1:1 Leadership Coaching


A strategic partner for leaders moving from individual execution to organizational influence.

Coaching with Choose to Lead is a private space to solve the problems that don't have an easy answer. We focus on pressure-testing your decisions, navigating tricky team dynamics, and building the specific habits you need to lead at the next level. This isn't just a place to vent; it’s a structured partnership for leaders who are actually in the thick of it.

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Who is 1:1 Coaching for?

This is for the leader who has mastered the technical side of their role but is now facing the "people" side of scaling. It’s for those moving from doing the work to influencing the work through others. If you are navigating a promotion, a restructuring, or a massive increase in responsibility, this is the space to catch your breath and calibrate.

What is Coaching?

It isn't a lecture or a "to-do" list. It is a high-level dialogue designed to sharpen your judgment. We look at the gaps in your current leadership system, test your assumptions about your team, and build the specific communication habits required to lead without burning out.

Partnership Details

Standard 6-month engagement with bi-weekly sessions.

Support between calls for quick gut-checks or urgent shifts.

Apply for 1-on-1 Coaching

Move from "working in the business" to "leading the business."

Frequently Asked Questions

  • We meet twice a month for 60 minutes. Most leaders find that the hour spent coaching actually saves them 5–10 hours of reactive firefighting and second-guessing later in the week.

  • Every session is a little different, but the rhythm is usually the same. We start with a real check-in, dig into whatever is front of mind, and work through it together. I ask the questions that help you see what you couldn't see on your own. By the end, you walk away with clarity and one concrete thing to act on. It's thinking partnership, not advice-giving.

  • No. Most of my clients are experienced directors and VPs who have hit a new level of complexity. At this stage, your technical skills are a given; your success now depends on your ability to influence people you don't directly manage and lead through a layer of other leaders.

  • Most partnerships begin with a six-month commitment. This provides enough time to move past surface-level fixes and actually install the new habits and systems that make leadership feel sustainable. Many leaders choose to extend after that to navigate their next expansion.

  • “Working with Kelleen has been such a meaningful experience. She’s helped me discover new tools and refine the ones I already had to better navigate my leadership challenges. What I appreciate most is how she helps uncover the real root of an issue and guides me to find the right way to work through it. Our conversations have also made me feel seen and understood — it’s been such a relief to know I’m not alone or “crazy” for the struggles I face. I’m so grateful for her insight, empathy, and the space she creates for honest reflection and growth."

    Andrea A., Global IT Director

  • "I landed my dream job and I don't think I get there without Kelleen. She redid my resume, helped me figure out a counteroffer I had no idea how to handle, and I felt confident the whole way through. Really glad I had her in my corner."

    Lawrence L., Senior Engineer

  • "I was dealing with a really stressful situation with a graduate program application and didn't know how to handle it. Kelleen helped me think through my approach in a way that felt strategic but also really human. By the end I felt prepared and clear-headed in a way I wasn't expecting. The outcome was great, but honestly what stuck with me was how much more confident I felt going into it."

    Amanda G., Graduate Student

  • "I was in the middle of a major career change and honestly didn't know which way was up. Working with Kelleen gave me a framework to think through where I was headed and the confidence to actually move forward. She has a way of meeting you where you are and helping you find clarity without making it feel overwhelming. I left our sessions with direction I didn't have before."

    Holly H., Senior Audit Consultant