Managing Difficult Coaching Relationships | Salestrong


Managing Difficult Coaching Relationships

In any type of relationship, the dynamics between the two individuals will have a significant impact on how successful that relationship is and this is no different for a coach/coachee relationship.  The challenge for many leaders required to step up and become a coach, is that they often have long-standing (and sometimes even problematic) relationships with those they’re required to coach.

So, how can leaders move beyond this to ensure they coach their teams effectively?

Why it’s problematic?

Coaching another person carries with it a huge level of responsibility and expectation.  The main purpose of a coach, after all, is to improve an individual’s performance.  Coaching becomes problematic if the relationship between the coach and coachee is strained or compromised, in any way.  Under these circumstances, both the coach and coachee are likely to experience any number of concerns – anxiety, apprehension, doubt, scepticism, unwillingness – all of which will only serve to negatively impact coaching outcomes.

Below I’ve highlighted the most common challenges when it comes to coaching relationships and offered some strategies for overcoming these:

Coaching a friend

Whilst this particular challenge tends to carry less apprehension for both parties than some others, there are guidelines that should be observed when coaching a friend if you are to avoid damaging either of the relationships:

  • Set ground rules at the outset – Be clear that you have two distinct roles, one as their friend and one as their coach.  You need to clearly differentiate the two relationships and ensure that each of you understands what is expected of each of you whilst you are engaged in the coaching process.
  • Maintain objectivity and avoid making assumptions – When you know somebody well, you will naturally have some pre-conceived ideas about how they might respond to a certain situation based on past experiences, but it is important not to let those influence how you coach them.  Instead, choose your wording carefully, try to think how you might phrase something if it were a coachee you knew very little about.
  • Maintain accountability – One of the key roles of a coach is to drive accountability to action, but this can get lost if the coach “makes allowances” or is more lenient with a friend.  Make sure you’ve covered off expectations regarding accountability when you set the ground rules at the outset.
  • Know when to step away – There may be occasions when you do not feel it is ethical to continue coaching somebody who is also a friend, perhaps because you are too deeply involved in either a personal, or work-related issue which involves your coachee, or because you feel the friendship is negatively impacting the success of the coaching.  Damage to either the friendship or the coaching relationship will, inevitably have a knock-on effect on the other relationship and it’s important that you are able to recognise and acknowledge when the coaching is no longer effective.

Coaching someone older/more experienced than you

Age and experience can both bring with them a sense of greater power so, when someone younger or less experienced is required to coach such an individual, the power balance shifts.  This can impact the coach’s confidence and can leave the coachee feeling resentful and patronised.

  • Start by outlining the purpose and aims of coaching – To be an effective coach, you do not have to have greater experience or knowledge than your coachee, you don’t actually have to be better than them at anything.  Rather, you need to have the ability to help them achieve their full potential; to look at situations and choices from different perspectives and to encourage them to step out of their comfort zone.  Set the tone by working together through the aims of the coaching, allowing the coachee to see that age/experience does not come into the coaching process and showing that you’re invested in their success.
  • Avoid the temptation to demonstrate your credibility – You may feel a need to justify your role as leader to someone who clearly has age and experience on their side but, be warned, this will only create friction in the relationship.  Instead, have confidence in your abilities – you were given this role for a reason – and avoid looking for opportunities to demonstrate superior knowledge.  Remember my first point, that an effective coach requires only the skills to be an effective coach, not to be more highly skilled or experienced in any particular field.
  • Give it time – When an external coach is employed by an individual, there’s no ‘history’ to work past, leaders looking to coach their own team members don’t have that same luxury.  Therefore, accept that you’re probably going to have to give it time.  Coaching relies on mutual trust and this can take a little time to build. Make sure you are consistent and accountable as the leader, both inside and outside the coaching sessions.  This will help you to build credibility with your team and strengthen coaching relationships.
  • Address the elephant in the room – Sometimes, whether this be in your initial coaching session or (if things don’t seem to be working), further along the line, you may just need to address the elephant in the room.  If you feel that the coachee is not open to the coaching relationship, hit the subject head on but, if you do choose to do this, keep emotions to one side, stick to facts and remain calm.

Coaching someone you’ve beaten to a promotion

In a study by Robert Half Management of more than 2,200 CFO’s, 19% reported that leading a former peer or friend was the hardest part of becoming a leader.  The obvious challenge here is resentment, particularly if the individual believes that they were the better person for the job.  Getting past this hurdle can be tricky and certainly, all of the tips highlighted above for coaching a friend, should be observed here.  In addition, this specific situation may benefit from the following:

  • Be consistent – Individuals resentful of your new position are likely to be looking for any opportunity to call you out.  Therefore, you need to be consistent in what you do and what you say you’ll do, particularly when it comes to them.  For example, given the strained relationship, it will be tempting to delay coaching sessions, reducing the frequency but, if anything, the opposite is required.  Stick to the commitments you make to them.
  • Seek out your own coach – This one may be somewhat dependent on your organisation’s culture and, specifically, your direct manager’s attitude to coaching but, having your own coach has two additional benefits in this situation.  Firstly, letting your team see that you too are a coachee can help to reduce misconceptions that you have ideas above your station now that you’re a leader (feelings which would typically accompany those of resentment).  Secondly, having your own coach, of course, gives you the platform in which to explore this particular challenge with your coach, who is more than likely to have been in the same situation at some point.
  • Don’t take it personally – It’s very easy to take this personally, to feel angry that the individual seems unable to congratulate, or be happy for you and holds you responsible for something, when you’ve done nothing wrong.  Try turning the tables and consider how you would have felt were the situation reversed.  Yes, you might counter that you would not have behaved in the same way, but it is highly likely that you too would have felt some resentment and anger.  Different people deal with situations in different ways, some just need a little longer to adjust.  Almost always, in this specific situation, the individual just needs some time to get over their initial feelings.

Coaching someone with whom you have conflict

Perhaps the most difficult challenge to overcome in relation to developing an effective coaching relationship.  This is going to require some serious thought and attention.

  • Don’t try to ignore it – There’s no sweeping this one under the carpet, carrying on as though nothing has happened, the two of you are going to need to sit down and talk about this.  Conflict arises from a difference of opinion which manifests into something more toxic and personal.  The only exception to this is where the situation was one that either involved (or should have involved) HR.  In such circumstances, my best advice is to talk to HR first, they may need to be involved in the initial conversation or may decide that it’s just not appropriate for you to be coaching this individual.
  • Be the bigger person – Perhaps with the passing of time, you might both feel able to meet in the middle but, in the absence of this and the pursuit of a way forward, as the leader, you’re going to have to accept that you might need to put your own opinion to one side and take the higher ground.  Whilst you may be reluctant to do this, fearful that it displays weakness, providing you demonstrate strong leadership and hold your team to account, there is no reason for this individual to perceive you as a weak leader.


For more on this topic, read our previous post ‘Do Sales People Really need Coaching?‘.

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