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Courtney Hills – an Alberta woman charged with stealing $950,000 from her employer – is one of Lee Chapelle’s clients. (Matt Gallagher)

For more than 20 years, Lee Chapelle drifted in and out of federal prisons, convicted of property-related offenses such as B&Es, auto theft and possessing a firearm. During the 1980s and 90s he became a regular fixture in prisons across the country.

“I was an idiot,” he now says. “Every time I came out, I’d reoffend.”

But once he realized there was a “considerable hole” in services provided to people charged or convicted of criminal offences, his life took a new direction.

Unlike for most ex-convicts, time spent in jail is not a liability in his new profession; in fact, it’s an asset. Chappelle does prison consulting. His expertise helps those charged with or convicted of crimes cope with the adversity of going through the justice system or to prison. It’s a highly specialized job in Canada – he is the only one doing it, he says.

In 2010, he founded Canadian Prison Consulting Inc., located in Toronto. “When I work with my clients, I really promote ownership, accountability, insight, remorse and it’s a long-term view,” he says. “I think the only way to beat the system is, first and foremost, not to be the victim, understand what brought you there and make sure you don’t go back.”

Chapelle recently made an appearance in How to Prepare for Prison, a documentary that takes a hard look at the lives of three individuals charged with crimes ranging from fraud to assault by strangulation. But rather than centre on the felonies, it focuses on the emotional turbulence the accused and their families face as they travel through the criminal justice system.

One of the film’s central characters, Courtney Hills – an Alberta woman charged with stealing $950,000 from her employer – is one of Chapelle’s clients. Chapelle is her confidante, the proverbial beacon of hope.

The accused are vulnerable, human. Anxiety ripples through characters and their families as the looming threat of prison casts a long shadow on their daily lives.

“My documentary was never about guilt or innocence,” director Matt Gallagher says. “It was always about what happens to people when they become ensnared in the legal system. There’s a world of pain that happens even before they get to court.”

Chapelle joined The Globe for a Q and A.

Lee Chapelle helps Courtney Hills navigate the criminal justice system in the documentary film How to Prepare for Prison. (Matt Gallagher)

Can you explain the nature of your work?

I do everything in my power to really clearly give [my clients] solid visual insight into what’s in store: what to expect, to remove all the unknowns, to give them a little bit of savvy beyond their years, if they’ve never been in before, to not stand out as someone who doesn’t know – or as they call it in the system, “the fish.” All the forms that are applicable on a daily basis in an inmate’s life, I provide them upfront and I explain how they’re used, how they’re able to do things, like make phone calls, have visits approved, how to apply for parole, a proactive foundation and how to do time as productively as possible.

Inmate etiquette and dynamics is covered a lot because there’s fear. Every jail and every prison follows a beat of a different drum, so what I do is groom people to essentially present as though they have a hell of a lot more experience than they do.

Courtney’s thought is that when she gets in, she’s going to ask for solitary confinement because she’s scared of potential violence. That’s often what I’m contending with and I cover a lot of ground on how to not be victimized and not sign up for solitary the moment they walk in.

She’s a big white girl and she, through her own homework, discerned that there was a high native population and she was concerned that maybe that would be hurtful to her. For her, questions were like, “How does it work, who am I going to be in a cell with, am I going to be in a cell alone and what are the daily routines?”

I really encourage the clients and their families to understand they will get through this, that they could come out the other side and be better. This could be the catalyst to a lot of good things.

You spent almost 21 years in prison yourself. Do you consider yourself to be living proof of the potential for change after prison?

I think my own personal history is a very clear inspiration in its own right because I made it through and I’m doing well today. It’s doable.

The film says your line of work is a “cottage industry.” What’s the scale of prison consulting in Canada? What about in the United States?

My understanding is that I’m the only one in Canada doing it. I would say we’re large scale. In the U.S. it’s been an industry for probably the past 20 years. There are firms down there that are really flourishing.

What’s it like supporting people who are about to enter prison?

For me, it’s very gratifying. You form really strong bonds. It’s an intimate relationship you form, with not just the person, but their families. There are people who are in very adverse circumstances. Something I stick to is not losing sight of what brought them to where they are and working towards that not happening again, but ultimately reinforcing that they’ll make it through this. I become the go-to person when prison is drawing nearer and nearer.

The film reveals that Ms. Hills has lost a lot: her house, career and fiancé. Are you still in touch with her? How is she doing?

I am. Since this occurred she took a job as a barista at Starbucks [while she waits for her sentence to begin]. She manages the floor in Calgary. But she’s terrified. She’s having a tough time right now. The longer this hangs over you, the more difficult. Not to say she’s a victim. This girl comes from a good background and I have no doubt in my mind she won’t put herself in a situation like this again with the price she’s paid thus far.

Do you think anything needs to change within the prison system?

Community corrections [when offenders serve time outside a prison and are supervised by a parole officer], I think, is maybe a direction that we can head in for people who aren’t a danger to public safety. It’s a lower cost to Canadians.

People like Courtney aren’t violent. I think we’ve lost sight of the public safety part. For predators and violent offenders, we certainly need consequences and prisons for that.

What did you think of the film?

I cried a few times. I found it very moving. I recalled moments with Courtney and it brought on an emotional reaction within me. It was well done. I think it was a really fair depiction of what it’s like to go through something like that and how difficult it is to be facing years of uncertainty. They captured it really well: What families go through, the collateral costs that most people don’t realize.

This interview has been condensed and edited.

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