How to get yourself in the right mindset before a difficult conversation

Which of these situations would be the most awkward for you?

  1. Breaking off an engagement;
  2. Asking a friend to pay back the money you lent them;
  3. Telling a colleague that their behaviour is undermining a team?

For many of us, the thought of having conversations like these is enough to make us wince.  Sometimes, people will do anything to avoid those tricky chats – like, marry, for example!


A simmering resentment may replace an honest chat.

Most of the time, people avoid having challenging conversations at work.  It’s so common that HR Directors I surveyed said it was one of their biggest headaches.  Yetunde Oladipo MA, Chartered MCIPD shared with me her process for checking your mindset before approaching these potentially uncomfortable conversations.

These 11 quick steps will help you discover how to approach a difficult interaction as well as find other options that may be just as effective.

If you’re prevaricating about approaching someone because you’re afraid you’ll bungle it or that it could blow up in your face, then this will have you realising what you can do to make the path smoother.

I’ve applied a real client situation (names changed) to this thought process.


The 11 questions to ask yourself before approaching a difficult conversation


1.  What is your dilemma?

“My manager, Florence, is not providing any guidance on a project, given to me by her Department director.  She’s also giving me the cold shoulder.”


2.  Can you consult with others?

“I hear through the grapevine that she’s been saying how she’d have preferred others to have had responsibility for this new initiative since they’ve been there longer.”


3.  What are your options? What are the consequences?

“I can ask colleagues for help with the project. Florence is hardly talking to me.  She’s probably sticking pins into a Voodoo doll at home, urging me to crash through glass doors.”


4.  Anticipate all the arguments.

“Having confided in another colleague, I realise Florence’s thinking would be difficult for her to rationalise to me in this context. Because of this, she’s dismissed or lied to me when I did try to raise the issue.”


5.  Reality check – do you have all the answers?

“I can’t argue with her if she thinks that those that are there the longest should be given opportunities, regardless of competence.”  This is her belief.


6.  Bias check – are you really open to their perspective?

“No.  My belief is contrary to hers.  We’d just end up locking horns.”


7.  How can the issue be reframed?

“She feels undermined because the director went over her head to give me this project.  It’s not personal.”


8.  Set intent.

“In this case, saying anything is futile.  I will focus on relationships which are more mutually agreeable. Easy to minimise contact and still have enough allies for my career not to be limited by her.”


9. Think about potential actions.

“Could be awkward asking her for a reference.  There are others in Senior Management, though, so it’s not an issue.”


10. Check your gut feeling.

“Now I’ve done all that, I don’t have a gut feeling.  My gut’s thinking about other things.  Food, right now.”


11. Plan of action.

“Enjoy my lunch.”



Your Action:

1.  Do you have a workplace dilemma, or working relationship you want to improve?

2.  If so, take 10 minutes to run through the questions before you deal with the issue.

3.  You’ve decided to have that difficult conversation?  Here are two techniques to help you.


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