Executive coaching starts with a conversation about where you are, what you want to change, and how you lead. From there, you and your coach define the work: the challenge to address, who should participate, and what useful progress would look like.
If you are considering coaching for the first time, you probably have practical questions. What happens in a session? How long do you commit? Will the conversations stay confidential? How do you know whether you need individual or team coaching?
This guide walks through those decisions, including how executive coaching with Ryan Coley at Sherpa Group begins.
What does executive coaching involve?
Executive coaching gives leaders a structured opportunity to examine their decisions, relationships, and habits, then put what they learn into practice.
A conversation might focus on a decision you keep postponing, a difficult relationship on your leadership team, or the responsibilities you need to hand over as the business grows. The work becomes more useful when you bring a specific situation and remain open to examining your part in it.
The International Coaching Federation describes coaching as a partnership that helps people explore possibilities and develop their own solutions. Your participation matters: you bring the context, make the decisions, and carry the work into your business. Read ICF’s explanation of professional coaching.
What happens in the first consultation?
The first consultation is a chance to understand your situation and decide whether working together makes sense.
At Sherpa, Ryan learns about you, your business, your current challenges, and your goals. The initial consultation is free and has no obligation. You do not need a polished presentation or a perfectly defined problem. Describing what keeps happening—and why it concerns you—is a useful starting point.
You might explain:
- A decision that has become harder than it should be.
- A conversation you and a colleague keep avoiding.
- A growth goal your current way of working cannot support.
- A change in your role that you have not fully adjusted to.
- Something you have already tried and what happened afterward.
Use the consultation to ask your own questions, too. How would Ryan approach the situation? What would participation require? What would you need to understand before agreeing to the work?
What happens during a coaching session?
A useful coaching session connects a real leadership situation with a clearer understanding of your choices and a practical next step. The exact conversation depends on your goals.
For example, consider a hypothetical founder who wants managers to take more ownership but reviews every small decision. A coaching conversation could explore which decisions genuinely require the founder, what makes delegation uncomfortable, and what authority the managers actually have.
A next step might be to define one category of decisions a manager can make independently, then observe what happens. That is an illustration of coaching work, not a Sherpa client story or promised result.
You can expect to participate actively. Clear examples, honest reflection, and willingness to try a different response give the conversation something concrete to work with.
Should you choose individual or team coaching?
Choose the format around where the work needs to happen.
Individual coaching may fit when you want space to examine your own leadership, clarify a decision, prepare for a transition, or change how you handle difficult conversations.
Team coaching may fit when the challenge involves how several leaders communicate, make decisions, resolve disagreements, or follow through together. A team issue deserves attention to the relationships and shared expectations within that team.
You do not have to settle this before the consultation. Explain who is involved and where the difficulty shows up. Ryan works with both individuals and leadership teams, and the scope is customized to the situation. Sherpa’s executive and business coaching options outline the ways to work together.
How long does executive coaching last?
Sherpa engagements can range from one or two sessions to an ongoing coaching relationship. The appropriate depth and duration depend on the situation and the work you want to do.
A narrowly defined question may call for a different commitment than an ongoing change in leadership responsibilities. Avoid choosing a duration simply because it sounds standard. Discuss what you want to address and what level of work is appropriate.
Before starting, clarify the proposed session frequency, duration, scope, and how you will revisit those arrangements. Ryan also provides support between sessions. Discuss what that support includes, how to use it, and the expectations around availability as part of your engagement.
How should you evaluate progress?
Define progress in terms of changes you can observe in your leadership and work.
A broad aim such as “become a better leader” needs more detail. Consider what someone could see you doing differently. Depending on your goals, you might discuss:
- Making a decision you have repeatedly deferred.
- Giving a colleague clear feedback instead of avoiding the conversation.
- Delegating a defined responsibility with agreed boundaries.
- Making ownership and next steps explicit after a leadership meeting.
- Following through on a commitment you previously struggled to keep.
These are examples to help you define your goals, not a standard Sherpa scorecard. Decide with your coach what is relevant and how to review it.
Coaching does not guarantee a particular business result. Revenue, retention, and growth have many influences. Look at your actions and decisions alongside the broader outcomes you care about.
What should you ask about confidentiality and cost?
Confidentiality and pricing should be clear before the engagement begins.
Sherpa’s executive coaching conversations are confidential. If a business is paying for an individual’s coaching, ask what information, if any, will be shared with the sponsor. For team work, discuss expectations among participants as well as with the coach.
The ICF Code of Ethics provides a useful professional reference: it calls for clear agreements about responsibilities, financial arrangements, confidentiality, and information sharing. Ask how those subjects are addressed in your own engagement.
Sherpa does not publish a fixed executive coaching price. Ryan can provide a case-by-case quote during the consultation once he understands the depth and scope of the work. Ask what the proposed fee includes and what would happen if the scope changes. You should have enough detail to make an informed decision.
How is Ryan’s background relevant?
Ryan brings experience with both people and business ownership to executive coaching.
He is a Licensed Clinical Social Worker, an executive coach with Novus Global, and a current multi-unit franchise owner. His clinical background informs his understanding of people and relationships; his ownership experience provides context for the responsibilities of leading a business.
Executive coaching remains separate from therapy. Discuss the purpose and boundaries of the engagement so you understand the role Ryan will have in your work together.
You can read Ryan’s background and credentials and explore his Novus Global coaching approach before the consultation.
How can you prepare?
Bring a few notes that make the conversation specific. This short checklist is enough to begin:
- Describe the situation. What is happening, and who is involved?
- Name the change you want. What would be different if the work were useful?
- List what you have tried. Include what helped and what did not.
- Identify constraints. Consider your time, responsibilities, budget, and deadlines.
- Write down your questions. Include format, scope, confidentiality, cost, and support between sessions.
You can also note what you are uncertain about. Finding a clearer description of the challenge can be part of the first conversation.
Frequently asked questions
Do I need a specific problem before starting executive coaching?
No. You can begin with a goal, a transition, or a sense that your current approach is no longer working well. Bring examples so the consultation can explore what needs attention.
Can executive coaching be just one or two sessions?
Yes. Sherpa engagements can range from one or two sessions to ongoing coaching. The scope and duration depend on your situation and goals.
Can my leadership team work with Ryan?
Yes. Ryan works with individual leaders and leadership teams. The consultation helps clarify who should participate and what the work should address.
Is executive coaching available virtually?
Yes. Ryan offers virtual coaching, with in-person options in Wake Forest and Raleigh, North Carolina. Discuss the format that fits your situation during the consultation.
How much does executive coaching with Ryan cost?
Pricing is determined case by case based on the depth and scope discussed in the consultation. Sherpa does not publish a fixed executive coaching price.
Start with the situation you are facing
You do not need every answer before reaching out. Bring the decision, relationship, or leadership challenge you want to examine, along with your questions about the process.
Start a conversation with Sherpa Group to discuss your goals and whether coaching with Ryan is a fit.