The Entry Point Into Coaching: A Practical Guide for Supervisors 

Supervisors today are expected to do more than manage performance — they are asked to develop people. As a result, many are learning coaching models like GROW, brushing up on EQ, and revisiting familiar tools such as SMART goals or SWOT analyses. 

And yet, a very practical question remains unanswered: 

How does coaching actually start with a direct report? 

Not in theory. Not in a leadership program. 
But in the reality of deadlines, meetings, capability gaps, and limited time. 

This article explores the entry point into coaching — where it fits, who sets the agenda, what it’s for, and how supervisors realistically integrate it into everyday leadership. 

Coaching Is a Leadership Stance, Not Just a Structured Conversation 

Most managers assume coaching begins when there is: 

• a formal development goal 
• a scheduled 1:1 
• a clear framework like GROW or SMART 

In practice, coaching begins before the model. 

The true shift is from directing work to developing thinking. Coaching is less about running a perfect process and more about adopting a leadership stance grounded in curiosity, accountability, and emotional intelligence (EQ). 

For example: 

• Managing: “Here’s what you should do next.” 
• Coaching: “What outcome are you aiming for, and what options have you considered?” 

The second response signals trust, ownership, and development — even if no one names it as “coaching.” 

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Who Sets the Coaching Agenda: The Employee or the Manager? 

This is one of the most common sources of confusion for supervisors. 

The reality is that both can — and should — initiate coaching, depending on the context. 

When the Employee Brings the Topic 

This is the most straightforward entry point. The employee might say: 

• “I want to develop my leadership skills.” 
• “I’m struggling to influence stakeholders.” 
• “I want to prepare for a future role.” 

These topics are often broad and not yet SMART. That’s normal. 

Your role as a coach is to help translate a general aspiration into something clearer: 

• What specifically do they want to be different? 
• How will success show up in observable behaviour or results? 
• What does “good” look like in the context of the business? 

This is where coaching, competency language, and SMART thinking come together — after the conversation starts, not before. 

When the Manager Brings the Topic 

Many supervisors hesitate here, worried they are “imposing” development. In fact, this is often where coaching has the greatest business impact. 

You might notice: 

• a recurring performance issue 
• a gap in collaboration or decision-making 
• strong technical skills but limited influence 

Rather than defaulting to feedback or instruction, you can open a coaching entry point: 

“I’ve noticed a pattern in how deadlines are being handled. I’d like to explore what’s driving that and how you see it.” 

This approach links coaching directly to performance, capability, and outcomes — not just personal growth. 

Is Coaching Part of the Flow of Work or a Separate Activity? 

Supervisors often assume coaching requires long, reflective conversations. In reality, effective leaders use coaching at multiple levels. 

1. Coaching in the Flow of Work 

This is the most underused — and most powerful — entry point. 

Short, informal questions embedded in daily interactions: 

• “What’s your priority in this situation?” 
• “What risks are you weighing up?” 
• “What did you learn from that outcome?” 

These moments build critical thinking, ownership, and EQ without adding time to the calendar. 

2. Coaching in Regular 1:1s 

1:1s are a natural bridge between operational management and development. 

A supervisor might say: 

“Let’s step back from the task for a moment — what capability do you think this project is stretching for you?” 

This connects day-to-day work with longer-term development, without requiring a full development framework each time. 

3. Dedicated Development or Career Conversations 

For promotion readiness, role changes, or persistent challenges, it helps to be explicit: 

“I’d like to use this conversation to coach around your development goals. Does that work for you?” 

This light “contracting” builds clarity and trust, especially when feedback, assessment, or future opportunities are involved. 

Do You Need a Coaching Contract — or Can You Just Coach? 

Formal coaching contracts are not required in most supervisory relationships. However, clarity of intention is essential. 

A simple check-in often suffices: 

• “Would you like my advice here, or would it help to think this through together?” 
• “Is this a performance discussion, or a development one?” 

These questions prevent confusion and signal respect — a core component of EQ-based leadership. 

What Can Managers Coach On: Technical Skills or Soft Skills? 

This is a false choice. 

Supervisors coach on both — the difference lies in how. 

Coaching Technical and Functional Skills 

Instead of giving answers: 

• “How did you analyse this?” 
• “What assumptions are you making?” 
• “What alternatives did you consider?” 

This develops problem-solving and judgment — critical leadership capabilities. 

Coaching Behavioural and Interpersonal Skills 

Common coaching areas include: 

• influencing 
• communication 
• decision-making 
• resilience and self-management 

Here, supervisors often draw implicitly on EQ: 

• “How do you think your message landed?” 
• “What triggers you in these situations?” 
• “What behaviour would have the greatest impact?” 

The coaching principle remains the same: the employee does the thinking. 

🎥 Video on Unlocking Success: The Coaching Chemistry Meeting

“I Struggle to Define Development Goals — I Don’t Know the Right Language” 

This is more common than most supervisors admit. 

You do not need perfect competency frameworks or polished HR language to start coaching. In fact, clarity usually emerges through dialogue. 

Useful entry questions include: 

• “What do you want more of in your role?” 
• “What feels hardest right now?” 
• “What would ‘success’ look like six months from now?” 

Once something tangible emerges, you can then apply familiar tools: 

• shaping goals into SMART objectives 
• using SWOT to explore strengths, risks, and development areas 
• linking insights to known competencies or role expectations 

The model supports the conversation — it doesn’t replace it. 

What Coaching Looks Like in Real Managerial Life 

In practice, coaching often looks like this: 

• A supervisor uses project debriefs to reflect on both results and behaviours. 
• A manager asks reflective questions instead of solving problems immediately. 
• A leader routinely links current challenges to longer-term capability building. 
• A 1:1 ends with, “What’s one thing you’ll try differently next time?” 

No formal coaching session required. 

Coaching Entry Point: FAQs & Cheat Sheet 

Do employees need to bring a coaching topic? 
→ No. Coaching can be initiated by either the employee or the manager. 

Does coaching have to be formal? 
→ No. Most coaching happens in short, informal moments embedded in work. 

Should I always use models like GROW or SMART? 
→ No. Use them as thinking aids, not scripts. 

Is coaching only about soft skills and EQ? 
→ No. Coaching applies equally to technical, functional, and strategic work. 

Do I need to agree a coaching contract? 
→ Only when stakes are high. Often a simple check-in is enough. 

What if I’m not confident in development language? 
→ Start with real work and observable behaviour. The language will follow. 

The Real Entry Point Into Coaching 

Coaching does not begin with a model, a form, or a perfectly defined goal. 

It begins when a supervisor chooses to: 

• slow down advice 
• ask better questions 
• and develop people through the work, not around it 

Everything else — GROW, SMART, SWOT, EQ — simply helps you stay in that space longer. Check our BOLDLY’s coaching skills for supervisors training program here: https://boldly.app/coaching-skills-for-supervisors  

AUTHOR: Cara Leverett

Cara works across strategy, social media and consulting, supporting organisations to build visibility and meaningful engagement in the coaching, leadership development and adult learning space .She is particularly interested in how coaching-led learning and HR technology can be combined to create meaningful behaviour change and scalable impact for leaders and teams. Her work sits at the intersection of strategy, creativity and innovation, with a focus on translating complex ideas into clear, engaging narratives. 

Drawing on a foundation in communications and creative problem-solving, Cara brings an innovative and considered perspective to her work across HR technology and digital learning platforms. She is curious about how organisations use digital tools, insight-led content and coaching experiences to support growth, performance and culture. Cara enjoys shaping ideas that resonate with senior HR, OD, L&D and talent leaders, and turning strategic thinking into content that connects and drives action.