👋 Welcome to ‘in your own words’ — a written series where we sit down with generalists from all over the globe to understand, in their own words, a little more about their story. The aim of this series is to amplify, inspire and learn from others who’ve walked squiggly paths.

Today, I’d like to introduce you to Katie Montbriand. During her 15-year career as a consultant and Fortune 500 leader, she’s become, by all accounts - an exceptional generalist. Through credit underwriting, marketing, product, operations, and Chief of Staff roles, each position offered a chance to grow and add tools to her leadership kit.

Let’s dive in! 🤿 

🎙Katie, in your own words, tell us your generalist story

Although I spent 10 years at one corporation, I reinvented my career in a zig-zaggy, generalist fashion every 18 months-2 years. I worked in everything from credit underwriting to marketing strategy, Chief of Staff, general manager, operations leader and more. I was an individual contributor and a leader of 100-person teams. I was Chief of Staff when a 1000-person organization came together. I led different parts of diversity recruiting and onboarding and coached associates across the enterprise. And then, it was time to fly away from my corporate nest. I almost left for a sabbatical twice, and finally did in 2021. I knew ‘corporate exec’ wasn’t my destination in life because I looked around and saw people not having a good time and didn’t want that for myself.

This career break was about deciding the life I wanted to live and building work into that life vs. the inverse. It’s important to me that I can live in 2 (or more!) places throughout the year, tap into my passions and talents, help people, have control over my time. So now I’m building two businesses that fit the bill.

🎙What are some of your favourite problems that you've solved as a generalist?

1) How to upskill people managers quickly

2) How to get a heavily tenured team (avg 10 years) to see a new vision for what banking operations could be (no more manual tracking and spreadsheets, move to controls built into technology solutions like automated retry logic and error reporting)

3) Expressing gratitude in the workplace - solutions were everything from a quarterly appreciation week where everyone got a budget to say thanks to colleagues, weekly appreciation threads in our team slack channel, letters of appreciation from leaders across the company, etc.

Ask me about how to make your appreciation meaningful. Really anything that sits at the intersection of humans, passion and business results. I love showing people what is possible and helping them get there.

🎙How has being a generalist worked in your favour?

Being a generalist means I’m not afraid to jump into new problems and be a beginner, because I never expect to have all the answers. This worked well in a corporate setting when I kept raising my hand to ask for new assignments in which I had no experience. I did, at times, feel like a square peg trying to conform to a round hole as people around me specialized and advanced quickly because of it. But looking back I’m so thankful for these varied experiences because they give me new perspectives.

Now, as a business owner it means I have a breadth of skills and the confidence to figure things out. In the past few months I have: learned how to do my own PR, built (and rebuilt!) websites, gotten pretty good at creating graphics, built an automated email sequence, researched sales tax laws, set up a CRM system. I’m always willing to give things a first try, and then call in the experts or ask for help if I truly can’t figure it out.

🎙Which role / job has been your favourite, and why?

Is it cheating to say that I love building my own business? 😃 I found two things that truly tap into my talents and passions and seeing them come to life is magical.

Going through the whole process of offer development, marketing, sales, delivery on a small scale is so cool. From my corporate life - I’m torn between Chief of Staff for a 1000-person team and leading my own 100-person team. I like both the advisor role and the leader role. While leading my own teams, I felt more control over the culture building and people development (which, of course, were my favorite parts).

🎙What moments or decisions have made outsized differences in your life?

1) Going to Barcelona for business school. There I met and studied with people from around the world, and for the first time in my life wasn’t part of the majority population. This experience taught me how beautiful it is when a diverse group of people work together with a basis of respect and understanding.

2) My sister died 7 years ago. At the time, I had gotten kind of lost as a human. I was working a lot, and not taking care of myself. After she died, I realized I was living a not-so-joyful life and went on a journey to get back to myself. Travel, adopting new healthy habits (like getting enough sleep, go figure!), therapy, writing and a lot of introspection got me through to my next chapter. It wasn’t pretty, but this was the first time I tapped into story in a powerful way - my healing journey had me on stage claiming my sister’s death as part of my own story.

3) Leaving my corporate job. It was like a comfortable marriage. Hard to walk away from something that I was good at, and that had pretty cushy benefits and compensation. Stepping out into the unknown and being comfortable saying: I know this isn’t the answer, but I don’t know what IS the answer yet. I had to go through that discomfort to get to where I am today.

🎙How have you honed in on your generalist skillset?

Mostly by trying a lot of different roles and putting myself in new situations every couple years.

Best practices or advice for generalists to connect cross-functionally with others at their company eg: engineers, finance, marketing etc

Be curious and be a partner.

I love to do immersive learning with other functions as a Chief of Staff. Actually sit with them and watch the work happen. Go to the call center, attend the demo, drop in on standup. This will help you see things from your partners’ perspectives and have a lot more empathy when you are trying to problem solve. You’ll also learn a lot about the things that matter to your customers.

There is no better feedback on a business policy than hearing a few customers call and complain to your phone agent about it! When they see you being actively interested in their work and understanding at least the basics of how it happens they will be more inclined to work toward joint solutions.

🎙Tell us about strategies you've undertaken to upskill

Some of my favorites:

1) I went to a Transformational Leadership program at Georgetown a few years ago. This was similar to their Executive Coaching curriculum but more focused on teams and how they work. It gave me a bunch of new perspectives and tools to use when leading change in an organization. It also forced me to learn about myself and confront some things that were holding me back.

2) Attending conferences about things tangential to my work. Hearing from thought leaders always sparks new ideas for me. Mobile world congress, DisruptHR, Galvanize from Fairygodboss are some that I enjoyed.

3) Understanding my own cycles of expansion and retraction. I go through seasons where I take in all sorts of new information, build connections and am ‘out in the world’. That is followed by a quieter period where I integrate and reflect.

🎙What do you wish the world knew about being a generalist?

It’s not that we can’t decide on a focus area, it’s that we decide more frequently than other people. Just because something is the primary thing today doesn’t mean we are married to it forever.

An example would be when I moved back to Minneapolis a few years ago. My midwestern friends would ask me ‘oh, so you’re HERE now?’, meaning, you’re done with your travels and now you are settling down. My response was: ‘I’m here NOW’ meaning: for the moment, I’m in this place. That doesn’t mean it’s going to last forever. Case in point: it’s been a few years and I’m moving again.

🎙What's the hardest thing / biggest challenge you've faced because of your generalist nature?

I get bored quickly. That looks like finding a new role every 18 months or wanting to move to a new city every ~4 years.

My search for novelty means I like new things and building, but am not great at being the long-term owner. I’m trying to address this tendency by living in 2 places during the year and starting 2 businesses. We’ll see if that works!

🎙What's your proudest moment or achievement as a generalist?

Launching a product that combines reflection/personal development, storytelling and art. The fact that I can use my journey to make it easier for others to find their way lights me up.

🔥Quickfire round

Recommend a book:

The Power of TED* (*The Empowerment Dynamic).

Recommend a podcast / movie:

Guilty pleasure: Scream Queens

Recommend an inspiring person to follow:

Mandolen Mull.

When I was chief of staff I built a cross-functional team of ‘culturists’ - a first of its kind. I pulled people from operations, data, marketing, and delivery and we listened to associate feedback and worked to transform the organization.

We got the leaders and employees talking in different ways (loved TINYpulse for this), got leaders on stage being vulnerable, addressed change curves, made learning opportunities accessible to everyone (like coach training for all our people leaders). When I look back, this was one of those very special confluence of people and passion that rarely happen in a career.

Find Katie on Linkedin, on Instagram or on her website.