What Happens In A Coaching Session
Support your people and strengthen your team with the leadership skills that will last a lifetime
Leadership is hard. It is high stakes, deeply human, and often isolating. Yet most leaders are expected to figure it out as they go, without much support, time to reflect, or feedback on what is actually working. Over time, these challenges can quietly erode morale, create confusion, and leave good people feeling burned out or unsure of where to focus.
That is where coaching comes in.
If you have ever wondered what really happens in a coaching session, or whether it is worth the investment, this is for you.
Whether you're exploring support for yourself or your team, this article will walk you through what coaching really is, what to expect, and how to know when the time is right. If you have professional development funds that expire at the end of the fiscal year, this is a valuable moment to invest in the people who make the work possible.
What Coaching Delivers
Clearer thinking and stronger decision-making
Healthier communication with their teams and peers
More confidence in high-stakes moments
Better stress management and emotional resilience
A stronger sense of purpose and momentum
The leaders I work with often describe the experience as both supportive and transformative.
Perhaps most importantly, they develop greater self-awareness. They begin to notice the patterns that shape their behavior, and they learn how to respond with intention rather than react out of habit.
"Jess did a beautiful job helping me understand and face some of the underlying reasons for my lapses in professional confidence. She's empathetic, curious, and constructive, and gave me personalized support during our sessions and resources that I continue to use. I can't recommend her more highly, whatever professional coaching you need”
When you grow in this way, your leadership becomes not just more effective, but the perspective and skills you gain serve you for life.
Here’s how you can get started:
One-on-One Coaching Kickstart Program
Most people in leadership roles are doing their best, often without the support, feedback, or space to grow into the kind of leader their team really needs. Coaching helps close that gap. It creates time to reflect, build self-awareness, and develop the practical skills that make leadership more clear, sustainable, and connected. When leaders feel supported, teams feel it too. Communication improves, alignment gets easier, and the work becomes more fulfilling for everyone involved.
In my Leadership Kickstart program, we start with a leadership assessment and a goal-setting session. From there, you receive three focused coaching sessions over two to three months, along with a clear and actionable plan to sharpen your leadership presence and build confidence in how you communicate, delegate, and lead.
Each session is structured but shaped by your goals. You bring the challenges you are facing, and I help you explore what is behind them. Together, we identify practical steps to move forward with clarity and confidence.
Leaders walk away feeling more grounded and more effective. They report stronger relationships, less stress, better decision-making, and a deeper sense of connection to their work.
“I have been able to achieve more at work in a month because of Jessica’s guidance than I had in the six months prior to our coaching sessions.”
Team Development Kickstart Program
Teams can struggle with unclear roles, slow decision-making, or a general sense of misalignment. Team development is a way to work through those issues together.
In my Team Kickstart program, we begin with a team assessment and a series of stakeholder interviews. This helps us uncover strengths, gaps, and opportunities. We then come together for a half-day workshop focused on building trust, clarifying expectations, and aligning on shared goals. After the session, I share a set of tailored recommendations to improve how the team works together.
Team coaching helps people get on the same page, reduce unnecessary friction, and build the kind of collaboration that allows everyone to do their best work.
“Working with Jess was incredibly valuable for us and our early-stage startup. She brought a thoughtful structure and exercises that gave us space to look at all aspects of our business in a one day intensive workshop. Jess is a talented coach and was particularly gifted at being a mirror that allowed us to see our business more clearly.”
How to Make the Most of Coaching
To benefit from coaching, you do not need to be in crisis, nor do you need to set time aside for a 3 day offsite. You only need to be curious and committed to your own growth.
Come to each session ready to reflect. Share what you are learning and where you feel stuck. Be honest about what is working and what is not. Coaching is most powerful when you are open to exploring your edges and willing to try something new.
The best coaching and team programs slot right into how you’re already working and serve as an anchor for you throughout your work week.
Coaching Is an Investment in the People Who Make the Work Possible
Most teams care deeply about their work and want to succeed together. But even the most dedicated people can struggle when communication is unclear, roles are muddled, or expectations are constantly shifting. Over time, these patterns can lead to frustration, low morale, burnout, and attrition. Often, this happens quietly, before anyone raises a hand to ask for help.
Coaching is one of the most meaningful ways to support the people who keep your organization running.
It creates space to think, to grow, and to build the skills that make work more sustainable and fulfilling for everyone involved.
“Because of Jessica, I now have a clear roadmap and a stronger sense of purpose, along with the tools to keep moving forward. I can’t recommend her enough to anyone looking for a coach who is not only knowledgeable, but also deeply invested in your success."
When you invest in coaching, you are investing in the long-term strength of your team. You are helping someone grow into the kind of leader who brings out the best in others, navigates hard moments with clarity, and leads in a way that creates energy instead of draining it.
Let’s Get Started
You can use this year’s budget to book a Leadership Kickstart or Team Kickstart package, even if the work begins next fiscal year. Both offerings are designed to fall below common procurement thresholds and are easy to initiate.
If you are not sure what the right starting point is, we can figure that out together.
You might be ready for coaching if:
You are taking on new leadership responsibilities and want a grounded place to grow into the role
You are managing a team where roles and ownership feel unclear, and you want to build stronger alignment
You are finding it hard to delegate without slipping into micromanagement
You want to give and receive feedback more effectively, while preserving trust
You are in a senior position and need time to step back, reflect, and make thoughtful decisions
Your team wants to work better together, but something is getting in the way—communication, coordination, or just too much happening at once
If any of these sound familiar, coaching can help.
And if your professional development funds expire at the end of the month, this is a good time to take action.
📅 Schedule a strategy call. We will talk through your goals, the context you are navigating, and what kind of support would be most helpful right now.
You do not have to figure it all out on your own. With the right support, work can feel more grounded, more human, and more joyful, for you and for the people around you.