Episode 76: Dealing With Procrastinators

You’re listening to The Less Stressed Lawyer podcast, Episode 76. Today, we’re talking all about dealing with procrastinators. You ready? Let’s go.

Welcome to The Less Stressed Lawyer, the only podcast that teaches you how to manage your mind so you can live a life with less stress and far more fulfillment. If you’re a lawyer who’s over the overwhelm and tired of trying to hustle your way to happiness, you’re in the right place. Now, here’s your host, lawyer turned life coach Olivia Vizachero.

Well, hello there. How are you? I am so excited to talk about today’s topic. So much of the time management content that I produce is geared towards helping people who struggle with time management; whether it’s reshuffling your schedule, planning your schedule inaccurately, not making a plan at all, or not honoring the plan that you make.

Those are typically the things that I touch on when I talk about time management. I help people who are in firefighting mode, constantly triaging emergencies, and running around like chickens with their heads cut off. Or I help people who are really frozen and paralyzed, procrastinating and getting in their own way, and sort of self-sabotaging in the process.

That’s a lot of what comes up when I talk about time management. But one of the things that I see with a ton of my coaching clients, especially some of my more senior clients who are at the partner level, they deal with other people’s procrastination.

Maybe that’s you. Maybe you’re listening to this, and you’re like, “Olivia, I love you. But your time management content really doesn’t resonate with me because I don’t struggle with this.” Okay, if that’s you, this is the episode you’ve been waiting for. Because chances are, if you don’t struggle with time management, you’re dealing with people that do struggle with it, and it is a major pain point for you.

It is a massive source of frustration, annoyance, resentment, and discouragement. It’s probably one of the least enjoyable parts of your job, having to interact with someone who procrastinates. So, I want to address this today so that you can really dial down your frustration and all the negative feelings that come up for you when you’re dealing with members of your team.

Maybe it’s even clients that you’re dealing with who procrastinate. But there are people in your life who are procrastinators and you’ve got all this negativity around their bad time management habits.

I want to walk you through really understanding what your judgments are about them, how you’re feeling as a result of having those judgments, how you show up as a result, and the result that ultimately produces in your relationship with procrastinator.

Then, I want to switch that and really figure out what do you need to be thinking instead. How do you want to feel instead? What do you want to do instead, to produce a different result, a result that serves you more? That’s what we’re going to talk about today.

I really want to give you a framework for how to navigate dealing with someone else’s procrastination. Right now, if you’re anything like most of my clients who are on the receiving end of someone else’s procrastination, it’s not going very well. You’re frustrated, the person who procrastinate is struggling, and you really don’t know how to work through this with one another.

I want to give you a framework for what to do, instead of whatever you’ve been trying. Because what you’ve been trying, if it’s like what my clients try, it’s not working. So, we’ve got to come up with a different approach, a different plan of attack, in order to hopefully get you different results.

Now, we can’t control another person’s behavior, you can only control your own. So, we can’t force someone to manage their time well. But if you show up, really with curiosity, and with an open, understanding mind, you can help someone problem solve what is ultimately driving their procrastination habit. We’re going to talk about that today.

First things first, though. I want to talk about the judgments that you have about the procrastinators that you deal with. I think now is as good a time as any to remind you that circumstances are neutral. So, someone getting something to you after it was promised, after the deadline, that is a neutral circumstance; it is not positive, it is not negative. It is neutral until you think a thought about it.

It’s your thoughts about that circumstance that determine how you feel. I promise you, this other person’s procrastinating, them turning in something late after a deadline, is not causing your emotional experience. So, let’s find the thoughts that you’re having, about the people that you work with, that are causing you to feel negative emotions.

A huge thought that people on the receiving end of procrastination have, a very common thought, is they tend to assume that the people who are procrastinating don’t care about the work. That they don’t care about turning it in on time. That they don’t care about their job. They just don’t care.

If you’re thinking that, you’re going to feel maybe offended or disrespected or frustrated. You’re going to feel some negative emotion if you’re thinking that the person doesn’t care. Now, I just have this core belief that people inherently do care. I believe that people inherently want to do good work.

So, if that’s not it, what else might be the reason that the person’s procrastinating? Let’s assume that they care. I’ve talked about this on the podcast a lot. I used to struggle with procrastination very severely. People who were on the receiving end of my procrastination, they were not happy about it. They had plenty of negative thoughts about my time management habits. And frankly, I don’t blame them. It made things more inconvenient for them.

Now, is that a thought? Yes, they chose to think it. I’m also going to choose to agree with it, it did make things more inconvenient. They didn’t get to review my documents when they wanted to review the documents. Based on their schedules, it really threw a wrench in things. It left people with less time to review my work than what they had wanted. It also made them look bad in front of clients.

Again, these are all thoughts, but they’re thoughts that the partners I used to work for would think, and I am not going to disagree with them. If I was in their position, I would probably choose to think the same thoughts. All right.

Now, that being said, if you’re going to choose to think negative thoughts, you’re going to choose to feel negative feelings. I believe a lot of people I used to work with, who were on the receiving end of my bad time management, believed that I didn’t care. I promise you; it couldn’t have been further from the truth.

The reason I procrastinated was because I cared so, so much. It was crippling how much I cared about doing a perfect job, about over promising and under delivering to everyone that I was working with, oftentimes with competing deadlines. I wanted to get everyone everything they wanted, at the time that they wanted it.

A lot of times that was in direct conflict with getting someone else something else that they wanted. I cared about doing a good job, and I would avoid getting started because I would be worried. I didn’t know what I was doing. I didn’t know how to approach the project. I deeply cared. I cared so much that it held me back and hung me up.

So, if you’re thinking the thought, about the people that you work with who are procrastinating, that they don’t care, I really want to offer you that that is likely not it. It’s very, very rare that someone’s procrastinating because they just don’t care.

You might be thinking that they should know how to manage their time. That’s another thought that’s very prevalent for people. If you don’t struggle with time management, you have a really hard time empathizing or sympathizing with someone who does. It just doesn’t make sense to you.

Just like my clients who don’t struggle with time entry, it breaks their brain when they hear that other people don’t enter their time until the end of the month. They just don’t understand how their brain is so different from another person’s brain, how their thought process is so different.

But I really want to offer you, just because you don’t struggle with this, if you don’t struggle with it, that doesn’t mean that no one should struggle with it. In fairness, no one ever teaches people how to manage their time. Okay? This is not a skill that we learned in school, at any point in school, all the way through law school. Nor is it something that law firms teach.

Now, I speak to a lot of law firms that come in, and do presentations on time management because no one else is teaching this stuff. Law firms recognize that there is a gap in the training, that there is a void that needs to be filled. I get to come in and speak at law firms all the time on this topic, in an attempt to fill this void.

Frankly, though, to be really honest, I’m getting ready to teach an hour-long masterclass on time management. It’s going to be incredibly comprehensive. But one hour is not enough to change the way that you manage your time. It’s an amazing starting point, and it helps us create a lot of awareness and learn some foundational tools and tricks in order to be better with managing time.

But I work with people on time management for weeks, and for months, until they finally get to the place where they’re really able to have a handle on managing their time. They know how to do it, and they’re implementing the tools that they’ve learned, that I’ve taught them.

It takes a lot of practice, and it’s a very messy process. They need to learn, then attempt, then fail, then tweak, then try some more, then learn some more, and adapt and keep going until they continue to get better and better and better at this. That process just takes time.

So, if you’re thinking that they should know how to manage their time, you’re going to feel kind of righteous, and again, frustrated. Maybe confused as to why they don’t know how to manage their time, like it doesn’t make sense to you. “I don’t know why this is a problem for them,” that might be a thought that you’re thinking.

If those thoughts come up for you, you’re going to be unnecessarily frustrated. So, I just want to offer you an alternate thought, that it makes sense that they’re not good at this, no one’s ever taught them how to do it. Okay?

You might also be thinking that people should get you work on time. Now, I’m not suggesting you give this thought up. If you are in a supervisory position, you might want to hold onto this thought. I just want to assure you, so long as you hold onto it and continue to think it and have this expectation that people get you things on time, and then they don’t get you things on time, you’re going to feel frustrated.

You’re going to feel offended. You’re going to feel angry, or resentful. You’re going to feel inconvenienced. So, you want to be really careful. Is this a thought that you actively want to choose to think, that people should get you work on time? Or do you want to replace it with a thought that maybe makes you feel curious? “I wonder why they didn’t get this to me on time?”

Tapping into that curiosity allows you to really explore what might have gotten in their way, and to help them problem solve and work through it so it doesn’t happen again.

I know another common thought that a lot of the partners that I work with have is, that they shouldn’t have to deal with this. If this is a thought that is coming up for you, you’re going to feel so righteous, and so annoyed, and really sort of exasperated throughout your day to day when you’re dealing with someone’s procrastination.

I just want to offer to you, if you’re in a supervisory position, if you’re in management, if you oversee other attorneys or other support staff, frankly, you should have to deal with this because you’re in the people management business. That is part of your job, managing people. That includes managing people’s flaws, okay? So, their bad time management actually is your business, and you’ve got to help them work through it.

Now, again, you, as they say, can bring a horse to water, but you can’t make it drink. You can’t force someone to manage their time better than they do. But you can help them understand why they’re struggling and find ways to support them in order to make improvements. Okay?

So, you want to do that. You really want to drop the entitlement that you have coming from the thought, “I shouldn’t have to deal with this.” If you are in management, this is literally part of your job to deal with this. Supervising other people, dealing with the things that they struggle with, and helping shepherd them through so they can stop struggling.

Those are some of the most common thoughts that I see on a very consistent basis. When people are dealing with procrastinators, they’re on the receiving end of someone’s bad time management habits. They think these thoughts and then they feel frustrated, resentful, confused, righteous, offended, disrespected, exasperated, annoyed, inconvenienced, bothered, angry, discouraged; all these different emotions.

If this is you, I want you to check in with yourself for a second. Think about the person whose procrastination you’re currently dealing with. What are your thoughts about them? What are your thoughts about them getting something to you after they promised it, after you asked them for it? What are all of the judgments you have about them?

Start to identify those thoughts. You can pause this episode and write them down, if you want to. Then ask yourself, how does that thought make you feel? How does thinking it make you feel? You’re going to start to see the direct connection between what you’re thinking about the person and how you end up feeling.

Now, what’s really important here, I want you to think to yourself, how do I show up when I’m feeling that way? How do I interact with this person? How do I manage this person? How do I deal with them? How do I act when I feel frustrated and resentful? How do I act when I feel confused?

How do I act when I feel righteous or offended or disrespected? How do I act when I feel discouraged and doubtful that they’re not going to be able to figure this out? When I’m feeling entitled that I shouldn’t have to deal with this? How do you show up? What do you do?

A lot of times, attorneys who are managing people, they will withdraw because they’re frustrated, they don’t want to interact with the person. So, they spend less time interacting with them, which is really the opposite of what’s needed in this situation.

People need more supervision. People need more mentorship and guidance. People need more support. They need your help to problem solve. Most people don’t know how to fix this problem themselves, that’s why they still struggle with it. That’s why it hasn’t gotten better.

If they knew what they needed to do in order to get better at managing their time, I assure you, they would do it. They really don’t understand what needs to change. So, they’re confused too. If you’re confused, and you’re avoiding dealing with them, and they’re confused, this isn’t going to get any better.

You also might talk down to them, be chastising or belittling. I’ve even seen situations where people will yell at someone when they’re turning in something late, when they’re missing deadlines. Remember, shaming someone does not lead to self-improvement, ever. So, that is not a strategy that’s going to work.

You might scare someone into a temporary, short-term blip on the screen, improvement. But it’s going to be temporary, it will not last because ultimately, when people are feeling badly about themselves, they begin to shut down. They show up in a negative way, not a positive way. Negative emotions don’t create positive actions. That’s not how it works.

Another massive mistake that I see people make when they’re dealing with procrastinators, is they simply tell them that they need to do a better job. This happened to me all the time. People would tell me, “Hey, Olivia, you just need to get better at managing your time.” I’m not disagreeing with them, they were right. I did need to get better at managing my time.

The problem is that it’s “good advice, poorly given,” as one of my former clients says all the time. I did need to do better, but I didn’t know what that meant. That was still very confusing for me. What does “do better” mean? I didn’t actually have the skills to manage my time well, so it was basically, not necessarily falling on deaf ears, but just falling on ears of someone who didn’t have the capabilities to really make an improvement, because they didn’t know the proper process for managing my time.

So it’s like, “Do better.” I’m like, “Yes, I will.” Then I go back to my office and I’m like, “I don’t know how to do better. What do I do?” Trust me, I had tried. I had bought every planner on the face of the earth; that’s not going to solve a time management problem. I had watched the YouTube videos, I had listened to the podcast episodes, I had read the books, I had followed accounts on social media, none of that was working.

It wasn’t until I really applied myself in a coaching capacity, and learned different coaching concepts, started practicing them in my own life, and then, through a lot of trial and error, that I finally got better at this. I feel like I learned some from my coaches.

But I taught myself so much of what I now teach my clients, and I really came up with a process that is foolproof, that works, when I teach people how to manage their time. It covers all the bases, and it really contemplates and addresses the discomfort avoidance that is a massive component of procrastination and time management problems.

You feel entitled to feel uncomfortable, and then you don’t take action because you’re not willing to feel that discomfort. I really have mastered the art of not just helping people plan their schedules, but teaching people how to feel their negative feelings. So, they’re able to move forward and take intentional action in spite of and despite them, which is the secret to managing your time.

So if you’re consistently having broken record conversations with the people that work for you, when it comes to their poor time management, you’ve got to check in with yourself.

Is what you’re saying to them actually helpful? What is it that they’re supposed to do with what you’re saying? Would they have any idea the first thing that they need to do, based on the instruction or guidance that you’ve given them? Telling someone to do better doesn’t create any clarity, and confused minds don’t improve. Okay?

Confused minds don’t move forward, they just spin and indulge in “I don’t know.” So, you’ve got to help people get out of that confusion, and get out of indulging in “I don’t know” by helping them problem solve.

You also might be complaining about the person to other colleagues or really dwelling on their “bad” behavior. This isn’t a morally bad thing, right? It’s just a judgment that it’s a negative thing that we’re dealing with, that we encounter in our work lives. Or in our personal lives, if you’re on the receiving end of anyone’s procrastination in your personal life, as well.

But, are you complaining? Are you dwelling? Are you spinning? Are you really stewing in the fact that you have to deal with this? That’s going to come from that thought of, “I shouldn’t have to deal with this.” Then, you keep dreading and dwelling on the fact that you do have to deal with this.

So, is that one of the actions that you take? What don’t you do when you’re feeling these negative emotions? I always love to flush that out, as well. You probably aren’t asking a lot of questions. You probably aren’t getting to the bottom of this. You probably aren’t seeing where people’s analysis is going awry. You’re probably not brainstorming different solutions with the person that works for you.

You’re probably not consistently communicating with them, coming up with different solutions, and troubleshooting what might work. What might help them make different decisions when it comes to how they manage their time, so they can start to improve.

So, check in with yourself. What do you do when you feel these negative feelings? What don’t you do? Start to compile that list. Then, let’s be really honest. Does it create a result that you want? If the result you want is best supporting the employee that’s doing work for you, who’s struggling with time management, if you want that, if you want to best support them, you probably aren’t going to do that by being dismissive.

By belittling them, by telling people to just “do better,” by yelling at them, by talking down to them, by judging them, by complaining about them, by withdrawing, by hiding from them, by avoiding negative conversations about their time management, by acting like it’s not that big of a deal and then silently cursing them, right?

None of that is going to lead to them getting better at their time management skills. So, even though we can’t control other people, you can control yourself. Really ask yourself, how would I want to show up? What would I want to be doing? What result would I want to create? I want to be the best support system possible, so they have the highest likelihood of overcoming their procrastination problem.

If that’s what you want to do, then we’ve got to make a change. We’ve got to change the way you think. We’ve got to change how you feel. And, we’ve got to change the way that you show up when you’re dealing with these employees.

Now, before we go into really examining those three things; the thoughts you need to be thinking, the feelings you want to be cultivating, and the actions you need to be taking; I want to do a check in here. Okay?

Because I consistently see this be a pain point between supervising attorneys, attorneys answering to supervising attorneys, direct reports, is that there are mismatched expectations. I always want you to take radical ownership and check in: Are you being unclear? Have you given someone a direct, very clear, very finite deadline or have you left it open ended?

If you’re leaving it open ended, we’ve got to fix that. We have to have clear, definitive cut offs for when work needs to be turned into us. What is the expectation? I used to struggle with this.

I joke with attorneys, when I come into law firms and speak to them, I always do a show of hands. Like, who here uses the terms “end of day” or “close of business.” Then we go through and we figure out what everyone means when they say that. Those mean a lot of different things to a lot of different people.

So, it might mean, to you, 5pm. It might mean 6pm, if you think the business day doesn’t end at 5pm. Maybe it runs a little bit later. Maybe you think it’s like 8pm, later on in the evening. Or you might think it means midnight, or 6:03am the following day, before the partner wakes up. Okay? We’ve got to be really clear on what you mean by that.

Because if you mean 5pm, someone else thinks that it means midnight. You’re going to spend that time, between 5pm and midnight, fuming because someone didn’t get you something on time. Then, the person who’s working for you thinks they haven’t even done anything wrong.

Same thing with responsiveness. Define responsiveness for your team. What does it mean to you? Tell them what you expect. Because if you expect someone to respond to emails the same day, or within eight hours or within an hour… You get to pick what responsive means to you.

Then, communicate that expectation. Versus your wanting a response in an hour, and the person who’s working for you thinks 24 hours is fine. You’re going to have so much unnecessary frustration simply because you have mismatched expectations, and you haven’t addressed them.

You haven’t been clear about what they are. We always want to create more clarity. A client of mine says this, I love this phrase, “Clarity is kindness.”

The other thing that I really want you to do, is check in with yourself about your expectation for the direct reports, the improvement process. What are you expecting? Let me promise you, this is not going to improve overnight. You are not going to have a conversation about this one time and then it immediately gets better, that is not going to happen.

People who struggle with time management struggle with time management. It’s not just a flip of the switch where they can just consciously make a decision and decide not to struggle with this anymore. There’s so much that goes into managing your time.

Learning how to accurately plan. Learning how to stop under estimating how long stuff takes. Setting boundaries. Saying no. Resisting the urge to people please. Controlling your calendar. Not allowing yourself to be interrupted. Not distracting yourself with other forms of entertainment.

Not procrastinating. Starting on time. Working without interruptions. Ending on time. Being disciplined to follow through. Allowing yourself to feel the discomfort that comes from working on stuff when you don’t feel like working on it.

This is a masterclass in life skills, in building discipline, in developing it, and then implementing it. Practicing this over and over and over again. It takes time to build the skill set. If you don’t have it, you’re not going to develop it overnight. It’s going to take a lot of practice. It’s going to require a lot of learning, a lot of consistent work, to make continuous and constant progress in this department.

If you want to help someone; I think here, you should be really honest. Do you want to help them get better at this? Do you want to help them problem solve? Is this something that you want to work on with them?

I know, you might be thinking you shouldn’t have to deal with this. But we’ve already established you do have to deal with this. If they’re on your team, and you want to continue to employ them, you want to continue working with them. So, you’ve got to decide, am I willing to commit to this, knowing it’s not going to be an overnight improvement? Knowing that it’s going to take more time than that?

If your answer is no, you’re allowed to have that be your answer. You’re allowed to say, “Nope, I don’t want to work with this person,” and then take the actions that you need to take in order to create that result.

Do you need to fire them? Do you need to ask to work with someone else instead? Do you need to bring different people into your matters, instead of just relying on the person who struggles with time management? You get to make up your mind. But I do want you to make up your mind.

And, I want you to make up your mind from a really realistic place. That this isn’t going to get better overnight. People who struggle with this, struggle with it. It’s going to take time for them to learn how to properly manage their time. Are you up for that?

If you decide you’re up for it, I want you to think about how long you’re willing to devote helping someone improve with this. Are you willing to give it six months? Are you willing to give it a year? I’d love to tell you that it’s going to happen faster than that, but in my experience it’s probably not going to happen faster than that.

There’s going to be a lot of trial and error, so are you up for putting in the time to help someone work through this? Decide on the amount of time you’re willing to give it, and then put your head down and go to work helping them.

Rather than every single day, day in and day out, being like, “They haven’t gotten it, yet. They haven’t gotten it, yet. They haven’t gotten it yet.” That is such a terrible way to support someone through learning how to not procrastinate. Because you’re going to constantly be frustrated that they haven’t caught on, yet.

Versus continuing to be supportive patient, calm, and really curious about what they’re struggling with now. Then, tweaking and iterating and constantly helping them get better. So, decide how long are you willing to work with them on this.

Then ask yourself, what is your process that you’ll follow for helping them improve with this? Now, the first step, is that you have to get yourself to a clean place. You can’t be interacting with the person who’s procrastinating from those negative emotions that I listed earlier.

If you do, it’s going to come across in the way that you communicate with them. So, we’ve got to get you to a cleaner place. The way that we do that is we change your thinking. First step is going to be to address your mindset. I want you thinking thoughts other than the ones we listed earlier.

Thoughts like, “We can solve this,” those going to make you feel really determined. Or the thought, “I wonder what’s causing this problem?” That’s going to make you feel really curious. Maybe you will be thinking, “They’ve never learned to do this,” so you’re going to feel compassionate or understanding.

You might need to think, “Shaming doesn’t lead to self-improvement,” and that might make you feel calm and patience. You might need to think the thought, “I’m in this for the long haul,” and then you’ll feel committed to helping them improve. Or you need to think, “We’re a team here, we’re on the same team.” That might help you feel really devoted or connected to the person. Okay?

Take a second and think about how you want to feel going into a conversation with the person. Do you want to be understanding? Do you want to feel accepting? Do you want to be calm? Do you want to be confident that you can overcome this, or at the very least optimistic that you can overcome this issue together by working with them?

Do you want to feel determined, motivated, connected, capable? Really think about how you want to feel. Then just simply ask yourself, what do you want to think in order to feel that way? What do you need to think in order to feel that way?

Start to identify your own new positive thoughts that you’re going to think, instead of the ones that you probably have been thinking. That’s going to help you get to that grounded place. That place where you can really be curious.

Then approach this with an open mind. From a place where you’re able to really assist and help them and support the person, rather than judge them, and give them a hard time and not be helpful. Okay? So, we’ve got you to a grounded place, that step one.

Step two, is we need to create an opportunity to have a conversation with the procrastinator. The first thing that I want you to establish in this conversation, is whether or not there is a problem. The obvious answer here, is that there is a problem. But we really need the procrastinator to also admit and be brought in on the idea that there’s a problem.

What I’ll see, a lot of times, is people want to dismiss that there is a problem to be solved. They want to pass it off like a fluke, like it won’t happen again. But that’s not really what’s happening here. If this has happened more than once, with the person that you’re working with, you know it’s not a fluke.

They’re going to potentially have a hard time fessing up that this isn’t just an accident and that it’s not going to happen again. People like to be overly ambitious and optimistic, and think that they’re just going to do better next time. Right?

You might also be hoping and wanting the person to just do better next time. So, it’s really easy to dismiss this, brush it off, cross your fingers and hope things just improve. But that doesn’t actually happen in practice. I want you to start the conversation by establishing that there’s a problem. Like, the deadline was missed, the person got something to you late. We need to establish that there’s a problem to solve.

From there, you need to ask questions. You need to gather a lot of information to figure out what the actual problem is. I want you asking questions because I need you to understand how they approach the work, what went wrong.

When you are just making assumptions about how they approached the work, you’re not gathering enough information to actually be able to spot where they went wrong in their approach. I promise you; you’ll be able to spot it if you don’t struggle with time management, and you’re far enough along in your career.

You’re going to be able to spot and see where they went wrong. You’re going to see that they waited too late to get started and didn’t give themselves enough time. Maybe they prioritized other work over yours, because they were people pleasing someone else or they over committed to you. They weren’t honest with you, because they didn’t want to “disappoint” you, even though they ended up disappointing you.

Maybe they underestimated how long it would take. Maybe they avoided getting started on it because they were confused, didn’t know how to get started, and spent a lot of time spinning their wheels. They didn’t come ask you for more direction because they felt embarrassed, especially because they probably should have started on the project sooner and didn’t.

So, you’ve got to ask questions. When did they start working on it? How long did they think it was going to take? What was their approach as they worked on it? Where did they get stuck? Did they come and ask questions? Did they not? Why did they assume it was going to take as long as they thought it would? Was their assumption incorrect?

You’re starting to flesh out where their analysis went wrong. You’re going to see if they needed to start a lot sooner. You’re going to see if they needed to tell you no, and be more honest with you. Or if they needed to come talk to you, ask questions, instead of struggle to figure something out on their own.

Once you’ve asked these questions, you’re going to clearly define the problem. What’s the problem that you both together need to solve? There are only four reasons people don’t get you work on time. They either didn’t make a plan to begin with.

They planned inaccurately and underestimated how long the task was going to take them.

Or they had a plan, but then they reshuffled their schedule to tend to another “urgent” matter. Maybe people-pleasing someone, or operating out of fear or guilt.

Or they just procrastinated. Why did they procrastinate? Were they confused about where to get started? Were they overwhelmed? Were they afraid they were going to do a bad job? What were their thoughts about the project? How were they feeling about approaching the project? What emotions were coming up for them?

So, those are the four: Not making a plan, planning inaccurately, reshuffling their schedule, and procrastinating. I want you to help them identify what went wrong. It might be a combination of those four different issues. Okay? You’ve got to identify what the problem is.

There also might be other problems. This doesn’t lead to why they didn’t turn it in on time, but other problems that make matters worse. So, not communicating with you. Not asking questions. Not communicating with someone else. They didn’t have capacity to do a different project when they were working on something for you.

So, do we need to work on communication here, as well? I really want you to clearly articulate the problem. Talk it through with them. You can explain the problem as you see it.

And I want you, the next step is, to figure out if they agree with that being the problem. Do they agree with your assessment of it? You can even have them articulate the problem. You can ask them, “What do you think the problem is?”

Now, a lot of people will want to answer that question with, “I don’t know.” That’s going to be the easiest escape route here. So, if someone says that to you, “Oh, I don’t know why I didn’t start on that earlier. Oh, I don’t know why I procrastinated. Oh, I don’t know why I didn’t come and ask you questions.”

I don’t want you to let their answer “I don’t know” stand. You’ve got to hold space for them to work through these questions and come up with better answers than “I don’t know.” So, you can say, “If you had to guess, what do you think it would be? If you did know, though, what might you say?”

Are those super coachy questions? Yes, they are. I use them with my clients all the time. But you can use them to work with people who you’re trying to help get better with time management.

You’ve established there’s a problem. You’ve asked questions. Now, you figured out what the problem is. You’ve agreed on it together, that that is the problem. Now, I want you to get their buy in? Do they want to solve the problem? You have to get their buy in. If they are not committed to solving this, it’s not going to work.

They’ve got to commit. They’ve got to step up to the plate. From there, you’ve got to come up with an approach for how are you going to solve this problem. Now, one thing I suggest, is that you meet with the people that are working for you, who struggle with time management, you’ve got to meet with them way more frequently than you do with people who don’t struggle with time management.

Would it be amazing if you didn’t have to do that? Yes, it’d be great. But doing what you’re doing isn’t working. So, we’ve got to change our approach. You need more interaction with those people. I highly encourage that you have standing meetings with them. Check ins where you force them to come with questions they have about the assignment.

I suggest that you have check ins on progress on the task, so you don’t create a situation where it’s possible for them to wait to the last minute to get started. You can also track someone’s time on a project, if you have access to their billable time. Have they started on it, yet? A lot of people will people-please you and say they’ve started on it. But if they haven’t billed the time yet, they haven’t.

Now, if people procrastinate with projects, they probably also procrastinate with billing their time. But stay on people about this, and ask them. You can actually go through this process with them, on their procrastination for entering their time.

Establish, is there a problem? Ask them how do they think about time entry? What emotions come up for them around a time entry, that leads to them delaying entering their time?

Their thoughts are going to be something along the lines of, “My other work is more important. I hate doing this. This sucks. I shouldn’t have to do this. It’s tedious. It’s time consuming. I don’t have time for this right now.” It’s going to be thoughts like that, and then they’re going to feel the negative emotions that are caused by those thoughts.

Then you can work through what exactly is the problem. Is it just that they need to feel dread and put the time in, anyways? Is it that they don’t have an approach for when they should enter it, and they need to make some decisions around entering their time?

Are they confused? Are they being perfectionistic? Do they think they need to enter all of the month’s time before they can start entering today’s time? Which is a terrible idea. You can just start entering today’s time instead of being perfectionistic about it, and worry about the backlog later. You want to ask questions to help discern these problems.

Once you’ve got a clear understanding of what the problem is, get their buy in so they want to solve it. Then agree on a process to solve the problem. What are you going to do with them, in order to see some improvement? I also want you to include the timeline for them.

Talk them through. “This is going to take a while. We’re going to consistently work on it for month after month after month,” And get them to buy into that, as well. It might mean heightened supervision. It might mean more frequent check ins. It might mean having to have uncomfortable conversations around their approach to projects and tasks.

But you’re doing it because you’re on their team, and you’re committed to helping them solve this problem, that they have now agreed that they face, that they have. They’ve also agreed to wanting to work on this with you, to help solve this problem, to address it.

I really want you to spend a second and think about, if you didn’t believe that it was shameful and bad to be bad at time management, how would you approach helping someone tackle this and improve?

If you didn’t think it was this moral failing, which so many people treat it as a moral failing, if you didn’t think of it that way, what would you do differently? You would diagnose and treat the problem instead of judging and ignoring it. Judging and ignoring it is what we do when we think something is shameful, okay?

So, check in with yourself. Are you guilty of being judgmental, but then also burying your head in the sand and not getting your hands dirty helping your team members work through their time management struggles, and working to help them solve these problems? If you drop your judgment, you can tap into being willing to help them diagnose the problem and to treat it.

You do that, again, by grounding yourself. Getting grounded first, then establishing there is a problem, asking questions so we can understand what’s causing the problem. We need to understand how they approach their work so you can issue spot.

Then we’re going to get really clear after asking those questions. What is the specific problem we need to solve and address? Get their buy in. Do they want to solve the problem? Then come up with an agreed upon plan for solving it.

Of course, last but not least, you evaluate, gather some data, implement the plan, and see what’s working, what’s not working, what do you need to do differently, and continue to iterate. Keep working this process. This is how you help someone work through their time management struggles.

Just like I’ve talked about in the past couple episodes, it is going to be messy. I highly recommend, too, if you’re dealing with someone who procrastinates, direct them to my podcast episodes. I have a very comprehensive time management series on how to manage your time.

I walk them through all the steps. I teach them the mindset. I teach them the strategy. I would highly recommend you listen to it, as well, so you can have conversations where you’re well versed in the strategy that I’m teaching. And, you have a framework that you can teach them, help them understand, troubleshoot, and talk through.

Definitely do that yourself, but also direct and have them listen to it as well. Have them partake in the process. You can ask them, “How do you think we should approach this? What do you think might work for you?” Let them buy in, let them participate in the solution process.

But if you see them doing something that you know doesn’t make sense, that you know is kind of the wheels going off the tracks, course correct. Bring them back to what you know to be true. Help them see where they’re thinking about it the wrong way, and then make your recommendation. You can explain to them why you are recommending what you are recommending. It’s coming from your experience, okay?

One of the things that I see people struggle with the most, is that they don’t plan backwards from the deadline. They underestimate how long something takes. So, I want you to teach them how you think about estimating how long a task takes. How you get clear on what something’s going to require from you. How you decide when to start working on something, so you ensure that you have enough time to complete it in a timely fashion. Think about how you approach your work.

As you ask them questions and learn more about the way that they approach their work, you’re going to see where their analysis leads them down the wrong path, where it causes the problem. Then, you can teach how they need to look at it instead. How to think like you so they manage their time better.

I hope this helps you dial down your frustration, because you’re causing your own frustration. I hate to break it to you. So, we’ve got to get you thinking differently about dealing with procrastinators. Then, we also have to get you dealing with procrastinators differently than you have been.

I want you to try this approach. Have much more open, honest, calm, curious conversations with the people that you’re working with. Help them problem solve, help them troubleshoot, get to the bottom of what’s not working. Establish that there’s a problem and then help them solve it.

They’re going to be so grateful to you, and you’re going to be so grateful to yourself because you’re not going to have to deal with this problem, if you put in the work to help people overcome it. Okay, I hope this helps you.

Also, don’t forget, I’m teaching a masterclass at the end of the month, September 29th, at 12pm Eastern, if you want to register for it. You can come learn what I teach, or you want your procrastinators that you’re dealing with to watch it as well. You can make it a whole, firm-wide event.

You can register for it at LessStressedSessions.com/signup. Or you can go to my Instagram, there’s a link there. We’ll also link it in the show notes to this podcast episode. Copy and paste it, and send it out to your whole team. That way, anyone who struggles with time management and procrastination can come and learn the proper process that I teach for how to properly manage their time.

Okay, that’s what I’ve got for you this week, my friends. I hope this was helpful. I hope you have a beautiful week, and I will talk to you in the next episode. Oh, one more thing. I almost forgot. Remember, I am doing a giveaway. If you would do me the kindness of reading and reviewing the podcast. If you’re just absolutely loving my content, it would mean the world to me.

As a thank you for leaving me a rating and review, I’m going to pick five people over the course of the month of September and October. At the end of October, I’ll pick five winners, and I will give away five distinct prizes. I hope you are one of the lucky winners.

If you haven’t left a review yet, go do that now. Thank you. It means the world to me. I can’t wait to pick names, and hopefully I pick yours.

All right, have a beautiful week. I’ll talk to you next week.

Thanks for listening to The Less Stressed Lawyer podcast. If you want more info about Olivia Vizachero or the show’s notes and resources from today’s episode, visit www.TheLessStressedLawyer.com.