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Guest Blog | How to Have Difficult Conversations

Top tips on how to approach a challenging career conversation

Tips on how to approach a challenging job or career conversation

…and how to avoid leaving a trail of disaster in your wake

Human Resources, Learning and Development Professional and Coach, Janet Henson-Webb, explains that there are two extreme approaches to difficult job and career conversations and shares some tops tips on how to handle them well.  

  1. Some people approach a difficult conversation like a ship in full sail.  They believe their direct, “let’s get it over with” approach demonstrates strength of character and courage.  They sail in and deliver the message quickly and succinctly, firing all their cannons at once, with little regard for either the recipient of the message or the context, environment and circumstances of the situation.  Meanwhile, to continue the analogy, the recipient of the message is usually bobbing about in a small boat having almost been upended by the galleon which has just sailed by or, if they’re really unlucky, they’re in the water surrounded by flotsam and jetsom.
  2. At the opposite end of the scale are those who procrastinate, who constantly put off initiating the conversation and who can never quite bring themselves to start it.  Their “head in the sand” approach, hoping that the “problem” will eventually go away drags the situation out, leaving matters unresolved, festering and infectious.

This may sound extreme but these approaches are surprisingly common.  

Here are some techinques to help you have a successful outcome

I would be the first to concede that effective communication takes skill and effort and what we’re seeing here is a typical example of the fight or flight response.  However, like all skills, fine-tuning your ability to communicate well and appropriately takes practice, preceded by some careful planning, preparation and rehearsal.  Here are some techniques to get you started.

Plan and Prepare

The starting place should always be your aim.

  • What is the intention of the message?
  • Why is the communication taking place?

Write this down and take time to define and refine it.

Now think about the recipient of the message.

  • What do you know about them already?
  • What are their communication preferences? Do they like a direct approach or will you need to work towards your message gradually?
  • Is there a best time of day to meet with them? You want them to be focussed and giving you their full attention.
  • Will your message be new to them or is it one of a series of ongoing discussions?
  • How do you anticipate they will react? Will they be defensive, hurt, angry, upset?
  • What will you do to respond to that situation? How will you defuse anger?  What will you do if they break down in tears?

You can’t plan for every eventuality but think through how the conversation might pan out based on your current knowledge of the individual.

  • Consider how you would feel and respond if you were in their situation.
  • Do your preferences correlate with theirs?
  • Think about where you might have to adjust your approach to take into account their views and experiences.


Not only do you need to be clear about what you want to say and how you are going to say it but you need to speak the words you’re going to use out loud.  This may sound like a step too far but you may well be surprised at what you come up with at the first attempt.  All manner of ill-judged words, phrases and interpretations come tumbling out and you’ll quickly realise that rehearsal is imperative.  Better to make your mistakes in private before the event.

  • Rehearsal gives you the opportunity to iron out any ambiguous statements.
  • It gives you time to find the right words for what you want to say.
  • It builds your confidence which is good for the recipient of the news as well as for yourself. No-one wants to sit opposite someone bumbling their way through a difficult conversation.  There will always be moments when you have to think “on the hoof”, choosing your words carefully and expressing them in the right way and this naturally introduces some hesitancy into your conversation.  But this is different from not planning, preparing and rehearsing in the first instance.

Final words...

Never, ever go into a difficult job or career conversation with someone without planning, preparation and rehearsal.   As the saying goes... to fail to prepare is to prepare to fail” .

This is the fourth blog from our Guest Blog Expert, Janet Henson-Webb, a Human Resources, Learning and Development Professional and Coach

Janet Henson-Webb, Transitions Consultant:


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