• Jess Annison

Case-study: Dealing with a difficult boss



One of my coaching clients, Phil*, has a difficult relationship with his boss. During our sessions it became clear to him that, whilst they'll never be best buddies, he'd like to have a better understanding of how his boss ticks, and how best to work together.



Through our coaching Phil and I discussed their recent interactions together. We talked through the conversations that seemed to go well and feel constructive, and the ones that went badly or fell flat. We talked through the thoughts, feelings and assumptions that were leaving him feeling frustrated, overlooked and sometimes disempowered.


Phil identified some patterns, both in their boss's behaviour and in their own. Phil was finding it particularly hard to get his boss to set clear priorities for the team. Instead, he compared him to "a magpie, always going after the next shiny thing". This was proving to be really frustrating for Phil: it meant that he often felt overwhelmed, and unclear about how to best direct his own team's efforts. As a result, he was disengaging from discussions about strategy and prioritisation, because he was pre-empting the "magpie" tendencies and the frustration it would cause.


By noticing those patterns and considering them with the help of transactional analysis theory, he has developed some alternative options for how he approaches difficult discussions with his boss. For example, Phil recognised that by disengaging from the discussions about strategy he wasn't standing up for his team's best interests (nor his own). Phil identified how he might best be able to constructively challenge his boss and help him focus: what words to use, how to frame the challenge, and when / where / with whom it would have the most positive impact. He put this into action between coaching sessions and, although one or two instances were still challenging, his boss responded really positively and openly thanked him for (in his boss's words) "reining him in".


Phil has experimented with a range of techniques between sessions, and we've reviewed what worked well and what needed further adjustment. Through the coaching he has developed a new understanding with his boss, and is having a greater impact in his role as a result. As part of his testimonial, Phil said "Jess quietly listens and then helps make sense of the chaos, by helping those solutions already within you rise up to a conscious level."


*Not his real name.


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