One-to-One Leadership Coaching

Leading people requires a different set of skills than being good at your job.

Maybe you’re managing people who used to be your peers. Maybe you’re avoiding a difficult conversation, struggling to delegate, or wondering how to hold someone accountable without becoming a micromanager.

You don’t have to work through it alone. My one-to-one leadership coaching gives you dedicated time to examine the challenge, explore your options, and develop a practical plan for what comes next.

We can work through situations such as:

Leading former peers and establishing professional boundaries.

Preparing for difficult conversations.

Setting clear expectations and following through.

Delegating without taking the work back.

Communicating with your team and your supervisor.

Developing your approach as a new leader.

Bring a specific situation. We’ll work toward a clear next step you can put into practice.

Before your session, you’ll complete a short questionnaire about your role, your challenge, and what you want to accomplish.

During our conversation, we’ll examine what is happening, identify what is within your control, and develop your next steps. When useful, I may also offer a practical framework or a perspective drawn from my leadership experience. I’ll distinguish that guidance from the coaching conversation.

You’ll leave with an action plan you helped develop—not a generic list of leadership tips.

I bring more than two decades of U.S. Army leadership experience, including communications, training, and organizational oversight.

I’m also the author of Life Skills You Didn’t Know You Needed and host of Tim Stating the Obvious. Through approximately 130 interviews with CEOs, executives, founders, and other leaders, I’ve explored how people lead, make decisions, and navigate challenges.

My approach combines thoughtful questions, direct conversation, and practical application. The goal is to help you develop your own judgment—not become dependent on mine.

One focused conversation about a leadership challenge you need to address.

Includes:

A short pre-session questionnaire.

One 60-minute private video session.

A written summary of the next steps we agree on.

One follow-up email exchange within seven days to clarify the plan.

Best for: preparing for a difficult conversation, thinking through a decision, or getting an outside perspective on a specific situation.

Six private sessions over 12 weeks to help you apply leadership skills to the situations you’re facing at work.

Includes:

Six 60-minute private video sessions.

An initial discussion to establish your goals.

Practical exercises or templates selected for your needs.

Written action steps after each session.

One email check-in between sessions, with a response within two business days.

A final review of your progress and next priorities.

Investment: $1,200 paid in full, or three monthly payments of $400.

Best for: newly promoted managers who want ongoing support as they establish expectations, build working relationships, and develop their leadership approach.

Schedule a complimentary 15-minute fit call to discuss what you’re looking for and whether my approach is appropriate for your needs. This is an introductory conversation, not a coaching session. There is no obligation to enroll.

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