How to have coaching conversations

September 17, 2021

People often wonder what separates an average manager from a great manager. While there are many variables, the ability to recognise the strengths and weaknesses of their employees, then coach them accordingly to produce improved results is key.

“There is one quality that sets truly great managers apart from the rest: They discover what is unique about each person and then capitalise on it.” — Marcus Buckingham

According to a recent study, only 30% of the US workforce are engaged at work. What’s more, research says that people who focus on their strengths every day are 6 times more likely to be engaged in their jobs, more productive and more likely to say they have an excellent quality of life. There’s a growing body of research to suggest that happiness can be coached, and in doing so performance reliably improves.

One of the best ways to do this is through coaching conversations. A coaching conversation is about asking the right questions help your employees come up with an answer their own way at the right time. Not every discussion you have with your team will be a coaching conversation, but if you can add the coaching conversation into your arsenal or improve the way you’re currently having coaching conversations, then perhaps you can cement your status as a great manager.‍‍

Implementing coaching conversations into your workflow, will therefore not only help develop your team and improve immediate performance. But, also help create future leaders, who can build on this success. So those are the reasons why you should start using coaching conversations, now here’s how to get started. Let’s start on a one-to-one basis and after that we will discuss how to do so with your team and peers.

How to have Coaching Conversations

Self Awareness

The goal of one-to-one coaching conversations is to make sure your employees are self aware, socially aware and can manage themselves.

Create self awareness with your employee by getting them to think about how their values and personality affects their work. We do this by encouraging our team to look over their Saberr profile and create their own personal profile (shown below) based on this.

Self Management

Have a conversation with your employee where you ask them:

  • Do you make the most of your strengths?
  • Do you have clear goals?
  • How do you deal with stressful situations?

If they don’t have answers to these questions, ask them to have a prepared answer by the next meeting you have with them.

Social Awareness

Another element of coaching an employee is making sure they work well within the team and take an interest in the people around them. Sharing their newly crafted personal profiles with each other is a great way to help team members get comfortable with their differences.

How often should you have a Coaching Conversation?

Having successful coaching conversations doesn't mean every conversation has to become a lecture or a time-suck. That is why we advocate regular check-ins with your direct reports to check their progress and see if they need coaching. During our research for CoachBot’s one-to-one feature, we found that monthly one-to-ones were the upper limit for effective check-in meetings and anywhere from once a week to once a fortnight is ideal. Marcus Buckingham suggests asking two simple questions weekly:

  • What are you working on?
  • How can I help?

This simple approach creates a regular discourse with your direct report that helps with work, not get in the way of it. It also helps to create an open environment where they feel they can come to you if they make a mistake and you can help them learn from it. This is what Harvard professor Amy Edmondson calls ‘Psychological Safety’ and what Google found to be the most important factor behind successful teams.

Coaching Conversations for Teams

Team coaching is about the team creating collective change — and successful team coaching conversations are about helping people understand how to work better with others to create this change. This is either by understanding relationships in the team to make conflict productive and useful, focussing on how people interact and communicate, or helping teams to clarify a shared purpose, goals and roles. It is of vital importance for everyone to be involved — so there’s collective accountability and shared benefit for everyone.

Relationships and Behaviours

Start with sharing the personal profile mentioned above to help create a discussion based around forming deeper relationships and a basis of trust in the team. Then look at how you work as a team day to day, small things like agreeing whether it’s ok to turn up to meetings late or committing to letting people speak frankly without holding back. A ‘behaviours’ exercise that works well is to agree what you as a team would consider the worst five behaviours a team could exhibit and commit to exhibiting the opposite — this creates a shared culture or a charter unique to your team.

Goals and Purpose

Next the team need to understand and agree on what they’re working towards before they get to work. An agreed set of short term (~3 month) goals and a shared purpose can help reduce conflict. In teams with strong trust they should feel free to challenge themselves and each other by asking “is what I’m/you’re doing today going to help us achieve our goals” if the answer is no then everyone in the team should be supportive in re-prioritising.


Discussing how you’re working as a team and regularly revisiting your purpose and goals is vital for continued success. The cadence of reflection will vary from team to team, with many agile teams meeting every day to discuss their work and reflecting every fortnight on their goals and progress. This might not fit into every teams schedule but taking time out every week to make some notes on how you’re working as a team and gathering together to feed that back on a monthly basis is a good minimum starting point. Building this habit of reflection is simple in principle but hard in practise, especially with mounting to-do lists. We spark these coaching conversations using CoachBot to prompt teams to reflect regularly and store reflection notes.

Linked to the Organisation

Make sure you link your team goals to organisational goals. Many organisations impose top down goals on teams based on the overall company strategy, if teams can translate these goals into their own language they become much more motivating.

Although these all seem like straightforward things to do in the workplace, continual learning through coaching conversations is an effective and uncomplicated way to improve performance. So try having a few coaching conversations with your direct reports, teams and peers and let us know how it goes!

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