What a career coaching session looks like

A coaching session walk through

Find out what it’s like to have a career coaching session with me, how you should feel during coaching, and how best to prepare.

Career coaching can feel vague from the outside. People often ask what actually happens in a session, what they need to bring, and whether they are “doing it right”.

Whether you are curious about coaching or already partway through a programme, here is what you can expect from working with me, and a few questions to help you get the most out of each session.

What happens in a coaching session

The discovery or chemistry session

Most coaching relationships start with a discovery session. This is a chance for us to introduce ourselves, understand what has brought you to coaching, and sense whether we are a good fit for each other.

We will talk about what you are hoping to work on, how I work as a coach, and what you need from the process. There is no pressure to commit. Coaching works best when there is trust, comfort and honesty on both sides.

You can book a discovery call with me here.

Defining goals and objectives

Coaching should have a purpose. Early on, we will define what you want from the coaching and what success would look like for you.

This might include:

• A specific outcome, such as a new role or a career pivot

• A way you want to feel, such as more confident or less stuck

• A capability you want to build, such as managing others or leading with authority

Alongside this, each session will have its own focus. You decide what you want to work on that day.

Expect questions, not instructions

Coaching is not advice-giving. I will not tell you what to do or make decisions for you.

Instead, you can expect a lot of open questions. These are designed to slow your thinking down, challenge assumptions, and help you articulate things you may already know but have not yet said out loud. I will step in with prompts at the right moment, especially when something feels unclear, circular or stuck.

Exploring what is getting in the way

A key part of coaching is understanding what might be blocking progress. This could be confidence, fear, values conflict, organisational dynamics, energy levels, or competing priorities.

We will explore these honestly and without judgement. The aim is not to label or “fix” you, but to increase awareness and choice.

Working through options together

I act as a sounding board. We will explore different options, pressure-test them, and consider what feels realistic and aligned for you. This is often where people gain perspective and realise they have more agency than they thought.

Action, accountability and follow-through

I am an action-based coach. Each session ends with clarity on what you want to do next, how you will do it, and when.

We will agree on what accountability looks like for you. This might mean checking in on actions at the next session, or simply naming them clearly so you take ownership.

How a coaching session should feel

A good coaching session should feel purposeful, but also human.

You should experience:

• Collaborative working – I do not tell you what to do or do it for you. Think of it like a personal trainer: we work together, but you do the work.

• Empowerment – you leave feeling more motivated, capable and confident than when you arrived.

• Clarity – on what your goals are, what matters most, and what steps to take next.

• Ownership – a sense that the goals and actions are yours, not imposed or borrowed.

• Allyship – you should feel understood, seen and supported, especially when discussing things you cannot easily say elsewhere.

If sessions consistently leave you confused, deflated or dependent, something is not working.

Five questions to ask yourself before a coaching session

These questions are useful whether you are at the beginning of coaching, halfway through, or approaching the end.

1. What do I want to leave this session with?
   This might be clarity, a decision, confidence, or a plan.

2. What feels most important or most uncomfortable right now?
   The thing I am tempted to avoid is often the most useful place to start.

3. What have I noticed since the last session?
   This could be progress, resistance, new information, or a shift in how I feel.

4. What decision, action, or conversation am I circling around?
   Naming this helps us move from thinking to doing.

5. What support do I need from this session?
   Challenge, space to think, reassurance, structure, or something else.

You do not need perfect answers. Bringing honesty and curiosity is enough.

Working with me

If you’ve come to this article thinking about coaching with me and this approach feels like a good fit, you can find more information about how I work, the types of coaching I offer, and how to book a discovery session on my webpage.