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Christine Sandman Stone

Christine Sandman Stone

Christine Sandman Stone is a Founder, Speaker, Author, Advisor & more

  • Location: Chicago, IL USA 

  • Title: Founder & CEO, Speaker, Author, Advisor 

  • Company name: Deliver At Scale 

  • University degree: MA Organizational Behaviour from Benedictine University; BA in Philosophy and English from Miami University

How does your usual day look like?

My day is a mix of moments – some silent, and some not. I start in peaceful silence - I make my first tea of the day and watch the sun rise over the buildings in downtown Chicago as I do my morning journaling. Next up is the workout that fits my day’s schedule best and getting ready for the day. One of my favourite things is to say hello to my husband who rises a little later than me; we’ve started this practice of standing and hugging each other in the kitchen. It’s impossible not to start the day smiling when the day’s start reminds you of love, light, and the plan for the day ahead.

The plan…Each day has a written plan, based on the weekly plan written on Sunday, with my OKRs for the quarter in mind. These patterns of planning help me make sure I am set to move fast, and with purpose.

Client work is the centre…A typical day will include client work – a talk on modern pressures on managers, a workshop on tech or career strategies with a large group, conversations with a leader on how to navigate an operations challenge, or a planning meeting to scope out future sessions.

Writing… If it’s a writing day, I find a place to settle, (get more tea), and work on the next book or article.

My city…I walk everywhere unless it will make me late.  Chicago is remarkable, and moving through it gives you a chance to reset your thoughts and feel the energy of the city.

Make the world better… Almost every day has ‘make the world better’ meetings. I mentor extensively, especially women in tech. It’s common for me to connect with someone at a coffee shop or on zoom to help them strategize a career change, prep for a promotion interview, solve a workplace challenge. In the last 3 years, women represented 46% of the layoffs in tech, but we were only 28% of tech to start. The hole got deeper AND we need better representative policy in companies, and in the world. My goal is to contribute to the gap closing in a material way.

Connection, food, and love… Many days have an evening event – the women’s mentoring co-op, a group that is discussion the future of work and so on. I plan ahead, and my husband will usually meet up with me and we will walk to a restaurant to get a meal after the day is done.

Silence again…I write the plan for the next day, have a chamomile tea, and complete the day’s journal – the process of recapping the day and the progress has a remarkable way of changing my dreams, and my rest.

What are the things you like the most about your job?

How hard and interesting it is – managing in today’s economy is a new terrain for everyone.

What are some of the skills you utilise the most in your day-to-day at work?

Critical thinking – When I speak or run workshops, I want hard questions that are new to me, and relevant to the audience, so we can find an answer that makes a difference.

What was one of your happiest days in your career and why?

I loved speaking in front of ~2000 women at the Grace Hopper women in tech conference; it’s great to deliver a talk successfully in front of a group of brilliant people.

What was the toughest career decision you ever made?

When I realized that my boss’ guidance to ‘smile more and ask fewer questions’ eroded the heart of my unique capability (I caught things others missed, and raised issues early). I realized I’d need to find a better-fit organization.

What is something you had to learn to become better at your work?

Humility. When you are an individual contributor, you get a leadership job because you were exceptional, but you have to set your bias about ‘your way’ aside to give your people freedom to do the job their way - headroom to grow and legroom to run.

How did you get to become an advisor and speaker?

35 years of pursuing hard, new things in both big companies and start-ups. I started as a technical architect 35 years ago designing computer networks, and then created a role for myself to implement those projects. Do you know what happens when you are great at leading technical work? You get the biggest/hardest assignments, then you get asked to save other projects that are in crisis, and then train others to deliver well. I’ve seen technology go through remarkable cycles of growth. My first company was small and privately-held. It was a great place to build technical acumen and expertise. VW/Audi, McDonald’s and Dell helped me build different capabilities, and in each role I was growing. ​At VW, I ran a PMO and created best practices (and drove a series of really lovely Audi manual transmission cars). VW had a wonderful management training program, and I learned for the first time about organisational development to lead teams. At Dell, I had my first turn-around opportunity, leading the worst ranked team in the US to first. All those VW-learned tools came in handy!

McDonald’s gave me my first chance to lead an Agile transformation (for non-tech folks, this is a complete change in how software developers work) and the opportunity to create the first multi-year technology roadmap for MCD North America. McDonald’s had a remarkable director-training program and a vibrant women in leadership community.

My last corporate role was with Groupon where in addition to leading my third Agile transformation, I led the global rollout of OKRs. OKRs are a modern strategic method for clarity and work alignment that many tech juggernauts use. I loved it – they helped me lead 1500 global technologists’ work priorization to remarkable results through the pandemic.

There’s a theme here. Each place has had something big and hard – delivering results in a pandemic for an experiences company, building strategy in operations-focused teams, turning around struggling teams, creating diverse talent pipelines. I can create something from nothing, and create the most lightweight best practices better than anyone else I have ever worked with. It’s my superpower.

The hidden theme is that I have 4 children and a husband. Being the best in my peer groups in each job gave me the opportunity to negotiate for workplace flexibility before it was common. I’d give talks about agile transformation, or technical career paths and the 3rd or 4th question into Q+A would always be – please go back: "How did you do it with 4 kids?"

I started sharing my dark secrets: hacks. Things like putting my kids to bed in their school clothes. Things like how I hyper-prioritise with my managers so I could help with homework each afternoon.

Those hacks are in my first book called The Parent Track: Work-life Balance Hacks to Elevate Your Career and Raise Good Humans.

What's the one piece of career advice you have for anyone interested in following your footsteps?

Pay close attention to what brings you pride and joy – those are indicators that you are performing excellently. Do more of those until you master it, and then do something else interesting.

What's your number one productivity hack / when or how are you most effective?

Number 1 hack: a written plan so I can jump in fully to work or an interaction with confidence I can come back to the plan. When am I most effective? Mondays and Mornings. By Friday afternoon, I am very entertaining, but not very effective.

What makes you gracefullyBOLD?

Being so fiercely oriented toward progress (change with measurable outcomes) in business, in life, in the world.

How do you spend your weekend or downtimes?

Our 4 kids are grown and live around the US – we travel to see them, and to visit places we didn’t get a chance to visit when we were busy being parents.

How do you deal with stress and build resilience?

I breathe and I am ferocious about getting enough sleep. Breath and sleep help me when an obstacle comes up – I have the energy to immediately think ‘Around? Over? Through?’ and start solving.

What would have been your alternative career path or alternative University degree?


Who is a female professional that inspired you along your career journey? What did she do / say / or what are the character traits and professional skills she uses.

I love Carla Harris, she gives a remarkable explanation of mentor versus sponsor, and it’s career changing. I reshare her advice every time I can. (Note: We love Carla Harris too, here is a TedTalk.)

If you could time-travel and meet any leader, who/where would that be?

I’d love to meet women like Ayn Rand, Marie Curie, Grace Hopper or Katherine Johnson who were all so successful in communities of men. I can’t imagine what hurdles they navigated as they moved toward their success.

Note from the Editor: (1) Ayn Rand (1905-1982) was Russian-born American writer and philosopher, best known for developing a philosophical system she named Objectivism. (2) Marie Curie (1867-1934) was a Polish and naturalised-French physicist and chemist who conducted pioneering research on radioactivity. She was the first woman to win a Nobel Prize, the first person to win a Nobel Prize twice, and the only person to win a Nobel Prize in two scientific fields. (3) Grace Hopper (1906-1992) was an American computer scientist, mathematician, and United States Navy rear admiral. (4) Katherine Johnson (1918-2020) was an American mathematician whose calculations of orbital mechanics as a NASA employee were critical to the success of the first and subsequent U.S. crewed spaceflights.

What's the last thing you learnt?

I continue to learn about data training sets for AI models, and the implications for all. The best writer in this space is Dr. Joy Buolamwini – her book Unmasking AI is terrific, and she writes and speaks extensively o the subject.

The one question we didn't ask you but you'd like to answer?

  • Question: "If you had a chance to have your own renaissance – what does that look like?"

  • Answer: I’ve started it now! Our children are grown, and each is financially independent, doing work they love, and choosing good humans to love. Now there is some freedom to carve a new path.

We sold our house in a more suburban area and moved to an apartment in the heart of Chicago. We walk to restaurants, plays, art shows, Lake Michigan (it’s a lake but so big you can’t see the other side so it’s like a small sea). I left corporate, and started my own company earmarking 30% of my time to make the world better, and 70% of my time to focus on work I love. I walk to meetings, and enjoy this deeply engaging work community. My husband works for a firm he loves, and either travels or works from home.

We travel for fun every month – sometimes for big trips (Dublin, Dingle then the Peak District; Montreal; Cayman Islands, last year) and small trips like to Boston, or hiking in Utah and to spend time with our kids who all live in different cities now. At some point, I want to live abroad for a month or two to work on a book in a small village somewhere. I’d love to build a house that our children can come to for peace and community, but we don’t know what location will work best just yet.

I want to have a studio where I can write and read and practice talks and a big garden outside.

I’d love to be able to work 20 hours a week, and leave the other hours for joyous pursuits. I’m working on those next parts.

One word answers & quick fire round. Let's go!

  • Your superpower: Pragmatic solutions

  • Favourite restaurant: Drawing Room at Chicago Athletic Club, Fabcakes on Wells, or the lobby of Soho House in Chicago

  • Book recommendation: For relaxing: 'Remarkably Bright Creatures' by Shelby Van Pelt, For learning: 'Mindset' by Dr Carol Dweck

  • Next holiday destination: Boston

  • Your hobby: Throwing parties!

  • Who inspires you: Stacey Abrams for her work on voting rights

  • Tea or Coffee: Tea

  • Red wine or White wine: Bourbon

  • Morning bird or Night owl: Morning bird

  • Cat person or Dog person: Dog person

Thank you Christine for sharing your journey & wisdom with us!

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