1:1 Leadership Coaching Services
One on One Coaching
Working with me one to one is a powerful opportunity to intentionally shape how you show up and lead. In our coaching you will be pushed to think differently, challenge limiting beliefs, explore blind spots, and get really clear on your leadership role and impact. Sound awful and also great at the same time? If so, we are a fit.
Our conversations are thoughtful, direct, and focused on progress, leaning heavily on proven behaviour change approaches.
Most coaching engagements are longer-term and focus on real leadership challenges over time. We can meet online, over the phone or in-person (in Vancouver).
We start with a slightly longer session to clarify your goals, and cater the ongoing coaching to meet your needs.
Curious?
My 1:1 Leadership Coaching Process
Every coaching relationship starts with a conversation. I offer a complimentary introductory call where we get to know each other, explore your goals, and determine whether we’re a good fit to work together.
If we decide to move forward, we begin with a comprehensive 2-hour intake session. This is where we take a deeper dive into your current reality, your leadership context, and the outcomes you want to achieve. Together, we co-create a clear, personalized coaching plan tailored to your objectives.
From there, the structure is flexible and designed to support meaningful progress. A common approach is to meet weekly for the first month to build momentum, then shift to biweekly sessions as you begin integrating what you’ve learned. Some clients choose to continue with monthly sessions for ongoing support and accountability.
My goal isn’t to keep you in coaching indefinitely. It’s to help you achieve your goals, build more expertise in your leadership, and develop the tools to move forward independently.
Common Challenges We Tackle in 1:1 Leadership Coaching
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I help leaders manage their teams with clarity and confidence—whether that means handling tough conversations, improving performance, or building stronger alignment. The focus is always on practical tools you can apply right away.
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When the stakes are high and time is tight, it’s easy to get stuck or overwhelmed. I work with you to create clarity in those moments, so you can make decisions you stand behind and lead with confidence, even in uncertainty.
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Conflict is a natural part of working with people—but it can feel uncomfortable and easy to avoid. I support you in leaning into those moments with clarity and confidence, so you can handle difficult conversations, rebuild trust when needed, and create a team environment where people feel heard and respected.
“Thank you so much for being you, and for helping me get to where I feel my absolute best. Without a doubt, you’re one of the, if not the, most influential and important people to come into my life. What I really value is that you have such a good ear and the outcome from our discussions. You are able to translate my own thoughts and feed them back to me in a comprehensive and thoughtful way that helped direct me where I needed to go.”
Frequently Asked Questions About Leadership Coaching with Jen Dowdeswell
Still have questions? Reach out anytime.
How do we meet?
Most clients appreciate the flexibility of zoom and phone call options. If you are local to Vancouver, we can absolutely meet in person.
What does the coaching relationship look like?
As annoying as this answer is, it depends. In a typical session, we start with what’s most present for you right now—whether that’s a team issue, a difficult conversation, or a high-stakes decision. We unpack what’s really going on, look at what’s getting in the way, and explore different ways forward. The goal is clarity: what to do next, how to approach it, and how to show up as a leader in that moment.
What happens in between sessions?
Between sessions, you apply what we’ve discussed in real situations. Then we use those experiences to refine your approach and build your confidence over time. The work is iterative—grounded in action, reflection, and adjustment.
How long does coaching actually last?
It depends on your goals. Many clients work with me over a few months to address a specific objective, while others choose to continue longer for ongoing development and support. The structure is flexible and evolves as you make progress.
Will this help with specific challenges I’m facing right now?
Yes. Coaching is grounded in your current reality—whether that’s a difficult conversation, team performance issues, or a high-stakes decision. We focus on what will make the biggest difference right now.
What does coaching cost?
I’ll walk you through options after our initial call, based on your goals and the level of support you’re looking for.