Leadership Development Facilitator and Coach (Part-Time)

Leadership Development Facilitator and Coach (Part-Time); North Chicago (IL); On-site; USD 39,000 - 83,000; Part time

Job summary

Aha! Leadership is seeking an experienced facilitator to join as a part-time employee to lead the majority of client workshops and leadership programs, both in person and virtually.

The role offers independence, visibility, and collaboration with a Project Manager for session logistics. The right candidate will have a minimum of three years of full-time facilitation experience or seven years in related learning roles, with strong communication skills and the ability to engage senior leaders.

Qualifications

• At least three years of full-time experience facilitating training or workshops for adult learners in a professional setting.
• Confidence leading groups of varying sizes and seniority levels, in both in-person and virtual formats.
• Natural ability to read the room, adjust in the moment and guide meaningful conversations.
• Engage skeptical participants with credibility, warmth and relevance.
• Strong communication and relationship skills, with a genuine interest in helping people grow.
• High degree of flexibility and calm, solutions-focused approach when plans change or issues arise.
• Detail-oriented approach to managing engagements, from updating project management tools to tracking participation.
• Willingness to weekly travel to client sites, primarily in Michigan and Illinois with some national travel.

Responsibilities

• Facilitate leadership development workshops, cohort programs and team sessions for corporate clients, both in person and virtually.
• Use a storytelling approach to facilitation with real-world examples and personal experience.
• Create a psychologically safe learning environment where participants feel comfortable sharing and practicing new skills.
• Prepare for engagements by learning client goals and tailoring examples to the group.
• Collaborate with Project Manager on session logistics and materials to enable focus on delivery.
• Provide 360-degree feedback assessments and debrief conversations to inform development steps.
• Offer one-on-one coaching to leaders with specific development goals.
• Keep courses current and help build new concepts when appropriate.
• Provide thoughtful feedback after sessions on group dynamics and themes for growth.
• Stay current on trends in talent development and bring insights to programs.
• Represent Aha! Leadership with warmth, professionalism, and consistency to clients.

Skills

Facilitation

Group leadership

Reading the room

Engaging skeptical participants

Communication skills

Flexibility

Travel readiness

Relationship building

Job description

About Aha! Leadership

Aha! Leadership is a small, close-knit, woman and minority owned leadership development firm that organizations bring in as an outside partner to deliver onsite and virtual training, coaching and assessment-based programs for their leaders and teams. We have been helping leaders grow since 2008, and most of our clients have been with us for years, which comes from the relationships we build and the care we put into every engagement.

About the role

We are looking for an experienced, warm and engaging facilitator to join our team as a part-time employee, leading the majority of our client workshops and leadership programs. This is a wonderful fit for someone who loves being in the room with leaders, who brings solid facilitation experience, and who wants the stability of a consistent schedule along with the variety of working with organizations across many industries.

We work hard to practice the same things we teach. We value curiosity, honest conversations and genuine care for the people in the room, and we believe the best learning happens when participants feel seen, challenged and supported all at once. Our facilitators are trusted to bring their own personality and experience to our programs, and we collaborate closely on content, share what we learn from each group, and celebrate the moments when something finally clicks for a leader.

Because we are a very small team with no large department behind the scenes, this role comes with a lot of independence and visibility. You will report directly to the business owner. You will also partner with our Project Manager, who handles session logistics and coordination so that your time and energy can go toward preparing for and delivering great sessions. The right person will be comfortable working with senior client leaders, including members of the C-suite, and taking ownership of their engagements from preparation through follow-up. Client needs can shift quickly, so this role also calls for a high level of flexibility, whether that means adapting to a change in plans, accommodating a last-minute request or problem solving in the moment when something unexpected comes up. If you enjoy the flexibility and connection of a small business and like knowing that your work makes a direct difference, you will feel right at home here.

What you'll do

• Facilitate leadership development workshops, cohort programs and team sessions for corporate clients, both in person and virtually. Topics range from communication styles, emotional intelligence and productive conflict to giving and receiving feedback, delegation, accountability, team cohesion, leading across generations and more


• Use a storytelling approach to facilitation, drawing on real-world examples and personal experience to make concepts memorable and relatable for participants


• Create an engaging and psychologically safe learning environment where participants feel comfortable sharing, practicing new skills and reflecting on their own leadership


• Prepare thoughtfully for each engagement by learning the client's goals, reviewing participant assessments and tailoring examples and activities to the group in the room


• Partner directly with our Project Manager, who coordinates session logistics, scheduling, participant materials and on-the-ground support, so that you can focus on preparation and delivery


• Administer 360-degree feedback assessments and lead debrief conversations that help leaders understand their results and identify meaningful next steps


• Provide one-on-one coaching to individual leaders with specific developmental goals, helping them focus on their growth areas, work through challenges and make meaningful progress


• Keep our existing courses current by updating content, activities and examples as needed, and bring in new concepts or ideas you believe would strengthen a program. Building new courses from scratch is not a core part of this role, although we welcome that experience if you have it


• Provide thoughtful feedback after each session, sharing observations about group dynamics, participant engagement and key themes that emerged, along with recommendations for continued growth


• Stay current on trends, research and best practices in the talent development space, and bring relevant insights into our programs


• Represent Aha! Leadership with warmth, professionalism and consistency, building strong relationships with the clients who return to us year after year

Schedule, Location and Time Off

Employment type: Part-time employee
Hours: 20 to 24 hours per week
Core schedule: Sessions are primarily held Tuesday through Thursday, though they may occasionally take place on a Monday or Friday at a client's request. Mondays and Fridays may also be used for travel, session preparation and follow-up work as needed.
Location: Detroit or Chicago area preferred; other locations considered for qualified candidates
Travel: Weekly travel to client sites, with travel time and expenses paid in accordance with the Aha! Leadership travel policy
Compensation: Competitive hourly pay based on experience. We are happy to share the pay range before our first conversation, so you can decide whether the role is a good fit before investing your time.
Paid time off: 18 days of PTO per calendar year, prorated in your first year
Paid year-end closure: Two paid weeks off at year-end, in addition to PTO
Paid holidays: Martin Luther King Jr. Day, Presidents' Day, Memorial Day, Juneteenth, Labor Day, Veterans Day, Thanksgiving and the day after Thanksgiving
Target start date: January 2027, but can be flexible

Aha! Leadership is an equal opportunity employer, and we welcome applicants of all backgrounds.

Required

• At least three years of full-time experience facilitating training or workshops for adult learners in a professional setting, or seven years of full-time experience in a role that included facilitation and learning and development


• Confidence leading groups of varying sizes and seniority levels, from frontline supervisors to senior leaders, in both in-person and virtual formats


• A natural ability to read the room, adjust in the moment and guide meaningful conversations, including the moments that feel a little uncomfortable


• The ability to engage even the most skeptical participants, including those who arrive with a “prisoner” mindset because they were voluntold to attend, and to win them over with a mix of credibility, warmth and relevance


• Strong communication and relationship skills, with a genuine interest in helping people grow


• A high degree of flexibility and a calm, solutions-focused approach when client plans change, last-minute requests come in or issues arise before or during a session


• A detail-oriented approach to managing engagements, from keeping our project management tool current and tracking participation to keeping all stakeholders aligned so that nothing falls through the cracks


• Comfort with weekly travel to client sites, primarily in Michigan and Illinois with some travel nationally, along with a valid driver's license and the ability to travel by air

Preferred

• Experience facilitating leadership development training specifically, or time spent in a leadership role yourself where you managed and developed people


• Experience providing one-on-one leadership coaching


• Experience administering and debriefing 360-degree feedback assessments


• Everything DiSC certification (Aha! can support certification after hire)


• Five Behaviors certification (Aha! can support certification after hire)


• Experience working with clients across industries such as manufacturing, automotive, healthcare and tech


• A background in HR, learning and development or organizational development


• Experience in curriculum or instructional design