00:01:26.390 – 00:01:49.750
White Collar Advice: Something we speak about at length—probably to the point where you want to pass out—is understanding the perspective of stakeholders: judges, prosecutors, case managers, probation officers. Chris has seen it from the other side.
Chris, let’s have an interactive discussion today. I’ll chime in, and if people have questions, they can put them in the chat along the right side.
00:02:03.470 – 00:02:07.809
White Collar Advice: What is the overarching role of the probation officer?
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Chris Maloney: Sure. Well, the overarching role is to be the eyes and ears of the court—you’ve probably heard that before.
00:02:15.731 – 00:02:20.699
Chris Maloney: The case falls under the jurisdiction of the judge, but the judge doesn’t have the time or ability to look into every case individually. So they rely on the probation officer to be those eyes and ears and funnel information to the court as certain judicial decisions have to be made.
00:02:20.750 – 00:02:42.709
Chris Maloney: This role doesn’t change much between Federal or State courts. It’s about gathering and verifying information that judges, and sometimes prosecutors, need to decide sentencing, whether conditions of release should change, or how supervision should be structured.
Probation Interviews and Reports
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White Collar Advice: Can you talk about the importance of the probation interview that leads to the probation report, and how someone can prepare properly for that report?
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Chris Maloney: Absolutely. As the defendant, the probation interview is your chance to communicate to the probation officer who you are—beyond the offense and your criminal history. Judges want to know before sentencing who this individual is.
00:03:27.470 – 00:03:43.740
Chris Maloney: They want to understand more than just the facts of the case or criminal history. They want to know, “Who is this individual? What struggles have they had? What issues may have influenced their decisions, such as mental health, substance abuse, or financial stress?”
00:03:43.800 – 00:03:50.530
Chris Maloney: The more information you provide to the probation officer to help paint a picture for the judge, the better. This helps the judge bring the human side into sentencing.
Why Preparation is Essential For The Probation Interview
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White Collar Advice: Why do you think, in your experience, that some lawyers dismiss the value of preparing properly for the probation report? Some will say there’s nothing to prepare for, that it’s just a five-minute interview, and that defendants shouldn’t stress about it. Can you touch on that, please?
00:04:49.950 – 00:05:05.700
Chris Maloney: Sure. Well, if you think back 10 or 15 years ago, guidelines controlled everything, at least in the Federal system. Unfortunately, it was very rigid. Sentences were driven by offense levels and criminal history, leaving little room for flexibility or individual circumstances.
00:05:24.100 – 00:05:52.459
Chris Maloney: Since the Federal guidelines became advisory, there’s now more room for the judge to consider human elements and go outside the calculated guideline range. But this flexibility means preparation is even more critical. Judges want to see thoughtful efforts from defendants and verified details about who they are.
Influencing Probation Officers Through Preparation
00:06:10.670 – 00:06:28.030
White Collar Advice: Let’s talk about influencing the probation officer, either at the interview, before, or just after. Our team talks about creating assets with the appropriate message to influence the probation report. What sort of assets do you suggest, or what types of messaging should a defendant convey to the probation officer?
00:06:46.370 – 00:07:02.980
Chris Maloney: Well, if you think back to the reasons you’re at sentencing, the court wants to understand why the crime occurred. Sometimes it’s financial motivations, but other times it could stem from substance abuse, mental health struggles, or family issues. Those are the things you want to bring up with the probation officer, along with supporting evidence.
00:07:02.980 – 00:07:25.749
Chris Maloney: For example, if substance abuse contributed to the offense, providing evidence of attending AA or similar programs allows the officer to verify that information. They can follow up by speaking to family members, clinicians, or even employers to confirm your efforts.
00:07:25.750 – 00:07:47.410
Chris Maloney: Without documentation or supporting testimony, claims can appear hollow. The probation officer’s role is to independently verify what you present to them. You can’t just tell a story—you need to provide them with the tools to validate that story and communicate it effectively in their report to the court.
Discussion Prompt:
- What steps have you taken to document and verify your efforts at rehabilitation, restitution, or personal growth?
Handling Trial Convictions and Victim Plans
00:08:06.290 – 00:09:17.990
White Collar Advice: Some people in our community have been convicted at trial, and their lawyers advised them not to provide anything to the probation officer for fear it could jeopardize an appeal. Is it possible to still provide information to the officer without affecting an appeal?
Chris Maloney: Yes, absolutely. I’ve worked with many people convicted at trial who went on to influence their sentencing despite concerns about appeal. You don’t have to address the offense directly. Instead, focus on personal struggles or the steps you’re taking to address issues, like attending therapy or working to make victims whole.
White Collar Advice: If there are victims, wouldn’t you agree that addressing restitution is critical? Some people focus too much on their own imploding life, but shouldn’t restitution and victim-focused plans take priority?
Chris Maloney:
Yes, 100%. If victims were created as a result of your actions, making plans to address restitution and demonstrating empathy for the harm caused should be a priority. Judges often look for evidence of sincere efforts to make victims whole.
Overcoming a Bad Probation Report
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White Collar Advice: Let’s say someone had a poor probation interview, and their report doesn’t reflect their efforts. What can they do to overcome this before sentencing?
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Chris Maloney: First, it’s important to know that a single bad interview doesn’t define your case. There’s typically ongoing dialogue with the probation officer, so defendants can follow up to clarify or provide additional information. You can even submit letters or evidence later to correct any gaps.
00:11:33.400 – 00:12:33.259
Chris Maloney: It’s also possible to challenge parts of the report through your attorney. After the probation report is drafted, defendants have an opportunity to file objections. These objections allow you to address inaccuracies or clarify anything that was misrepresented. The judge ultimately reviews these objections, so it’s a vital step to ensure your voice is heard.
Discussion Prompt:
- If your probation report contains errors or omissions, what steps will you take to clarify or correct them?
Preparing for Long Sentencing Gaps
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White Collar Advice: Due to COVID and other delays, some cases have seen sentencing hearings scheduled years after the probation interview. Should someone request a new probation report if years have passed?
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Chris Maloney: Yes, absolutely. If a significant amount of time has passed, the probation officer should update the report. You don’t want outdated or incomplete information going before the judge.
00:15:29.410 – 00:15:46.089
Chris Maloney: Ideally, the officer will proactively seek updated information, but it’s perfectly appropriate for the defendant to request an updated interview or provide additional documentation showing progress made since the initial report.
Importance of Record Building
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White Collar Advice: While in prison, how can people continue building a record to influence their probation officer and improve their supervised release terms?
Chris Maloney:
Actions during incarceration matter. If, for example, someone cited substance abuse issues at sentencing but didn’t address them in prison, probation officers and judges may question their sincerity. Participating in educational programs, earning certifications, or attending therapy demonstrates accountability.
Building a Record During Incarceration
00:18:18.530 – 00:19:13.370
White Collar Advice: Let’s say someone is in prison for three years. How can they use that time to create a positive record that probation officers will look at favorably when they start supervised release?
Chris Maloney:
Anything mentioned at sentencing as a mitigating factor—whether it’s substance abuse, lack of education, or employment struggles—should be addressed while incarcerated. If someone argued for leniency due to addiction, but there’s no record of participating in treatment or self-improvement programs, probation officers will notice.
Completing programs shows that you’ve made an effort to address the root causes of your crime. It’s not enough to claim improvement—you need documented evidence of your efforts, such as certificates of completion or reports from counselors.
Supervised Release: First Steps
00:18:27.380 – 00:18:51.950
White Collar Advice: When someone comes home and begins supervised release, the probation officer will look at their probation report. How important is that report, even years after sentencing?
Chris Maloney:
The probation report serves as the starting point for the officer assigned to supervise you. It contains details about your criminal history, personal background, and sentencing factors, so it shapes their initial understanding of you.
If the report is thorough and shows a clear plan for rehabilitation, it gives the officer confidence that you’re serious about reintegrating into society. If it’s vague or missing critical details, it can lead to stricter supervision.
00:19:11.600 – 00:19:29.560
Chris Maloney: For example, if the report mentions ongoing struggles like addiction, but you didn’t address those issues during incarceration, the officer may assume you’re not prepared for success. On the flip side, a well-documented record of progress sets the tone for more flexible supervision.
Halfway House to Home Confinement
00:24:00.920 – 00:24:11.559
White Collar Advice: Some people turn down halfway house placement because they’d rather stay in the camp. Is that a mistake?
Chris Maloney:
Turning down halfway house time is not advisable. Halfway houses are a transitional step meant to help people adjust to life outside prison. It’s an opportunity to secure employment, arrange housing, and demonstrate stability before fully reentering the community.
00:24:11.650 – 00:24:33.869
Chris Maloney: Declining halfway house placement can also be seen as rejecting a program. This may make it harder to build trust with probation officers or case managers, who may view the decision as a lack of effort to reintegrate. Even if the halfway house has challenges, such as geographical inconvenience, it’s worth taking advantage of this resource.
Travel Restrictions on Supervised Release
00:37:27.660 – 00:37:32.160
White Collar Advice: Are you allowed to travel while on probation? What are the requirements, and does it matter if restitution is still owed?
Chris Maloney:
Travel during supervised release is possible but requires approval. Domestic travel must be approved by your probation officer, while international travel requires approval from the judge.
00:37:32.300 – 00:38:11.880
Chris Maloney: Officers evaluate travel requests based on factors such as compliance with restitution payments, stable employment, and adherence to other conditions. If you’re behind on restitution or struggling with compliance, it’s unlikely travel will be approved. Conversely, if you’ve consistently met all conditions, officers are more likely to approve reasonable requests, such as work trips or family vacations.
Common Probation Violations
00:55:32.810 – 00:55:46.089
White Collar Advice: What are some common probation violations that could get someone sent back to the halfway house or even prison?
Chris Maloney:
One of the most frequent violations is moving without permission. Even something as simple as changing your address within the same city requires approval. Moving without notifying your probation officer is a serious violation that can result in being sent back to the halfway house or to prison.
00:55:46.410 – 00:56:03.889
Chris Maloney: Other common violations include failing to attend scheduled meetings, traveling outside the judicial district without approval, and not complying with court-ordered programs. Each of these violations, even if minor, damages trust with your probation officer.
Ending Supervised Release Early
00:41:49.230 – 00:41:57.149
White Collar Advice: What’s the process for getting off supervised release early?
Chris Maloney:
The most effective way is to demonstrate consistent compliance with all conditions and show that supervision is no longer necessary. Probation officers can advocate for early termination by recommending it to the judge, which carries significant weight. Alternatively, your attorney can file a petition for early termination, but the judge will still consult with your probation officer for their opinion.
00:41:57.870 – 00:42:05.760
Chris Maloney: The best-case scenario is for the probation officer to proactively recommend early termination based on your demonstrated accountability and progress.
Final Reflections
Chris Maloney emphasized that success during probation and supervised release requires preparation, consistency, and clear communication. By staying proactive and addressing issues early, individuals can create opportunities for reduced supervision and smoother reentry into society.
Discussion Prompt:
- What steps are you taking today to ensure long-term success on probation or supervised release?
Justin Paperny
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