The Changing Nature of Progressive Discipline: A Developmental Approach for Disciplining Senior Executives and Middle Managers

The evolution of progressive discipline among senior executives and mid-level managers shows itself in its developmental focus while accounting for legal compliance.

As the author of 101 Sample Write-Ups for Documenting Employee Performance Problems: A Guide to Progressive Discipline and Termination from HarperCollins Leadership and American Management Association Books (https://bit.ly/4ajQK4f), I’ve had the pleasure and opportunity to influence the employee relations field and help frontline operational managers and business owners and executives improve their leadership communication significantly. After all, even if you have an MBA from a top school, they don’t teach “leadership in the trenches” on a practical basis. And the fine points of disciplinary documentation—including according workplace due process and avoiding situations where your disciplinary documentation could actually be used against you or your company in court—scare enough executives to avoid documentation altogether.

But it doesn’t have to be that way. . . Documented disciplinary interventions can be easier and simpler than you think. Further, they go a long way in dis-incentivizing plaintiffs’ attorneys from accepting cases in the first place. After all, “Did they ever put anything in writing?” is one of the first questions that a plaintiff’s attorney will ask when considering taking on a new case. Likewise, disciplinary documentation can be used in court to demonstrate that a company had “good cause” to justify a termination decision. Even more significantly, disciplinary interventions work: they reset expectations, document training opportunities and other employer interventions to make matters better, and when done correctly, help workers course-correct so that performance improves and termination can be avoided.

That being said, the nature of progressive discipline is changing, especially for senior executives and middle managers. The Covid-19 pandemic introduced remote work, and “managing the unseen” became a just-in-time leadership skill that caught many organizations off guard. In CEO priority surveys since the early 2020s, “emotional intelligence” has been catapulted to a top-five priority. Why? Because the ability to bond with people, build strong relationships based on trust and respect, and to strengthen communication and collaboration across the enterprise became the strongest paths to ensuring that employees working remotely were doing their best work and operating at peak performance.

Understand that the post-Covid reintegration period will likely last five years, and fallout from the pandemic will continue to change the way we do business through 2027. Organizations are reinventing themselves as we speak, focusing on culture, retention, employee engagement, and discretionary effort. Disciplinary measures and systems actually impact and influence corporate culture. In fact, a number of organizations are focusing on making disciplinary efforts feel less punitive and more developmental. This blog article explores fundamental changes to the progressive disciplinary strategies within your organization, particularly when the need to discipline senior executives or middle managers arises. But I begin with a huge caveat, depending on how your workforce is structured:

·         If your workers are governed by a union’s collective bargaining agreement, elements of this more collaborative and developmental approach may not pass the smell test if you take adverse action (especially termination) against a union employee based on the suggestions that follow. Therefore, speak with qualified labor counsel about incorporating any elements of the approach that follows, as it may contradict the union contract or inadvertently set precedent in creating more "disciplinary steps" than your contract requires.

·         If your workers are mostly hourly, consider speaking again with qualified employment counsel before implementing these changes. You’ll likely need to change the language in your employee handbook and announce some of these changes before moving forward. Much will depend on your state employment laws and inclination to favor workers (California) or employers (Texas), for example. Much will likewise depend on your industry and your employees’ willingness to litigate, fake workers’ compensation injuries when disciplined, and the like.

·         Finally, much will depend on your willingness to adjust your progressive disciplinary practices to reflect a more open, transparent, and trusting culture.

In this article, we’ll focus on building a developmental approach for senior executives and middle managers engaged at some stage of the disciplinary process. Why? Because they tend to have a much stronger sense of “career” than hourly employees; they'll more likely appreciate the approach to a shared and respectful experience in this space without taking advantage of it; and because most companies fail to document disciplinary matters for this particular workforce cohort, making litigation a more significant threat (since the company can’t defend its actions in the litigation arena with little if any documentation in place).

Simply put, in a dynamic post-Covid landscape, the concept of progressive discipline is undergoing a significant transformation. Once primarily viewed as a punitive ladder of escalating consequences, it's evolving into a more nuanced, developmental process, especially when applied to senior executives and middle managers. This shift reflects a broader organizational understanding that discipline, when handled thoughtfully, can be a powerful tool for fostering a respectful culture, enhancing professional development, and ultimately, strengthening corporate performance. It’s not a punitive framework or “paperchase” to remove people and protect the organization’s flank: instead, it can morph into a program that embraces a more developmental, coaching-oriented approach and that has a profound impact on individuals and the entire corporate culture.

The Traditional View of Progressive Discipline: A Punitive Ladder

Historically, progressive discipline has been a linear, step-by-step process designed to address performance issues or behavioral infractions. It typically begins with a verbal warning, escalates to written warnings, and then to termination (i.e., a "three-strikes-before-you're-out" approach to notifying workers of continuing problems). The underlying philosophy was rooted in deterrence and compliance: employees would correct their behavior to avoid harsher penalties. For lower-level employees, this model often served its purpose, providing a clear framework for addressing issues.

However, applying this traditional, often rigid, model to senior executives and middle managers presents a unique set of challenges. These individuals are often long tenured, possess deep institutional knowledge, and hold positions of significant influence. Their mistakes, while potentially more impactful, are rarely a result of a lack of understanding of basic rules but rather stem from complex factors such as strategic misjudgment, leadership style issues, or communication breakdowns. A purely punitive approach risks alienating valuable talent, fostering resentment, and overlooking the underlying causes of the issues.

The Modern Paradigm: Discipline as Development

The modern approach to progressive discipline, particularly for those in leadership roles, looks to reframe it not as a path to punishment, but as an opportunity for growth and recalibration. This developmental perspective recognizes that:

• Leaders are Learners: Even the most experienced executives can benefit from feedback and guidance, thereby perpetuating a "continuous learning culture".

• Context Matters: Performance issues at senior levels are often multifaceted and require a deeper understanding of the situation, organizational dynamics, and individual motivators. Think of it as a “high stakes, high support” type of mindset.

• Retention of Key Talent: Losing a senior executive is costly, not just in terms of recruitment but also in lost institutional knowledge and disruption to strategic initiatives. A developmental approach prioritizes retaining valuable talent through improvement.

• Cultural Impact: How a company handles discipline for its leaders sends a powerful message about its values and culture. Likewise, companies that avoid documenting discipline and otherwise “surprise” leaders with termination decisions send an equally powerful (although negative) message about its values and culture, leaving employees to divine by their superior's actions whether they're performing well or even wanted.

This shift doesn't mean abandoning accountability. Instead, it means enhancing accountability by stepping in where most organizations tend to look the other way or sweep matters under the rug. It’s all about integrating accountability within a framework that prioritizes coaching, support, and clear pathways for improvement. Likewise, this makes it much easier for the executive “dispensing” the disciplinary action to feel more comfortable doing so. The alternative—avoiding confrontation at all costs—diminishes in value because the leader now gets to play coach and mentor, not just unilateral decisionmaker and disciplinarian.

The Key Elements of Developmental Progressive Discipline

Several key elements define this more modern, nuanced, and developmental approach to disciplining senior executives and middle managers:

1. Early Intervention and Proactive Feedback: The most effective discipline is often that which is never fully implemented. Regular, honest, and constructive feedback should be an ongoing part of the managerial relationship. For senior leaders, this can include 360-degree feedback, annual performance reviews, quarterly professional development touch-base meetings, and informal, real-time feedback. Addressing minor issues before they become major impediments is crucial. This proactive approach helps identify potential problems early on, allowing for course correction without the need for formal disciplinary action. Plus, it builds trust based on accountability and transparency so that leaders never have to worry about questions like, “Does my boss like me?” or “How am I really doing in my boss’s eyes?” Put simply, it helps employees do their best work every day with peace of mind.

2. Clear Expectations and Performance Metrics: Before any disciplinary process begins, it becomes paramount that expectations are crystal clear. For senior roles, these expectations often go beyond quantifiable metrics to include leadership behaviors, cultural alignment, ethical conduct, and strategic contributions. Ambiguity at this level can lead to misunderstandings and disputes. In short, where gaps in communication exist, people fill in those gaps with assumptions. And that’s where teams get misaligned and things fall off the rails pretty quickly. Regular reviews of ongoing expectations and their alignment with organizational goals are vital.

3. Coaching and Mentorship: When performance or behavioral issues arise, the first step should often be to offer coaching or mentorship. This might involve assigning an external executive coach, pairing the individual with a senior mentor within the organization, or providing access to leadership development programs. The goal is to equip the individual with the tools, skills, and insights needed to overcome their challenges. This demonstrates an investment in their success rather than an immediate move towards punishment. Remember as well that “career and professional development” remains one of the top five priorities for Gen Y Millennials and Gen Z Zoomers—the slight majority of your current workforce as of this writing in 2026 but soon to become the vast majority when Boomers fully exit the workplace around 2030.  

4. Performance Improvement Plans (PIPs) with a Developmental Focus: While PIPs have traditionally been seen as a precursor to termination, in a developmental model, they are reframed. For senior leaders, a PIP should be a robust, collaboratively developed plan that outlines specific, measurable goals, identifies resources for support (e.g., training, coaching), and establishes clear timelines for improvement. It should focus on skill development, behavioral changes, and strategic contributions. Regular check-ins and adjustments to the PIP are crucial.

5. Transparent Communication and Due Process: Transparency is vital at all stages. The executive or manager must understand the nature of the concerns, the evidence supporting those concerns, and the potential consequences. They should be given ample opportunity to present their perspective, ask questions, and contribute to the solution. A fair and unbiased process, often involving HR and senior leadership, is essential to maintaining trust and credibility. This also helps mitigate legal risks associated with unfair dismissal.

6. Support for Behavioral Change, Not Just Compliance: Punitive discipline often focuses on achieving compliance – ensuring the performance improves or a particular behavior stops. Developmental discipline aims for sustainable behavioral change, addressing the root causes. For a senior leader, this might involve helping them understand the impact of their communication style, strengthening their emotional intelligence quotient (“EQ”), or enhancing their strategic thinking capabilities. This requires a deeper engagement than simply issuing a warning.

7. Escalation with a Focus on Re-evaluation: While the process aims to be developmental, there may be instances where issues persist despite coaching and support. In such cases, escalation is necessary. However, even then, the focus should be on re-evaluating the individual's fit for the role, their alignment with organizational values, and exploring alternative pathways, rather than simply moving towards a predetermined punitive outcome. This might include reassignment, demotion to a non-managerial role, or, as a last resort, separation from the company.

Impact on Corporate Culture: Respect, Trust, and Accountability

The way a company handles discipline for its senior leaders profoundly impacts its corporate culture:

1. Fostering a Culture of Respect: When discipline is approached developmentally, it signals that the company respects its employees, even when they make mistakes. It demonstrates a belief in their potential for growth and improvement. This respect trickles down, encouraging managers to adopt similar approaches with their own teams, creating a more empathetic and supportive environment. Conversely, a punitive approach for leaders can breed fear, discourage risk-taking, and foster a culture of blame. And under no circumstances should the issuance of a “PIP” infer that termination is imminent: to do so would destroy cultural norms and significantly damage your company’s credibility in court.

2. Building Trust and Psychological Safety: Leaders who feel supported through challenges are more likely to trust their organization. This trust is crucial for psychological safety, where employees feel comfortable speaking up, admitting mistakes, and taking calculated risks without fear of severe retribution. When leaders are given opportunities to make themselves “vulnerable” (in a healthy sense) and learn and grow from their errors, it creates a precedent that encourages others to do the same, fostering innovation and creativity, open communication, and cross-organizational collaboration—again, three of the top five priorities of CEOs in survey after survey.

3. Enhancing Accountability: Paradoxically, a developmental approach can enhance accountability. When individuals are invested in their own improvement, and when the process is transparent and fair, they are more likely to take ownership of their actions and commit to change. Punitive measures, on the other hand, can sometimes lead to defensiveness and a focus on avoiding blame rather than true accountability. A developmental approach clarifies that accountability is about living up to expectations and continuously striving for improvement, not just avoiding penalties. In short, it fosters a sense of self-motivation and positive change “not because you have to but because you want to.” Yes, this stuff really does work. . .

4. Strengthening Leadership Development: Integrating discipline with professional development means that leaders are continuously growing. Issues that arise become learning opportunities, sharpening their skills and preparing them for future challenges. This continuous development pipeline strengthens the organization's overall leadership capabilities, ensuring a robust and adaptable management team. It teaches executives how to pivot and lean in rather than resist and self-justify. It removes much of the drama surrounding communication about substandard performance or inappropriate workplace conduct.

5. Modeling Desired Behaviors: Senior executives and middle managers are cultural exemplars and role models. How they're treated when performance issues arise sets a precedent for how all employees are valued. If leaders are given opportunities to learn and develop, it models a culture of continuous improvement and resilience. This also reinforces the idea that leadership is a team sport—a journey of ongoing learning, not a destination of perfection.

With all this being said, I’ll stand behind my original premises: first, that constructive confrontation and documentation are far superior to a lack of communication or avoidance (where managers “divine” from their superiors’ actions or avoidance that they’re no longer wanted); second, that leaders respond well to course correction if it’s delivered fairly and constructively, increasing the chances that accountability and self-motivation can thrive. Why? Because the evolution of progressive discipline from a purely punitive mechanism to a developmental one is a testament to the growing understanding of human capital's value in the modern corporation.

For senior executives and middle managers, this shift is particularly significant. By embracing a framework that prioritizes coaching, mentorship, clear expectations, and supportive improvement plans, organizations can transform challenging situations into opportunities for growth. This not only benefits the individuals involved, offering them a chance to recalibrate and re-engage, but also profoundly shapes the corporate culture. A developmental approach to discipline fosters an environment of respect, trust, and genuine accountability, ultimately strengthening the organization's leadership, resilience, and long-term success. In this new paradigm, discipline is no longer just about addressing problems; it's about cultivating potential and building a more robust, adaptive, and human-centric workplace.

Yet Legal Challenges Remain. . .

While a developmental approach to discipline is culturally superior, the courtroom remains a place where "magic words" and rigid procedures often dictate the outcome of a wrongful termination lawsuit.

Therefore, a purely developmental approach will not inherently satisfy the courts if it replaces formal notice of termination risk. In fact, failing to include the "magic words" about potential termination can significantly increase a company's legal exposure. What magic words, you ask?

“Failure to demonstrate immediate and sustained improvement may result in further disciplinary action, up to and including termination of employment.”

Ah, but doesn’t that absolutely kill the spirit of everything we’ve outlined above in terms of accountability and self-motivation? Yes, in many ways it does. But remember, we’re building the plane while flying it. This is a developing behavioral science, not something codified in stone--not because it's in any way inferior but because it simply hasn’t made its way thoroughly through the courts or made its mark on “case law” to a significant degree. Therefore, you have to proceed with caution—even with executives and managers who are totally career focused and engaged.

The Due Process Trap: Development vs. Notice

Plaintiff attorneys frequently argue that their clients were denied due process. In a legal context, due process in employment usually boils down to two things: Notice and Opportunity.

1. Notice: Did the employee know exactly what they were doing wrong and—critically—did they know their job was at risk?

2. Opportunity: Were they given a fair chance and a reasonable timeframe to fix it?

The danger of a "developmental-only" approach is that it can be too "soft" in its messaging. If a manager uses terms like "leadership journey," "growth opportunity," or "skill-building" without ever mentioning that the executive's employment is in jeopardy, a court may find that the employee was misled into believing they were simply in a training phase, not a disciplinary one. As such, the plaintiff attorney could argue that their client was "denied due process" because they didn't understand the consequences of their actions or that their job was in immediate jeopardy of being lost.

Those "Magic Words" and the Law

Courts generally do not require specific phrasing like "up to and including termination" as a statutory requirement, but they do look for unequivocal warning.

• Ambiguity Favors the Employee: If your policy or the specific PIP document is ambiguous, judges often interpret that ambiguity against the employer.

• The "Surprise" Factor: Courts hate "surprise" terminations. If the documentation shows months of coaching but zero warnings of dismissal, a jury is likely to view the eventual firing as "capricious" or "pretextual" (i.e., a cover-up for a different, perhaps illegal, reason, based on your ex-employee’s / plaintiff’s protected status, including age, race, or other factors).

But Aren't Senior Executives Treated Differently?

For senior executives and middle managers, the legal standard is often slightly more flexible for the employer, but the stakes are higher. Before you jump too quickly to the employment-at-will or “senior executive defense strategy,” remember two things:

First, employment-at-will exists in the courtroom, not in the workplace. Yes, you can terminate anyone “at whim” if they’re employed “at will,” but they can likewise sue you “at will,” and you won’t necessarily have any defense to fend off such a claim. Remember, employers use the “employment-at-will affirmative defense” at the hearing stage of litigation to win a “summary judgement” (i.e., immediate dismissal of a case). However, if the case “survives summary judgment” and proceeds towards the trial stage, the employer is generally expected to show “good cause” to justify the termination.

Most judges and arbitrators argue that “if it wasn’t written down, it never happened.” And voila—your company ends up getting sued on the plaintiff attorney's terms rather than your own (which would not have been the case if you had a clear documentation trail outlining the problems and missed expectations that ensued). Without documentation, most companies settle “out of court” rather than proceed to trial for fear of putting compensatory or punitive damage awards in the hands of untrained jurors. Looked at another way, without an appropriate paper trail (documentation), a company isn’t just flying blind—it's essentially walking into a courtroom unarmed.

As far as the “Senior Executive Defense Strategy,” courts often give companies more "business judgment" deference when firing a leader for "cultural fit" or "strategic misalignment." However, if that leader has an employment contract that requires "Cause," the lack of formal progressive discipline (with the "magic words") can make it nearly impossible to prove "Cause" in a breach-of-contract suit. All headaches that could have been avoided with substantiated documentation in place. . .

How to Bridge the Gap: The "Iron Hand in a Velvet Glove" Approach

You can maintain a developmental culture while protecting the company legally by integrating "Notice" into the "Development" portion of your documentation.

1. Separate "Coaching" from "Formal Discipline"

Clearly label the stages. You can have a "Developmental Coaching" phase that is purely supportive. However, if that fails, you must transition to a "Formal Performance Improvement Plan." The transition itself serves as a legal signal that the stakes have changed. The individual then understands the heightened consequences of failure to improve and the fact that their position may now be in immediate jeopardy of being lost (i.e., a core element of workplace due process).

2. The Developmental Warning

You don't have to be clinical or cold to be legally safe. You can embed the "magic words" within a respectful context:

"We are fully committed to your growth as a leader and are providing [Coach Name] to support this PIP. However, we must be clear that this is a formal process. Failure to demonstrate immediate and sustained improvement in the areas outlined will/may result in further action, which could include the end of our professional relationship."

3. Document the "Opportunity to Cure"

An "Opportunity to Cure" in employment law is a contractual provision requiring an employer to formally notify an employee of performance deficiencies or policy breaches and provide a specific, defined period to correct these issues before facing termination. It acts as a due process protection, allowing for remediation to avoid "for cause" termination or litigation. Plaintiff attorneys win when they can show the "improvement goal" was a moving target. To satisfy a court:

• Be Specific: Don't just say "improve leadership." Say "improve 360-degree feedback scores regarding 'Directness' by 20%." Outline KPIs (Key Performance Indicators), KBIs (Key Behavioral Indicators), KRAs (key result areas), OKRs (objectives and key results), C-SAT (customer satisfaction), or other criteria that directly and objectively tie the executive’s or manager’s role to the business.  

• Set Timelines: Give a clear 60 or 90-day window. Note that if you’re concerned about this window appearing to “guarantee” employment for that specific period of time, you could amend your “magic words” caveat to include, “If at any time within the following x days you fail to meet the terms outlined above, termination may result” or something similar. (It’s best to check with your HR department or qualified legal counsel when it comes to such wording, especially if you suspect the individual may be litigious.)

Summary of Legal Reality

If you abandon the "magic words" entirely, you are essentially gambling that the employee will never sue. In a wrongful termination suit, a developmental approach without clear warnings of termination looks like bad management to a judge—it suggests the company wasn't serious about the problem until the moment they decided to fire the person.

In reality, it’s likely more about the organization failing to engage in potential confrontation. I’ve always said, “The path of least resistance is avoidance,” which explains why many leaders look the other way or sweep matters under the rug when it comes to addressing substandard performance or inappropriate workplace conduct, especially with other executives. I've also advised managers and senior leaders during training workshops that avoidance of a lawsuit isn't a pure strategy unto itself. Understand that getting sued from time to time is the price of doing business in corporate America: what's important is that you get sued on your terms, not theirs. Progressive discipline creates a documented record that dissuades plaintiffs' attorneys from accepting new cases on the front end and holds the potential to eliminate or significantly mitigate damages in court on the back end. You can't get much better than that in terms of a legal ROI (return on investment), especially if it contributes to your firm's perception as a fair and objective arbiter of employee disputes or performance and conduct challenges.

Consider this revised approach to discipline a “both-and” rather than an “either-or” imperative. You can be both encouraging and supportive of a leader's turnaround while demonstrating due process with those “magic words” once the coaching escalates to a Performance Improvement Plan (PIP), which in many organizations is treated as the equivalent to a final written warning. To simply play the “good guy” and avoid the disciplinary consequence language could land your organization not only in court but settling on the courtroom steps for fear of facing a jury’s judgment in the “David versus Goliath” atmosphere of employment litigation. (And yes—your ex-employee is David in this scenario, while your company is the big bad “Goliath”—at least that’s how it will be explained to a jury.)

The evolution of progressive discipline in our post-Covid world reflects openness and transparency, accountability and self-motivation, and a focus career and professional development. Therefore, integrating discipline with professional development will never steer you wrong when working with senior-level and operational managers unless you fail to escalate matters appropriately when transitioning from the "coaching and mentoring" stage to the formal disciplinary stage. Make that distinction clear, and you'll likely cut down significantly on the number of times you'll need to move to that formal disciplinary stage in the first place.

But remember that the documentation itself is your key lever and leverage in any post-termination legal activity. Therefore, your best strategy will likely combine both: coach based on career and professional development but document to accord workplace due process and minimize legal claims for wrongful termination and (subsequent) discrimination. This winning combo can be a game changer both in terms of enhancing culture while minimizing legal exposure.

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