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How To Run an Effective Coaching Session

Hilary Johnson

Product Lead | Growth Advisor @ ustwo Freelance

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4 Articles
Hilary loves leading healthy and productive teams that collectively deliver product impact. Hilary is currently working with ustwo and The Body Coach to help people achieve their fitness goals.

If you are a technologist working in the world of product development, it’s likely that you’ve come across coaching in recent  years.

Coaching is now a well established mechanism for helping people work towards their goals and reach success.

In product management, more and more product people are looking to coaching. Product coaching helps these practitioners  sharpen their skills, overcome challenges and enable them to work towards their objectives.

Many product team managers are enthusiastic about introducing a coaching approach in their teams too.

Are you keen to apply coaching principles within your organization or team? Maybe you’re getting your own product coaching practice off the ground.

Either way, it can be difficult to know how to approach coaching effectively as you’re starting out.

As coaches, we want to help people get the most out of sessions.  It’s therefore important to approach sessions with structure and forethought.

To run an effective coaching session, think  about how you structure them before, during and after.

But first, what exactly is coaching?

What is coaching?

Coaches help individuals reach their goals by sharpening their skills and supporting them in navigating challenges.

There are all kinds of different coaching, depending on someone’s area of work and goals. But the principles around how to run an effective coaching session are universal.

In product coaching, product practitioners work with a coach to become more effective in their role. This often means building better products.

Some of the areas coaches and product people  work on include:

  • Product knowledge: e.g. User and Customer Knowledge, Data Knowledge, Business and Company Knowledge, Product Operational Knowledge

  • Process skills and techniques, e.g. Product Discovery Techniques, Product Optimization Techniques, Product Delivery Techniques, Product Development Process

  • People skills and responsibilities, e.g.  Team Collaboration Skills, Stakeholder Management Skills, Leadership Skills

If you’re managing other product managers, there’s a good chance you’ve already used some coaching techniques in one form or another.

Coaching helps managers work with their team members to solve problems and work through challenges. Coaching is a great way to support and guide team members in a non-directive way.

You may have come across private coaching too, which has gained popularity over the years, and not just in product.

A private coach might go a bit broader and support a product practitioner with designing a career plan and working out steps to get there. A private coach can provide a perspective that is different to someone within your own organization.

They might also be able to help with more sensitive topics, like a lack of confidence or feeling blocked.

What is a coaching session?

A coaching session is the process of meeting with a coach to work through challenges. Often a session will be a one-to-one meeting between the coach and an individual.

Usually a session is structured around working towards a specific goal. A typical coaching session usually lasts between 30 minutes and an hour.

I find it best to keep them under an hour to keep everyone’s energy and focus high.

No matter the area of coaching, a well structured session will help work towards goals.

How to structure a coaching session?

I like to think of my coaching sessions as I approach product development. In product development, we approach product challenges with outcomes to work towards. We also break those outcomes down into pieces to move bit by bit towards a given outcome. I approach coaching in the same way.

I recommend setting up objectives and success metrics early on in a coaching relationship. This will mean that you can tailor  sessions with clear goals. Of course, working towards goals takes time.

One coaching session is usually not going to mean instantly unblocking a practitioner in an area.

But using a good session framework helps both the coach and the product manager see incremental progress.

Here is the coaching session structure I use when coaching clients. This framework usually helps drive meaningful conversations and leads to progress towards goals.

Before the coaching session

Before meeting, I encourage product people I work with to start thinking about the session ahead.

I’ll typically send out some questions beforehand. I encourage the individual to have a think about them in advance and jot down some notes in a shared document.

Some of the questions I like to ask are:

  • How have things been going since our last session?

  • Have I made any progress towards my goals since our last session?

  • What key problems or challenges do I want to focus on in this session?

  • What actions do I have to report on?

Asking questions in advance gives a product manager the time to reflect and come to the session with clear areas to work on.

The responses to the questions also help me better prepare for the session.

During the coaching session

It’s important to prepare a loose structure beforehand. If you don’t, you run the risk of running off topic and lacking direction.

A coaching structure helps you keep on track and help an individual make progress.

Here is a framework I usually use to structure one-on-one coaching sessions:

  1. Recap of any outstanding actions or progress

  2. Identify a goal for the session

  3. Work towards the goal

  4. Identify any learning or actions to take forward

  5. Conclude the session

1. Recap of any outstanding actions or progress

Spend a bit of time reviewing anything actionable that came out of the last session. For example, a product manager might have taken an action to try out a new prioritization framework.

Download Now: Get our eBook on Mastering Prioritization

You might agree to review how this went for them and whether there are any key takeaways.

2. Identify a goal for the coaching session

Invite the product manager to identify what they want to look at in the session. 

You may already know this if they’ve done some preparation.

Either way, it’s worth acknowledging what areas you’ll be focusing on.

Discussing a session goal will help the product manager feel involved in the process and take ownership of the session. It also helps you ensure that you’re working on a meaningful theme.

3. Work towards the goal

Explore the challenge or area that the individual wants to work on.

Explore possible solutions together. Coaching is non-directive, so the focus is often on listening and asking powerful questions.

If you’re working through tactical areas (e.g. skills) a coach often puts their ‘teacher’s hat’ on.

They’ll draw on their product knowledge to support the product manager to resolve a particular challenge.

4. Identify any learning or actions

Work with the person to identify any actions to take that will help them move towards their goal. Remember that coaching is non-directive.

This means that the product person needs to own the actions and feel comfortable taken them on.

Discuss how they might hold themselves accountable to the actions.

5. Conclude the coaching session

I like to spend some time briefly summarizing learning, actions, and any shifts in perspective at the end of the session.

It is the coach’s responsibility to keep sessions on track. You can gently let the product practitioner know if you’re veering off course and suggest returning to the session goal or theme.

Coaching sessions don’t always follow a neat plan.

Staying 100% on track is not always possible. For example, a practitioner may have wanted to work through product metrics at the beginning of the session.

But perhaps they get distracted by a difficult interpersonal issue at work.

The focus then may switch throughout the session. If this issue is important to them, a carefully planned out session might go out the window. In this case, I acknowledge that you are agreeing to change the focus.

This way, nobody will feel shortchanged at the end of the session.

Try to stick to a framework and keep on track. But remember that everything doesn’t always go to plan. Stay flexible - if you don’t get to cover some areas, you can always follow up asynchronously.

What does a good coaching session look like?

A good coaching session is one in which a person is unblocked or moves incrementally towards a goal.

Here are some other indicators of a good coaching session:

Impact

The areas you work through in a coaching session should ladder up to the practitioner's overall goals.

This will help keep the focus. It also leads to impact.

An individual will be taking incremental steps towards their goals in  a single session.

Guidance

A coach encourages the product manager to uncover the answer themselves, rather than telling them what to do. This helps them learn and grow.

In domain-specific coaching like product coaching, coaches are usually experienced practitioners.

They may draw on their experience and knowledge to help resolve a particular challenge.

For example, a product manager may be struggling with setting OKRs.

A product coach might recommend an approach to setting OKRs, based on what the coach has successfully used in the past .

Ultimately, it will be up to the product manager to try the framework out if they think it is relevant to them.

Openness

Product Coaching is not limited to sharpening skills, or the “tactical”.

Often, product managers share challenges around lacking confidence, lacking direction or feeling blocked. Discussing this requires being vulnerable.

A good coaching session is one where the individual feels at ease, comfortable and supported. In this environment they can raise sensitive issues that might be important to work through.

Energy

A one on one coaching session requires energy and focus from both the coach and the individual.

An effective session is one in which a coach tracks attention and engagement. A coach can adjust the session as needed, if energy is waning.

They will also try to keep the session positive in tone. This doesn’t mean that you shouldn’t discuss difficult or challenging topics.

It means that  a good coach supports the product manager with solutions and errs on the side of a positive outlook to help motivate them.

Personal ownership

Good coaching sessions result in learning, new ways of looking at things or actions to follow up on.

It’s important to encourage an individual to take ownership and accountability for actions rather.

When a product manager arrives at solutions and actions that they feel ownership over, they will be more likely to follow through on them.

Effective coaching sessions require forethought and structure.

Be deliberate about how you structure your coaching sessions.

This will ultimately result in individuals making effective progress towards their goals.

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