Crossing The Chasm: Making The Leap To The C-Suite

September 27, 2021
Kendall Holbrook

You have an opportunity in front of you to take on a role in the C-Suite, but are you ready to make the leap? As part of the Grace Hopper Celebration in their Anita Borg On Demand Studio, I will explore the mental leap you need to make to say YES to a top slot in an organization. Whether the role is that of a COO, CFO, CTO, President, or even CEO, all eyes will be on you. If you have the education, experience, and desire, you can make the leap! View my presentation at You can also chat with me live during my Speakers’ Corner Q&A session on Wednesday, September 29 at 1PM ET/10AM PT.

As women, we know that we often sell ourselves short and not give ourselves enough credit for what we know or what we can do. When readying yourself for top leadership positions, there are three components of readiness and a fourth stage to help guide you in your new role. These four parts apply regardless of the size of your organization or the exact role label.

  1. The Fundamentals: Education and Experience – You look good on paper; you have the degree(s) and you worked the necessary roles to help you develop the right skills. The first step to any new role, especially a C-Level role, is your education and experience. Is it the type of company that requires a high level of education or was it founded by someone who was self-made and rolled up their sleeves to build the organization? What are the demands of the role? Have you carefully observed others in the desired role? Once you have carefully examined the role in this way, do you believe you are a fit? Can you perform most of the functions? Do you do some of the tasks already in your current role?
  2. The Extras: Your “Board of Advisors” – We know that no one gets to where they are alone, and it is no different for those in the C-Suite. You must have a strong network of coaches, mentors and sponsors who have helped prepare you for this type of role along the way. It may be made up of friends, professional executive coaches, managers, or other leaders you can trust. Although all your “board” members are key, having a great mentor during your job prep and search may be key because they will know you best. Your “board” can support you as you make the decision on your readiness as well as helping you sort out the types of organizations and roles that might be the best fit for you. Do not underestimate the self-belief and confidence this process may require. Your “board” is perfect for helping to reinforce your confidence and is the “extra” component needed before you make the leap.
  3. The Big Decision – An opportunity opens up; it is brought to you, or you identify it as part of a search. When you look at the role description, the size, goals, and strategy of the organization, how do you know if this is the right position for you? If you have the Fundamentals covered and have incorporated the Extras, you are likely ready, but what does ready mean? Does it mean you check off all boxes at 100%? No. Ready means you can do most tasks and are able to be proficient in all tasks with some coaching and time. You must allow yourself to be “new” in a new position. You mentor or other members of your Board of Advisors will be there to support you in this.
  4. You Made the Leap, Now What? – You are a brand new “C”, and you may not feel like you know exactly how to operate in your new role. That is normal, you just need a little time to find your way. You should approach this new role in the way you have always approached new roles.
    • When in your new position, or even before you get there, you should read everything you can, meet with your team, meet with other colleagues, and leads from each department, go to all the meetings, etc.
    • Build relationships throughout the new organization. Leverage an outward mindset and seek to learn about those you work with and how you can assist them and their role in assisting you.
    • Leverage your mentor, or potentially find a new mentor who knows the role you are now in. You might consider finding an executive forum or an informal group of executives with similar positions to be able to have a safe group to discuss challenges with.
    • Find an executive coach. A professional to keep you accountable to yourself is a great addition to your toolbox.
    • Focus on continuous learning. Soak up as much information as you can about leadership, operations, etc.


Starting your new role at the executive level isn’t dissimilar from when you first started your career. Once you are comfortable, you will be able to make the role your own. Learning, collaborating, growing, and focusing on creating positive outcomes will help define your legacy and set you up for continued and future success.

To view my on-demand presentation, visit and search for Kendall Holbrook. You can also view the slides that I use in my presentation by visiting my GHC page on our website. I hope to meet you on Wednesday at 4PM ET/1PM PT at my live Q&A session!

#DareTo #Innovate #Elevate #Transform #WomeninTech


Kendall Holbrook

Chief Executive Officer

Dev Technology