#591 No Regret Skills: How to Make Better Decisions

8 Sep 2026 · 35 min · 11 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

“No regret skills” for squiggly careers, focusing on decision making (part 1 of a two-part series; part 2 covers adaptability).

Guests

None. Hosts Sarah and Helen (Squiggly Careers podcast).

Guest backgrounds

Not applicable—no external guests; the episode borrows ideas from Frank Bowley (Head of Skills England) and poker decision-making author Annie Duke (Thinking in Bets; How to Decide).

Key claims

No regret skills stay useful across scenarios; decision making helps career outcomes and builds trust. Don’t judge decisions by outcomes; score confidence probabilistically; use “truth groups” to challenge assumptions; categorize decisions by stakes (routine/considered/strategic); update judgments with new information; use backcasting (time-travel) to plan what you need to do for future confidence.

Notable examples

Confidence scoring for Helen’s PhD decision (e.g., 55%); team post-it/chat confidence rounds; a prototype decision they changed after low confidence; routine vs strategic examples like weekly meeting choices vs a CEO interview; backcasting for PhD success (research, real projects, new conversations/opportunities).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding No Regret Skills

0:45 to 3:38

Discussion on the concept of no regret skills and their relevance in careers.

“I was like, it's something that I have remembered and repeated, but we should obviously credit the individual as well at the same time.”

The Importance of Decision Making

3:38 to 6:00

Exploring decision making as a critical no regret skill in careers.

“I think the risk is because the hot right now skills, so let's use AI as an example, because they get a lot of attention, I think it is easy to under invest in no regret skills.”

Poker Principles for Decision Making

6:00 to 8:10

Applying poker principles to enhance decision-making skills at work.

“Okay, so the no regret skill that I think is important for everyone investing in is decision making.”

Interactive Decision Making Exercise

8:10 to 14:00

Engaging in a fun activity to reinforce decision-making concepts through poker.

“going to take some conceptual things about poker principles and poker parallels for decision making.”

Exploring Decision-Making Tips from Annie Duke

14:00 to 20:17

Learn how to make better decisions using insights from Annie Duke's work.

“something I'm not that familiar with that I can see play out at work.”

The Importance of Truth Groups

20:18 to 24:38

Understand the role of truth groups in enhancing decision quality.

“Let's see how the writing goes because I feel like that really derailed us last time.”

Categorizing Decisions: Routine, Considered, and Strategic

24:39 to 28:00

Discover how to categorize decisions and allocate your focus accordingly.

“I feel like the zero jeopardy given you're making me go through all of them um decision menu a A decision menu.”

Strategic Decision Making Insights

28:00 to 29:16

Learn how to prioritize and protect time for significant strategic decisions.

The Concept of Backcasting

29:16 to 30:48

Discover the technique of backcasting and its application in decision making.

“And I don't, yeah, I don't think, I think I was good at the last one, the trust one.”

Applying Poker Principles to Decisions

30:48 to 32:48

Understand how poker strategies can enhance decision-making across various contexts.

“I think we might have done this, but called it something else before.”
Show all 11 chapters

Personal Views on Decision Making Skills

32:48 to 34:06

Reflect on the value of decision-making as a no-regret skill and personal priorities.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Hi, I'm Sarah and I'm Helen and this is the Squiggly Careers podcast where every week we borrow some brilliance from a person, a place, even a letter the other week if you've not caught up with that episode and we try to turn that curiosity into useful action for you and your squiggly career. So something different with this episode is that we're going to do it as a bit of a two-parter. So the thing we're borrowing brilliance from is a sticky statement, something that I overheard at a conference I was at recently. And we are going to take that sticky statement, which is about the idea of having no regret skills.

0:35And Sarah and I are both going to teach each other one of those skills. So in today's episode, I'm going to be talking about the no regret skill of decision making. and in next week's episode Sarah is going to be talking about the no regret skill of adaptability so maybe let's get started with where I heard about this skill from and why it's a relevant one for you and your squiggly career so what do you think today's is is it a concept is it a statement it's something I heard someone say what would you what do you think we are are we borrowing brilliance from him or the statement or the concept what do you think I think it's a well Well, for me, when you described it to me, it was a sticky statement.

1:13Okay. I was like, it's something that I have remembered and repeated, but we should obviously credit the individual as well at the same time. So today we are borrowing brilliance from a sticky statement. And the sticky statement is no regret skills. This came from someone called Frank Bowley, who is the head of skills England. And it was at an event I was at, Learning Power 100, where they were talking about different organisations that are doing brilliant things in learning. And Frank stood up to talk about like what was happening in skills, almost like a macro level, like zoom out, this is what is happening with skills.

1:48And someone in the audience said, you know, because you've got all of this data around skills and what we need to know, you know, if there was like one or two skills that you think are important for us to be investing in, what would you say they were? And Frank stood up and he said, look, I've not got a crystal ball. He was really honest. Like I can't predict the future. we talk about scenarios in Skills England. And then the statement, the sticky statement, he said, but what I can see is that there are a set of no regret skills. And regardless of the scenario that plays out, these skills are consistently useful across all of them.

2:23And you know, when you're writing your notes, I was like, no regret skills, underline once, underline twice. I was like, there's something in that. Well, we have so many conversations with companies around the world and skills has been a hot topic for a while now. But I do think people get a bit confused. You know, they're like, well, which are the skills I should be investing in? I think you do get some shoulds, some should skills. I think there's sometimes a difference between, well, what are the skills that I enjoy? What are the skills that I want? And then there's maybe what are the skills that my organization wants me to have?

2:52Like, how do I match those two things together? And then one of the things I have seen really consistently is a really long list of skills. Yeah. And then it's really hard to know where to start. So you see, sometimes I've seen like 20, 25 skills. and then they'll you know companies might say oh you know but obviously you can't be good at all of these and I'm like well what but which ones do I need to be good at am I meant to be putting more energy and investment into some of these areas so I just I found the no regret skills really refreshing because I think one you understand it fast I'm like okay I get it and I think in the context of a squiggly career developing in different directions loads more scenarios jobs we don't know that are going to exist yet.

3:32These no regret skills, I feel like they're worth investing in. They're always going to be useful. You can't lose, which I think is helpful. Agree, agree with all of it. I think the risk is because the hot right now skills, so let's use AI as an example, because they get a lot of attention, I think it is easy to under invest in no regret skills. And I think in terms of your squiggly career consistency, these are the ones that you're going to take with you like from role to role move to move the no regret skills are the ones that are probably going to be quite constant but I think it is very easy to just almost like miss out on when you could invest in and improve on them because with so much attention and noise goes towards the hot for now ones yeah so I think by the shiny skills yeah and I think naming your no regret skills like for for me and I think there's probably a set that are pretty universal which is what we've tried to focus on today but I think individually just thinking about what what am I like hot right now skills but also what are my no regret skills and just making sure that you are investing and improving in those areas you're getting feedback on them yeah spending time developing them I think that is an important um commitment for your career over the long term so what we decided to do because I don't know I think we wanted to have some fun with it is we both picked a no regret skill so we like we chose one for ourselves and the idea is that we are going to sort of teach I use that word loosely yeah loosely and lightly teach the other person that skill or share that skill in a way where if you think oh that's a helpful no regret skill for me you can learn along with us um and even if you think it's not a no regret skill there's probably something you can take from from both of these areas maybe the way that we're going to bring these no regret skills to life you could apply that in like if there's another skill that you're like oh that's that would be one of my no regret skills yes you could take how we are doing this with each other i think we've been quite creative yeah i can't wait um and so i should say that sarah and i we know the skill that so i know the no regret skill sarah's working on she knows mine um but we haven't we haven't taught each other this skill yet so it's gonna be live so we didn't practice we didn't practice or rehearse i know a bit more about your one because you shared it beforehand and there's a couple of kind of books that we'll reference um but i refuse to share my script with you before i'm so intrigued keep listening i don't know what's coming you looked really tense and i was really trying to reassure you like i know it's gonna be fine but i also know it won't work well if if i share it beforehand so let's go for yours first because i'm excited by your props you've got props i have got props um so if you're watching you'll see this and if you're listening i'll describe it i've got some playing cards i love i love a card game i've got some praying cards but they're not normal playing cards as i I will explain.

6:18They're squiggly playing cards. They're squiggly playing cards. They're squiggly skill playing cards. Okay, so the no regret skill that I think is important for everyone investing in is decision making. Okay. And let me give you the context for why I've decided to choose decision making. I mean, that's really meta, but just go with it. I think that in our careers today, we are having to make more decisions. but I think specifically we're having to do that with more information than ever like there's opinions and insights and information because in AI suddenly you've got this other thing that's informing your decisions so it's just like well I've got to make quite a lot of decisions my careers are longer so I'm perhaps making more career decisions the pace of changes is accelerating so I've got to make quicker decisions so there's that moreness then that's compounded by well there's more information to inform that decision and then I think there's more uncertainty so So for me, this ability to make better decisions, I don't want to say make good decisions, I think make better decisions, better decision making as a skill, I think is a really valuable thing for us to invest in.

7:26And I think it not only helps hopefully your career because better decisions lead to better outcomes. I also think it creates confidence from the people that you work with. So if you know that I have a good decision making skill, I think that creates confidence. Yeah, trust, confidence. And I guess decision making is useful, which is probably why it's a no regret skill. It's useful in your role. Like we all make decisions in the jobs that we do and it's useful for your career. So, you know, it kind of works in both contexts, which is quite helpful. It's a double win for your development. I love it.

8:00Okay, help me be a better decision maker. Okay, so I've borrowed some brilliance from the world of poker. Okay. Which is why the cards... I don't know how to play poker, I should say. Okay, well, you're not going to... Okay, I'm not going to learn that. going to take some conceptual things about poker principles and poker parallels for decision making. This is informed by a poker player called Annie Duke. I think she's quite famous in the world of poker, but not being a Texas Hold 'em expert, I'm not actually up on Annie's game. But she has written two books on decision making. One is called Thinking in Bets and the other one is called How to Decide.

8:34And so I borrowed some ideas from her to help us improve our decision making skills but before I get into that I kind of wanted to talk about these sort of poker principles and parallels with decision making at work so I've got four um which I think even without someone playing poker this makes sense I think you can tell me not um so in poker you have to make a decision without seeing everybody else's cards so you have to decide what card to play without being able to know what cards you're holding and actually the parallel at work there is you will often have to make a decision at work without having perfect information.

9:10You're not going to know. Almost all the time, right? Yeah, so that's our first kind of poker parallel. Our second one, it's quite interesting. The best play doesn't always win the hand. In cards, a good decision can still lead to a bad outcome because luck and other people influence what happens. You're in control of the decision you're making, but you're not in control of the other things that are happening. and the work, the parallel is, don't judge the quality of a decision solely by the outcome. You've got to think whether it was the best decision you could have made at the time with the information you had available.

9:47Yeah, that's particularly useful because I think sometimes you can get very attached to outcomes. You know, you made a decision, you go to a meeting, someone more senior disagrees with you and you think, oh, I made the wrong decision. Now, you might have done, but actually were there things that you just didn't know about uh did somebody go into that meeting before you and present some new information were you a bit just unlucky did you were you talking to someone senior at the end of a really long day yeah you know like so there's all these kind of things that could get in the way of feeling like you've actually done a good job with your decision making that are out of your control yeah i quite liked it because i think you might be you might tell yourself i'm i'm not good at decision making but actually if you've got if you follow some of the things we're going to talk about in developing the skill then that is you making a good decision but you're not always in control of the outcome so i like that and this one's interesting so in poker most hands are folded so you're playing a game and you don't try and win every hand it says professional players spend much of the game deciding not to play because they know that every hand is not every hand is worth the risk and at work the parallel is good decision makers don't chase every opportunity they know what deserves their time and attention and what doesn't yep I quite like that in our day I'd be like well that's not worth my time that's not a decision that I need to get involved in or be part of that's a decision that warrants my attention I think I find that one hard Miss Control Freak?

11:11No but I didn't I didn't used to find it hard until we ran a company together and I think now I find that one way harder even today actually I let go of being part of some decisions that I knew that you had already made and someone in our team said she was basically waiting for me yeah probably thinking Sarah's a control freak probably she'd never say that um but being like and I only say it in jest um but she was like going but what are your decisions and so I was like well no because Helen's already done it and and like so I did let go of it but even then I found it quite hard I was like I paused and was like is this definitely the right thing to do it's so pretty because i have such a low decisions i have such a kind of low need for control that i'm like it's fine if you want to make a decision it's fine i kind of i have an opinion but i don't have like a need for control if you know i mean i need to be heard but i don't need to be in control of it you've already made those decisions so hopefully they were good ones um here's our first uh our fourth sorry uh principle and the parallel so the fourth principle in poker is that new cards change the situation so good players continually update their judgment as new information is revealed.

12:25So being a poker player sounds quite cool. The parallel at work is that actually good decision making requires you to stay open to changing your mind. Better decisions come from responding to new evidence, not defending old assumptions. Yeah, I think that's really useful, isn't it? That's like hold your decisions lightly and stay open. It's a tricky balance, isn't it? Because I think when you do make decisions, it's really important to commit to them and to champion them and you've got to you've got to get behind a decision I think that really matters because decisions need momentum but then there may be examples of where someone does suggest something different or there is some new data or something external changes and what was a good decision is no longer the right thing and it's sort of having that continual openness to scanning and spotting and you know being brave enough to change your mind yes yeah and that recognition that i'm making the decision based on this data and that data has now changed so i can change my decision yes i think that's not being seen as a weakness yeah or a bad thing but i think if you explain the criteria for which you came to a decision i think that means that you might you won't lose credibility then if you change because you say well the criteria has changed so my decision has changed whereas if it just looks like you're flip-flopping from one to another then that's that's the thing inconsistent inconsistent The assistant looks a bit weak.

13:47Do I get to play with the cards yet? You do get to play with the cards. But the reason I want to do the parallels because you might think, sometimes I think sometimes this can feel gimmicky, you know, like poker parallels. But I actually think there are some strong things in decision making for that, something I'm not that familiar with that I can see play out at work. So what I have done is I have looked at Annie Duke's work and she has many recommendations on decision making as I've sort of dived into her work. And I've picked four, which I have written on these cards. I get to pick a card, any card.

14:14Yeah, I mean, we're going to go through all four tips. but the order of which we do them is determined. It's a game of chance. Okay. Okay, so you can pick. Can I lean forward and pick? Yeah, lean forward and pick and then you can tell me what it says on your card and then I will explain this to you. I'm enjoying this. Okay, so which one have you got first? Scare confidence. That's cool. Your confidence. Okay, you know new data, my not very clear writing is a new piece of paper. I was thinking that can't be scared, but I can't work out on it. Okay, this is going to get more entertaining. Because of mine.

14:46But I got a queen. Yeah, there you go. You got a queen. Sorry, tell me about score confidence. Score confidence. Okay, so I'll do a what this looks like in poker and then what it looks like at work as a kind of way of talking about it. So what poker players do... You've got me giggling now. So when poker players don't think in terms of right or wrong, every decision that they're making is based on probability because they're playing the cards. So they are like, okay, what's the likelihood I'm going to win here? Somebody having an ace or whatever. Yeah, someone's already played three queens. So what's that going to mean?

15:17That bit I don't think I'd be very good at. You've got to work out like percentages, right? Yes. Well, actually, we're coming on to percentages, but it doesn't have to be, you don't have to come, it's not a formula, but I do think poker players probably almost are playing with a formula. They know how many cards are in a pack. They are knowing how many have been played. And then, so they have a level of confidence when they are playing a hand that they are aware of. Okay, they're not just throwing the cards down. They've got confidence. and what Annie says who is our kind of decision making guru for this is that thinking in probabilities reduces overconfidence and it also encourages humility so that you're not being cocky about a decision and you're also saying actually you know I'm playing this and I'm not 100 % sure if I'm going to win so the point at work when you're when you're going to make a decision i think first of all self-score and then consider whether you would communicate that confidence score to the people that you're making the decision with so i don't know what was the decision let's bring it to life what is a decision that you are making about i don't know personal professional at the moment what feels like a decision you've made uh to start a phd that felt like okay okay this is a big decision yep we'll come back to actually types of decisions it depends what card you pick next um okay so phd is a decision so what we'd be doing now is you would be self-scoring but you're going to share it because how confident are you that that is the right decision for you to make as a percentage yeah out of 100 55 oh interesting okay so um If you're comfortable sharing, what would make you more confident in that being the right decision?

17:01When you and I have spent more time together figuring out how the PhD will support the work that we really care about. So the conversations that we're going to have, the specifics of the projects that we're going to do, because at the moment it's quite a nebulous. It's easy to say, right, oh, we're going to start a PhD. but there's a lot we don't know the don't know notebook is long and having we've also had some initial conversations and it's the academic world is a very different world and very different to our world and so I think what would increase my confidence is sort of us starting to do that translation from well what does the academic world need from us as part of this process but also what do we need from this process like for ourselves like intellectually but also for the work that we care about to make squiggly careers better for everyone what's going through my mind is i mean rather because i could now mirror back my confidence level and we could talk about why they're different or why they're not but i guess the more important thing for people listening is that a team conversation about your confidence score so let's imagine you're launching a new product or a service or a process, like everyone go around the room.

18:17You could even put it on a post-it so that you're not, you know, you haven't got bias as it goes around the room. Like put your confidence score on a post-it note, kind of put it up, or you could type it in chat if you're doing it virtually. And then you could discuss like, oh, you could basically see the difference. And then you could discuss the outliers, someone who's a lot less confident, someone who's very confident, and then say collectively, what would help us to increase our confidence score? That would help you to make a better decision. what's interesting is we had an example of this last week where I don't think we had that language but we looked at some we'd mocked up something that we were thinking about creating and I looked at it and I thought my confidence score in this now is 10 percent 15 percent like I actually think we need to change our decision you had looked at it and thought the same and we had actually talked to each other and we'd come up with a different kind of way of viewing something but then And interestingly, someone in our team who's also working on it kind of after the fact said, having looked at that example of what it might be, she'd obviously also felt quite low confidence in the decision to make this prototype.

19:20And she was almost relieved that then we were doing something different. And I was like, oh, well, if we had, but that probably like created a bit of like anxiety, a bit of angst. And you also might get there quicker. You know, if we had all said, OK, we've seen this prototype. What's our confidence that this feels like the right thing to do? I wonder if it would have fast tracked everyone if we'd have all gone 10%, 15%. Because I think we would have all been about the same. And then actually, I think that's reassuring. It's not, I don't find that demotivating. But I almost think individually we'd all got there, but none of us have talked about it.

19:53I think you can get to loads of different outcomes with it. Either we're all really low and it's like, thank goodness we've all called it. Let's sort it. Let's call it. Or we've got these outliers. And then I think that's interesting. That's a learning opportunity, isn't it? You know something, if you had seen that and you said, well, I'm 80 % and I said, I'm 15. You're like, right, well, you know something I don't know or you're seeing something that I can't see. Really helpful. Yeah, so I like that one. I do. Are you ready for your next one? I'm enjoying picking the cards. Okay, pick a card.

20:20Okay. Let's see how the writing goes because I feel like that really derailed us last time. Okay, I can read this one. Truth groups. Truth groups. Okay, so poker context here. Professional poker players review their hands with other players to improve the quality of their reasoning it's not about finding the right answer but it's about that it's about the logic of a decision and so this would be in the context of work this is you've got a big decision to make so let's take phd okay you've got a big decision to make this is about your truth group so you this is where you would find some people that might challenge you the point of these people is they're going okay well what do you want it to do for you what might get in the way um like in back to the what assumptions are you making so they're kind of asking you questions that you might not be asking yourself and I think the more that you do this for different decisions you might be able to stop patterns like repeated patterns because maybe I'm just like shiny object maybe I have these conversations with people about decisions I'm making about a new job or a new project or something and I start to spot a pattern in those groups that I'm being led quite a lot by shiny objects so let's take a decision could be the PhD or another one um because maybe you've already done this I do think you are quite good at this oh yeah I was gonna say I think this is my I don't think you'd call it like truth groups what would you call it I probably connect it to you know we talk about personal board and have you got the right people around you the questioner because I do think I have that and I definitely I'm always very confident and comfortable sharing decisions or reflections on something I'm trying to make a decision about with that group of people very fast you're brilliant at it and I get fast feedback and I really appreciate it and I think people quite enjoy it because it's quite fun to get involved with other people's decisions you know like they've not got to worry about it right they can just be a critical friend yeah um and so I did I think this actually is my default response to hard decisions new ideas like so new like hard decisions and new decisions but not like everyday decisions I think I use it for like those they're usually like they feel significant in some way I see you do it I've seen you do it with chapters of our book for example and you'll just do it on whatsapp right a lot of the time you do this often quick ways that you will get some I did it last week with four people so that prototype I talked about that we killed and replaced with something different I sort of had an idea for what the different was and within 48 hours I had voice noted five people including you um but almost the other four probably more important because they were sort of outside of our world and just went this is the thought like what connects what's useful what doesn't make sense and actually I could hear in people's listening back to people's voice notes back to me and it's good because it's a flexible and quick way of doing it so people can respond like when it works for them um I love hearing like what people repeat back to you um I like how people respond in different ways so like one person sent me three voice notes they sent me one which was like their first thoughts then she was walking her dog for a bit and then obviously had some more she like stopped and she was like this is why walking is good and then left me few more and then she obviously thought of like one other challenge like a day later where it was like one of my friends um Rob who did read chapters of learned like a lobster for us um and is my kind of probably strongest critical friend he just comes back so he's such a fast thinker but he's also a really critical thinker so i always really believe him yeah because if something doesn't work or there's holes in it i do trust that he will he will spot them um and so yeah this this for me really helps me with decision making and judgment yeah i think this connects to judgment as well so i guess for everybody else this is you've got to first of all name a decision what's the decision you need to make you've got to demonstrate your thinking for the decision so this is how I'm thinking about it and then you've got to go out to a couple of people who've probably got a slightly different context or skill than you you don't want the people who are just going to go great idea you really want the critical friends like a Rob who can just challenge your thinking a little bit um we like that one I do I do like all right you've got two you've two left 50 50 that I've card odds now all right what we got I feel like the zero jeopardy given you're making me go through all of them um decision menu a A decision menu.

24:45Okay, so the point here is, this is quite an interesting thing without us not knowing a lot about poker. Professional poker players don't spend the same amount of time on every hand. Some are straightforward. Others deserve much more thoughts because the stakes are higher. And so the context applying this to our careers are we're all making loads of decisions every day. You've got micro decisions, major decisions. The point is to distinguish the decisions you are making and treat the time you spend on them differently rather than being overwhelmed because that can be just exhausting. And so there are three categories that could be helpful here.

25:24There is a routine decision. This is everyday limited consequences. Considered benefit from a bit of discussion. And then strategic, these need longer, might even need a process, a criteria for them. So if we think about maybe to bring this to life, the question in our minds is how much thinking does this decision deserve? Yeah. But let's apply that to real stuff. So what would be a routine decision? This is an everyday decision with limited consequence. I suppose maybe what meetings happen when within a week. Okay. So meetings in a week, probably internal ones, maybe some external ones. How much thinking does that deserve?

26:06well so the the right answer i suspect is not much of my time yeah but i don't think that's what i do okay um yeah so i don't think i get that right because i think sometimes i probably around control uh because you're very if i think about how you approach that same decision it's really different to me like i dive into that i probably micromanage that a bit um probably have a real point of view about how I want my time to like to look and so I don't let that go so that probably does take up it's a sort of every day should be low like low input yeah and there's somebody in our team whose job that is yeah um but I don't think I do that very well so I guess the point here hey that's interesting reflection but the point here is if you're spending too much time on routine decisions it's taking it away from the one we're trying to get to which is a strategic one so that's a good I almost feel like for me the thing that I need to somehow learn to do is that once I'm in something I find it really hard to then not you know almost like apply the same level of rigor across everything if I'm not in it I'm okay you know almost like if I'm not even part of it yeah then actually I'm happy to like live with if you were sorting it I would just be like oh okay fine it's fine I'm not I'm not in it so I either need to be like I'm either like a hundred percent or zero percent and I don't think that's very helpful because that's not life right all right consider decisions so these are ones that benefit from a bit of discussion maybe evidence what would be an example um if you and i were both delivering for the same learning partner yeah um like the same content but maybe we're delivering at different times because of time zones i'm always like you and i do try to make sure that we connect on those things just to make sure we're being consistent any insights from spending time with those groups you know like it's a considered decision like is there anything i need to change when i deliver the same session this afternoon as the one you delivered this morning so if i ask you the question how much thinking does that kind of a decision deserve and then my second is and are you spending the right time on it right now um i think we do spend about the right amount of time on it i think sometimes we leave it too late so you know we we realize a bit last minute that we needed to do that and then we would always do it but i think probably like anticipating that yeah would help us yeah okay so kind of pre-empting the considered decisions yeah based on your diary last one strategic decisions so significant consequences difficult to reserve reverse if you get these ones wrong what would an example of that be um well I was in my non-executive job interviewing for a new CEO last week and that felt very important um and to your point there was a criteria and there's more than one person and it's very rigorous and multiple stages and felt you know the person leading that company really matters right so that felt really strategic and if I reflect on your diary because I know I you know I could literally see it did feel like you gave that decision the time it deserved because it was blocked out it was protected and actually if I look at your diary over the last couple of weeks of doing that that did that was probably the single dominant thing in your diary over a couple of weeks so um how much thinking does it deserve significant amount because it's a strategic decision and you protected and planned for that so I think they're sort of zoomed out for everybody else is to categorize the decisions you're making like I would just have a little table and I would think about what are all the routine decisions what are all the ones that are considered what are all the strategic ones and then reflect on how much time do I think it deserves and how much time am I actually spending on these things right now yeah I think the sort of the I wouldn't want to recommend a matrix because no one needs more matrices because you apart from me you create them for everyone but you know that It does feel like within a week, there's some sort of like time decision matrix of like, how much time does this deserve, given like the impact of that decision?

29:58And I don't, yeah, I don't think, I think I was good at the last one, the trust one. But this one is one where I think I could get better. I think I don't spend enough time on strategic decisions because it makes me think about, are we clear about the strategic decisions we need to make? Yeah. And therefore it's then hard to dedicate the time to it. So, you know, I think the point is you'll get to different reflections, but it's a way of prompting it. Do you like to choose the last card? Pick this one. Pick me. Pick me. OK, what might that one be? I feel like there, you just weren't even, you were like, holy, I'd leave really far.

30:29Oh, some time travel. I've got very low cards, two threes and a two. So Annie says that good poker players think through different scenarios before they commit to a decision and they consider how they'll respond with new information. so they can almost imagine themselves in a future and think, what do I need to do now? That actually has a term that I hadn't heard of before. It's called backcasting. Have you heard of that? No. No, I haven't. I think we might have done this, but called it something else before. So the idea of backcasting in the context of a decision-making at work is you imagine yourself at some time in the future.

31:04So let's take a decision. Let's make it real. Give me a big decision. The PhD. Okay, we'll take the PhD. so you've got to imagine future you okay um this decision has gone well yeah what when would this when would you know this has gone well you're at 55 now when you're like 100 this has gone well so not the so not necessarily completed just you feel i've made the right decision this is a right decision when is that okay in like 12 months time then i would want to feel confident i made the right decision okay so what we want to do now is back casting is for you in 12 months time for you to feel 100 % confident that you've made the right decision, what would you need to be doing today over the next couple of weeks and months for that to be your future reality?

31:49Okay. So I think I would have to have spent more time reading the research and got excited about the insights that I was discovering. I would need to have worked on at least one project with a company so because then it feels real life so there's like a research point there's like a real life point and it would need to have opened up new conversations and opportunities to increase the reach and relevance of squiggly careers that don't exist today and I know that's a very specific thing to you and me at the moment but I in listening to you it makes me think that the confidence score and the time travel together are really useful because you have like where am I now and then you go okay let's use some backcasting take me to when you're 100 % confident and then is it why it's called backcasting because you work back you work backwards it's not I guess the forecasting is just going forward but I know it's a funny term but you kind of I know I do get it we saw I think we've sort of done it you sort of project and then yeah think about what do I need to do now it's like visualizing and then kind of come back again isn't it um that's all I have for you but I would love your reflections on like poker principles to inform decision making well I think it is a perfect example of why borrowing brilliance makes things more playful and fun and I think you could do that as a you know like as a team like team conversations around decision making really helpful um and I think everyone decision making is like universal and so I think there will be things that people listening will already do well on decision making so it's like that's great and then I think there will be other areas like I started to reflect on or like okay well that's probably where I get stuck with decisions so where you know it's like where do you get stuck where are you too slow or where are you too speedy um you know I think all of those things like will be different for different people but I can I can see how it's um I can see how it's a no regret skill it wouldn't make my list oh decision making wouldn't make your skill no interesting but I think it depends what your filter is I can I can understand the argument for why you would include decision making but if I was doing it from a very selfish perspective like selfish skills and I was thinking okay I'm going to choose three yeah no regret skills decision making wouldn't be in my top three all right well pitch pitch yours to me hi everybody hope you enjoyed part one of our no regret skill series next week we're going to be back with the second part which is where we're going to be talking about the no regret career skill of adaptability make sure you are signed up for our newsletter you just want to go to squigglynewsletter.com it comes out every Tuesday it's the easiest way to stay on top of all of our links to learn everything we create for our Squiggly Career community and if you are a Squiggly Career supporter you definitely want to get our newsletter so just go to squigglynewsletter.com and we're back for more No Regret Skills next week

From the publisher

With so many skills competing for our attention, how do you decide which ones are worth investing in?

In this episode, Helen and Sarah explore the idea of 'no regret skills' – skills that will stay useful whatever the future of work looks like. In the first of this two-part series, Helen borrows brilliance from poker player and author Annie Duke to explore decision-making and shares four practical ways to get better at it.

🎯 What You'll Learn
– How confidence scoring can improve your decisions
– How a truth group can challenge your thinking
– How to decide which decisions deserve more of your time
– How back-casting can help you make better decisions
– Why a good decision doesn't always lead to a good outcome

Next week, Helen and Sarah explore another no regret skill: adaptability.

For questions about Squiggly Careers or to share feedback, please email: [helenandsarah@squigglycareers.com](mailto:helenandsarah@squigglycareers.com)

Need some more squiggly career support?

1. Download our free career tools: https://www.amazingif.com/toolkit/
2. Sign up for our Skills Sprints: https://www.amazingif.com/squigglysprints/
3. Sign up for our Squiggly Careers Newsletter, a weekly summary of the latest squiggly career tools: https://bit.ly/squigglynewsletter_pod
4. Order our new book Learn Like a Lobster: https://www.amazingif.com/books/
Learn more about your ad choices. Visit podcastchoices.com/adchoices

More from Squiggly Careers

All 128 episodes
#591 No Regret Skills: How to Make Better DecisionsSquiggly Careers · 35 min
Listen in VO