The Power of Coaching Conversations

16 June 19

Using coaching techniques can be a very effective means for managers to deal with the issues people bring at work.  It doesn’t require a formal structured coaching approach and can work well when used by itself or alongside other approaches such as giving feedback.  The main coaching skills of question-making and listening are valuable in many work situations whether you call it coaching or not.

The key to using these techniques is to consider how the individual you are working with may respond and the particular scenario you are dealing with. For some people and situations coaching techniques may not work well and you are better off giving direct feedback. For others you may start with coaching questions and then move to feedback or advice if it’s apparent the coaching approach isn’t working.

Listed below are five common scenarios where a coaching approach could be beneficial with guidance on good question making and tools to use for each. Remember that situations are rarely as they first appear and when it comes to issues with people there are usually a variety of contributory factors.  A wise manager will take time to explore these contributory factors.

1: Managing My Workload


We all know the impact a heavy workload can have on performance and wellbeing at work. The volume or nature of work and competing deadlines often causes people to feel overwhelmed and out of control, with the result that the quality of work and personal wellbeing suffers. Different people will have different thresholds for the amount and type of work which affects them, but everyone can benefit from support as to what to prioritise and how.

Example questions to help people work through issues related to workload:

  • Describe a typical day at work?
  • How do you currently choose what to work on, when and how?
  • How does your approach compare to other approaches in the team?
  • On a scale of 1-10 (10 being the best) how successful are your approaches?
  • What needs to change?
  • Who is really good at prioritising work and managing workload?
  • What can you learn from this person?
  • How could this person help you?

Useful Tools

Tools such as the Importance/Urgency grid are a useful way to enable someone to reflect on their activities and prioritise. This tool is based on the tension between things that are important, and things that are urgent, and the belief that when we can distinguish between the two we can use our time more effectively.


Its popularity is often attributed to US President Dwight D. Eisenhower, who said, “I have two kinds of problems: the urgent and the important. The urgent are not important, and the important are never urgent”. The ‘Eisenhower principle’ therefore allows people to avoid the natural trap of focusing on activities that are urgent but not important, and instead work on the important activities that will bring long term success.


To use this tool, a manager can invite the individual to list all the items on their work list. The individual then reflects on this list and categorises according to what is important, urgent, or neither using the grid. The aim is to have the majority of tasks land in quadrants 1 and 2, i.e tasks falling into quadrant 4 should be questioned “is this something I should be doing?”. Tasks that fall into quadrant 3 should be dismissed as not relevant.


2: Confidence Issues


Many people present with confidence issues which impact on their ability to deliver at work and enjoy a sense of achievement. This is often at the root of many issues people bring and should always be treated with respect and sensitivity.

Managers always have to find a balance between supporting and challenging the individual and inevitably this balance will shift according to the individual and the issues they are facing.  Individuals with confidence issues will often benefit from a stronger emphasis being placed upon support. There are several strategies that are useful in these scenarios which help to avoid making assumptions and ensure the experience for the individual is positive:

  • To check whether confidence issues are present the manager can play back observations to the individual, using the individual’s language, and check reactions.
  • Enabling the individual to visualise a time when they felt empowered and more confident as a way of remembering their true strength and potential, instilling a sense of personal belief.
  • Empowering the individual by switching roles. The manager and individual physically swap seats. The manager pretends to be the individual and plays back what they have heard so far and then asks for advice.
  • Acknowledgement followed by words of encouragement and praise. Still resisting the temptation to be too directive but reaching out on a human and compassionate

Example questions and phrases to help individuals with confidence issues:

  • How do you feel about tackling this issue?
  • You have used the words “worried…..concerned… uncertain…exposed” when describing the situation. How do you feel? How would you like to feel?
  • Tell me about a time when you were at your most confident at work: what was happening, who were you with, what were you doing, how did you feel?
  • I am now you….the problem is xxxx….my concerns are xxxx. As my manager what advice would you give me?
  • You strike me as a considered, values-driven person who cares deeply about the quality of your work and your relationships with colleagues. I would encourage you to feel good about the contribution you are clearly making and take on board the positive feedback you have already received.

Useful Tools

There are many tools, advice websites and programmes available through a simple internet search.  The essence of building confidence with individuals at work is to provide a safe space to listen, learn and practice and progress at the right pace for them. You can read more here


3: Relationships With Others


For the majority of people, the relationship with key colleagues is one of the most important parts of a successful work life.  A coaching approach can be particularly helpful in this scenario.

Issues shared are often related to:

  • The individual trying to get to know their colleague and coping with a communication style that is different to their own
  • Getting constructive feedback on a piece of work
  • Poor communications through email or in difficult meetings
  • My colleague is always too busy to pin down for a conversation
  • Poor decision making
  • They don’t prioritise what’s important to me

Example questions to help people explore their relationship with others.

  • How well do you know your colleague?
  • Describe his/her communication style?
  • What matters to her/him the most? What motivates her/him?
  • What does your colleague know about you?
  • How have you explained your current challenges?
  • What has s/he heard?
  • What change do you want to see?
  • What do you want your colleague to do?
  • What would stop you asking for this to happen?
  • How else can you connect with the wider organisation?
  • To what extent is his/her style reflected in other people in the organisation?
  • Who or what influences this person the most?
  • How can you make the most of this knowledge?

Useful Tools/Models

Tools such as Radical Candour can be helpful in helping to understand their relationship and communications with colleagues.  Good questions to start with would be ‘how directly are you communicating with your colleague?’ and ‘how much do you care about how they are getting on?’.


4: Managing Difficult Behaviours


Many managers face challenges with behaviours in the team that they and others find disruptive or unacceptable.  For more serious behaviours of this type, HR conduct policies may apply.  In many cases the behaviour is best addressed through an informal discussion between the manager and the individual.   There is no one or simple way for a manager to approach this.  However, a coaching approach could work if the individual is sufficiently self-aware and reflective.  If not, a manager may prefer direct feedback.


If a manager is taking a coaching approach, one approach that we have found to be consistently effective is the use of questions to enable the individual to step into the shoes of others and gain greater insight into the impact of their behaviours. A deeper understanding of someone else’s experience is always helpful for increasing self-awareness.

Example questions to help an individual put themselves in someone else’s position and to build self awareness more generally:

  • How do you think other people experience you when you are very busy, focused on a piece of work, receiving your feedback….?
  • What feedback might team members give you about how you work with them?
  • When you and X were debating options for a project this morning, how do you think they experienced you?
  • What aspects of the way you work make you a good team worker and what aspects might you need to work on?

Useful Tools/Models

Tools such as Johari’s Window can help identify how individuals can become more self-aware.

In the discussion, the manager could explore the open and blind spot quadrants through open questions.  Most people are not fully blind to disruptive or difficult behaviours but they may not be aware of their impact.  A good question to ask could be ‘Think about a recent situation where your interactions with a colleague didn’t go well – why might they have responded in the way they did?’


Sometimes, the coaching approach doesn’t work and you need to move into feedback.  Take care to do this thoughtfully and sensitively.


5: Managing Poor Performance


Poor performance, whether a one off for a piece of work or more widely, is a frequent scenario for managers. Unfortunately, many managers don’t deal with this effectively and avoid the discussion until it becomes more serious. As with most issues, a timely and skilful intervention can minimise the likelihood of a bigger problem in the future.

As with the other scenarios, managers should consider the approach that is most likely to work for the individual.

Where a manager adopts a coaching style for a one-off issue, here are some good example questions.

  • How would you rate your performance on that piece of work?
  • What went well with that presentation and what could you improve?
  • If you had the chance to start again, what would you do differently?
  • If you were the manager giving feedback for that report, what would you say?
  • How will you get an A grade for similar work in the future?
  • What learning are you taking out of that experience?

Where the performance issues are deeper and more sustained then dealing with them is likely to be best done through HR processes. However, a parallel or subsequent coaching approach can help an individual focus on the actions required to improve.  Managers need to consider how they preserve trust and may need to work on rebuilding this following a performance process.

Some example questions are as follows:

  • What aspects of your performance do you most need to focus on?
  • What are the barriers you need to overcome and how will you do that?
  • What could you do differently outside of work to help inside of work?
  • What else can help you achieve your goals?
  • What do you need from me to help you achieve your performance goals?
  • How do we work together to ensure you develop?





I’ve worked with Norman for nearly seven years and have seen first hand his ability to think and act strategically while at the same time setting high standards for operational delivery.  He fully understands how to support the development of a high performing board and get the best out of people in the workforce.  We’ve worked together on some difficult issues and Norman has always impressed by his ability to find practical, viable and successful outcomes.

Bryan Portman – Non Executive Director, Moss Bros & Chair, Family Action