Executive Coaching
Lead with greater impact — without losing yourself in the process.
Leadership today demands more than ever: complex decisions, relentless change, competing priorities, higher expectations, and teams that need both empathy and accountability.
Pressure doesn't just affect how leaders feel. It can change how they lead — pulling even highly successful leaders into constant activity, reactivity, over-control, isolation or ways of working that simply aren't sustainable. And that can affect not only the leader, but their team, their decisions and organizational performance.
Carey-Ann Oestreicher, MBA, Master Certified Coach (MCC), helps leaders step out of the noise, see what may be getting in the way of their greatest impact, and make meaningful shifts in how they lead. Drawing on more than 15 years of executive coaching, her experience as a former Corporate Vice President, and her proprietary Human Leadership™ methodology, Carey-Ann combines deep coaching expertise with a practical understanding of what it takes to lead when the stakes — and the pressure — are high.
Coaching is highly personalized and may focus on navigating change and uncertainty, increasing strategic impact, strengthening executive presence, building trust and accountability, developing teams, navigating difficult relationships and decisions, or creating a more sustainable way to perform at a high level. Carey-Ann's Human Leadership Dashboard™ provides an additional lens for recognizing where pressure may be influencing five critical leadership capacities: Intention, Impact, Trust, Connection and Self-Leadership.
The result: stronger leaders who think more clearly, lead more intentionally, create greater impact through others, and are better equipped for the demands of leadership today and what's coming next. Because Human Leadership isn't the softer side of performance. It's a competitive advantage.
An Executive Coaching Experience Built Around You:
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Getting To Know You
No two leaders — or leadership challenges — are the same. Each executive coaching engagement is customized around you, your leadership context, and the outcomes that matter most to you and your organization.
Every engagement begins with a conversation. We'll explore what's happening in your leadership right now, what you want to strengthen or change, and what you're hoping to achieve through coaching. It's also an opportunity for us to get to know one another and determine whether we're the right fit.
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Your Leadership Development Plan
Together, we turn insight into focus by identifying the leadership shifts that will create the greatest impact and develop clear, meaningful coaching objectives connected to both your own aspirations and the needs of your role and organization.
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Discovery & Leadership Assessment
During our first session, we go deeper to understand you as a leader — your strengths, challenges, values, patterns, pressures and aspirations. Your engagement includes a comprehensive Discovery Session, along with carefully selected assessments and reflection tools to build greater self-awareness and identify meaningful opportunities for growth.
Carey-Ann may also draw on her Human Leadership Dashboard™ to explore where pressure is currently influencing how you lead and where greater Intention, Impact, Trust, Connection or Self-Leadership could make a difference.
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360 Feedback & Stakeholder Perspective
Where appropriate, coaching includes a 360° assessment to better understand how your leadership is experienced by others. This may include confidential stakeholder interviews conducted by Carey-Ann or The Leadership Circle Profile™, a comprehensive 360° leadership assessment.
For organization-sponsored coaching, Carey-Ann also connects with the leader's manager and/or appropriate organizational sponsor to understand the broader leadership context and desired outcomes.
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Executive Coaching & Real-World Application
Through eleven private, 50-minute coaching sessions, you'll have a confidential space to step out of the day-to-day demands of leadership, think differently, challenge assumptions, work through complex situations and translate insight into action.
Between sessions, you'll put the work into practice — through conversations, decisions, leadership experiments, reflection and practical actions designed around your goals.
Carey-Ann also provides ongoing email support throughout the engagement when challenges or opportunities arise between sessions.
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Measure Progress & Leadership Impact
Development should create meaningful change.
We'll revisit your objectives throughout the engagement, including a midpoint progress review, to understand what's changing, where you're seeing impact and what still needs attention.
At the conclusion of the engagement, we'll reflect on progress against your original objectives, the shifts you've made in how you lead, and how you'll continue building on that growth beyond coaching.
Ready to Explore Executive Coaching?
Whether you're a leader considering coaching for yourself or an organization exploring coaching for one of your executives, let's start with a conversation.
What Clients Are Saying…
“Through listening, thoughtful questions and balanced advice, Carey-Ann helped me focus on gaining perspective and developing capabilities to help me grow as a leader for improved personal and professional effectiveness. I’m confident in the value she will bring to any coaching investment.”
— Leigh Brown, Human Resources Vice President, RBC
“Carey-Ann is an amazing Executive Coach. She has taught me to be more mindful and resilient. Through my work with Carey-Ann, I am better able to handle the pressures of my current and future leadership roles. Life during COVID-19 has become unpredictable for so many of us, but I feel I have learned new things about myself through my coaching with Carey-Ann as well as some tools to help me better navigate this time. A great investment in leadership!”
— Audrey Ancion, AI Institute Canada Leader, Deloitte
“Carey-Ann is an outstanding Executive Coach. Her focus on the whole person and highly empathetic approach are only part of her strength. She is also great at teaching mindfulness exercises that really simplify and clarify the real issues and challenges. I have found my work with Carey-Ann to be very enriching and would recommend her as a coach without reservation.”
— Thomas Webb, CEO of Weave Risk Solutions
“I had the pleasure of working with Carey-Ann two years ago. She was very transparent with me from the start. Didn't sugar coat anything and stated that some of the work would be very difficult and it was. I also had an instant connection with Carey-Ann as our lives, careers had many similarities. I worked with her for six months and it was transformational for me. We are still in contact and I am grateful every day for the work Carey-Ann did with me.”
— Jane VanderPlaat, Vice President, Client Services at CUMIS and Co-operators Life Insurance Company
“I really enjoyed having Carey-Ann as my Executive Coach. She helped me both personally and professionally as I was moving into a new role, and truly helped me identify my priorities and potential. Carey-Ann was great at listening, asking questions that guided me to new insights, and she even laughed at some of my attempts at humour! I felt relaxed and at ease with Carey-Ann, and she managed that tricky balance of keeping me honest with myself while also helping me validate my intentions and objectives. Working with Carey-Ann, I feel I was able to get a faster start in my new role while learning a great deal about myself, my thinking, and how to be a better leader.”
— Bruce Palmer, CEO and President, Pro-Demnity Insurance Company
“Carey-Ann is an exceptional coach and leader. I've had the opportunity to work with her and to see others flourish through her coaching. Carey-Ann's strong business and communications background, coupled with her excellent coaching style, holistic approach, and amazing ability to gently zero in on issues, are some of her strengths. I highly recommend Carey-Ann.”