A coaching conversation
‘What do you think is going on there?’ I asked.
My client stared at the screen, absorbing the chat on MS Teams and trying to make sense of it.
‘It’s like something’s changed. One minute, they were very receptive to the project. Next, they seem disinterested and detached… almost curt.’
‘Why do you think that is?’
He considered this for a moment, looking thoughtful.
‘Perhaps it’s not me..’
‘Go on’
‘Well, I think she is behind the project, but reading this back again, it looks as if something has happened to change her mind. It’s not that she’s fobbing me off or becoming dismissive. I’m wondering, what is she not saying? Maybe she is under some kind of pressure?’
‘That’s a possibility. ‘ I said, ‘What do you want to do about that?’
His expression changed. You could see the lightbulb go on.
‘It’s been a while since we’ve had a proper chat, ‘ he said. ‘She’s hard to pin down and extremely busy. I’m going to reply and suggest we have a coffee. Perhaps I can find out what’s really behind her communication. And if I find out what the problem is, I can offer to help.’
Conversation in the Digital Age
I’m interested in how we can have more effective conversations and how digital communication can facilitate better conversations. We spend a significant amount of time on digital platforms and communicating via various channels, such as MS Teams or Slack, or through ephemeral messaging services like WhatsApp. So, how can we utilise technology to help us find our voice?
My client and their stakeholder had that conversation by the way, and it had a positive outcome for both. Yet, it would have been easy to continue communicating digitally and avoid an in-person, honest conversation. The digital space, however, allowed my client to analyse the communication from their boss and gave them time to consider what might be driving the behaviours and what to do about it.
Language and Ashby’s Law
Sometimes, we can read too much into the tone of digital communications, but it does give us time and space to analyse both the structure and the content of people’s language.
Are they Proactive (short sentences, direct) or Reactive in style (long sentences, indirect)?
Are they focused on People or Tasks?
Are they talking about Change or Sameness?
Are they Open (saying what they mean) or Closed (holding something back)?
We can then decide how to adapt, showing flexibility in our approach to achieving good outcomes.
- Flexibility in our language – responding to their language
- Flexibility in our mindset – becoming the host of conversations that matter
- Flexibility in the environment – where and how the conversation takes place
Flexibility is a concept I often explore with clients trying to manage a complicated relationship. The individual who shows the most flexibility in the conversation tends to have the most control over the outcome. It is based on systems theory, something called Ashby’s law. I have seen many clients achieve success by choosing how to use the digital space and then stepping into the conversational space. They become the host of their conversations to create better outcomes and relationships.
How else can we leverage the digital space and utilise AI specifically?
Framing your conversation
In my e-book, “Find Your Voice,” I outline a conversation model I call “The Frame.” It helps people tackle difficult conversations by framing the start of any conversation. Usually, people find the opening the hardest part, and I find that once we find the words to start a challenging conversation, the rest is much easier. In preparation for a recent webinar, I decided to run my model through Chat GPT to test it :
Thanks, John — the framework you’ve developed provides a gentle yet clear structure to open up meaningful conversations It looks like it’s designed to balance honesty, empathy, and clarity — ideal for navigating sensitive or essential discussions.
Great, so I asked it to create examples using my frame. Here is just one example it came up with:
How do I approach a colleague where tension exists?
I wanted to talk to you about some of the tension I’ve noticed between us during project check-ins.
I know you want the project to succeed and that you bring a lot of experience to the table.
I think that some of our recent interactions have felt a bit combative, and it’s starting to impact how I contribute.
So, what I wanted us to talk about is how we’re working together and whether there’s anything we both need to say or reset.
If we can do that, I think it’ll make the rest of this project a lot smoother for both of us — and maybe even more enjoyable.
I’ve been using AI as a test bed for approaches and getting instant feedback. I’ve used it to approach tricky or sensitive issues, negotiate opportunities, and effectively pitch services or position my offers. It is well worth testing your approach to conversations or any other form of communication using digital tools.
Instant Feedback
Perhaps digital and AI, specifically, can help us find our authentic voice. Many tools are available to help us become the confident, assertive, and persuasive people we deserve to be.
I once helped a client role-play a situation in which they felt subjugated by a colleague’s behaviour. The colleague wouldn’t acknowledge or even look up from their computer when they went to them for information. You can imagine how this made my client feel.
In the role-play, the client noticed their body language and how they entered the room. I was also able to provide specific behavioural feedback. By replaying the scenario, we developed a new, improved approach that incorporated more positive language and physiology. It gave them the confidence to approach their colleague with purpose and assertiveness, and get the result they wanted.
These days, we can now turn to simulated environments that provide similar immediate feedback, helping us practice our skills. Something like Orai.Com can give us feedback on:
- Pace
- Filler words
- Energy
- Facial expression
- Conciseness
- Pausing
- Confidence.
The potential for digital feedback is enormous and can only accelerate.
Creating a Thinking Environment
Finally, most of you will have used AI tools to capture conversations, using tools such as Co-Pilot, Otter or Zoom Companion.
These are a game-changer in bringing quality to our conversations, and they are brilliant in the coaching and collaborative arena.
On a practical front, it saves us time writing stuff up. It also clearly captures what has been discussed and agreed upon, removing a potential source of conflict and mistrust.
This allows both parties to engage fully, creating a better thinking environment and providing each other our fullest attention. We deserve it after all.
And when the conversation is over, you can reflect on the themes that arise, the barriers and enablers to a good outcome, and consider your own language and communication structure. How did that go?
Develop better conversations.
The digital tools and strategies above help us to be better hosts of our conversations. They enable us to choose when and how to use the digital space and to develop effective and human interactions.
- Prepare with Precision – digital tools will help you organise thoughts and clarify intent.
- Practice with Feedback – simulated environments can build confidence in delivery.
- Perform and Reflect – real-time and post-conversation tools are already enhancing our conversations.
I encourage you to find your voice and use AI and other digital tools to have those conversations that matter to you.
About the author: John Drysdale is an executive coach, trainer and facilitator within the sector and coach to SME business owners to help them grow their business. He runs an ILM centre and trains people to become qualified coaches. He is also a certified trainer/coach with Asentiv© the world leaders in relationship development and referral marketing. Living in Scotland he enjoys running, walking in the beautiful surroundings of Fife and is a keen music lover and musician. He has recently published his book entitled ‘Find your voice’.