Conversations are endemic in business. Most of us have several, perhaps dozens every day. Some as simple as a catch up over coffee, some as complex as a full day discussion to assess and respond to a newly presented challenge. In the middle are the regular workplace discussions we have to measure progress, solve tactical issues, make minor decisions or course corrections and so on.

Trying going a day at work without a conversation: you’ll find incredibly frustrating not to mention isolating.

Despite the prevalence of conversations in every aspects of our lives we rarely give much thought to how effective we are as a conversation partner. It’s also rare that we seek out or are provided with training or guidance on how to develop and master this skill. We truly take it for granted.

How then do you assess, do my skills need a tune up? Could I move ahead faster at work, get better results, achieve more, if my skills were better?

We think there are four core skills to develop if you want to focus on being an excellent conversation partner at work:

  • Questioning
  • Active Listening
  • Summarising
  • Challenging

In the rest of this article we’ll define each of these and give you a handy way to assess yourself against each of these skills.


For questioning we rely on a definition from Lani Watson at the University of Edinburgh:

A question is an information seeking act.

Think about that for a moment, it actually covers a wide range of situations. The information may be knowledge you want, or confirmation of something or that alternatives have been considered. You may be asking for yourself so that by answering someone supplies you with information or you may be asking someone to prompt them to reflect on something in order that they seek out new information for themselves.

How would you assess your own questioning skills? One way is by the quality of the answers you get. If you find that you’re asking questions and first time, most of the time you get good answers then you are most likely asking questions that are easy to understand and well designed to get at the information you want. A second way is by the reaction. If you are used to your conversation partners using phrases like “oh, that’s a good question” or “I’ll need to think about that” chances are you are asking thoughtful, insightful questions that are helping your conversation partner to reflect or to see things from a fresh perspective.

Active Listening

Our definition of active listening is our own:

Active listening is where the listener is required to make a conscious and fully focussed effort to listen and understand what the speaker is saying. In doing so they must understand the full message.

We all know the term active listening and we all assume we’re good at it but the reality is more than ever our environments are full of distractions and maintaining active listening is harder than ever.   

How then would you assess yourself here? Once again we suggest two rules of thumb. First is to be brutally honest with yourself. Try to keep track, how often during a conversation do you tune out to mull over something else, or because you caught sight of a notification on your phone or heard a noise in the room next door and began to speculate on the source? It’s so easy to that if you are honest you’ll find you are tuning out more often than you’d like. In the second case stop yourself at any point in a conversation and ask yourself, what was the last really important point that was made? If you can answer with 100% confidence every time then you can be confident in your active listening skill level. But if not then perhaps there is room for improvement?


We have a very concise definition of summarising as befits the topic:

Summarising is the process of expressing the key points of a conversation in a concise and easily understandable fashion.

In our view summarising is a critical, yet often overlooked conversation skill. The ability to replay, in either your own words or the words of your conversation partner as the situation demands shows an ability to understand, allows for mutual agreement to be reached quickly and demonstrates respect. We should all have this skill at our fingertips.

To assess your own ability to summarise ask yourself two questions. One, do I consciously plan for the use of summarising in my conversation at work? If you are like many people you neglect this skill and don’t make it a key feature of how you operate. Two, in any conversation, at any obvious point when your conversation partner has paused at the end of answering a question or outlining a situation or plan ask yourself, could I summarise, in my own words, in no more than a few bullet points, all of the key points that were made since I last spoke? If the answer is yes you are in good shape. But if the answer is no, or sometimes, then you have a significant opportunity to set yourself apart by mastering this critical skill.


Our final skill we define as follows:

The process by which we interact with a someone in a spirit of positive dialogue in order to question their thinking or beliefs in order to assist them to derive insights, ideas, options and avoid pitfalls in their situation.

Another often overlooked skill. Indeed many of us are actively concerned about challenging others in the workplace. Yet by our definition it’s clear that by avoiding the use of challenge we do ourselves and the people we are speaking with a big disservice. Properly used an effective challenge is one of the most positive things you can do in any conversation.

As with summarising being honest with how often or consciously you challenge today is essential to understand both your attitude to and current levels of benefit from challenging. In addition to this self-reflection the key way to assess the effectiveness of your challenges is to note how often by challenging you move the conversation into a new, more effective direction or how often you help to unstick a situation where your conversation partner can’t see beyond their current predicament.

Wrapping Up

Getting good at conversations isn’t something most of us consciously think about or plan for yet the benefits of investing in our skills are significant. Every journey of personal development begins with an honest assessment of where we are today. I hope these 4 quick self -assessments will help you assess you own skills and give you some pointers to areas where you may be able to improve.

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