
Jessica Chaikowsky
Consultant | Content Development
Jessica has spent her 20+ year career focused on bringing both rigor and compassion to how companies acquire, onboard, assess, and develop their people. She works with individuals and people managers as a coach in the classroom and at a strategic level, consulting with executives and HR leadership teams. Jessica carries a toolkit packed with expertise in learning design and facilitation, change and project management, and a deep curiosity about human behavior and communication.
She has worked for Nortel, Nav Canada, the Canadian Management Centre, Starbucks, and Aecon, and she has consulted with national and international clients across multiple industries during her six years with Deloitte. Her business acumen and passion for the “future of work” provide a long-term perspective, balanced with the pragmatism needed to coach leaders on execution.
Jessica holds a B.A. in English Literature and Philosophy. She earned her TESL certification while teaching English in Ukraine in the mid-1990s and received her Executive MBA in 2010. She also holds certifications in change management, adult learning, and various 360-degree and psychometric assessments. Currently, she is an independent consultant, developing and delivering leadership programs, assessing and coaching high-potential leaders, and advising on talent assessment and development strategies.
Outside of work, Jessica enjoys singing jazz and owns a wine-importing and education agency.
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Don’t Call It Strategic Planning If Nothing Changes
Strategic planning is one of those phrases that sounds impressive in a boardroom but often fails to produce meaningful results. Too many organizations go through the motions—workshops, PowerPoints, dashboards, only to return to business as usual. If nothing changes after a strategic planning session, can we really call it “strategic”?