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How to Find & Qualify the Best Executive Coach (10 Questions)

by Thuy Sindell, PhD. and Milo Sindell, MS.

Executive coaching is an extremely effective method to quickly up-level a leader’s skills, boost team productivity, and increase overall company effectiveness.

When it comes to executive coaching, progress is a just few coaching sessions away. When you find & hire an executive coach - the right executive coach - performance achievements unlock, organizational impact is felt, and company goals are achieved.

However, it can be difficult to choose the right coaches who will truly take leadership development to the next level and provide a level of coaching that is not only transformative for the leader but also leads to measurable business impact and executive coaching ROI.

There are an estimated 50,000 thousand executive leadership coaching experts out there, yet only a small percentage of these coaches are able to deliver the results that leaders, Human Resources (HR), and companies depend on.

Read on for our comprehensive guide for individual leaders and HR Professionals on how find, identify & hire the right leadership coach for your organization and measure the impact of this investment.

Executive Coaching Stats

According to Forbes, over 70 percent of those provided a coaching opportunity by their business improved work performance, built better relationships & had better communication skills.

Furthermore, companies that offered executive coaching to the leadership teams reported an 86 percent return on their investment.

HR professionals report that employees who embrace coaching services are less likely to procrastinate and are more likely to achieve their goals than employees who do not receive coaching.

How to Find & Qualify the Best Executive Coach

What is Executive Coaching?

Executive coaching is the process of a leader & coach working together over the course of 3-12 months to achieve a specific set of objectives. These objectives often center on specific behavior and leadership competencies. As part of the coaching process, specific objectives and business metrics can be linked to successful changes in behavior.

The Executive Coaching Process

Traditionally, the coaching process begins by getting a baseline of the leader’s current strengths and opportunities through a 360 assessment. Additional assessments can also be used to further understand specific personality traits and conscious/subconscious motives that influence a leader’s behaviors.

From these assessments, 2-3 three objectives are identified. An alignment meeting takes place between the coach, leader, leader’s manager, and HR partner. A development plan is completed outlining goals, metrics, and expected benefits of attaining the goal.

It’s critical to ensure all stakeholders and leadership are aligned on the executive coaching goals & process. Once the entire team is aligned the coaching can be initiated & meetings proceed to take place at regularly scheduled intervals.

How to Find & Qualify the Best Executive Coach

How to Maximize Your Coaching Investment: Our Framework for Finding & Evaluation the Best Executive Coach for Your Needs

In the ever-evolving landscape of business leadership, the journey to becoming an exceptional leader is a perpetual one. One of the most effective tools for accelerating this journey is executive coaching.

Executive coaching offers personalized guidance, helps hone leadership skills, and unlocks untapped potential in high-level leaders.

However, finding the top leadership coaches to choose from and identifying the perfect executive coach for your specific needs requires a meticulous approach that takes into account various factors.

This article presents an in-depth framework to assist Human Resources professionals and individuals in identifying, evaluating, and selecting the right executive coach and coaching firm for their specific needs, what to look for when choosing an executive coach, and important questions to ask when hiring an executive coach. See our process below.

How to Find & Qualify the Best Executive Coach

1. Self-Assessment: Unveiling Leadership Goals

Individual Leaders - A thorough self-assessment forms the cornerstone of effective executive coaching. It’s not only about acknowledging your strengths but also confronting your vulnerabilities. Reflect on past experiences, challenges, and feedback to identify areas in which you aspire to grow.

By understanding your leadership goals, you lay the foundation for a targeted coaching journey that brings out your best self. For instance, consider instances where you faced obstacles in decision-making or communication, and aim to address these through coaching. This introspection not only drives personal development but also enhances your ability to articulate your coaching needs to potential coaches.

HR Professionals - While individual leaders embark on their journeys, HR professionals have a unique opportunity to conduct a macro-level self- assessment of leadership needs within their organization. This requires collaboration with various stakeholders, including senior management, department heads, and teams, to gather insights into the skills and competencies needed at different levels.

Through surveys, interviews, and data analysis, HR professionals can ascertain the overarching leadership challenges that coaching initiatives should address. By involving key stakeholders in this process, HR can ensure that coaching efforts align with the strategic objectives of the organization and address critical leadership gaps.

How to Find & Qualify the Best Executive

2. Define Your Criteria: Identifying Essential Traits

Individual Leaders - As you outline your criteria for an ideal coach, prioritize their experience over credentials. An experienced coach who has weathered leadership challenges can provide insights and strategies that align with real-world scenarios. Additionally, consider their communication style – do you prefer direct feedback, a more empathetic approach, or a balance between the two? This criterion ensures that the coaching experience aligns with your preferences and learning style. Also, examine whether they possess a background in your industry or have dealt with similar challenges to what you’re facing. This industry alignment can facilitate more relevant guidance tailored to your leadership role.

HR Professionals - Define criteria that resonate with your organization’s leadership development strategy. Consider a coaching firm’s track record in driving measurable change within diverse leadership roles. Assess their ability to customize coaching programs, as this ensures that coaching initiatives adapt to the unique needs of different leaders and departments. Collaborate with various departments to create a comprehensive checklist of traits that align with your organization’s leadership culture. By involving a cross-functional team in this process, HR can ensure that coaching efforts cater to the distinct needs and nuances of different departments and leadership levels.

How to Find & Qualify the Best Executive

3. Research and Referrals: Leveraging Networks

Individual Leaders - Networking not only exposes you to potential coaches but also offers insights into the coaching process itself. Engage with industry events, workshops, and online communities to gather recommendations and first-hand accounts of transformative coaching experiences. Participating in leadership seminars or webinars allows you to connect with other leaders who may have engaged in coaching and can share their experiences and recommendations. Additionally, consider seeking mentors within your industry who can guide you in selecting a coach aligned with your aspirations.

HR Professionals - Leverage your professional network to gather recommendations for coaching firms. Collaborate with industry peers to exchange experiences and insights about different coaching providers. Look beyond the surface and inquire about the long-term impact of coaching engagements they’ve been part of. Reach out to colleagues in the HR field, attend industry conferences, and tap into online HR communities to gather a diverse range of referrals. Engage with professionals who have first-hand experience with specific coaching firms to gain valuable insights into their methodologies and impact on leadership development.

4. Credentials and Expertise: A Blend of Experience and Skill

Individual Leaders - While certifications may offer a sense of credibility, prioritize practical experience. A coach who has navigated leadership challenges can offer real-world insights that resonate deeply. Inquire about their journey, the leadership roles they’ve held, and the complex situations they’ve managed. These stories not only inspire but also build confidence in their ability to guide your growth. Additionally, seek coaches who engage in continuous learning and stay updated on the latest leadership trends. This commitment to ongoing education showcases their dedication to staying relevant in a rapidly evolving business landscape.

HR Professionals - Evaluate coaching firms not solely based on the number of clients they’ve served, but the depth of impact they’ve made. Look for firms that showcase a spectrum of case studies across different industries, demonstrating their versatility in addressing various leadership challenges. Review their consultants’ profiles and explore their backgrounds to ensure they possess the requisite experience and expertise to address the multifaceted leadership landscape within your organization. Consider engaging in conversations with potential coaches to gauge their ability to contextualize their experience to your organization’s needs.

5. Compatibility: Forging Rapport

Individual Leaders - The coaching journey is intimate, requiring a harmonious relationship between coach and leader. During initial conversations or discovery sessions, pay attention to how comfortable you feel sharing your aspirations and vulnerabilities. The coach’s ability to create an environment of trust and psychological safety is pivotal for the coaching relationship’s success. Ask about their coaching style and approach to ensure they align with your communication preferences. Additionally, discuss any specific leadership challenges you anticipate facing to evaluate their ability to address these challenges effectively.

HR Professionals - Beyond individual rapport, consider the compatibility of the coaching firm with your organization’s culture. Do their values align with your company’s ethos? Are they equipped to understand and integrate your organization’s unique leadership dynamics? Request insights into how they have successfully navigated diverse organizational cultures in the past. Inquire about their process for customizing coaching programs to align with the cultural nuances of your organization and its leadership development goals.

6. Track Record: Showcasing Impact

Individual Leaders - Request specific examples of how a coach has propelled leaders like you toward growth. Inquire about the challenges those leaders faced and how the coaching intervention led to tangible improvements. A coach who can substantiate their impact with concrete anecdotes instills confidence in their ability to guide your journey. Ask for references from previous clients and engage in conversations to understand the scope of transformation achieved. Inquire about the duration of these changes and how the coach supported the sustained development of their clients.

HR Professionals - When evaluating coaching firms, request data-backed success stories that highlight their ability to drive organizational change. Look for firms that present quantifiable improvements in leadership effectiveness, team dynamics, and overall organizational performance resulting from their coaching engagements. Discuss case studies in detail to discern how they aligned coaching strategies with organizational objectives. Additionally, seek insights into how they measure and track the long-term impact of their coaching initiatives on leadership development.

7. Customized Approach: Tailored to Needs

Individual Leaders - Every leadership journey is unique, requiring a coaching approach that aligns with your specific goals. Seek coaches who demonstrate a willingness to adapt their methodologies based on your individual strengths and challenges. A cookie-cutter approach rarely yields transformative results. Discuss specific scenarios you’re dealing with and inquire how they would tailor their coaching to address those situations. Inquire about their process for assessing your current leadership style and identifying areas for improvement.

HR Professionals - The coaching solution you choose should integrate seamlessly with your organization’s existing leadership development initiatives. Look for firms that have a proven track record of crafting tailored coaching programs that address the specific needs of different leadership levels and roles. Collaborate with the coaching firm to co-create a roadmap that aligns with your organization’s long-term leadership strategy. Additionally, inquire about their methods for assessing the unique leadership challenges within your organization and tailoring their coaching approach accordingly.

8. Chemistry and Trust: Foundation of Progress

Individual Leaders - The coaching relationship thrives on trust. Evaluate potential coaches not only based on their expertise but also on the comfort and trust you feel in their presence. A coach who can establish an environment where you’re comfortable sharing your struggles and aspirations is primed to guide meaningful growth. Discuss confidentiality measures and express any concerns you may have about sharing personal challenges. Additionally, explore their approach to handling potential conflicts or differing viewpoints that may arise during coaching.

HR Professionals - For coaching engagements to succeed on an organizational level, it’s imperative that the coaching firm can foster trust with leaders at all levels. Choose a firm that emphasizes building a strong rapport with leaders, ensuring a safe space for honest conversations and growth. Inquire about their methods for facilitating open dialogue, managing sensitive topics, and fostering a culture of trust within coaching engagements. Additionally, discuss their approach to handling any organizational challenges that may surface during coaching.

9. Communication Skills: Guiding Growth

Individual Leaders - Communication is the conduit through which coaching insights are exchanged. Seek coaches who exhibit active listening, empathy, and the ability to pose incisive questions that prompt self-reflection. Effective communication bridges the gap between insights and actionable steps. Inquire about their approach to providing feedback and how they ensure that their guidance is understood and integrated into your leadership practices.

HR Professionals - Consider coaching firms that prioritize open and effective communication. A coaching engagement’s success hinges on the coach’s ability to navigate diverse leadership styles and personalities within your organization. Inquire about their communication strategies for working with leaders at different organizational levels, ensuring that their coaching insights resonate and drive growth across the organization. Additionally, discuss how they handle feedback and maintain ongoing communication throughout the coaching journey.

10. Goal Setting: Pathway to Achievement

Individual Leaders - Collaborate with your chosen coach to establish SMART (Specific, Measurable, Achievable, Relevant, Time-bound) goals that form the roadmap for your coaching journey. Clear goal setting ensures that you are not only growing but also progressing toward tangible outcomes. These goals serve as the compass for your coaching journey, guiding both you and your coach on the path to success. Additionally, inquire about their process for adapting goals as circumstances evolve, ensuring the coaching remains aligned with your development needs.

HR Professionals - Emphasize goal setting as a foundational aspect when engaging with coaching firms. Firms that excel in crafting coaching programs aligned with specific organizational goals demonstrate a strategic approach that permeates throughout the organization. Discuss the process for collaboratively setting goals that align with your organization’s strategic objectives and leadership development initiatives. Additionally, explore how coaching firms ensure that the goals set at the beginning of the engagement remain relevant as the organization’s needs evolve.

11. Flexibility and Accessibility: Adapting to Needs

Individual Leaders - Life is dynamic, and so is leadership. Inquire about a coach’s flexibility in accommodating your schedule, personal circumstances, and evolving priorities. A coach who can adapt ensures that coaching remains relevant amidst changing circumstances. This flexibility not only makes the coaching journey more convenient but also underscores the coach’s commitment to your growth and development journey.

HR Professionals - A coaching firm’s ability to customize its approach to fit different leadership roles, schedules, and challenges within your organization showcases their commitment to providing a flexible and impactful coaching solution. Inquire from successful professionals about their methods for tailoring coaching engagements to the unique needs of different leaders and departments. Additionally, discuss how they handle unforeseen changes in organizational priorities and how their coaching approach adapts accordingly.

12. Contract & Fees: Transparent Agreements

Individual Leaders - Before committing to a coaching engagement, first gain clarity and a comprehensive understanding of the coaching process. Clarify the frequency of sessions, their duration, the fees involved, and any supplementary resources provided. A transparent agreement sets clear expectations and avoids surprises down the line. This transparency not only builds trust but also ensures that both parties are aligned on the terms of the engagement.

HR Professionals - Choose coaching firms that are forthright in discussing costs, contract terms, and the scope of services covered. Transparent agreements prevent misunderstandings and lay the groundwork for a productive collaboration. Engage in thorough discussions about the financial aspects of the coaching engagement, and inquire about any potential additional costs that may arise throughout the process. Additionally, discuss their approach to addressing any changes in scope or unexpected circumstances that may affect the agreement.

13. Gut Feeling: Trusting Instincts

Individual Leaders - Intuition plays a crucial role in selecting a coach who resonates with your aspirations. If you sense a strong connection and have great coaches and believe in their ability to guide your growth, your intuition is likely steering you toward a compatible coaching partnership. Pay attention to how you feel during initial conversations with potential coaches and trust your instincts to guide you toward the coach who aligns with your values and objectives.

HR Professionals - Your intuition comes into play when evaluating coaching firms. A strong resonance with a firm’s values, approach, and commitment to driving meaningful change indicates a promising partnership. Trust your instincts as you engage in discussions with representatives from coaching firms. Consider whether their approach aligns with your organization’s culture and whether you have confidence in their ability to contribute to your organization’s leadership development goals.

14. Measurement & ROI: Quantifying Success

Individual Leaders - Inquire about a coach’s methodology for tracking your progress and assessing the value added to your leadership journey. A coach who integrates measurement and assessment into the coaching process ensures that growth is not just anecdotal but measurable. Discuss how they plan to gather feedback from you and your colleagues, as well as how they intend to translate these insights into quantifiable measures of success.

HR Professionals - Prioritize coaching firms that possess a robust framework for measuring coaching outcomes. Demonstrable ROI through quantifiable metrics underscores a coaching firm’s commitment to driving tangible organizational growth. Inquire about their approach to measuring the impact of coaching on leadership effectiveness and organizational performance. Explore their methods for gathering feedback from leaders and teams and how they translate these qualitative insights into quantitative metrics that showcase the value of coaching initiatives.

How to Find & Qualify the Best Executive Coach

What Questions Should You Ask a Potential Executive Coach in an Interview?

When investing in a coach, it’s important to properly research potential subjects and make sure they fit your business needs as closely as possible.

Asking good questions during interviews allows you to gain further insight and makes the decision-making process much easier.

Wondering what questions to ask an executive coach when selecting & interviewing potential coaches? The following questions will provide a baseline for vetting and identifying the best executive coach for your leaders & company.

1. What’s Your Educational Background?

The point of this question is straightforward: To understand the coach’s formal education, coach certification, and interests. Certification should not be a requirement of whether or not you work with them. A certified coach is not mandatory - many of the best executive coaches are not certified and instead have hands-on leadership experience.

2. What Coaching Methodology Do You Use?

There are a number of different executive coaching methodologies. The important aspect of this question is to determine that 1., the coach actually follows a process and 2., understanding how the coach achieves results. Often, many coaches will not have a methodology and approach coaching as an open and fluid process. We have found that having a methodology is vital to effective and clear coaching results.

3. How Many Leaders Have You Worked With?

A qualified executive coach should be able to provide data on how many leaders they have coached and businesses they have helped, and the outcomes of their engagement.

You will want to hear from the coach the results the leaders experienced as well as the impact of the coaching on team and business results. Without a measurable outcome achieved an engagement with an executive coach is a waste of time and money.

4. How Do You Define Executive Coaching Success?

One of the most important aspects of choosing the right executive coach is the return on investment for the company. There must be a way for the HR director and the executive coach to measure how successful the investment into the coaching engagement was.

Ask the coach how they measure coaching success. You and your executives will need to see tangible measurements of success in order to confirm that you are getting the best return on your investment.

5. Have You Ever Coached a Leader Where You Were Not as Successful as You Had Hoped?

Every executive coach encounters clients that are challenging and even resistant to coaching. Learning about how the coach addresses challenges will provide insight into their style, persistence, and how they work.

6. How Do You Handle Confidential Information?

The relationship between leaders and executive coaches must be one of trust and confidentiality.

The executive coach must be seen by the leader as independent from HR and business.

That said, the coach should share information with HR if it relates to the safety, legality, and liability to the company.

7. Can You Describe a Time Your Coaching Pushed Someone Out of Their Comfort Zone?

In order for executive coaching to be successful, people need to be pushed. In some cases, this may push people out of their comfort zone. The best executive coaches meet their executive clients where they are and should provide the type of coaching that they need. This often requires the coach to challenge the executive to confront certain realities, challenges, and push the leader to grow.

8. What Coaching Experience Do You Have in My Industry? If You Don’t, Share How Your Experience is Still a Fit?

Executive coaches with experience in the same industry will have a deeper understanding of the factors that exist in that particular industry. However, keep in mind that choosing a coach simply because they have experience in the industry is not always the best option. More often than not, executives face the same challenges no matter the industry. Your goal is to identify the best executive coach no matter what. Not the best coach who has also been an electrical engineer in the aerospace industry.

9. How Did Coaching Impact Your Life?

Coaches need support too, and the coach chosen should be able to explain how a coach changed their life.

The answer to this question should reveal passion, engagement, personal development and reveal how they approach the executive coaching method.

10. How Do You Screen Your Clients? In What Situations Do You Say “No” to Taking On a Client?

Good coaches know how to screen organizations they assist in order to be sure they will be a good fit and be able to provide measurable results.

An executive coach who coaches clients at a high level should recognize what types of personalities work best with the methods they use and be honest about whether the organization considering them is a good fit.

Ask them to describe the perfect client to get a more in-depth understanding of their coaching style and application. Ask the coach under what circumstances will they not take on a client. Also ask if they have ever fired a client and if so, for what reasons.

Executive Coaching ROI

Executive coaching has proven to be an invaluable asset for the growth & development of senior-level executives in the corporate world.

According to the International Coaching Federation, the size and revenue of the worldwide coaching industry continues to grow. As the leadership landscape evolves, the significance of executive coaching services and the coaching industry grows exponentially.

But knowing how to maximize business coaching investment and selecting the right executive coach to fit the specific needs of your organization is essential to achieving the long-term success desired from executive coaching.

When you hire an executive coach, to maximize your coaching investment, the coaching journey needs to mirror your specific goals, values & aspirations. With the right coach or coaching firm, individual leaders can become beacons of influence, while organizations can cultivate empowered leadership cadres that navigate change and drive growth.

If done correctly, executive coaching can promote rapid transformation within your company’s existing leadership structure and provide lasting value for your company or organization.

As you embark on this transformative voyage of career coaching, the guidelines explored in this article serve as a compass, guiding your decision-making process with clarity and confidence, illuminating your path, and steering you toward the boundless potential that effective executive coaching can unlock.

Want to Hire an Executive Coach? Start the Process Today

Whether you’re a poised individual leader seeking personal growth or an astute HR professional shaping organizational leadership dynamics with your strategic planning, when you decide you want to hire an executive coach, the journey of selecting the right executive coach is pivotal.

Start the process today with the best executive coaches in the business.

If you need guidance on the process, don’t hesitate to reach out to us; Skyline G has a team of executives ready to provide assistance in all areas related to executive coaching ROI, armed with an understanding of the importance of investing in yourself and/or your organization through executive coaching, as well as a clear roadmap for selecting the best-fit coach, we can help you take charge and start this journey today.

At Skyline G we’re committed to finding creative solutions for unique challenges faced by C Suite executives. Contact us today to learn how the best executive coaches in the business can help create better leaders and drive positive change at your organization.

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