Have you ever had to have a challenging conversation and not known how to go about it?

Whether you call them difficult conversation or constructive conversations or courageous conversations, what we are really talking about is a conversation that you might normally want to avoid.

That might be giving someone feedback that’s a bit challenging, talking to someone where you have a different perspective, talking to someone who might come across very aggressively and just knowing how to deal with it.

Are you thinking, I am not sure I know what a constructive/brave or courageous conversation then it might be useful to reflect on the following:

Do you find you are having a conversation about someone?  If you are not talking to them but are spending time talking about them to someone else, then you are probably in a place where you are avoiding having a difficult conversation?.

If that is the case, the next step is to prepare for it.  As with most things making it feel more manageable and being able to prepare for it will not only make for something that feels less uncomfortable it will also have better outcomes.

Once you feel prepared, go into the conversation with a positive constructive mind-set.  If you are going to go in that anxious, stressed mind-set then the chances are that will then be felt by the other person and that might influence some of their behaviours.

Where are you on the OK- Corral (see below)?  For a conversation to be valuable and not descend onto an argument you need both to be in the top right hand corner:  Assertive or Actively constructive.  This means you are both OK and not one of you in defensive or aggressive places that can lead to destructive arguments.

The OK Corral


To allow for the other person to be prepared, ask for their permission, in a non-confrontational way ask if you may give them feedback.  Give the person enough time to recognise that it’s going to be a really helpful and constructive conversation.

When sharing your thoughts or feedback be mindful of your language, you can inadvertently say things you do not mean.  Watch out for the use of “but”.  For instance, “you have done a really great job, but there is something I need to talk about”.  Replacing the “but” with an “and” “you have done a really great job, and there is something I need to share”, means that you do not negate the first positive part and are building on that positive base.

And then avoid thing like passive aggressive phrases where as I have said before, or with all due respect.  Be truthful.  It it essential that the difficult conversation is constructive, that you’re honest and that you are thinking about how that person is going to receive your messge.   And then allowing them to provide their thoughts around it.

Finally think about it as a joint solution where it’s not about what they are going to do but what are you going to do together.

In summary:

  • Prepare your thoughts and be in an Active Constructive mindset.
  • Recognise where they are in the OK corral (see above).
  • Describe the situation as a problem to be solved jointly.
  • Don’t assume you know what someone else is thinking.
  • Encourage them to share how they felt about the situation.
  • Listen, give attention and ease.
  • Acknowledge what they said and the impact that the situation has had on them.
  • Ask open questions to help expand the conversation.
  • Ask for permission when providing feedback: “May I give you some feedback”
  • Respond don’t react: recognise your emotions, consider your response.
  • Avoid the use of: “BUT”, Why questions and “As I said before” phrases.


Consider doing these things.


  1. Build a rapport with the person, get to know what works for them
  2. Consider what you are going to say
  3. Ensure you seek permission before doing so
  4. Be impartial, this is not what about what you think but what you observe
  5. Be consistent and persistent
  6. Be willing to receive feedback


And avoid these to ensure you have a successful outcome.


  1. Make light of your feedback or undermine the feedback being given
  2. Be aggressive or passive aggressive
  3. Use it as an excuse to address issues you have, this should be about areas they wish to address
  4. Ignore the behaviour – you are therefore complicit in it!
  5. Treat everyone the same, people respond to different types of feedback


As with most things the more often you do the more comfortable you will be and therefore the better the overall outcome. Don’t let it become a big issue, nip things in the bud!


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