How To Have Successful Workplace Conversations

A three-step guide you can implement.

Jane sat down with her line manager, excited about the conversation ahead. She had many ideas about moving the project forward and looked forward to brainstorming their next steps. She thrived on collaborating with others and innovating to create a meaningful impact.

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As the meeting began, she realised it was going to be nothing like what she had imagined. Her heart sank as she listened to the list of must-dos and how-to dos flying her way. She tuned out as her line manager started talking.., “Now Jane, I have been thinking, and this is what we need to do….” Jane knew this was her cue just to shut up and listen and do as she was told. She wondered as she listened about how she would grow as a leader if she were to spend her time just following instructions!

Have you been in Janes’s position? Have you been the line manager? From my personal experience, I would say ‘yes’ to both, at different times.

Liz Wiseman, the author of Multipliers, suggests the role of a leader has shifted —moving away from a model where the manager knows, directs, and tells,
toward one where the leader sees, provokes, asks, and unleashes the capabilities of others. That is what Jane was looking for in her line manager. For Jane, her desire drove her expectations for interactions with her line manager, and she experienced disappointment when that expectation was unmet. It is an easy fix that leans into the concept popularised by Brene Brown in Dare To Lead. It’s a simple concept, yet many leaders find it hard to implement. Clear is kind.

Several things are happening here for the leader and the team members that create this complex system of conversational behaviours. As we unravel the complexity, one thing must be at the front of our minds. Great conversations start with you.

A research study out of Stanford University around communication in the workplace indicated that 9 out of 10 conversations missed the mark. Now, that is a rather
disturbing statistic. However, there is a relatively simple reason why this happens.

I see two common mistakes that impact the quality of the conversation. The first and most common mistake occurs when participants enter the conversation with different understandings about the purpose of the conversation. One participant has already decided what needs to be done. Their intention is to advise. The other person expects to contribute their ideas and thoughts, be heard, and feel valued. The second mistake occurs when we assume everyone thinks the same way as ourselves.

Here are three steps you can take to set your conversations up for success

Step 1 – Decide what kind of conversation is needed.

Use the conversation compass to navigate a shared conversation. Four types of conversations are outlined in the conversation compass, an adaptation of the conversational dashboard proposed by Judith Glasser in her book Conversational Intelligence. These four conversations are summarised below:

The big idea is that conversations are more effective and efficient when people are in lockstep and enter the conversation from the same space.

Step 2 – What is the best way to approach the conversation?

An advantageous way to use this model is with the following questions of reflection.

Think about you – What is your best approach?

Things to consider:

  • Is there scope for sharing ideas or is the decision already made, and all you need to do is inform others of the decision?
  • Is this conversation informational or transformational?
  • Is it action-orientated or opinion-orientated that required influence?

Think about the other participants — What might the other person expect in the conversation?

Things to consider:

  • Do you expect them to want to contribute ideas, or will they expect you to provide the information?
  • Will they have an opinion, or do you expect them to not really care in this case?
  • Is this an area of growth for them? What do you think they need?

Step 3 – How will you communicate that intent to the other person so you are both starting on the same page?

Things to consider:

  • Think about the context of the conversation.

Consider how the context may impact the other person so you can identify how to invite them into the conversation
and make it safe. This step aims to prevent differing expectations from arising in conversations. Framing what is expected in the invitation creates the space for both to step into the conversation from the same place. When you start together, three things happen.

  • You create safety
  • You stay curious and minimise unhelpful conflict.
  • The gap between intent and impact is decreased by outlining expectations and naming the kind of conversation at the outset.

Here is how you do it,

  • TELL – I’d love to chat to let you know… what will happen next in project x.
  • ASK – I’d love to chat and hear your thoughts
    about our approach to project x.

See the difference?

Follow these three steps and you will set your conversation up for success before you start.

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Tabitha Leonard


Tabitha Leonard, creator and founder of coaching intelligence NZ is a certified communication coach known for creating school cultures where approaches to communication propel performance. She is obsessed with supporting leaders to communicate with the brain in mind so they can nurture exceptional educators. She can be contacted at Tabitha@tabithaleonard.com