Supervisor Coaching

Practical, one-on-one leadership development for supervisors and managers. Practical, one-on-one leadership development for supervisors and managers.

Promotion is a decision. Preparation is a responsibility.

Knowing the work and leading the people are different responsibilities. A promotion gives someone authority. It does not provide every skill needed to use it well.

Montgomery Hassell’s Supervisor Coaching provides individualized development for new supervisors, emerging leaders, and experienced managers who need focused coaching. The work centers on their responsibilities, development needs, and real workplace situations.

We offer four- and six-session engagements. Each coaching session lasts no longer than one hour.

Promotion is a decision. Preparation is a responsibility.

For new and emerging leaders

Prepare for the responsibilities that come with leading people: setting expectations, supervising former peers, giving feedback, addressing performance concerns, and following through. Coaching provides a place to ask questions, learn the fundamentals, and practice before facing the situation at work.

For experienced supervisors and managers

Work on specific challenges such as avoiding difficult conversations, communicating under pressure, listening before reaching conclusions, delegating responsibility, or holding people accountable consistently.

The objective is not to lower the standard. The goal is to improve how the supervisor leads people while maintaining that standard.

Four or six sessions. A defined development focus.

Four-session engagement

Focused coaching around a clearly defined development need, with instruction, practice, and workplace application.

Six-session engagement

Additional time to work through development priorities, practice leadership situations, review workplace application, and reinforce the learning.

We discuss the need and recommend the appropriate starting point. Sessions are scheduled by agreement, with time between meetings to apply the work. No coaching session exceeds 60 minutes.

The scope, schedule, fee, and sponsor communication are agreed upon before coaching begins. Additional coaching may be arranged when appropriate.

How the coaching works

Understand the person and the situation

We begin with organizational leadership to understand the concerns, expectations, and support available. A validated behavioral assessment and individual discussion help identify the participant’s strengths, natural tendencies, and development needs.

We consider the participant’s perspective alongside the organization’s concerns, then establish a practical development plan with clear, observable objectives.

Teach, prepare, and practice

Sessions combine applicable leadership concepts, honest feedback, and practice. The participant works through realistic situations: what to ask, how to listen, what needs to be clear, and how to follow through.

The first time a supervisor practices a difficult conversation shouldn’t be with the employee.

Coaching provides an opportunity to prepare that conversation, try an approach, receive feedback, and work through it again.

Apply the learning at work

Practical assignments connect the sessions to the job. After the first session, each meeting begins with a review of previous learning, assignments, workplace experiences, and questions. Current concerns become part of the discussion rather than being set aside for a generic lesson.

Review progress and reinforce the work

We review progress against the agreed objectives and identify what needs continued attention. Communication with organizational leadership follows the arrangements established in advance and addresses progress, next steps, and reinforcement on the job.

One leadership standard: Grace & Truth

The coaching is grounded in a practical standard for how leaders treat people and address what needs to happen.

Grace

Listen, understand, and value people while preserving dignity and respect.

Truth

Establish clear expectations moving forward, accountability, consequences, and follow-through.

Grace is not avoiding a difficult issue. Truth is not permission to be harsh. Leaders are expected to do both: understand the person and address the responsibility.

This standard applies at every level of the organization—not only to the person receiving coaching.

Clear responsibilities on all three sides

Montgomery Hassell

We provide the development plan, practical instruction, preparation, candid feedback, and opportunities to practice. We assess progress honestly and identify where further work is needed.

The participant

The supervisor is responsible for participating, considering feedback, completing agreed assignments, and applying the concepts at work. Coaching requires more than attending the sessions.

Organizational leadership

Leadership is responsible for modeling the expectations, providing appropriate resources and authority, reinforcing the desired behavior, and holding the supervisor accountable. Coaching does not replace the supervisor’s manager.

We are responsible for the quality of the coaching we provide. Individual behavioral change and organizational performance improvement cannot be guaranteed.

Your coach: Tim Prillaman

Tim Prillaman is Senior Managing Director of Montgomery Hassell, Inc., a former senior human resources executive, author of The Narrow Path to an Engaged Workforce™, and creator of the Tailored Leadership™ leadership development system.

His approach draws on decades of practical work in leadership development, employee relations, performance management, and organizational effectiveness. He has worked with supervisors and managers when employee concerns, performance expectations, and operating demands all needed attention.

“My role is to be honest about what needs attention, teach what applies, and help the supervisor practice using it. The objective is not just to understand leadership. It is to apply it when the situation gets real.”

Questions before getting started

Do we need to purchase Tailored Leadership?

No. Supervisor Coaching stands on its own. It may complement Tailored Leadership or your existing development efforts, but no other program or book is required.

What information is shared with the organization?

Confidentiality and communication boundaries are established before coaching begins. The participant and organizational sponsor understand what will be shared and how progress will be discussed.

What falls outside the coaching engagement?

Supervisor Coaching is professional leadership development—not psychological counseling, an HR investigation, or a substitute for management decisions. Employment decisions remain the organization’s responsibility.

Start with a conversation about the need.

Tell us about the role, the development need, and what you would like the supervisor to handle more effectively. We will discuss whether coaching is appropriate, which engagement makes sense, and what each party should expect.