These questions are changing my life


Hey friends,

I recently re-read The Coaching Habit, and it’s now my top recommendation for anyone who wants to give better advice.

I’m usually quick to jump in with a solution when people tell me their problems. But apparently being a good mentor is more about listening hard and asking the right questions.

So here are six questions from The Coaching Habit you can use the next time a friend or colleague asks you for advice. Working with my team, I’ve been amazed by the power of the right questions to get clarity on things.

🥊 The 1-2-3 Opening Combo

🧠 1. The Kickstart Question: What’s on your mind?

This gets to the heart of the conversation. It’s another way of saying let’s talk about the thing that matters most. The person we’re talking to will be relieved on multiple levels:

  1. we’ve skipped the small talk
  2. we’re letting them immediately address the main issue
  3. they’re being listened to.

A good way for us to deepen the conversation (once we’ve discovered the main problem), is to ask which one of the three P’s they’d like to discuss:

  1. Project – the technical content of their problem.
  2. Person – issues with colleagues, family, etc.
  3. Pattern of behaviour – are they getting in their own way?

This gives us a good framework to start any coaching/advice conversation.

🤔 2. The AWE Question: And what else?

Asking and what else? stops us from diving in with advice after hearing someone’s problems.

It also gets all of the issues on the table, because the first-level answer to what’s on your mind may not address the biggest issue.

For example, with a little prodding, ‘I feel like Jane doesn’t listen to me’ could turn into ‘and actually, I feel like no-one in the flat really listens to what I have to say’. Having even a little bit more context makes our advice-giving at least 20-30% better.

Asking an extra question also buys us some time to think about our answer… 🤫

🔍 3. The Focus Question: What’s the real challenge here for you?

Everyone loves fixing problems, ticking them off on the to-do list. But we rarely stop to ask “are we solving the right problem?”*

When we ask what’s the real challenge her for you?, we give our conversation partner time to slow down and think about what their real problem is, before they put loads of work into a possibly pointless solution.

This also saves us from discussing multiple problems, and going round in circles.

*People can spend days fine-tuning a Notion PKM or Task Manager template, before realising that it doesn’t actually solve any of their real problems.

🚀 Three Next-Step Questions

So now, the conversation is flowing and we’ve discovered the main issue. The next three questions give some forward momentum to your conversation.

🎯 4. The Foundation Question: What do you want?

Sometimes the person we’re talking to will know their problem inside out, and recognise the challenges… but still not know what they actually want to happen.

I sometimes call it the Goldfish Question because it often elicits that response: slightly bugged eyes, and a mouth opening and closing with no sound coming out. – The Coaching Habit

Asking this question might do a few things for our conversation partner:

  1. Answer the question for them: “Oh, I guess what I really want is X. I’ll go get that done.”
  2. Get to the heart of their problem: “Hm. I guess what I really want is to move to the US. Then all of my problems would be solved”.
  3. Give them the confidence to finally make a request: “Actually Ali, what I really want is for you to stop using me as a guinea pig for your weird coaching methods”.

We have to pay attention at this point: ever answer has a subtext. It’s usually one of what Marshall Rosenberg calls The Nine Self-Explanatory Needs.

🦥 5. The Lazy Question: How can I help?

If we haven’t already got a clear request from asking what do you want, then how can I help should do the trick.

More importantly, this question is efficient. It stops us from kind of doing what the other person wants, but not accurately enough that it’s actually useful.

And remember – you don’t have to say “yes” to requests, or solve everyone’s problems. You can always guide people through their own problem-solving process: “what have you tried so far? What are your first thoughts? OK, that all sounds good, any other solutions?”

🎓 6. The Learning Question: What was most useful for you from this conversation?

This last question is partly so we can improve as advice-givers by getting feedback on what worked and what didn’t. But asking the Learning Question has a few other benefits:

  1. It frames the conversation as something positive, shifting both of us into growth mindset mode.
  2. It makes the person we’re talking to actively recall the whole conversation in their mind, which reinforces any lessons they learned.
  3. It makes things more personal and shows that we care about their feedback.
  4. It also sneakily reminds people that you’re pretty helpful person. 😇

By narrowing it down to the most useful thing, we’ll also get 90% of the feedback value in probably half the time. And we’ll definitely get feedback, because (unlike “was this convo helpful”?) it’s not a yes/no question.

This book has massively levelled up my advice skills. 📈

Have a great week!

Ali xx

🚀 Learn How To Kickstart Your YouTube Channel (for free)

Not many people know this – I have a free 7-day email course called Part-Time YouTuber Crash Course. It’s for anyone who wants to kick-start their YouTube channel. We’ve recently revamped the whole thing, adding Notion templates, downloadables, and interactive assignments to help you get your channel off the ground.

It’s also a nice intro if you’re considering enrolling in my Part-Time YouTuber Academy, which launches next Monday 🚀 Anyways, the email course is free, takes 7 days to complete, and you can sign up by clicking this link.

♥️ My Favourite Things

📕📗📙 Shakespeare and Company  I was in Paris last weekend and had a browse in this bookshop near Notre Dame. Tbh I want to spend more time serendipitously reading in bookshops, instead of getting my recommendations exclusively from Twitter. In fact, now that I’m running a medium-sized business I need to build time into my day to go do random stuff, and not get locked into a corporate structure.

🎙️ Podcast – Nathan Barry on My First Million. Been getting back into podcasts and revamping my Castro setup. I really like the level at which the My First Million guys have their conversations. Some podcasts skew too beginner heavy, with questions like “what struggles did you have starting out”, but they keep it pretty raw and real, so it genuinely feels like being a fly on the wall. This episode with Nathan Barry (founder of ConvertKit, the email service provider I use to send out Sunday Snippets 💕) was particularly good.

📝 Tech – Apple Magsafe Duo. My uber-handy portable wireless charger, which now lives in my bag. It flips out and lets me charge two Magsafe devices at the same time, eg iPhone, Airpods or Apple Watch. A bit overpriced, but that’s sadly the life of an Apple fanboy like me.

✍️ Quote of the Week

Never say anything in writing that you wouldn’t comfortably say in conversation. If you’re not a person who says “indeed” or “moreover,” or who calls someone an individual (“he’s a fine individual”), please don’t write it.

From On Writing Well by William Zinsser. Resurfaced using Readwise.

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