The Powerful Conversation
- Difficulty
- Moderate
- Time to result
- ~days to results
- Steps
- 7
- Confidence
- —
Simon's repeatable structure for a coaching conversation, demonstrated live on Ali. It runs broad before tactical, on the logic that tactical knowledge is freely available on Google and YouTube yet almost nobody applies it — so the constraint is energy, mindset and resources, not information. The sequence is: gather data by asking what success and freedom specifically mean to this person, step into their world, then move them into "the land of possibility" with a what-would-be-possible question. Simon then listens for their own language as evidence — a hedging "could", a tone that drops — and reflects it back. The conversation only closes when a vague intention becomes a named action with a calendar slot and a follow-up date.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Offer the experience
Rather than explaining coaching, invite the person into one: ask what they're doing next week and whether they'd be interested in having a powerful conversation together. Then stop.
Pro tip Simon built his early practice by attending as many events as possible and making this exact offer whenever he heard someone describe a challenge.
- 2
Start broad, never tactical
Address the broad issue — energy, mindset, resources — before any tactic. Simon's reasoning is that you can hand someone all the tactical know-how and they still won't act, so there must be a reason underneath, and everything flows from that point.
Watch out Diagnosing at the tactical level (leads, ads, funnels) wastes the session if the person has no baseline energy to execute.
- 3
Data gather to step into their world
Ask what is important to them and then define their words: what does freedom mean to you, what does success look like specifically. Simon compares it to Sherlock Holmes sitting a person in the armchair opposite and asking questions to unpackage what is in their mind before solving anything.
Pro tip Treat this stage as data collection only — resist the urge to advise while gathering.
- 4
Ask what is important about it
When they name a goal, ask what is important about that goal. This surfaces the real driver — in Ali's role-play, the podcast idea turned out to be about lifelong learning, not podcasting.
- 5
Move into the land of possibility
Ask what would be possible for them if they had the freedom, the time, the fulfilling work — the future-state question that energises rather than analyses.
Pro tip Scale questions ('how important is this, one to ten?') expose the gap between what someone says they want and what they're actually prioritising.
- 6
Reflect their own language back
Listen for hedging and for tone. Simon caught Ali using 'could' repeatedly and re-asked the question as 'what will you do', and separately noticed Ali's tone lift describing squash and drop describing his personal trainer.
Pro tip The best question can't be prepared — it only appears when you're genuinely listening to what the person just said.
- 7
Convert to a calendar commitment and a follow-up
Ask what one thing, however small, they will do before you next speak — then get the calendar out and pin the exact hours. Close by naming the follow-up conversation.
Pro tip Ali's commitment went from 'I could watch a video' to '3-4pm Sunday, video; 4-5pm, plan' in under two minutes of specificity pressure.
Watch out Without a stated follow-up, the accountability that makes the whole structure work disappears.
In the wild
Ali plays a doctor a year into the job, curious about music and starting a podcast but convinced there is no time. Simon asks what is important about starting a podcast, and the answer surfaces lifelong learning as the real driver. He asks how important taking a step is, one to ten — Ali says two. Then: how long have you been telling yourself 'when I have the time'? Eight years. What would have happened if you'd taken small steps eight years ago? Finally Simon reframes it as importance rather than time, and pins Ali to a named YouTube video and a plan in specific Sunday hours.
→ A vague eight-year-old intention became two scheduled one-hour blocks and a follow-up conversation the next week.
After a talk at a company in Canary Wharf, a manager who had only attended because it was hosted in his building approached Simon and said what he'd heard made sense, but why should he listen — what was the incentive to apply it. Simon didn't argue. He asked when was the last time you felt truly happy. The man paused, which told Simon a great deal, then admitted the cars he'd bought and the investments he'd made had been great for a while but he didn't think they made him happy. Simon's only follow-up was: what does that tell you.
→ The manager shifted from sceptical to genuinely interested in what could be possible for him.
Common mistakes
Collecting a bank of questions in advance
Simon says new coaches hunt for the right list of questions to ask. The best question can only present itself in the moment, from listening — a pre-loaded script stops you stepping into the other person's world.
Accepting 'I could' as a commitment
Conditional language signals no decision has been made. Simon rephrases to 'what will you do between now and next week' and then demands the exact calendar slot, because an unscheduled intention is not an action.
Solving the tactic instead of the block
All the tactical material is already free on Google and YouTube, yet very few people apply it. Answering the tactical question leaves the actual reason for inaction untouched.
From the transcript
“what would be possible for you when you have that freedom”
“I'm noticing the word could a lot I'm going to rephrase the question again what will you do between now and next week”
“great let's get specific get your calendar out when exactly will you be blocking out time to watch that YouTube video”
From the episode
Life Coach: Why Your Energy Drives Your Success In Life - Simon Alexander Ong
Simon Alexander Ong