How to ask your employer to cover coaching sessions

90% of my clients have their employer cover the cost

Most companies and organizations have professional development budgets. If you’re in a leadership or management role, many are willing to go beyond conferences and trainings for 1:1 coaching, especially when you make a solid case for how it will benefit them.

Here’s a compelling stat: 30-40% of Director-level leaders and above are actively working with a coach. Data on nonprofit, NGO, and social enterprise leaders is less abundant, but there is evidence of coaching gaining traction in these sectors as a way to address the unique challenges leaders face, including resource constraints, burnout, and complex stakeholder management.*

Why Coaching Is a Win-Win

When you work with a coach, you gain tools to:

• Lead with greater clarity, confidence, and resilience.

• Tackle challenges proactively instead of reactively.

• Strengthen your influence and relationships at work.

It’s not just about leveling up for you. Investing in your highest-impact people pays off big time—boosting culture, retention rates, and overall outcomes.

an email template to get the ball rolling 👇

Hi [manager name],

I would like to work with an Executive Coach, and am wondering if [company/organization name] is open to covering the cost of my coaching sessions?

Lisa Higgins runs a coaching practice where she works with leaders and teams to unlock doors to growth, cultivate relationships that work, and grow the inner skills required for long-term success and impact.

Lisa’s 1-on-1 coaching program spans 6 months and includes:

• 2 private (60 min) coaching calls/month

• Unlimited email support between sessions

• Enneagram assessment and CliftonStrengths assessment

Each session is customized to my goals and has action items between sessions. It’s designed to improve my skills as a leader [might state a goal or 2] and to benefit [company/organization in X ways].

The cost of the program is [$x,xxx]. You can read more about Lisa’s offerings here.

What do you think?

Thank you,
[Your name]

*Many fellowships and grantee programs are incorporating coaching and emphasizing its transformative impact on well-being, human capacity, and mission advancement. If you want support advocating for funder support contact me.

Unlock New Possibilities with the Enneagram

When you find yourself spinning, feeling frantic, overly urgent, or stuck—it is a sign you are hanging on tight to a version of how things should or need to be. There is nothing wrong with having a vision or a goal in mind, but it is impossible to be your most creative and compassionate self when you clinging to control.

Each Enneagram Type has a tendency to hold tightly to a narrative of how they and the world should be.

What new possibilities open up when you let go just a little bit?

Type 1 - I release driving myself and others to be perfect.

Type 2 - I release caring for and helping others before myself.

Type 3 - I release the need for others to deem me successful and accomplished.

Type 4 - I release my focus from what is missing or lacking.

Type 5 - I release the need to withdraw until I have full and complete understanding.

Type 6 - I release preparing for all the uncertainties and worst-case scenarios.

Type 7 - I release the need to seek new and exciting experiences.

Type 8 - I release needing to be strong and in control.

Type 9 - I release the need to avoid conflict.

Connect with me to learn more.

Read about the Enneagram as a game-changing tool for leaders and teams here.

Listening Filters by Enneagram Type

A filter is an internal lens that influences what we hear and how we respond. If we are not aware of our filters, we can miss the speaker’s true intent, their underlying emotions and needs. It takes awareness to see and courage to let go of our listening filters. And doing so is a key ingredient to connecting and communicating effectively.

Our Enneagram Type reveals common (not prescriptive) listening filters. Do you recognize yourself here? In your next conversation, check to see what you might be filtering for. Then ask yourself, “What does the speaker want or need from me as a listener?”

TYPE 1 - Ones tend to filter the world through the lens of perfecting and correctness. They listen for errors, inconsistencies, and areas that need improvement.

TYPE 2 - Twos tend to filter through the lens of relationships and connection. They listen for cues on how they can help or support others.

TYPE 3 - Threes tend to filter through the lens of success and achievement. They listen for opportunities to excel, gain recognition, and enhance status.

TYPE 4 -Fours tend to filter through the lens of identity and authenticity. They listen for expressions of individuality, emotional depth, and unique perspectives.

TYPE 5 - Fives tend to filter through the lens of knowledge and understanding. They listen for information, patterns, and insights that help them make sense of the world.

TYPE 6 - Sixes tend to filter through the lens of security and trust. They listen for signs of safety or potential threats, seeking reassurance and certainty.

TYPE 7 - Sevens tend to filter through the lens of excitement and possibility. They listen for opportunities for fun, adventure, and new experiences.

TYPE 8 - Eights tend to filter through the lens of power and control. They listen for signs of strength, authenticity, and they may challenge anything they perceive as weakness or injustice.

TYPE 9 - Nines tend to filter through the lens of harmony and peace. They listen for common ground, how to avoid conflict and maintain connection.

Connect with me to learn more.

Read about the Enneagram as a game-changing tool for leaders and teams here.

Why the Enneagram

I often hear from clients how “spot on” the Enneagram is in revealing their self-sabotaging patterns and how “game-changing” it is for uncovering the root of conflicts with colleagues and partners.

In contrast to other assessments that look at behavior, the Enneagram examines motivation–why you think, feel and act the way you do. There are 9 Enneagram Types. Your Type is not a box you are stuck in, but rather as a starting point. A place to begin understanding your emotional and mental patterns - to see the paths you travel frequently–to consider what’s working, what’s resulting in deeper connection, peace, and creativity–what’s blocking you. Working with the Enneagram then provides a map (quite literally) for growing beyond limitations, for self-leadership, and for understanding and building healthy relationships.

LEADERSHIP DEVELOPMENT

Most assessments say, “Here are your strengths! Yay!” but neglect to mention the fine print: when strengths go into overdrive, they can become liabilities. You might find yourself careening toward burnout or unintentionally straining relationships. The Enneagram takes a different approach. It helps you nurture your strengths in a balanced and intentional way, while also shining a light on blindspots and overcoming unseen barriers to your goals. Most importantly, it cultivates authenticity and connection—both at work and at home.

For one of my clients, an Enneagram 2, this meant learning to trust her intuition and inner knowing. She was a deeply empathetic leader, but her tendency to help everyone left her stretched thin. Through our work, she discovered how to balance her natural compassion with decisive action. By letting go of the need to solve every problem for every person, she not only delivered better on her organization’s mission but also freed up precious time and energy to truly enjoy her work—and her life.

The Enneagram is especially valuable when emotions and stakes are high. It helps you restore balance, gain clarity, and take courageous action while staying deeply connected to both yourself and your team. I worked with a bold and decisive Enneagram 8 leader who thrived in high-stakes situations but often struggled with team dynamics. Their intensity sometimes left colleagues feeling overshadowed or unheard. Through the Enneagram, they realized their drive to protect and take charge came from a deep desire to see everyone succeed. By cultivating self-awareness, they learned to dial back their intensity and create more space for collaboration. This shift restored trust and balance in the team while empowering them to act courageously with the full buy-in of their colleagues.

The Enneagram also offers profound insight into your team members’ strengths, how they respond under stress, and what makes them feel valued and purposeful. These insights can transform performance conversations into opportunities for growth and connection. One manager I worked with had an Enneagram 7 on her team who brought incredible energy and creativity to brainstorming sessions but struggled with the follow-through required during long execution phases. Under stress, this team member often shifted focus to new, exciting ideas, unintentionally leaving others to carry unfinished work. The manager, through the lens of the Enneagram, recognized that this behavior stemmed from the 7’s need to avoid feeling trapped or bored. By acknowledging their contributions and involving them in energizing aspects of projects—like ideation or client engagement—the manager also introduced clear accountability structures to keep tasks on track. This approach made the 7 feel more purposeful and valued while creating a better balance across the team, ensuring projects started and finished with equal enthusiasm.

TEAM DEVELOPMENT

Integrating Enneagram insights into team dynamics not only enhances effectiveness but also nurtures stronger relationships and sense of belonging across the group. You can dig into your team’s core values, strengths, gaps, and blindspots to uncover the hidden forces at play. One leadership team discovered that their struggle with innovation was rooted in an unspoken discomfort with tension. In a group where everyone valued harmony and avoided conflict, they hesitated to “rock the boat,” even when it was stifling progress. By recognizing this dynamic, they introduced intentional practices and rituals that helped them surface disagreement in a constructive way. This simple yet powerful shift deepened trust and fostered a growth-oriented culture—one that embraced individual contributions while strengthening the team’s interdependence.

The Enneagram also helps leaders spot gaps in team composition and challenges that may be holding the team back. One manager noticed that no one on her team was naturally inclined to question assumptions or challenge the status quo. This gap, once identified, led her to recruit someone with a more critical, analytical perspective. The result? A more balanced and effective team—one that felt seen and valued and was empowered to approach problems with a diversity of thought.

Working with the Enneagram builds emotional intelligence and equips your team with the tools to foster psychological safety, inclusivity, and trust. By weaving Enneagram insights into the fabric of your team’s development, you’ll create a culture that not only embraces diversity, equity, and belonging but also delivers exceptional results.

A note on my approach: My work with the Enneagram deeply considers our cultural identities, life experiences, and socialization. Recognizing that our formative experiences of seeking safety, belonging, and security vary greatly based on factors such as family, religion, race, class, and gender, I tailor my approach to honor and integrate these diverse identities. 

I offer Individual and Team Enneagram Reports. Connect with me to learn more.

Preparing for a Hard Conversation: 4 Questions To Ask Yourself

How can I make this conversation a little easier and still get my message across? It's one of the most common things I coach clients through. These 4 questions (I won't call them simple!) will make your next hard conversation easier and a lot more generative - for you and for them:

1. What feelings do I have about this person/situation?

2. What does 100% responsibility look like for me?

3. What is my desired outcome? Be specific. Clear is kind.

4. Am I prepared to listen with the same attentiveness with which I want to be heard?

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1. What feelings about this person/situation do I have?

Acknowledging and working through your own stuff enables you to show up to the conversation calm, confident, and responsive instead of reactive. Giving your emotions (energy in motion) some space helps keep them from hijacking you during the conversation. Learn more about the importance of leaders feeling their feelings in this video from The Conscious Leadership Group.

2. What does 100% responsibility look like for me?

Leaders are often tempted to take either more or less than their share of responsibility. Consider this question carefully. Try separating facts from judgments and assumptions. Get objective feedback from a mentor or coach. Taking 100% responsibility keeps you from falling into the trap of blaming, complaining, fixing, or giving up. It also helps you get clear on your desired outcome.

3. What is my desired outcome? Be specific. Clear is kind.

Defining and anchoring in your outcome throughout the conversation will keep you focused and productive, and help stabilize the emotional dynamic. For example, 

• You’re having this conversation because you need to give feedback that’s not so fun to share, but you’re giving it to them because you’re committed to their success. 

• You’re having this conversation because something needs to change.

• You’re having this conversation because you’re committed to making the relationship better.

Read more about “Clear is kind. Unclear is unkind.” from leadership guru Brené Brown.

Consider the concept of Radical Candor from author Kim Scott. 

4. Am I prepared to listen with the same attentiveness with which I want to be heard?

We all want to be met with generous and curious listeners. Your goal is to bring this attitude to the conversation - rather than the common traps of listening to fix, diagnose, defend, calm, debate, or correct. Attentive listening is a fundamental tool for leaders to build trust, to create inclusive and equitable environments, to gain valuable insights and enhance problem-solving.