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Squiggly Shortcut: 5 Questions That Will Transform Your Career Conversations

January is always a good moment to pause, think about the big picture and zoom out when we’re thinking about the future and direction of our career. In today’s shortcut, Sarah shares 5 questions to help you have useful career conversations whether that’s with your manager, a friend or with yourself.

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Episode Transcript

Podcast: Squiggly Shortcut: 5 Questions That Will Transform Your Career Conversations

Date: 15 January 2026


Sarah Ellis: Hi, my name's Sarah and this is a squiggly career shortcut.

 

And in today's shortcut I'm going to be talking about five questions to help you have useful career conversations. And you can use these questions in a few different ways.

 

You could use them to prepare for a career conversation you've got coming up. So to do some thinking beforehand, maybe you're a manager who's having career conversations with their team. You could send these questions out beforehand, get people to pick one or two that feel most relevant for where they are right now.

 

Or you could just use these as coach yourself questions. You could just ask yourself these questions.

 

But I'm recording this in January and I think it is a good moment for us to pause to think about the big picture and to zoom out a bit with our career, just to make sure that we are kind of looking ahead so that then we can also think about, well, what does that mean for me today in the role that I'm doing and the job that I'm in?

 

So question one, what do you want to be true in 12 months time that isn't true today? I love this question. It gets you to practise fast forwarding, doing a bit of mental time travel and visualising because you're asking yourself things you want to be true that aren't true today. This typically tends to be about doing something for the first time, so something new and being a beginner or making a change. If you find any of these questions a bit daunting or intimidating to get started with, please, please don't worry. That was lots of people's initial reaction. Maybe put the question down on a bit of paper, set yourself a timer for three minutes and do a three minute mind map for one or a couple of these questions just to warm up your thinking. Remember, most of us don't do our best thinking, like sitting at our desks. Maybe go out for a walk and think about one of these questions, or go and sit somewhere different and scribble down some notes.

 

 Question two, when do you feel most fulfilled in the work that you do? So this is really reflecting on what gives you energy and what do you enjoy? If I was answering this, I would talk about kind of creating with my co founder, coming up with ideas, solving problems together. Those are some of the things I really enjoy. And those often spark other thoughts, like how often do you feel fulfilled? Are you getting to use those skills and strengths really frequently? Are there more opportunities to do the things that you really enjoy? Maybe not just in your Job, but also in your team or in your organisation or industry.

 

Question 3. Which confidence Gremlin gets in your way the most at work at the moment, we all have lots of gremlins, those beliefs that hold us back. Fear of being found out, fear of not being smart enough, fear of conflict, if you're me. But which is the one? So rather than kind of worrying about them all, which is the one that you think shows up the most? Where and when does it show up? It's very rare that they're there shouting really loudly all of the time. So can you spot the specific situations? So for me, previously this would have been my conflict. Gremlin gets in the way the most when I'm surprised by disagreement. Use that question to sort of spot, like when your gremlin is kind of coming out to play in an unhelpful way, because, again, that can prompt you to start thinking about, well, what could you do to cage it, doing that for yourself. But if you're in a career conversation, often other people might have ideas or even they might just be able to support you in those moments where that gremlin is sort of shouting loudly.

 

Question 4. I think this is my favourite one. What are you curious to learn more about in the next three months? So I kept the window here a little bit shorter than a year, but because I think we're curious about lots of things and sometimes really big goals are too far away, not good for us to get started with. So kind of one thing that you're really curious, you're intrigued and you're interested in. So I shared actually on LinkedIn this week. I'm really curious to learn more about systems thinking. I know a bit, but not enough to be able to describe systems thinking in a simple and straightforward way to someone else. So I feel like I need to improve my own understanding before I can start to apply it. But I see it pop up in lots of different places. But I don't, you know, I want to. I want to dive a bit deeper into it for myself.

 

And then the fifth question, and this is going kind of beyond even the next 12 months. If you weren't doing what you do today, what opportunities and possibilities would you like to explore? So it's kind of letting go of, you know, how you see yourself today in your job title and your role and your day to day, and just really thinking creatively and just imagining the different roles, maybe the different organisations. If you really want to dive into that a little bit more, we do a scanning exercise that we talk about in how to explore your progression possibilities in that podcast episode where you take lots of data from different job descriptions to give you some ideas. Because I appreciate that is always a really big question. Helen and I actually asked ourselves that question last week to test it out and it did take us both a moment. But then actually once we got started we could think of loads of other things. And that's despite the fact we actually really love what we already do.

 

So those five questions for you what do you want to be true in 12 months time that isn't true today? When do you feel most fulfilled in the work that you do? Which gremlin gets in your way the most at the moment at work? What are you curious to learn more about in the next three months? And if you were doing what you do today, what possibilities and opportunities do you want to explore and are you intrigued by?

 

So I hope you found those helpful. Whether you're mind mapping, having a career conversation with your manager, going for a walk and talk with a friend, and if you've got any other brilliant career questions that you find really helpful, feel free to connect with me on LinkedIn and message me. I'm always looking to increase my bank of useful Squiggly career questions, but that's everything for today.

 

I hope you are finding these Squiggly career shorts useful. You can email us at any time. We're helenandsarah@ squigglycareers.com.

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