The Right Way to Manage Rule Breakers

Summary

HBR IdeaCast: The Right Way to Manage Rule Breakers

Podcast: HBR IdeaCast
Episode: The Right Way to Manage Rule Breakers
Date: June 16, 2026
Host: Alison Beard
Guest: Michael Gill, Associate Professor at Oxford Saïd Business School

---

Episode Overview

This episode focuses on a crucial—and often misunderstood—leadership challenge: how to manage rule breaking within organizations in a fair, effective, and even constructive way. Michael Gill, whose research synthesizes insights from 250+ studies over four decades, joins Alison Beard to dig into why employees break rules, how leaders can respond more skillfully, and when breaking the rules might actually be a positive force.

---

Key Discussion Points & Insights

Rule Breaking Is Increasing—and Not Always for the Worse

• Workplace rule breaking is common and rising.
  • "The Ethics and Compliance Initiatives 2023 Global Business Ethics Survey reported that 65% of employees around the world said they had observed misconduct at work. And that's up from 60% three years earlier in 2020." —Michael Gill [02:26]
• Possible factors:
  • Rise of remote work (less oversight)
  • New technologies, especially AI, creating gray areas
  • Unclear whether this reflects “moral decline” or just changing conditions [03:34]

Four Types of Rule Breaking: Understanding Motivation is Key

Michael Gill’s research identifies four main drivers for why people break rules:

1. Self-Interested Rule Breaking:
   "This is when people break the rules for their own self interest... maybe they fudge their expenses or bypass approvals so they can get a bonus." [04:44]

2. Pro-Social Rule Breaking:
   "This is when employees break rules to try and help other people... For example, an employee might disregard a rule and provide a bonus to a valuable customer who had bad service." [05:36]

   • Memorable moment:
     Alison: “I like those kind of rule breakers.” [06:25]

3. Corrupted Rule Breaking:
   "This is when people are breaking rules not because they want to, but because they feel pressurized or threatened or coerced in some way by their colleagues or their boss..." [06:28]

4. Edified Rule Breaking:
   "This is when people break rules... for a higher purpose or to do something they think is right. For example, people working in healthcare who break an organizational rule to help a patient." [06:50]

Leaders’ Common Mistakes in Managing Rule Breaking

• Assuming all rule breaking is self-interested and punitive action is needed
  • "If we’re always assuming it’s... self interested, then you’re going to have all sorts of problems." —Michael Gill [07:25]
  • Punishment can backfire if the motivation was not harmful

Practical Advice for Managers

Diagnosing Motivation

• First, ask why rules are broken

  • “Underneath it all is the premise of asking and trying to understand why.” —Michael Gill [08:24]
  • Patterns of repeated rule breaking signal issues with the rule itself

• Create psychological safety

  • Allow anonymous or safe forums for employees to share why rules are broken [09:31]

Choosing a Response

• Punish when rule breaking is self-serving and harmful.

  • “If someone has obviously self interestedly and knowingly broken a rule that is for their own benefit... then punishment is entirely appropriate.” [10:33]

• Show compassion and educate when the motivation is not self-interest.

  • “Rather than punishing, it’s more about educating and explaining.” [11:17]

Rethinking Rules Proactively

• Don’t encourage rule breaking, but use it as information.

  • “Organizations need rules and they should be supported and enforced. But if people are breaking rules, they are sending a signal...” [12:01]

• Update outdated or unworkable rules.

  • If a rule is often broken, it may no longer fit real operational needs

Should Leaders Ever Encourage Rule Breaking?

• Be careful not to encourage rule breaking directly.
  • “My view would be probably not to encourage rule breaking, but to be really sensitive to when it does happen and to try and revisit the rules to understand when those rules are not fit for purpose.” [14:16]

Detecting Hidden Rule Breaking and Silence

• Invite anonymous feedback or use intermediaries.

  • “Invite people to speak, whether it be anonymously, or through other people or... a representative, and to share their ideas.” [15:11]

• Mystery shoppers/observers can reveal rule issues.

Senior Leadership’s Role

• Model openness and honesty about rule challenges.

  • “Be honest and admit as leaders when they have broken rules or made mistakes, because that encourages other people to speak up...” [16:42]

• Reduce the distance between frontline and leadership.

  • “Can those leaders spend time on the front line, however briefly... to get a sense of why employees might feel the need to break rules?” [16:42]

---

Notable Quotes & Memorable Moments

• “When your employees are coming to you and talking... about why they felt they had to break a rule... you’ve built a culture and a climate where people feel willing and able to talk to you... That trust... would suggest to me that you’re doing a really good job.”
  —Michael Gill [18:04]

• “If you have talented and committed employees, employees you really value, but they keep breaking a rule or the same rules, they are sending you a really strong signal.”
  —Michael Gill [19:39]

• “Before a rule is even broken, it would be really useful to speak to the people who will be most affected by those rules and to ask them, do you see any contradictions in what we’re asking you to do and these rules?”
  —Michael Gill [20:32]

---

Important Timestamps

• [02:26] — Survey data showing rule breaking is increasing
• [04:44] — Gill’s four motivations for rule breaking
• [07:25] — Leaders’ error: default to punishment
• [10:33] — When punishment versus compassion/education is appropriate
• [14:16] — Should leaders ever encourage rule breaking?
• [16:42] — C-suite’s role: show honesty, bridge the gap
• [18:04] — Signs of a strong feedback culture
• [19:39] — Being curious about repeated rule breaking
• [20:32] — Proactively questioning rule contradictions

---

Conclusion & Takeaways

• Understanding why rules are broken is the starting point—not all violations are equally problematic.
• Patterns of rule breaking may signal rules that need updating.
• Managers should focus on curiosity and open communication rather than jumping to punishment.
• Leaders at all levels should model honesty and bridge the front line–C-suite gap for better rule management.
• Constructive dialogue about rules can strengthen organizational culture and performance.

---

Further reading:
How the Best Leaders Respond to Rule Breaking (HBR article by Michael Gill)

Transcript

[Alison Beard]

Deal's not just another payroll platform. It's one your team might actually enjoy. Hr IT and payroll together finally built in house built for peace of mind. VisiT-E-E-L.com HBR. Marketers know how it feels to invest in something that seemed incredible but didn't live up to the hype. We optimize for impressions, but then don't see any revenue. Instead, get the highest ROAS of all major ad networks with LinkedIn ads, spend $250 and get a $250 credit. Just go to LinkedIn.com IdeaCast Terms and Conditions apply.

[Michael Gill]

Hello everyone, I'm Michael Gill and you've tuned in to the Harvard Business Review ideac. Don't worry, I have Alison Beard with me here as well.

[Alison Beard]

Hi everyone.

[Michael Gill]

But we wanted to switch things up a bit today because I recently contributed to an HBR article about rule breaking in organizations and how leaders can manage it.

[Alison Beard]

And so, while Adi and I typically

introduce all of our episodes, our producer Mary agreed to let Michael bend the rules in this instance.

But Michael, how should I deal with

this rule breaking of yours?

[Michael Gill]

Well, one of the main findings of my research is that when it comes to dealing with rule breakers, the first thing to do is really understand the motivation behind the behavior. And for me, it was to prove that rule breaking isn't always a bad thing. In this case, it maybe got listeners more interested in the topic.

[Alison Beard]

I certainly hope so, and I want to dig into that and much more. But first, let me properly introduce you. Michael is an associate professor at the University of Oxford Said Business School. And his research, a synthesis of more than 250 studies across four decades, was

featured in the HBR article how the

Best Leaders Respond to Rule Breaking. Welcome to the show that you've already opened, Michael.

[Michael Gill]

Thank you very much for having me.

[Alison Beard]

Okay, so how big a problem is this for leaders right now? Are employees and managers breaking more rules

than they have in the past?

[Michael Gill]

So we have different pieces of evidence that suggest that rule breaking is very commonplace and in many instances, on the rise. So for example, the Ethics and Compliance Initiatives 2023 Global Business Ethics Survey reported that 65% of employees around the world said they had observed misconduct at work. And that's up from 60% three years earlier in 2020. And in the United States, more than half of workers reported seeing rule breaking, and prior surveys found much lower levels. So that does suggest that the problem is increasing. To understand how common or frequent this is is really difficult because lots of organizations, for obvious reasons, don't want to talk about it. But with the evidence that's out there, and certainly in my study, we can see that rule breaking is happening in all sorts of organizations in all sorts of places and industries around the world. And it is really common. And I think one thing to reflect is if you've ever encountered rule breaking, and I suspect most people have.

[Alison Beard]

Yeah.

And I imagine that there are a couple trends that might have led to an increase in rule breaking. You know, I think of remote work which means less oversight. I think of people using new AI tools in ways they shouldn't or aren't sanctioned by the organization. So I'm hoping it's that not just like moral decline.

[Michael Gill]

I hope so too. I think that you're absolutely right. I think with the rise of new technologies and new tools and soften areas of grey where people are not sure whether or not you can do this and organizations might not fully understand what their rules are dictating. Absolutely. It could be driven by issues of AI. And I'd like to think that there isn't a sustained moral decline. But I do think that people will break rules for all sorts of reasons and sometimes that will be for self interested reasons and sometimes it will be because they're trying to help people. And the technology we're now embracing can make all of those different explanations just as valid as they've always been.

[Alison Beard]

So you said not all rule breaking is bad. What exactly did you find in your research about that in terms of different motivations?

[Michael Gill]

The nub of the research article is that there's a lot of different research about rule breaking and it's across the fields of management and sociology and economics and criminology. But these different literatures tended to offer different explanations for why people break rules, but didn't really speak to one another. So what I've tried to do in this study is to pull all those different explanations together. And really when you look at across all these different literatures, there are four main types of rule breaking explanations. And I'll just quickly run through those. So the first one is self interested rule breaking. This is the rule breaking that most people are really familiar with. This is when people break the rules for their own self interest to get themselves something that will benefit them. So for example, maybe they fudge their expenses or bypass approvals so they can get a bonus. That's the most well known type of rule breaking and that's typically what most managers think about when we think about rules being broken. But there are three other types. And the second is called pro social rule breaking. And this is when employees break rules to try and help other people. So this might be to help a customer or to speed up a process or to help a colleague who's stuck. And an example of this might be an organization has a formal rule that says you can't give a refund if a customer has received bad service, but if a customer is really valuable, an employee might disregard that and provide a bonus.

[Alison Beard]

I like those kind of rule breakers.

[Michael Gill]

They sound great. They sound great. And there are two others. And the third one is called corrupted rule breaking. And this is when people are breaking rules not because they want to, but because they feel pressurized or threatened or coerced in some way by their colleagues or their boss to break a rule. And then the final type is edified rule breaking. And this is when people break rules again, not for themselves, but usually for a higher purpose or to do something that they think is right. So, for example, that might be people working in healthcare, people breaking an organizational rule if it helps a patient, for example. And the article's trying to say there are all these different types of explanation. And if we want to understand rule breaking, we need to understand that there are lots of different motivations for why it happens.

[Alison Beard]

So what are the biggest mistakes that leaders make when it comes to responding to rule breaking in their organizations?

[Michael Gill]

Yeah, so I spend quite a bit of time with different organizations and have worked with quite a few in a pro bono capacity on rule breaking. And one of the most common is that is an almost default assumption, not across all, but across many managers, that if someone's broken the rule, they should be punished. But the problem with that is twofold. Number one, it misrepresents why people are breaking rules. So we've just touched on the different types of explanations, and if there are four types, and we're always assuming it's one, in this case self interested, then you're going to have all sorts of problems. And the second is if you respond to someone being self interested and assume everyone is self interested by punishing them, then that can have really negative consequences as well in organizations.

[Alison Beard]

So what advice do you have for managers who are trying to better discern the motivation of a certain person's rule breaking before they react or punish?

[Michael Gill]

There's several steps, I think, that managers could look to do, but underneath it all is the premise of asking and trying to understand why. And for many employees who break rules because they're trying to help the company or because they're trying to help colleagues, or because they think they're doing the right thing, they will be more likely to offer up an explanation. And to try and explain to others or their boss, their leader, their manager. Why they've done can be tricky. Of course, there'll be lots of instances where employees don't want to share and that leaves managers with a problem. But also, if people continue to break the same rule over and over again, that's also sending a really strong signal to managers and leaders that maybe they need to think more carefully about how that rule is being used. And is it really working in practice with the day to day realities of work?

[Alison Beard]

Yeah.

So, as you say in the article, it's key to look for patterns in rule breaking. How can managers begin to notice those patterns? If it's sort of an accumulation of anecdotes, or is there data analysis that could be done?

[Michael Gill]

There's a whole host of ways that different managers might choose to approach it. The first is giving people a forum where they could share instances with you of why they might break rules. So giving people an opportunity where they might feel psychologically safe, where they know they might not be punished, or some forum in which they can share and explain why things are happening. The second is really to look for patterns. So as you touched on there, why might certain rules be broken? Well, if the same rule is being broken again and again, or a certain department continues to break the rules, then that's really interesting and that can lead to conversations about why that's happening. Ultimately, whatever the approach, it's about trying to gather more data and to understand the motivations behind the rule breaking before reaching to react.

[Alison Beard]

And once you've determined a person's motivation or a set of people's motivations, what are the different ways that you might handle the situation? Situation depending on your diagnosis.

[Michael Gill]

Yeah. So I think it will of course depend on what you understand to be the motivation of that rule breaking. But if we take two extreme ends of the continuum, one is punishment. One is if someone has obviously self interestedly and knowingly broken a rule that is for their own benefit and is harming the organization in some way, then punishment is entirely appropriate if they're aware of the rule they've broken and of the consequences. And I think most managers are aware of disciplinary action and how that can unfold. But there is also the other end of the spectrum, which is, first of all, many people break rules without fully understanding why, or as we've spoken about, maybe they felt pressurized. And in those instances, it's really helpful to offer some Compassion to try and help someone understand why they shouldn't be breaking this rule and the consequences of it. Rather than punishing, it's more about educating and explaining. And the benefit of a compassionate approach when people aren't breaking the rule for self interest is that they are more likely to be willing to then stop breaking the rules or to share their insights about how that rule can be changed and improved.

[Alison Beard]

What would you say to an organizational leader who says we have rules for a reason? If we go into this sort of pattern of trying to understand why people breaking rules and then maybe changing them, it's just going to lead to chaos.

[Michael Gill]

The first thing to say is I wouldn't recommend that any rule breaking should ever really be encouraged by managers, at least not directly. Organizations need rules and they should be supported and they should be enforced. But if people are breaking rules, they are sending a signal to management about something important and that tends to be that the rules may no longer fit the operational realities. Now, it may be that some people break rules again for self interested reasons, and if that's the case, and that's clear, then absolutely enforce the rules and use punishment as appropriate. But if a rule has been broken over and over again, and that is an issue, then that speaks to a more fundamental problem about the rule itself rather than the rule breakers.

[Alison Beard]

Let's be honest, most HR platforms aren't exactly a joy to use. Deal's different. It's AI native, keeps you compliant and grows with your team, whether you're five people or 50,000 HR IT and payroll on one platform that just works. See for [e-mail] that's D E-L.com HBR.

[Relativity AI Advertiser]

Legal teams are under more pressure than ever. More data, more complexity, more scrutiny. They need AI built for the realities of legal work. For more than a decade, Relativity has invested in AI built specifically for legal teams designed to meet legal standards and support defensible decisions. The result is explainable AI that handles tedious tasks, so judgment and critical decisions stay where they belong with you. Relativity is the AI platform for legal work. Learn more at relativity.com ideacast.

[Alison Beard]

Are there instances when people actually should encourage rule breaking? You know, I think of the old Facebook saying, move fast and break things. Like we're in a period of such dynamic change that actually we want people to be challenging rules.

[Michael Gill]

I think there's a benefit to encouraging people to consider and reflect on the rules and to ask people why rules don't work or perhaps how could they change or develop. But I think there's a real risk in encouraging rule breaking, that you can set a precedent whereby people then continue to break rules and they might at the start break rules that you want them to break, or lesser rules, if you will. But the risk then is that people continue to break rules that you don't want them to break, or more foundational or fundamental rules. So my view would be probably not to encourage rule breaking, but to be really sensitive to when it does happen and to try and revisit the rules to understand when those rules are not fit for purpose.

[Alison Beard]

And you also advise leaders to try to figure out what they aren't being told, sort of when people want to break a rule, but haven't yet, maybe. So how do you do that?

[Michael Gill]

That's a great question. So it can be really difficult because for all sorts of reasons, people don't want to speak up in the workplace, especially to their bosses, managers, leaders. One thing and one option to managers is to invite people to speak, whether it be anonymously, whether it's, or whether it's through other people or through a representative, and to share their ideas. Others are to use things like surprise, we call them mystery shoppers in the United Kingdom. But having people go into the workplace and experience it either as a customer or an employee, and then feedback their experiences in a way that's removed from the everyday employee to managers. And then another option on top of those is really simply to try and just sketch out with your team if they think there might be rules that could be broken or if it's a possibility and why they think that might happen in a safe environment. And again, the underlying principle is just to try and flesh out what could cause people to break rules and then how likely is that to happen?

[Alison Beard]

It sounds like this is a problem that should be mostly dealt with by frontline managers, you know, a boss dealing with their direct reports. But is there anything that higher level leaders in the organization, maybe the C suite, can do to ensure that everyone's treating rule breaking in the right way?

[Michael Gill]

I really believe that this is a very senior level issue. And I think in the C Suite and indeed at all levels, there are several things that leaders can do that would have a profound impact on rule breaking. I think one thing is to be honest and admit as leaders when they have broken rules or made mistakes, because that encourages other people to speak up and share their experiences about why they felt they had to break a rule or why they didn't understand a rule. And I think that spirit of openness and honesty requires real leadership. And it can have a really profound impact on getting other people to speak up. And I think the other thing as well is to try and make sure that that gap between the front line and the C suite can sometimes be closed. Can those leaders spend time on the front line, however briefly, to try and get a sense of why employees might feel the need to break rules, even if it's for the benefit of customers or their colleagues? Because in the abstract, it can be quite obvious to many senior leaders that rule breaking is wrong. But in the practical, lived experience on the ground, it can make much more sense.

[Alison Beard]

How do you know when you're doing a good job, both dealing with the bad kind of rule breaking and then also learning from the good kind?

[Michael Gill]

I think that when your employees are coming to you and talking to you about why they felt they had to break a rule, and they did or they didn't, and even better, why they think they might be able to change the rule in some way and can offer you ideas, I think at that stage, you've been really successful because you've built a culture and a climate where people feel willing and able to talk to you about how rules can be recrafted or redeveloped without being hidden away from you. And that trust, that level of openness between employees would suggest to me that you're doing a really good job. And the next step on from that would be as a manager, a leader, you are prepared to revisit and reconsider rules rather than just sticking to them steadfastly.

[Alison Beard]

So why did you get interested in rule breaking? Are you a rule breaker yourself?

[Michael Gill]

No, no. I am very much a geeky academic, so I like to follow the rules very clearly. The reason I got quite interested in rule breaking was because I was approached by several different firms initially in a pro bono capacity, and we were talking about several issues the firms are facing. And some of these firms spoke honestly about issues of rule breaking and asked me to come and talk to them about it. And in doing so, I reviewed the literature. And that also, I think, reflects the point that this is a real issue that organizations are facing right now.

[Alison Beard]

Is there any other advice that you have for leaders on how to stay on top of rule breaking in their organizations?

[Michael Gill]

Yes, I have one key recommendation, which is I am advising managers to be curious. You know, for example, if you have talented and committed employees, employees you really value, but they keep breaking a rule or the same rules, they are sending you a really strong signal, and that is likely to indicate some sort of tension between what they're being asked to do. Or expected to do every day and the structures of your organization. And don't just assume you know why people are breaking rules. Try and find out and as a bare minimum, try and have a conversation with those people.

[Alison Beard]

What are some specific questions that you think you know, either CEOs or frontline managers should be asking?

[Michael Gill]

I think before a rule is even broken, it would be really useful to speak to the people who will be most affected by those rules and to ask them, do you see any contradictions in what we're asking you to do and these rules? I think that's one broad set of questions. And another question would be, if you do see any contradictions, can you see alternatives or can you think of different ways in which we could approach this? Again, showing a curiosity not just for the motivations of employees, but also about the rules you employ every day in organizations.

[Alison Beard]

So what's next for you in studying rule breaking in this type of behavior?

[Michael Gill]

The interesting thing is it's so hard to get access to firms who want to openly discuss rule breaking. As you can imagine, no one really wants to talk about it. So any direction that we could get people who would be willing or open to discuss rule breaking, I think would really help us, at least from a research point of view, to understand more about why this happens and how to address it.

[Alison Beard]

Terrific. Well, Michael, thank you so much. It's been a pleasure talking to you about this.

[Michael Gill]

Thank you so much for having me today.

[Alison Beard]

That's Michael Gill, an associate professor at the University of Oxford said Business School. You can learn more about this research in the HBR article How the Best Leaders Respond to Rule Breaking. If you found this episode helpful, please share it with a colleague. And be sure to subscribe and rate IdeaCast in Apple Podcasts, Spotify or wherever you listen. If you want to help leaders move the world forward, please consider subscribing to Harvard Business Review. You'll get access to the HBR mobile app, the weekly Exclusive Insider newsletter, and unlimited access to HBR Online. Just head to hbr.org subscribe thanks to our team, Senior Producer Mary Du Audio Product Manager Ian Fox and Senior Production Editor Kristen Murphy Romano. And thanks to you for listening to the HBR IdeaCast. We'll be back with a new episode on Tuesday. I'm Alison Beard. Let's be honest, most HR platforms aren't exactly a joy to use. Deal's different. It's AI native, keeps you compliant and grows with your team whether you're five people or 50,000 HR IT and payroll on one platform that just works. See for [e-mail] that's D E L.com HBR.