In Part 1 of this series, we explored why executive coaching is a relevant development choice for leaders navigating complexity, rising expectations, and fewer built-in supports inside organizations as budgets are scrutinized in the learning function. We focused on what coaching can deliver: clarity, self-awareness, accountability, resilience, and a trusted thinking partnership.
Understanding how coaching actually works is the next step. The process itself is often discussed in abstract terms, which can make it difficult to know what to expect or how to evaluate whether coaching is right for you. This article takes a practical look at what happens inside a coaching engagement, how coaching conversations unfold, and what to consider when choosing a coach.
The Coaching Process
Most executive coaching engagements follow a structured rhythm rather than an open-ended or ad hoc approach. Coaching typically begins with an initial contracting and discovery phase, during which you and your coach clarify what your “north star” will be – the overarching goals you want to work on throughout the engagement. Even if you do not exactly know this as a defined sentence or paragraph, your coach will skillfully help you ascertain “what good looks like” by the end of the engagement.
In many engagements, this early phase includes the use of assessments or 360-degree qualitative feedback reports. These may involve leadership style inventories, personality or strengths assessments, or confidential feedback gathered from managers, peers, direct reports, and key stakeholders. At Evolved People Coaching, we offer assessments such as DiSC, Five Behaviors of a Cohesive Team, and the Hogan Leadership suite as well as comprehensive qualitative 360 stakeholder interviews and thematic feedback reports. The purpose of these tools is not evaluation or performance management, but insight. They help surface patterns, blind spots, and discrepancies between how leaders see themselves and how others experience them.
When used well, assessments and 360 feedback provide a shared data set that informs the coaching plan. They help focus the work on what will have the greatest impact, grounding coaching goals in both self-perception and external feedback.
From there, coaching sessions typically take place every two to four weeks and last between 60 and 90 minutes. Each session builds on the last, creating continuity and momentum over time. Sessions often include reflection on recent experiences, exploration of current challenges, examination of patterns or assumptions, and agreement on actions to test before the next meeting.
However, it is the action and work between sessions that really creates the forward momentum. Leaders apply new approaches, experiment with behaviors, seek feedback, and reflect on outcomes. This between-session application is where coaching moves from insight to meaningful change.
Most engagements last between three and twelve months, depending on the scope of goals and the complexity of the leader’s context. Some leaders engage a coach for a specific transition or challenge, while others work with a coach across multiple stages of their career.
What Actually Happens in Coaching Sessions
Coaching conversations differ from consulting or mentoring conversations in one important way: the focus is not on advice-giving. Rather than telling you what to do, a coach uses questions, reflection, and observation to help you think more clearly and see situations from new angles.
You might be asked questions such as: What feels most important here? What outcome are you aiming for? What assumptions are shaping your response? What are you saying “no” to if you say “yes” to this? What would it look like to experiment or bring curiosity to those challenging moments?
Over time, this style of inquiry helps leaders strengthen their own capacity for reflection and decision-making. Many leaders find that they begin asking themselves these questions outside of coaching sessions, applying the thinking process independently.
In addition to asking questions, a coach acts as a mirror. They may reflect patterns they notice, for example how you talk about success, where you hesitate, how you frame challenges, or where energy rises or drops. These observations help close the gap between intention and impact, allowing leaders to make more deliberate choices about how they show up.
The Coach–Client Relationship
At the core of effective coaching is a relationship built on trust, confidentiality, and partnership. Coaching conversations are confidential, even when the coaching is sponsored by an organization. This confidentiality creates psychological safety, the ability to speak openly about uncertainty, doubt, and complexity without fear of evaluation or consequence.
The relationship is also collaborative. You set the agenda for each session, decide what to work on, and choose which actions to take. The coach’s role is not to direct your career, but to support your thinking, challenge your assumptions, and help you stay aligned with your goals.
This partnership is what makes coaching distinct from mentoring, consulting, or performance management. The value lies not in expertise about your job, but in the quality of thinking the relationship enables.
Choosing the Right Executive Coach
The effectiveness of coaching depends heavily on the quality of the fit between coach and client. While there is no single “right” coach for everyone, several factors matter consistently.
Professional credentials provide a useful baseline. Certifications from organizations such as the International Coaching Federation (ICF) indicate that a coach has completed formal training, adheres to ethical standards, and has been assessed on coaching competency. While credentials alone do not guarantee quality, they signal a serious commitment to the profession.
Relevant experience is also worth considering. Some coaches specialize in particular industries, leadership levels, or types of transitions. Depending on your situation, experience in a similar context may help a coach understand your challenges more quickly. That said, strong coaching skill often matters more than industry expertise, as effective coaching centers on facilitating your thinking rather than providing content knowledge. Nicki Gilmour, our founder and head coach believes there is value in working with coaches who also have a background in social-organizational psychology, social work or clinical psychological or adult learning in addition to being a certified coach. Nicki states,
“Executives are part of a wider eco-system of other humans and their behaviors. This along with cultural norms around how work gets done, and other factors such as management practices, policies, systems and processes, means the work is powerful when seen through context of the team, manager and company itself. Empowering people to map the ‘systemic enablers and disablers’ when navigating their success in addition to looking at optimizing how they show up, creates impactful results.”
Chemistry and trust are critical. Coaching requires openness, reflection, and a willingness to be challenged. At Evolved People Coaching we offer a complimentary initial consultation or chemistry session. Use this time to notice whether you feel heard, whether the questions prompt new thinking, and whether the interaction feels both supportive and stretching. We have a range of coaches who have different styles (DiSC/Insights) and personalities and even backgrounds to ensure you get the right person to be able to be honest and vulnerable in the private sessions. We have an associate pool of ten coaches who we trust.
Finally, consider logistics and structure. Coaching is most effective when it fits realistically into your life. Discuss session frequency, format, and expectations upfront. Most coaching today occurs virtually, offering flexibility in both scheduling and access, but structure and consistency still matter. Face to face still matters and can be done, but virtual also works as well.
A Foundation for Making the Most of Coaching
Understanding how executive coaching works helps you engage more intentionally — whether you are considering coaching for the first time or refining an existing engagement. Coaching is not a passive experience. Its impact depends on clarity of goals, quality of the relationship, and the leader’s willingness to reflect, experiment, and apply insights in real time.
In Part 3 of this series, we will turn to how leaders can make the most of their investment in coaching. We will explore how to approach coaching with intention and practical next steps for beginning a coaching relationship that genuinely supports your growth.
If you are ready to start, please book in with Nicki Gilmour to have a complimentary call to explore your goals and challenges and be matched with the right coach here: BOOK SESSION
By Jessica Robaire, writer for theglasshammer, executive coach at Evolved People Coaching
