Why Coaching Often Fails

Alexandra Cory
Alexandra Cory
Scrum Master
Posted on
Jun 24, 2022
Updated on
Mar 16, 2023
Table of Content

Learning how to Coach is straightforward; learning when to Coach is the tricky part 

As a Scrum Master, coaching is an important part of my role. I encourage colleagues to keep an open mind and consider all the potential options and approaches to solve a problem or accomplish a goal. I also challenge any assumptions they’ve made and aim to identify limiting beliefs that might be holding them back. 

“Generally speaking, what coaches do is anchor people to their own internal strengths; they inspire organizations to dream beyond their plans. They apply emotional and intellectual intelligence to the long haul of life and work” - Hudson (1999) The Handbook of Coaching

I found learning how to coach to be simple enough, but judging who to coach and in which situation much more difficult, as it’s not as obvious as you might think. Scrum Masters, Agile coaches and other servant leaders have many other roles to play aside from a coach; teacher, mentor, change agent, impediment remover and facilitator. They need to use their best judgement to decide which role they play at any given moment to best serve their colleagues. 

When coaching causes frustration

The value of coaching isn’t communicated and questions are deemed unnecessary.

I’m very conscious that coaching employed in the wrong scenario can be frustrating for the recipient. I’ve experienced it firsthand, allowing myself to be coached out of politeness rather than benefiting from the process, before leaving the conversation feeling slightly patronised and misunderstood. I’ve picked up on signs of irritation in others during and after coaching; sighs, eye-rolls, clipped or sarcastic responses to questions, comments afterwards about being interrogated and complaints about endless open-ended questions. Popular coaching models such as GROW require the coach to ask a series of open-ended questions designed to help the coachee define their Goal, clarify their current Reality, explore Options and eventually Wrap up with a plan of action. Working through the questions in such a model can be very valuable to someone who is open to coaching, but can otherwise be quite tedious. 

The Intention to coach isn’t clear and questions are taken out of context.

Coaching questions can be taken out of context when someone doesn’t feel in need of coaching or doesn’t realise the intent behind them. Imagine you are coaching a colleague who’s dealing with a specific issue. You might ask questions like, “What alternatives could you consider?” to determine whether they have ruled out potentially viable options on account of assumptions or beliefs that could be challenged. Your colleague might suspect your question is leading somewhere, perhaps to an alternative approach you already have in mind. They may wonder whether you doubt the validity of their proposed approach or lack faith in them personally. If you are open with colleagues about your intention to help them through coaching, and explain your coaching methods, it can help avoid confusion and gives you both the opportunity to discuss whether coaching could be valuable to them at that time. 

When to Teach or Mentor rather than Coach 


Coaching involves:

“Unlocking a person’s potential to maximize their own performance. It is helping them to learn rather than teaching them." - John Whitmore - Coaching for performance (2003) 

Before coaching someone, it’s worthwhile to consider whether they have the knowledge they need to be capable of setting and achieving their own goals or solving a problem through coaching alone. There may be a need for teaching initially, otherwise asking open-ended questions in the hope of teasing out some ideas may make them feel as if they’re failing a test.  


Similarly, we should consider whether mentoring would be more appropriate than coaching.  If people are new to their role, they may benefit from a more experienced team member acting as their mentor to provide specific advice and guidance which wouldn’t be within a coach’s remit. A coach remains neutral and keeps their opinions to themselves, whereas a mentor can share their thoughts and feelings about things and give more direction.

"Mentoring is (the) process whereby one senior individual is available to a junior; to form a non-specified developmental relationship; to seek information from; to regard as a role model; to guide the performer; to provide feedback and appraisal; to teach all the facts that will enable the individual to perform effectively in an organization.’ Nigel MacLennan." - Coaching and Mentoring (1999) 

Teaching and mentoring go hand in hand. Teaching imparts the initial knowledge, and mentoring helps with putting it into practice, which can be very beneficial when it comes to complex work such as software development

When neither teaching, mentoring, nor coaching fit the bill

Sometimes the best way to support colleagues in their time of need is neither through coaching, teaching, nor mentoring. We don’t always need advice or guidance when we’re faced with a challenging situation; sometimes we might simply need someone to listen, empathize and perhaps pick us up by showing faith in our ability to get through it. 

Who are the obvious candidates for coaching?

Obvious candidates for coaching have the knowledge and experience required to achieve more, whether it be progressing in their role or overcoming challenges, and they are usually the most enthusiastic about receiving coaching. 

Often those who are first in line for coaching are the most confident and ambitious, while their less confident counterparts, who are perhaps more in need of coaching, shy away from it due to fear of being pushed too far out of their comfort zones. Coaching can help them see themselves and their situation from a different perspective and adopt a more positive “can-do” mindset.

People don’t always stand out as needing coaching; however, in an Agile organisation, with a culture of continuous improvement, it’s safe to say that anyone can benefit from it. Coaching encourages them to regularly set and achieve new goals. Also, let's not forget that anyone, even the least obvious candidates, can have a bad day and benefit from coaching to regain their optimism. 

Does more experience reduce the need for Coaching?

Even the most experienced people have something to gain from coaching in a culture of continuous improvement. In some cases, more experience can create a greater need for coaching. When someone has worked in the same role or organisation for a long time, they may become set in their ways, complacent and perhaps resistant to change. A coach can reignite their passion, empower them to challenge the status quo and push themselves out of their comfort zone toward new goals.

Knowing when to Coach requires intuition

We can use our intuition to help us judge the best opportunities to employ coaching. By  perfecting the ability to read a room we can pick up on negativity, signs of dissatisfaction, resignation or defeat that can tell us when colleagues are putting up with something they’d rather change, and hopefully could change, with the help of some coaching. 

Once an opportunity has been spotted, we need to draw on intuition to help us approach it at a good time. For example, if someone is still reeling from discovering a serious issue when you attempt to coach them, they may not be particularly receptive to it. They may need some time to calm down and gather their thoughts first.


Coaching can be valuable to anyone regardless of knowledge, time in their role or character – as long as they have sufficient knowledge and experience to be coached to their own conclusions and are in the right frame of mind to be receptive to it (which you can influence through making your intentions clear, building a trusting relationship with them, and through considerate timing). 

Some tips for learning when to coach:

  • Get to know people: their character, knowledge, experience, strengths, weaknesses, and motivations.
  • Read the room: observe behaviors and notice signs of dissatisfaction, resignation, and resentfulness indicating a desire for change.
  • Feedback: Request feedback on your coaching afterwards. Was it useful? Was it well-timed? etc. 
  • Coaching: Coaching is a two-way street, and you need to set the candidates’ expectations and receive their consent. 
  • Aim: Make sure the problem to solve or goal to achieve is well defined so there is a clear target to aim for. 

About the author

Alexandra Cory
Scrum Master

Experienced Scrum Master with a varied background working with software development teams in a number of sectors including digital agencies, finance, publishing and eCommerce. Helping teams to transition from Waterfall to Agile, implement Scrum and successfully scale Scrum in rapidly growing organizations. Passionate about empowering teams to self-manage, build trust and optimize their ways of working to become high performing teams.

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