WOW 180 | Deadline Management


Effective leadership isn’t just about setting deadlines; it’s about empowering your team to own them and thrive, finding the balance between support and accountability. For today’s episode, hosts James Carrier and Jane Stewart continue to dive deeper into the intricate world of leadership challenges. This time, they tackle a multifaceted issue many managers grapple with—meeting deadlines and fulfilling responsibilities within a team. They reflect on the balance between empowering team members to take ownership and providing the necessary support to ensure tasks are completed effectively. Throughout the episode, they dissect the dynamics of managing a team member who constantly misses deadlines, highlighting the roles of clear communication, shared expectations, and more. Tune in now and get equipped with strategies to foster productivity, accountability, and growth within your team!

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Management Challenges: Responsibility, Organization & Ownership

Before we get into this episode, I want to remind you of all the great stuff on our website at Over there, you can check out all the online seminars and workshops we do as well as our team development programs. You’ll also find articles on topics to help you thrive at work. That’s Now, let’s get onto the episode.

What are we talking about, Jane? What’s our series? What’s our focus?

This is the next episode in a series that you and I have been doing together around management challenges. It’s like looking at some of the common things that we talk to managers about that are causing them challenges in their management work. We talk it through. We talk a little bit about our own personal reflections and whether we’ve experienced it. We also talk a little bit about what we might do in the scenario. We’ve also been inviting audiences to send in their management challenges, and this is one that’s been sent in. We are going to share a little bit about how we approach these things.

I think of this as agony for leaders and managers or something like that, whatever the challenges people face. We’ll chat about them. What we’re doing is we’re chatting about it from a personal perspective. What have we experienced? What might we do? What might we think about? This is very much us stepping into those conversations and reflecting as we process and chat it through. It’s been an exciting set of shows to do. We’ve got a new management challenge now, Jane, as you said something that one of the audience sent in. I’ve got a specific challenge I’d like us to think about. Would you like to introduce the challenge? What’s the high-level focus for this episode? Is there any more detail on it?

In this episode, we are talking about a situation where you’re in a management team and someone in your team is not taking responsibility for where they need to improve. We know there are scenarios where you are managing someone, they’re a valuable member of staff, but they’re not getting everything right and you keep trying to fix things for them. You give them all the tools. You tell them what you want them to do. You suggest ways they might be able to do it differently, yet nothing happens. They’re all very enthusiastic. They’re like, “Yes, I’m going to try that. I think that will work,” and nothing actually happens.

In this particular scenario, we were talking about what was shared with us where you’re managing someone and they’re not great at organizing their own work. They sometimes miss deadlines. They’re not getting some of the tasks done. They’re doing other work great, but they’re not consistently meeting deadlines, communicating those deadlines, their progress, and then getting the work they’ve been asked to do done.

You’ve had this conversation with this person. Yes, there’s acknowledgment like, “I know I’m not getting this right. What do you think I can do?” As a manager, you’ve said, “There are few things you can do here.” That person’s gone away and nothing’s changed. The situation is, as a manager, how do you step away from constantly trying to fix everything for them? Instead, how do you find a way that encourages and helps them to take responsibility for what they need to change and indeed to change what they’re doing?

That’s the scenario we were shared with. It’s something that we’ve picked out of the audiences’ comments because, certainly, it’s something we hear quite a lot in management training. I’ve also got some personal experience of it in certain situations. I’ve also worked with individuals who’ve had this challenge, both as the manager and the individual who’s maybe not quite getting things right. James, what about you? Is this something you’ve experienced?

I was reflecting on this when it came in. It’s certainly something that’s very much been in the sphere of my working life, this piece around how you help people take accountability for stuff. How do you help people own what they’re doing so that they have responsibility for it, deliver on it, and meet their deadlines in the work that I’ve done to meet the quality requirements as well? It’s something that I have seen. I’d say I’ve not experienced something exactly like this myself.

Generally, I’ve been fortunate enough to work with people who tend to be fairly structured and clear on what they’re doing. Maybe that’s because the majority of my work has been with accountants. The people that make it through the accountancy training process tend to be people who are organized. That’s one of the key criteria. The majority of people that I’ve worked with haven’t demonstrated exactly this type of situational behavior, but I’ve certainly worked with people outside of the accountancy world who have, coached people who have, and spoken to people about this.

There are a couple of aspects that came to my mind when you were talking about this scenario. One is how do we understand and help an individual change? There’s something about us as leaders and managers that’s important here as well. Is there something that we need to change as leaders and managers in terms of our approach, behavior, and mindset as well?

I don’t know if I heard you use the phrase here, but I’ve heard you use it before, this phrase of being a bit of a rescuer. Sometimes we can be the rescuer and block somebody from some of their own poor behaviors by stepping in and helping them when things could be going wrong. There’s a piece around helping somebody to develop, but there’s also a piece around helping ourselves develop as leaders and managers.

In short, I have observed this quite a lot and I’ve got a couple of thoughts about it. It’s an interesting thing. Like you say, it’s the type of thing that people ask us a lot. When we speak to people in various programs and one-to-one conversations, people often want help improving something akin to accountability and ownership within individuals in their team, which is a broader area than just this, but it’s something that crosses over with this.

I was pausing a little bit because I was reflecting on your comments about working on ourselves as managers and leaders. I’ve spent a disproportionate amount of time saying to people, either clients or even friends and colleagues, “You can only manage your own side of the conversation. You can only manage your own side of the contract. You can only manage your own side. You can do other things to influence and lean on or leverage psychological research and management research to help other people. Fundamentally, you can only be accountable for your own behavior and actions.”

You can absolutely do other things to influence and to lean on or leverage psychological research and management research to help other people, but fundamentally, you can only be accountable for your own behavior and action.

I don’t know whether it’s the time of the year, but I’ve seemed to be talking about that a lot lately with people. That’s interesting and relevant here as well. I’ll come onto that when we get onto a bit more about what we do, but it’s important to recognize that dual responsibility as a manager of the job still needs to get done. We’ll talk a little bit about that as well.

I’ve got one other question. As we’ve been speaking about this, I’ve been thinking a little bit about myself. Myself being that person who maybe didn’t always have accountability or didn’t understand or something like that. I’ve got a couple of thoughts or snapshot moments from my own career where I felt like I’ve had a realization that’s helped me move more toward that ownership type of piece. I was wondering if you’ve been the same. Have you ever been the person who’s maybe struggled with accountability or ownership or things like that?

I’ve struggled less with accountability and ownership than I have with the actual challenge that was sent to us, which is the organization and meeting deadlines. That sounds slightly contradictory. What I mean is I’ve never had problems with standing in front of anyone and saying, “I’ve screwed up. I’ve missed deadlines. I’m taking ownership.” In fact, to the point where probably unhelpfully, sometimes I take on ownership of other people. It’s the bit about only being responsible for my side of things is a big thing. Certainly, as you know, James, I have huge challenges around meeting deadlines, particularly when they’re an ingredient to something else.

Sometimes they’re not. Someone else needs me to do stuff and I still don’t get it done because I’m like, “I know when this needs to be in.” I have some sympathy for it, but it also makes me a little bit more confident in saying what is and isn’t in the sphere of the people who’ve helped me and the people who’ve held me accountable, and what they should and shouldn’t expect of themselves.

The people have held me to account but have also allowed me to talk about it, process it, try things, and fail things, things haven’t worked, some have and some haven’t, some things worked sometimes, and some things don’t. They’ve let me go through that process. That’s interesting because the industry matters in this space. If you’re an accountant or if you are a nuclear physicist on a submarine, if you’re an industry with high-reliability needs, in other words, things go wrong and people die, it is a very different scenario and you have a very different space for being able to look, learn, and fail about this stuff. You need different processes in place as well. I have some sympathy for both sides of the coin, but it probably also makes me a little bit blinkered about seeing it because I see it from my perspective.

It’s a great perspective to bring. Let’s bring some different perspectives and see where we go. It sounds like there’s some rich thinking in that space. We’ve both got some reflections and thoughts on this type of context. If you were a manager in this context we’re speaking about and somebody was having some of those difficulties managing their time or presenting that way, you had spoken to them about it, you had some concerns, but things hadn’t changed, what would you think about at that stage? What would your next steps be? What would the questions you ask yourself be? How would you reflect? What might you do going forward from that point? Why don’t we start with, “What questions might you have? What things would be open?” Let’s then go on to look at actions.

In my perspective, if I’m sitting in the manager’s chair and I’ve got someone working for me, let’s call them Ripley, and Mr. Ripley is not meeting deadlines consistently, not getting the work done, and not telling me about what’s going on, even though I’ve consistently sat down and given them tools, there are a number of questions I’d be asking myself before I start this conversation.

One is, “Are the things I’m asking them to do actually needed?” There is a real thing where we get into this habit of asking for things that would be nice to have some jobs. Therefore, it doesn’t mean they shouldn’t do them, but it is important to understand, “Are the things you’re asking them to do meaningful? Do they understand why they matter?” That then links to something like the SBI model we’ve talked about before, which is thinking about what the situation is, the behavior, and the impact. Even if you’re not going to share it with them yet, what is the situation where this is going wrong? What is the behavior? What is the impact?

WOW 180 | Deadline Management

Deadline Management: There is a real thing where we get into this habit of asking for things. That would be nice to have some jobs and therefore it doesn’t mean they shouldn’t do them, but it is important to understand the things you’re asking them to do.


The thing is, it’s much easier I think to talk about what people are doing that could be done differently than what they’re not doing. For example, trying to understand what they’re doing instead of that work. Either you think this person is not doing any work or enough work in the time that they should be or you think they’re prioritizing something else. If it’s the first, we are not talking about bad organization. We’re talking about effort, laziness, and motivation.

Let’s assume for the minute that they are doing stuff, and they’re not doing the right stuff. They’re not doing things like getting things over the line, hitting the deadlines, and stuff like that, or they’re spending too much time on something so it’s not getting finished in time. It’s then a conversation about understanding what they were doing instead of the things you wanted them to be doing. They’re slow at stuff, in which case it’s a conversation about how they need to get faster at stuff.

From the example that was presented to us, it’s that they’re poorly organized and they’re not meeting deadlines. If they’re poorly organized, generally, that means they’re doing something else when they should be doing the things you want them to be doing in the wrong order. It’s rare someone says, “They’re poorly organized” and they actually mean they’re not doing any work.

There’s something about what are they doing instead and why they’re doing it because that’s a much easier conversation. It’s much more likely to bear the fruit of finding out what’s going on in someone’s head. It’s much easier to say, “You didn’t hit the deadline for this. Tell me about what you were doing instead.” “I was working on this and this.” “Why did you choose that work?” You then get into, “It’s because it’s the work I enjoyed. It’s the work I thought was more important. It’s the work that I get credit for.” Quite often with this stuff, it’s about choices and about what they’re doing.

As you said, that, “What were you doing instead?” conversation can be a wonderful opener to all kinds of other things. It puts the ball back in that individual’s court and it can raise all kinds of things about prioritization, pace, quality, and things like that. That’s an interesting way. One of the questions is, what else is somebody doing? What’s our current state of what’s happening in this? From there, there are some branch conversations along the lines of, “Why did you choose that? How long did that take? What were the outcomes of that? In hindsight, was that the right thing for you to have been prioritizing?” those types of things. “What else are you doing?” is a good question to build on. Is there anything else that you’d bring in to think about?

It’s quite hard for me because I relate to this quite a lot as a person who sometimes lets people down. There’s so much in my head. There are a couple of obvious things that I’d be aware of. Generally, this particular type of challenge is less about stepping in and constantly helping people and more about the organizational side of it. Quite often, they can be symptoms or concurrent with neurodiversity, types of neurodiverse conditions, particularly ADHD, there’s a huge number of people walking around under their nose. If you do know that the person that you are talking about is neurodiverse, then it is a very different conversation because there are lots of great materials out there. There are lots of websites. Someone like the genius within NCIC has helpful tools around that stuff. That’s a very different conversation.

I do think that knowing someone and the level to which you know what works when you delegate to that person generally is important. I’d be thinking about, “Where have they got the work done?” before, “Where has it been? What did I do differently with that person?” It is helping them do a little bit where they’re thinking for them if they’re struggling with it. I also think there’s a bigger thing, which is, “What’s the job? How are you holding that person accountable for that job?”

The point that was sent to us was like, “I feel like I’m constantly trying to fix it for them.” That’s where I’d be thinking about it’s worth reading up on transaction analysis a little bit because there’s some interesting thing of being this rescuer or this parent figure that comes in and goes, “I’ll fix all this for you.” I relate to that. New people started in the first organization, and I’m the first manager, I was like, “Let me fix it all for you. Let me lay it out all neatly.” I didn’t give them space and time to process.

There is a difference between giving someone space and time and leaving them on their own unsupported, and giving people space and time and discussing and monitoring how that progress is happening. I’m going to say something somewhat challenging. I’m not sure where you sit on this. I am massively passionate about coaching skills for managers, but people sometimes confuse coaching skills for managers for, “I’m going to leave them on their own.” They get that bit wrong about when people need direction, when people need support, and when people need to be given details.

There is a difference between giving someone space and time and leaving them on their own unsupported.

The third thing that I was going to talk about was the tools that work for you rarely work for anyone else. Sometimes that’s literally because we’ve got autonomy as a thing. We like it when we find our own tools, but also, what works for you James doesn’t work for me. What works for me doesn’t work for you. It doesn’t work for Laura who works with us.

The example that we were given is, “I’ve given them loads of tools well.” Did any of those tools work for that person? If they didn’t, then it’s not the right thing. You have to keep trying things with that person, but that person needs to be coming back to you and saying, “I tried this. This is what happened and this is why I don’t think it’s worked so I’m going to try something else.” That only works if you create and hold that person accountable for trying. That means dates in the diary conversations. It means, “This isn’t working and I can see that I’ve missed deadlines.”

For me, that’s when we’ve talked about this before on this show on the management challenges. It’s about transparency. Where are those deadlines so everyone can see they’re being missed? It’s very easy to bury your head in the sand and pretend it’s not happening. If you’ve got a dashboard somewhere with a task list and that task list’s got things that aren’t finished, it’s got someone’s name against them, and that’s visible to everyone or to that team, it’s a much easier thing to manage and it’s much easier to self-manage.

I’ve got a couple of thoughts back on a few of them, and then maybe 1 or 2 other things that I’ll share as well. When we were asking about that, you talked about, “Is your work meaningful and does it need to happen?” That’s an interesting starting point. Probably, there’s a little bit of subjectiveness around that, which can make it a little bit of a nuanced difficulty. What is a quality standard that needs to be met? How important are deadlines? How meaningful is the underlying work?

People might have different views on that. That can be something that’s, in the back of my mind, that subjectivity of meaning. There can be differences in that. I wanted to touch on that. I love the shout-out for the SBI model. We might touch on that a little bit later on. Your point about neurodiversity is interesting. Again great shout-out to genius with NCIC. That’s an interesting thing here.

When we’re looking at what are they doing instead, part of me also wondered if there’s something about, “Are there different stages of work at which people maybe struggle more than others? If there’s a deadline being missed, what is the work that the deadline being missed relates to? What type of worker activities are involved in here?” Potentially, I know that some people find it much harder to do work with a blank page than they do with a concrete plan, or to do the final stages of work versus another middle stage of work. Trying to get a little flavor and understanding of where in that larger process of work is this happening could be interesting.

Different people need help in different stages or benefit from support in different stages. The stages are important things to think about. When it comes to your point about people perceiving coaching as abandoning people to do stuff, there is nuance around empowerment and support. For me, it can sit within the coaching approach, but I can very much see why sometimes it doesn’t. Make sure that the empowerment and leaving people to have autonomy, accountability, and to own this stuff is supported by your support as a manager.

WOW 180 | Deadline Management

Deadline Management: Different people need help in different stages or benefit from support in different stages.


At times, that is direction. For example, some people struggle with an early-stage piece of work with a blank canvas. People can struggle. If you say, “Here’s a deadline to do something,” they can never get past that blank canvas because they need some help and support doing that structuring. What you’d end up with is, as a leader or manager, identifying substages in work where a little bit of support, guidance, or guide-railing could help accelerate this. Minor input could help provide the support and guidance that would unlock individuals. Understanding those stages is important.

As you were talking, I had another thought. I wonder about the role of organizational processes in this and the nature of work that exists within this as well. Some work where it’s repeated on a more regular basis, certainly in the finance world, some aspects of work are very procedural. For a lot of a month-end type of financial work, there will be a very detailed process flow of what happens, at what date, at what timeline, on what file, and to whom it’s sent to. It’s all defined in working days. I don’t know how people know this, but there is a working day minus 5 or minus 4 all the way down to flipping over to the new month and you have working days 1, 2, and so on. Each day has a series of tasks that are defined within it.

Within that type of structure where there are predefined processes around a cyclical delivery, there isn’t so much space for individuals to not be able to be organized and meet deadlines because the whole current and momentum of an organization is anchored around process, timeline, and day. I wonder if there’s a role or something to consider for proceduralization, I don’t know if that’s even a word, of what’s going on in here. Those are a couple of reflections back on what you had. Do you have anything you want to build on that?

I could talk about this forever because there are so much what-ifs in this. It’s very hard to give anyone an answer. Your point about the process is important. There are a couple of things that triggered off in me. Generally, it is your point about where is the problem in the work, map out the work process, and go, “Where do they get stuck?”

Where do they see they get stuck as well? What’s their perception?

That’s an important conversation because my experience of smaller organizations is there’s not nearly enough of their work that has standardized workflows or work processes. They misunderstand how easy that would be to do. They think it’s a whole project. Sometimes it’s literally writing on scrap paper, “This is the order we’re doing,” taking a photo of it, sticking it on the wall, and then ticking it off every time we’ve done it. It doesn’t have to be like that.

You can tweak it a bit. You can start that way. If you want to make it better, then you can.

Acknowledgment is an issue. That also made me think of two things that we do a lot in our Doing More By Less Seminar, which is around task acceptance and task delegation skills. One of the things that we know and we talk about quite a lot is task acceptance. I am hands up admitting that for the longest part of my career, I didn’t do this. We know that when someone accepts something onto their task list, they write, they speak, or they do something that says, “Yes, I own this.” They’re more likely to get it done.

When we send someone an email to say, “I’d like you to explore and find three options for charity to give to this year,” if we send that email, that person has something to add to their list without them accepting it in that organization. If you make the norm in the organization that it’s only accepted when they write back to you and say, “Yes, no problem. Here’s the date I’ll get it done by,” If they have to tick it on a shared board, or if they verbally have to say to you in a meeting, “Yes, I can do that,” even better if you say to them, “I’d like to give you this piece of work, is this something you can do? If so, by when?” that increases your chances. I like task acceptance. I also think good task delegation.

We talk about it a lot more in detail in the seminar. We talk about what the supervisory need is. Once you’ve delegated it, what access do they want from you or what are you going to ask from them for accountability, updates, and progress information? If I had an experienced member of staff who didn’t have any of these issues, I would probably say to them, “Let’s make supervision on a needs basis. You email me when and if you need help in this project.” If I had a junior member of staff who only started and was in their first job, I might say to them, “We are going to meet every week. I want you to come with a list”. If it was their first week in the organization and they didn’t know where anything was, I might say to them, “I wanted you to email me the minute you get stuck on something because we know there’s going to be loads of stuff you don’t know to start with just for the first week.”

It’s about what that supervisory element is. I also want to share one thing that might help around the rescuer thing. I have a problem with repetitive tasks that I build up in my head sometimes as much more challenging and more time-consuming than they are. I put them off. I used to do that with the operational budget of the charity I worked at. My boss who you’ve met online, Russell, we’ve done an episode with him about ethical working and ethical leadership. Russell locked me in. Once a month, he would take me away from the office. We would meet somewhere for two-plus hours. I knew the only thing I would have to do was to go through the budget with him. The night before, I would do the budget.

Let’s be clear, I never got better than doing it the night before, but it was always done the night before and I always had to report to him on it. It was painful for the first 4 to 5 months we did it. Eventually, it became a habit. He wanted me to take ownership of it but he also knew it had to be done. He made a decision that he was going to put a lot of time and effort into it. Crucially, he made it clear that the reason he was doing it was because he needed to write the financial report for the board and it needed to be done each time and we needed to know how much money we had. It never got better, but it got done.

With the specific response to the audience, it depends if this is all the stuff or some of the stuff. With me, it’s not all the stuff. Some stuff I do is not an issue. I get it done. It’s done straight away. It’s always the odd thing that suddenly becomes like this massive awful and, in my head, it becomes much bigger than it is. I’d be interested in your reflection, James. In the world of accountancy, it happens less, more processes. If this happened within our working environment now and you were managing the person, what do you think you would do?

A lot of the things that we’ve spoken about cross over with this. I would probably step back and think it was my fault because that’s my default place. It’s me. “It’s not them, it’s me.” That’s my go-to type of thinking in things like this. I’d probably build out and try and explore a little bit more. In this scenario, a bunch of that stuff’s been done and those conversations have been had. I would try and reflect a little bit more and think things like, “What’s for broader context? Is there anything else going on in this individual’s life? Is this new? Is this a change? Has this always been the case?” I would think about those stages. What work does this relate to? Is it relating to a stage? Is it relating to a specific type of work?

I’d want to understand or ask myself what level of pressure is the individual under. Are they under high pressure, which means that they’re strained or stressed and consequently find it hard to think clearly? With that, I wonder if the total amount of demand being placed on this individual is realistic. What is it that we’re doing that maybe supports this? Is for demand realistic and associated with the demand? It’s not just for the volume of work, but it goes back to that point around clarity. Do they have the right amount of clarity they understand why the work matters?

If the answer to all of those things comes back they’re not under excess strain, the amount of clarity is there. As a leader and manager, I’m making clear why this matters. I’m communicating and delegating effectively. I’m providing a reasonable amount of check-in, support, guidance, and helpful challenge conversations. If, as a leader and manager, I felt that all of those things were being met, then I’d start to wonder about whether or not this was the right role for a person or if it was time for them to think about what’s right for their career and whether they’re in the right role.

Realistically, that’s probably where I’d end up if I’d explored all those other avenues. I’d then start to look at things like, “What are the things that the individual enjoys doing? What types of work do they thrive when trying to perform? What do they see their strengths as? What are the capabilities they enjoy using?” I try and see whether those are mapped up to what’s being asked of them. If not, there are a couple of things you could try and do. You could start to look at job crafting, shaping, and adjusting the role into something that fits that individual.

If this is an individual that, otherwise, we value and think brings great things to what we’re doing, how can we change and flex the demands placed on them as an organization to help them thrive so they’re more fulfilled and we get more delivery and better performance from them. I’d start to think about that. If there was no other way, then I’d start to look at what can we do to help this individual find a role that does give them a chance to use their strengths.

Maybe moving to a different organization, different function, different team, whatever it is internally or externally. That’s probably where I’d go. It is about starting to think about performance management to document some of this and move to those more difficult conversations about it being time to move on. That’s where I am. What about you?

At its simplest, and as a manager, I’m like, “Does this person understand what the job is and accept what the job is? Does this person understand they are not fulfilling the job? Does this person want to fulfill the job? Can they fulfill the job?” If the answer to that is no, do we need to change the job, change the person, or help the person find something else? One of the challenges is if you as a manager keep rescuing someone, you’re not rescuing them. You think you’re rescuing them because you think you’re giving them solutions. A) They’re not solving it. B) You’re basically saying it doesn’t matter.

There are no consequences. There’s no motivation to change this because this person is saying, “You are not getting the job done the way I want it. That means not getting the job done. Therefore, we need to look at how this is going to be fixed. If we can’t fix it, then we are faced with a real challenge here because you are not getting the job done, which means I need someone else to do the job or you need to change what you are doing.” That’s a difficult conversation. You have to be gentle around it. I’ve always said this. I said this in the episode about bad behavior in meetings as well. If you have let things go for a very long time and if you said, “Yes, you do need to improve” and that’s it, then you need to give this person a chance to find a new way.

If you as a manager keep rescuing someone, you think you’re rescuing them because you think you’re giving them solutions as they’re not solving it. But you’re basically saying it doesn’t matter. There are no consequences. There’s no motivation to change this.

For me, that would be starting by saying, “Things aren’t getting done. Until they do, every week for the next three months, we’re going to sit down and check your to-do list together. You’re going to drop me an email with your to-do list. I’m going to look at your to-do list if it’s online, which is the ideal. I’m going once a week and I’m going to pop some notes and questions about what’s going on. I want an email every time you miss a deadline. Here’s where the deadlines are written down. Here’s where we’ve agreed with them.”

You need a shared information point that you both agree with. It’s important, no matter what this is, whether this is about the organization, missing deadlines, the quality of work, or whatever it is. There needs to be an agreed truth of what is needed to be done and when. Otherwise, it’s easy to slip away. I’ll give you a very specific example. You and I can agree and say, “When do we need to get this done?” We might say next week. I will go away, and in my head, I’ll be like, “We said we’d do it next week. We haven’t told the client that. As long as I’ve done it by the end of Monday the week after, that’s a legitimate thing.” I then have to remind myself, “No, we said this week. I’m going to go and write it down somewhere as Friday or Thursday.”

It’s because generic terms don’t work for people. Lots and lots of people, when you say next week, you might mean by the beginning of next week, I might mean by the end of next week. I might mean Friday or Monday doesn’t make any difference because all our clients are Monday to Friday. Suddenly, it’s drifted and you haven’t done anything about it and other stuff is getting on your list.

That shared truth of what you’ve both agreed is happening and when. Therefore there is a truth about what’s been missed, it’s not been justified, and it’s not been called out. I would say the biggest thing is calling it out and carving a conversation about it. A real add-on about it is like, “Let’s look at the list. This is done. This isn’t done. Was it a capacity issue? Was it a prioritization issue? Was it something else? Was it prioritization? Let’s talk about what I would’ve liked you to do differently.”

We talk about sometimes an information center, huddle board, or we’ve got a range of different things that we use as tools to do that. Having that shared truth often in a public place, within the team, public within the team is a useful thing. We’ve covered a lot of the stuff in here. There’s some great reflection in here. I’ve got one other tangential piece that I’m going to bring, which is a cul-de-sac, a curve ball, or cutting their way. I’ve got a reflection, which is sometimes about the quality of what we do need. What is good enough?

Clearly, in this instance, it seems like in the example that good enough is not being met in terms of this, but there is a whole piece around, “How good do we need to be? Are we sometimes as leaders and managers looking to ask for more than we need?” That’s something in my mind here. What is good enough? Where do we need to get to with good enough? One of the things that sticks in my mind is that being a leader and manager is a lot easier when everybody that works for you is great. Sometimes we’ve got to work with people who aren’t excellent. If we aspire to have everybody around us be excellent in terms of performance and potential, then that’s an unrealistic expectation for us as leaders and managers. Also, here’s something I think is true. If everybody working for you has huge potential and is a great performer, chances are they’re not going to be working for you for very long, and that brings a whole set of other challenges to it. There’s something in that balance that is worth bearing in mind. I feel like we often aspire to always get to the stage of having wonderful people, but I don’t think that’s often a reality. Maybe that’s just my thought. What do you think about this?

Being a leader and a manager is a lot easier when everybody works for you is great.

I do agree. What I see mostly is managers and leaders blaming people for organizations under-resourcing them. I don’t mean with money or time, although I do see that in workflows and work processes. The practical example I would give you is, all too often, I hear people criticizing the way in which projects are managed, but the people have no skills, no experience, and no training in how to do that. Critically, they’ve got rubbishy IT equipment either hardware or software. They’re trying to manage everything off Google Sheets. No shade to Google Sheets. Google Sheets is amazing, but it’s not the primary project management tool something else might be that has a CRM system that’s more advanced. Google Sheets is amazing, but you need to know how to set it up. You need to know how to link spreadsheets. You need to do all of that stuff.

It shows up when I work with businesses that employ someone from a bigger business previously who has been a star performer, but they have been a star performer in a business that has enormous HR project management, risk management, processes, and all of that support around them. There are pre-existing ways of doing things and they come into a much smaller organization that doesn’t have any of that, and the manager’s like, “They were great XXX PLC. Now, they’re here over at a little family business. What’s the problem?” They were great in an environment that was already tooled up for them. What you are now doing is asking for a very different set of skills. You’re asking someone to be able to make sense of the chaos, implement processes, and then stick to them. That is a different skill.

I wanted to flag that because I see that a lot. The number one reason I see it is businesses committing to do too much, trying too many products, or if it’s nonprofit, trying too many projects or too many initiatives, spreading themselves too thin, not doing things well, and not correctly working out the level of work it’s going to take to keep things on. You talk always about new projects, runners and riders, and stuff like that. When you get a new project, it’s to say, “The first nine months, we’re going to set it up.” No one says, “By the way, it’s going to take someone half a day a week to properly manage it afterward.” It falls behind, and then it’s harder to catch up.

I wanted to flag that because sometimes the solution is not just about the individual. The solution is about how is this team functioning and what are the things we can do. I also totally take on board the point you were making about different people being at different levels of good at different things. I think it matters. I’ll be honest, I’ve seen people be brilliant in some jobs, and the same person you are like, it’s not the right job for you in the way that you are being asked to do it.

WOW 180 | Deadline Management

Deadline Management: Sometimes the solution is not just about the individual. The solution is about how is this team functioning.


That’s us getting to the end of this. We’ve covered a whole load of stuff in there, bringing a lot of different thoughts and ideas from concepts. These are all things that individuals can look up and learn a little bit more about, from things like transactional analysis, performance management, the SBI feedback model, coaching, job crafting, task acceptance, and task delegation, to things like observation and conversations with people to understand where they’re struggling and where they’re performing in terms of the steps of a process they’re going through and the types of work. We’ve touched on neurodiversity.

We’ve talked about the importance of having shared information centers and a shared version of the truth of what is asked and what is being missed. We’ve talked about the fit of an individual to a job, whether it fits with them, the skills that they bring, and the things that they want to use. We’ve talked about the fact that this isn’t just on individuals to change, but sometimes we as leaders need to do less rescuing and maybe let people stand on their own two feet in a supported way and sometimes fall over a bit themselves so that they do learn some of those lessons.

We’ve also reflected on the broader demands placed on people, whether or not those are realistic and sustainable and whether those need to change, as well as the importance of thinking about for broader context that the individual is in, and whether they have other stresses and strains placed upon them that make it harder for them to navigate in this space.

Reflecting on that, one of the key takeaways for me is that, in this context, if I were here, I would start with some of that listening a little bit more about exploration and then trying to find out if I could change, if a person could change, if their role could change, and if we could change their role. If not, then it would be a conversation about how we help somebody move onto a role that would help them be fulfilled, use their strengths, and deliver well. That’s my reflection on this. Do you have any other reflections? Anything you want to share?

WOW 180 | Deadline Management

Deadline Management: If a person could change if their role is changed, then we could change their role. And if not, then it would be a conversation about how we help somebody move on to a role that would help them be fulfilled and use their strengths and deliver.


It’s an interesting conversation because it would be very easy to give a simple answer, which would be, “Set up regular meetings, have an agreed list of what needs to be done, make sure they understand the impact of what’s not happening, and leave them to report to you on a weekly basis of where they leave and fail so you have a shared agreement of how they’re missing the mark.” Don’t get me wrong, that’s not important. It’s important, but there is so much more that will be helpful if you are genuinely intent on helping this person be better.

A regime of weekly reporting meetings on deadlines adds a whole layer of stress and anxiety to somebody’s existence, which can have all kinds of detrimental effects.

The one thing I was going to mention was if you look at agile working practices or process ones like scrum or something like that, picking and choosing the bits of that, whether it’s a huddle, whether it’s things like that that’s going to work for people, is helpful. Looking at some of the project methodologies out there, don’t apply them wholeheartedly if they’re not the right thing for your business, but picking and choosing what are the things that would help us move this forward could be helpful as well. It’s a hard one because there’s so much to it and we don’t know a lot of the detail, but like everything, it always starts with trying to understand the conversation and understand what’s going wrong rather than trying to throw solutions at it.

Why don’t we leave it there? It’s been an interesting conversation. Hopefully, it’s helpful for the audience that recommended it. If you have any other management dilemmas you’d like us to discuss, please email them at It’s a great email to use. We’ll pick those up. It might take us a few weeks or months, but we will get onto them. With that in mind, it’s time for us to say goodbye. It’s goodbye for me.

It’s goodbye from me.

I wanted to say thanks for tuning in to the whole episode. If you enjoyed it, if you have a question, or if you just want to say hi, you can find us on Twitter @WorldOfWork_IO. Don’t forget, you can also find out more about what we do, including our online seminars, workshops, and development programs on


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