Debra Chantry-Taylor: Why Priorities Fail in Real Businesses & What Strong Teams Do Differently
In this episode of Better Business, Better Life, Debra Chantry-Taylor breaks down why so many leadership teams keep setting priorities that never quite land.
In this episode of Better Business, Better Life, Debra Chantry-Taylor breaks down why so many leadership teams keep setting priorities that never quite land.
Drawing on hundreds of leadership sessions, Debra explains that priorities usually fail not because teams are lazy or uncommitted, but because the system is working against them. Too many priorities, vague outcomes, “forever” initiatives, and reliance on external factors quietly erode confidence, trust, and momentum.
Debra unpacks what strong teams do differently. They limit priorities to three to seven clear, finishable goals per quarter. They write SMART priorities, protect focus time, assume interruptions will happen, and use weekly check-ins to realign rather than panic. She also tackles common leadership traps like founders changing direction mid-quarter, teams chasing perfection instead of progress, and the hidden cost of never finishing anything.
This episode is a practical reset for leadership teams who want fewer priorities, cleaner execution, and the confidence that comes from actually finishing what they start.
CONNECT WITH DEBRA:
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►Debra Chantry-Taylor is a Certified EOS Implementer | Entrepreneurial Leadership & Business Coach | Business Owner
►Connect with Debra: debra@businessaction.com.au
►See how she can help you: https://businessaction.co.nz/
►Claim Your Free E-Book: https://www.businessaction.co.nz/free-e-book/
Episode 258 Chapters:
00:00 – Introduction
00:35 – Why Priorities Fail in Businesses
01:36 – Patterns of Priority Failure
02:39 – Clarity and Prioritisation
03:47 – Strategies for Effective Prioritisation
04:54 – Handling Forever Priorities and External Dependencies
07:32 – Managing Interruptions and Trade-offs
09:31 – Audience Questions and Answers
15:25 – Weekly Meetings and Balancing Flexibility with Accountability
Debra Chantry-Taylor is a Certified EOS Implementer & Licence holder for EOS worldwide.
She is based in New Zealand but works with companies around the world.
Her passion is helping Entrepreneurs live their ideal lives & she works with entrepreneurial business owners & their leadership teams to implement EOS (The Entrepreneurial Operating System), helping them strengthen their businesses so that they can live the EOS Life:
- Doing what you love
- With people you love
- Making a huge difference in the world
- Bing compensated appropriately
- With time for other passions
She works with businesses that have 20-250 staff that are privately owned, are looking for growth & may feel that they have hit the ceiling.
Her speciality is uncovering issues & dealing with the elephants in the room in family businesses & professional services (Lawyers, Advertising Agencies, Wealth Managers, Architects, Accountants, Consultants, engineers, Logistics, IT, MSPs etc) - any business that has multiple shareholders & interests & therefore a potentially higher level of complexity.
Let’s work together to solve root problems, lead more effectively & gain Traction® in your business through a simple, proven operating system.
Find out more here - https://www.eosworldwide.com/debra-chantry-taylor
SUMMARY KEYWORDS
Leadership teams, priority failure, clarity, execution, fast growth, family businesses, focus, capacity, confidence, progress, accountability, weekly meetings, team health, financial targets, business improvement.
SPEAKERS
Debra Chantry-Taylor
Debra Chantry-Taylor 00:00
I always say that if everything is important, nothing is important. Less is more, but less but obsess. The goal is a leadership team that gets better at choosing, better at predicting, better at defining and finishing what matters most. So most leadership teams I work with genuinely care. They're smart, they're committed, but they're busy as hell, and yet, quarter after quarter, their priorities don't land, and it's not because people are lazy. It's not because they don't want it badly enough. It's because they're playing a game that quietly stacks the odds against them.
Debra Chantry-Taylor 00:35
Hi and welcome to another episode of Better Business, Better Life. I'm your host, Debra Chantry-Taylor, Taylor, and I'm passionate about helping entrepreneurs and their leadership teams lead their ideal life, for me, that is a life where you're doing what you love with people you love. You're making a huge difference in the world. You're being compensated appropriately for the value that you bring, and you have time to pursue other passions. And so in this podcast series, I talk about how we can actually achieve that create a better business, to create a better life. And today I'm going to be talking about why priorities fail in businesses, and what you can do to ensure that priorities get achieved. Let me start this week with a confession. So most leadership teams I work with genuinely care. They're smart, they're committed, but they're busy as hell, and yet, quarter after quarter, their priorities don't land. And it's not because people are lazy. It's not because they don't want it badly enough. It's because they're playing a game that quietly stacks the odds against them. This week, I saw a post that nailed something we don't talk about often enough. Thank you to my colleague, Chris Jones. After nearly 700 leadership sessions, he saw that some patterns have become impossible to ignore. So let me go a little bit further. So the pattern is the same, whether I'm working with an established business that's hit a ceiling, whether I'm working with fast growing businesses where everything is moving so fast that the wheels are falling off, or if I'm working with family businesses who are juggling business ownership relationships, all of those beautiful things, and the pattern is the same in terms of it's the priorities that just don't land. And when priorities don't land, then the trust quietly erodes, confidence drops, frustration builds, and leaders start questioning people instead of the system. And so today I want to talk about why priorities fail in real businesses, and what strong leaderships can do differently to get better over time, not perfect, just better. So let's clear this up really early, effort is almost never the issue. In established businesses, people are grinding doing long hours, but they feel stuck in fast growth. Businesses, people are just sprinting to keep up. And in family businesses, people are not only carrying the operational load, but they're carrying an emotional load as well, and you can see it. The hard work is everywhere, but what's really missing is clarity. Hard work without clarity creates busy teams, conflicting assumptions, endless meetings and very little progress. And of course, different parts of the business define success differently. So sales will push for growth, ops pushes for stability, finance pushes a control, and founders push revision. And when those priorities aren't clear, everyone fills in their gaps with their own version of what matters most, and that's when execution starts to fracture. So the most common trap across any business is taking on too much, too many priorities, or priorities so big that they really should be broken down into a 12 month strategy, not a 90 day commitment. Established businesses tend to hit the ceiling because they keep piling new initiatives onto an already stretched system. Fast growing businesses do it because optimism runs ahead of capacity. We'll figure it out as we go. We'll build the plane as we take off. Becomes the operating model and family. Businesses often do it because saying no feels personal. But no matter what the reason they do it for the result is exactly the same. Teams are underestimate how much time, how much energy and attention real focus requires, and everything slows down. Strong leadership teams. They do something really uncomfortable. They reduce the list, fewer priorities, smaller priorities, realistic priorities, not because they lack ambition, but because they understand capacity and they know that clarity creates confidence. I always say that if everything is important, nothing is important. Less is more, but less but obsess. So let's have a look at some of the issues that we have around priorities or 90 day rocks, often they're not specific enough, because if you can't tell clearly whether something is done or not done, it's not a priority, it's a talking point. And I always like to use the analogy of those of you who've listened to my show for a little while. I love champagne. I love breaking up a bottle of champagne to celebrate. And so if something is done, I will know when to open that bottle of champagne. Problem is, if you're not sure whether something is done or not, it's really hard to actually do that. So this shows up differently in different businesses. In established businesses, they'll hide behind broad initiatives like improve efficiency, fast growth businesses default. A whole let's build the plane. While we're flying it, we can't commit to one thing. We need to do a whole bunch of stuff, otherwise the plane will fall out of the sky, and the family businesses soften that language to avoid conflict, because they don't want to have conflict with their family members. The common denominator, though, is still the same. It's vagueness. Good priorities describe what will be completed, not a theme, not a direction, not a hope, but specific priorities that will remove debate, reduce the politics, and create momentum. And clarity is not about control, it's leadership. Like I said, clarity creates confidence. Another thing that I see is the Forever priorities, and these are the ones that quietly kill morale. It's kind of work in progress, but it's dressed up as a quarterly priority or a rock marketing, systems, culture, governance. Are they important? Absolutely. Are they finishable this quarter? Rarely. They're ongoing work. They're business as usual. And so when you choose priorities that never end, the team stops believing that completion matters. Everything feels half done. The energy drains, and they lose the passion for those priorities. So what strong teams do is they break that forever work into clear finish lines, not improve systems, but let's map the current process and identify the top three constraints. By the end of the quarter, completion builds their confidence. Confidence builds momentum, and the momentum builds trust. The next biggest execution killer is priorities outside of your control, so it's one of the biggest execution killers. You're waiting on someone else. So if you think about this again from the three lenses in established businesses, it's often senior leadership or the board in fast growth businesses, it's suppliers, investors or key hires. And in family business, it's owners, siblings or legacy decision makers. And when priorities rely on someone else's behaviour, they will stall. So what strong teams do is they shift the focus. They define the priorities around what they actually can complete. And that's where the 80% rule matters. So the old Pareto 80% 20, you just have to go with 80% don't aim for perfect outcomes. We aim for meaningful progress. And progress compounds. Waiting doesn't so don't wait till it's 100% wait till it's 80% and just get on with it. Another issue is when something else showed up. So, you know, the plan was really solid, but then reality intervened. This is the fighting fire stuff, customer issues, people problems, market changes, operational surprises. So here's the difference between what struggling teams do and what strong ones do. Struggling teams pretend interruptions won't happen. Strong teams assume they will. They leave margin, they block focus time. They use weekly meetings to realign instead of panic. And most importantly, they make trade offs explicit. If something new comes in, something else must come out, otherwise, your priorities will quietly decay. And I always say to my teams, yeah, you've got to remember that, yeah, 80% of your time will be spent on business as usual. There's going to be stuff that pops up where you have to fight fires. But if you haven't blocked out 20% of your time and actually blocked it out in your calendar and made sure it's there for you, then it will get filled with other things. And so the best thing you can do is go through your calendar every week, book out that 20% of your time, which is about a day a week. So is it two half days? Is it a couple of hours every day, whatever it looks like, but make sure you've got that time blocked out, that you can still assume that there's going to be some firefighting, some stuff happening, but at least you've actually got some time blocked out, which means you can actually deal with it. And let's be honest, priority completion, as Chris said, it's a muscle, you know, it's something you have to work out over time. You cannot just sip a protein drink and expect that you've got muscles the next minute. So this is the reframe that most leaders actually need. Getting good at completing priorities is not about motivation. It's not about discipline. It's not about hiring better people. It's a muscle established businesses will need to rebuild it after years of drift, their muscle has actually deteriorated the fast growth. Businesses need to develop it while scaling and family businesses need to strengthen it while managing emotion history. And just like muscle in your body, it takes time, it takes repetition, it takes patience, and, most importantly, consistency. So let's look for progress over perfection. Every single quarter, it's part of the reason why we come back together every 90 days to talk about where we're at, what's worked, what hasn't worked. It's all about building that muscle and learning from all of our mistakes, but also from the great things that have happened. And the goal isn't flawless execution. The goal is a leadership team that gets better at choosing, better at predicting, better at defining and finishing what matters most.
Debra Chantry-Taylor 09:41
So if priorities keep slipping, don't default to blame. You need to start asking yourself better questions. Where are we overloading ourselves? Where are we being vague? Where are we pretending forever work is finishable? Where are we outsourcing control? Where are we waiting on others? Where are we leaving no room for reality, the fighting fires, the thing. That will pop up. You don't need a perfect quarter. You just need a quarter that is better than the last, and that's how strong businesses are built. Now I did ask my chat, GPT d2 to come up with some off the cuff audience questions, which I thought I haven't even looked at them, so I've literally just pulled them up on screen now and I'm going to answer them. So the first one is, how many priorities should a leadership team have really have every quarter? And this is simple, three to seven priorities. Three to seven rocks every quarter. They've got to be smart rocks. They've got to be specific, measurable, achievable, realistic and time bound. And the reason it's three to seven because less is more people can't focus generally on more than about three things. So really, three to seven less is more less, but obsessed. You need to be obsessed about your profitability, of your company, achieving your numbers and getting your rocks done. What's the difference between ambition and overload? So this is an interesting one. I think that it's you know, ambition is where you're the eternal optimist. You really want to go faster, but if you try to do everything, it won't work. You'll just overload your team. They'll become overwhelmed. And so by doing less and focusing on it doesn't mean that you can't do more once you've completed that, but that laser, sharp focus on those two or three priorities will mean you actually get them done, and then you can add more to it. When you put in a whole bunch of priorities, people will just become overwhelmed. Nobody will know what is important. How do you reset priorities when everything already feels urgent? To me, that comes down to the leadership team being really, really clear on what will actually move the needle. Because if you keep doing the same thing, you'll keep getting the same results. I always say, if nothing changes, nothing changes. And so you've got to think about, do we want to just keep fighting fires all the time? And if we don't, then we have to change though we do things. So you have to think very carefully about where you're going to find the time to do this block that timer in your diary, and then get back together as a team and look at your list and go, Look, we didn't get five rocks done this quarter. Let's get it down to three, and then we've got real priorities we can work on. Next question, what do you do when founders keep changing direction mid quarter? You can see, I'm reading this for the first time. That made me laugh. What do you do when founders keep changing direction mid quarter? Every founder, every visionary I've ever worked with, myself included, we'll try and change direction mid quarter. It's the role of the integrator and the leadership team to kind of keep this on track. And so if you're really, really strong on where you're headed, using your vision, traction, organiser, knowing where you're headed, you know what your 90 day priorities are. There's no need to change. 90 days has actually gotten a heartbeat. So what I always say is that just get them to hold off on that thought. Put it into the long term issues list. Make sure that it's there. 90 days is not long, even in a fast paced environment, even in a fast scaling company, if we keep changing direction all the time, mid quarter, the team gets confused. Nobody wears what they're doing. So just stick at what you've agreed to, and then you've only got another from 90 days before we can actually look and changing that so integrators, keep the founders on track, keep them enthused and excited about the idea. Maybe give them some homework to do. Hey, that's a fantastic idea. Why don't you go and do some research on that and come back to us and keep that idea kind of bubbling away. It'll either disappear because the vision or the founder will forget what they were wanting to do, or it'll start to develop a much deeper understanding of what they want to do, which means when we come to our next quarterly review, we can then bring that into the next 90 days. Number five, how do you handle priorities when different functions want different outcomes? This is they're all about team health and teamwork, really, if you think about when I spoke about the different areas of the business have got different priorities, but at the end of the day, the company has got a really clear direction, and everything that each of those functions should be doing should be supporting that company vision. That's why we have a VTO at the company level, which talks about the direction of the organisation and the rocks that fall into the departments from that are to support those overarching goals. And so really, that's about clarity. Clarity creates confidence, getting your team on the same page, knowing where the business is headed, they will all come into line in terms of what needs to be achieved. Number six, what's the biggest mistake fast growth companies make with priorities? The biggest mistake they make is probably taking on too many I see that they, you know, they just see that they've got to do lots of things because everything is moving so fast, but you actually need to slow down to speed up. And so you're not going to got to look at your priorities and go, we really only need probably less for a fast growth company, in some respects, less do less obsess about it, get it done well, and then you can always add more to it, but don't start something new until you finish what you set out to do. Number seven, how do you stop forever initiatives from killing momentum? Well, as I said before, those forever initiatives break them down into bite sized chunks. It's human nature that we love to celebrate success. So if you. Got a rock that really isn't a rock, and it's just a forever initiative, if we never actually achieve the done, it just feels demotivating. So let's break into small, bite sized chunks for the 90 days. Set a really clear goal. What can we get to? Where can we execute to date up to this point, and then we can celebrate that success, and celebrating that success will give the inspiration the motivation to actually keep going the next quarter. Number eight, what role do weekly meetings really play in execution? So this is the level 10 meetings in EOS. I think they're genius, because, as a person who at university would always procrastinate and leave things right to the last minute, if you think about it, and 90 days, it feels like a long time. It goes in a heartbeat, but it feels like a long time. And so you think, I've still got time, I've still got time. I've still got time. When you're having a weekly meeting and you're checking in every single week, you're actually being held accountable for it, and it's reminding you of what you need to do and whether or not you truly are focusing on it. And so for me, personally, in my business, is when I attend my level 10 meetings and I have to review whether my rocks are on track or off track. By saying it's off track, it's a genuine realisation that, hey, you know, I've really got to do something about this. And so it gets me back into that focus of, okay, what is the small bite sized chunk I can do this week to start moving that forward? And if we just keep taking bite sized chunks every week, we'll get there. Number nine, how do you balance flexibility with accountability? Hey, look, I always say that EOS is a framework. It's not rigid. It's designed to give you a framework to actually help you. You don't have to complete a rock. You know, for rock, if you're going through a rock and you get to a point where you go, this is a complete and utter waste of time, then stop it. You don't have to complete it, as long as you have really good reasons understandings about that, and that's why we come back every 90 days and say what worked and what didn't work. So there is flexibility. You can have flexibility. You can have account and still have accountability. We just need to, in that, you know, in that weekly meeting, discuss with the team why we don't think it's worthwhile completing, and then we park it. It's very it's perfectly okay to park rock, stop rocks, decide they're not worth doing. So I think it's easy personally. What's different about priority setting in family businesses compared to non family businesses? To be honest, I don't think there is a difference here. I think that at the end of the day, a family business is just another business, and a business needs to have a leadership team that's on the same page, that knows what they're doing, who's got clear priorities. So really, there is no difference in that number 11. How do you rebuild trust after repeated missed priorities? I think you've got to have the tough conversation. I think you could actually kind of, you know, talk to the person about why have we missed it, talk to the team about why have we missed it. Are we being unrealistic? You know, the amount of times I sit in a 90 day quarterly review and people go, Hey, we didn't get our rocks done. Why is that? We set them too big. We set too many. Just learn from that. Failure is never a failure unless you haven't taken something from it. So when you look at supposedly failing your rocks, what you should be doing is, okay, we didn't do it. What can we learn from it? What can we take forward? How do we just moving forward? And as long as you're always doing that and not pointing the finger, you didn't get this done, if there's a genuine reason, then we talk about it and we learn from it. And number 12 is the final question from my chat. GPT, what does good enough actually look like in execution? Good enough. To me, it looks like we have set three to seven priorities for the quarter. They are bite sized chunk pieces of work that actually move the needle, and we've got to the point where we have achieved what we set out to do. And that's not really good enough. That is just what should be expected in a business. So for me, it's like less is more. Get clear about what success looks like. Commit to it, focus on it, obsess about them, get them done. And then what you'll find in your 90 day kind of review is you'll have hit your numbers. You'll have hit your profitability. You've done all of your rocks. But more importantly, you're creating a business that is improving every single quarter. And if you imagine, if you just take one or two or 5% improvement every single quarter by the end of the year. You know business, it's absolutely flying. So that was the off the cuff audience questions 12 rather than 10. So I guess for me, it's really about breaking things down. The last thing I would like to say is that a lot of teams think that their rocks have to be due at the same time as their their quarterly targets and numbers. Financial targets and numbers, I really think they shouldn't be I think they should be due either before or afterwards the last two or three weeks of a quarter. You all the team, should be focused on hitting your financial numbers. You should be focused on hitting your revenue numbers, focusing on your profitability numbers that last fast sprints to make sure we actually hit those things. So if you're trying to do that, as well as trying to actually achieve your rocks at the same time, again, if everything's important, nothing is important, you've got too much on so I always recommend sure you have to have financial quarters. We've got things called the IRD and the tax department who expect us to follow certain financial quarters, but they're arbitrary dates that. That they have come up with, the tax department has come up with. So why not make your rocks due a few weeks beforehand or a couple of weeks afterwards? That way you've actually got a sprint to the finish line of the quarter financially to make sure we hit our numbers. And then you've got a sprint towards your rock priorities, which is that is also 90 days. It also means you get a full 90 days to actually focus on both of those things. So that's my interpretation of the stuff that Chris Jones shared on his LinkedIn post. Really, it isn't rocket science. It's just be clear about you where you're going
Debra Chantry-Taylor 20:30
if you know where you're going, break it down into bite sized chunks. Make sure they truly are achievable in those 90 days, and don't get distracted. You. You.
















