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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Andrea Weiss

helps you in your leadership.



Jonno White

7 Questions with Andrea Weiss

Name: Andrea Weiss

Current title: Founder & CEO

Current organisation: The O Alliance

After a 30+ year career with some of the world's largest fashion brands, Andrea founded The O Alliance, a consulting network with global reach focused on the digital transformation of commerce. Her enterprise level clients include major retail and CPG firms on 4 continents.

7 Questions with Andrea Weiss


1. What have you found most challenging as a CEO or executive of a large enterprise?

Leading remotely has presented totally new challenges of team building. As the leader of a large, distributed organization, adapting quickly, using multiple collaboration tools and ensuring top to frontline are aligned to execute well in the changing dynamics.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

My story started at the bottom. I worked in almost every role inside a retail company, and always had a plan to reach a general management role. After attending business school, I stepped back into the business, accepting the most challenging operations roles. By achieving and turning around difficult situations and understanding the workforce, I was well prepared when I was elevated to President and ultimately CEO.

3. How do you structure your work days from waking up to going to sleep?

I am very planful about my days. I rise early to allow time for morning exercise/walk, and then read several global business and news feeds. I review my daily calendar and ensure I am prepared for my meeting, Zoom sessions and calls. I try to wrap by 6 or 7 PM and whether I am traveling or working from home during COVID19, I always end every day with dinner or a long call with my husband.

4. What's the most recent significant leadership lesson you've learned?

During COVID19, the lesson of kindness and empathy required by a leader was really accelerated. It has been so important to sincerely ask about the health and wellness of your team. I don't start any session without asking how everyone is feeling, to ensure we are all aware of our colleagues.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The Fountainhead by Ayn Rand was the book that helped me most understand the power of the individual. It gave me the courage to stand up for my beliefs and to understand the powers that attempt to derail.
I also recently read Braving the Wilderness by Brene Brown, which is also a current book on leadership courage.

6. How do you build leadership capacity in a large enterprise?

With a plan! Leaders need diverse experiences, developmental opportunities to stretch themselves and to demonstrate leadership capacity.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

I recall taking an assignment as CEO at a new company. I inherited a very siloed organization and the executive offices were almost like bunkers, lined up side by side, but with few windows or open work areas. Knowing my own style and the need to facilitate open, cross functional communications, one of my first moves in the first 100 days was to not simply have an "open door policy". I had the wall opened up to my office so that the entire executive floor would see how I worked, who I met with and when I came and went.
This became more than changed the culture.

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