How to Have Courageous Conversations - Part 1

You need more than ‘guts’ to tackle difficult conversations at work, you need tools. Tool #1 is understanding the personality you're dealing with.

by Philippa Thomas 0 Developing yourself
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People are often wary of being too ‘courageous’ in their communications at work, in case they’re perceived as aggressive and rude. It can be intimidating to confront difficult situations and engage in a tough conversation. After all, most of us don’t want to be considered rude or disrespectful, so we sometimes find ourselves agreeing to things we really shouldn’t. However, by avoiding that tough conversation, the problem isn’t resolved - just deferred. On the other hand, when we do attempt to say ‘no’, especially to a domineering character, we can find ourselves in a stressful conflict situation, which can seriously damage our working relationships.

However, a courageous conversation doesn’t have to be confrontational. The key is having the confidence to be straight-forward and strong – but respectful too – if you have an opinion to voice or problem to address. With the right tools at your disposal, you’ll find you don’t have to be a courageous super-hero after all.

Tool #1 – Personality Preferences

Your first step should be to start thinking about the Person you need to be ‘courageous’ with, reflecting on their personality and range of ‘normal’ behaviours. It’s highly likely that they will fall into one of these four categories:

  • Thinkers/Analysers – are logical and unemotional. They want facts and accurate information, but work at a slower and more reflective pace. They are unlikely to be swayed by you just being nice to them.
  • Directors/Drivers – are dominant, impatient and fast-paced. They are bottom-line, get-it-done-now people and are likely to be found in your senior management team!
  • Socialisers/Expressers – are the people-persons, but they also like a fast pace. They are fun, talkative and flexible but don’t like to hang around too long.
  • Relators/Amiables – are affable and easy-going people-persons, more laid back than the socialisers. They prefer not to make decisions quickly and can need a lot of support in doing so. Primarily concerned with the needs of others, they like to believe that they’re ‘doing the right thing’ at work.

When preparing for a difficult conversation with one of these types of people, you’ll find it helpful to check with our simple list of key Do’s and Don’ts below.


DO: Be thorough and well prepared; demonstrate through actions rather than words; be systematic, exact and organized; describe a process in detail and explain how it will produce results; ask questions to let them show how much they know; provide details and analysis with solid, tangible, factual evidence.

DON’T: Spring surprises on them; fail to present good data; dismiss their ideas


DO: Talk about desired results; keep communication business-like; recognise ideas rather than the individual; be precise, efficient, and well organized; provide clearly described options with supporting analysis; argue on fact, not feelings, when disagreement occurs.

DON’T: Discuss feelings; waste time with small talk; fail to get to the point; be unsure of your facts.


DO: Allow discussion to flow and occasionally go off topic; be entertaining and fast moving; be interested; avoid conflicts; compliment them; allow them to get things off their chest.

DON’T: Be boring; be unfriendly; ignore them; take too long to get to the point.


DO: Be warm and sincere; show a personal interest; allow them time to develop trust in you; move along in a slow, informal manner; listen actively; discuss personal feelings in the event of a disagreement; support the relationship above all else.

DON’T: Force your point; rush them to make a decision; ignore their feelings; just focus on the task.

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