Event Summary 11.23.2021

Women Leading in Technology: A Conversation with Deb Cupp, President, Microsoft US

A virtual event hosted by Minnesota Technology Association.

Women Leading in Technology - A Conversation with Deb Cupp, President, Microsoft US Event Summary

On November 9th, Jessica Albrecht, Courtney Plude, and Emily McDonough attended the Women Leading in Technology (WLiT): A Conversation with Deb Cupp, President, Microsoft US event hosted by Minnesota Technology Association. The virtual event was facilitated by Robin Brown who asked Deb a series of questions. Below is a brief insight into some of those questions followed by her perspectives.

What are some of your favorites?

  • Peloton workouts – Deb starts each workday with a Peloton workout
  • Current Favorite Book: Dare to Lead
  • Current Favorite Movie / Show: Ted Lasso

How do you remain flexible and ensure equity for all employees in a hybrid work environment?

  • We are all learning, and allow for flexibility
    • Frequent polls and surveys
  • Talking with multiple companies / clients on their approach to hybrid work
  • Continuous communication and transparency
    • Communicating that we need to be agile

How are companies retaining talent?

  • Knowing that the biggest challenge is being able to remain equitable for all
    • Seeing clients’ employees pivoting and employees are saying they want something more
  • Organizations need to keep listening and learning and determine how they are going to create action

We heard about the Great Resignation, can you please share more information on that?

  • See it as the great shuffle of talent
  • Believe that the environment is going to settle over the next six months to a year
  • Microsoft, as well as all industries, will continue to learn and adapt over this period
    • Reiterated that it will be key for organizations to continue to listen, learn, and act on their learnings

What was your path to where you are now?

  • Started in sales
  • Incredible passion for customers and learning from each experience / journey
  • Selling created a level of curiosity – that there are always opportunities to do it a little bit differently each time

What was your biggest challenge?

  • Figuring out what I wanted to do and where I want to do it
  • Making sure I understand myself and what I am passionate about
  • Learned it’s okay not to be passionate about what others want you to be passionate about
  • Staying true to your values

How did you get your seat at the table?

  • Great mentors
  • Practice and leaning into discussions that are uncomfortable
    • Taking steps to work through the uncomfortable
  • Getting feedback – “How did I show up” – sometime feedback is tough, but it is key to everything

What do you look for in a mentor?

  • Individuals that have the same values
  • People that she admired
  • People who are going to challenge your thinking

Did your mentor list shift over your career?

  • Yes!
  • Her board of directors / mentors shifted throughout the stages of her career
  • Each of the mentors have pushed her in different ways
  • Mentor shifts were based on what is important at a point in time in life

What is the most important lesson?

  • Need to be authentic!
  • You must be you!

We appreciate the opportunity to have participated in this event and look forward to attending more Minnesota Technology Association events in the future.

To learn more about insights we gained from attending this event or to connect with a Trexin Advisor, please click here.

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