they handled a similar issue in the past. You’re there to help them be the best version of themselves in their job.
GS: How does being a generalist help in your role?
AD: As a Chief of Staff, I context switch between functional areas, topics, and business units multiple times each day. I need to be comfortable with every area of the business. A great Chief of Staff can comfortably sit down at any table in the organization and hold their own. I’m not a marketer, but I’ve made it a point to know just enough to be dangerous in a marketing meeting or any other functional area meeting.
This also means working with a diverse set of personalities and working styles. As a generalist, I’m curious and open, so I can handle the variety of topics and working styles quite easily. I’m also constantly synthesizing and making connections, so I recognize patterns that might be hidden to people who strictly stay in their one functional area.
GS: What should executives look for in a Chief of Staff?
AD: The relationship doesn’t work without trust. The principal needs to commit to being open with the person so they can build a trusting relationship. He or she also needs a certain level of self-awareness before hiring a Chief of Staff: what about themselves are they looking to supplement, amplify, and buffer.
A Chief of Staff has to pass the airport test with flying colors. Would you want to be trapped in an airport with this person for a whole day? You’re going to be glued at the hip while working together, so you need to be able to clearly communicate, trust one another, and be able to laugh together!
GS: What makes an effective Chief of Staff?
AD: The best Chiefs of Staff live 2–3 steps ahead of their principal. They think and act proactively about what needs to be done to make the next few steps as efficient and smooth as possible. Like a good driver, they’re paying attention to what’s ahead of them on the road ahead while simultaneously navigating what’s immediately in front of them.
Effective Chiefs of Staff are incredibly humble. This role is 100% about serving your principal and doing whatever it takes to help them be successful in the organization. No job is too small for a Chief of Staff and there is no room for an ego.
GS: What would your advice be to someone who is looking to become a Chief of Staff?
AD: Follow me and my hashtag on Twitter! I’m trying to make #futurechiefofstaff stick :)
I recommend reaching out to current Chiefs to get firsthand information about the role from as many people as possible. The role is different in every organization and for every leader, but there are some common elements. Be honest with yourself when you listen to the conversations. Does working behind the scenes sound fun or frustrating? Do you hate getting interrupted at work? I love to talk about the role and encourage anyone interested to reach out to me.
Try taking on more in your current role. Ask your leader what you can take off their plate and push yourself into other areas of the company to get as broad a perspective as possible. Volunteer to take notes for your boss in a meeting and then drive the follow-up from that meeting. See if you enjoy that type of work and then seek out more of it. I’ve met many Chiefs who have created the role for themselves after taking on a variety of work and demonstrating the value of the role to their boss.
Thank you, Alicia. Great perspective and insight into applying generalist skills in a very specific job title. If you want to learn more about Alicia’s career as Chief of Staff, please be sure to check out her blog and follow her @artfulconcern.
