C4S1: Orientation Before Orientation

You’ve offered the job. Your Mentee has accepted. Now what? At this point, your Mentee will likely be in prison for another 1-2 months before being released, however there is still plenty to do to help ensure the transition from incarceration to employment is as smooth and streamlined as possible. Think of this part of the process as orientation before orientation.

Not-So-Standard Procedure?

For traditional hires, job orientation is usually done in-person and online. In most cases, the process of covering company policies and benefits and filling out paperwork is a familiar, standard procedure. It’s important to remember that for your Mentee—soon to be employee—this may not be the case.

Depending on the length of their sentence and/or previous work experiences, many of our TRP Fellows may be unfamiliar with parts or the entirety of a typical job orientation. They may not know they need to have a driver’s license or Social Security number with them on their first day. In fact, they may have to get those forms of identification altogether upon their release. They may not know about tax withholding. They may not know how to pick a health plan, retirement plan, or what equipment or uniforms your company provides or doesn’t. They may not have a computer to complete potential online portions. This 1-2 month period, prior to their release, is an excellent time to discuss topics like these and start realistically framing what those first weeks of employment will look like for both parties.

Update Your Team

In addition to preparing your Mentee, we recommend using this point in the process to check in and update your other employees on the progress you’ve been making as well as the estimated timeline for your new employee’s arrival. As we shared in Chapter 1, having your leadership team and other employees feel included and excited about this addition can be a gamechanger for creating a positive and successful transition.

Plans, Arrangements, and Communication

As you’re working on orientation before orientation with your Mentee, we will be helping them make the necessary plans and arrangements for things like IDs, housing, transportation, and other essential needs upon reentry. Additionally, we’ll help you coordinate their “first day of work” logistics (e.g. where, when, needs etc.).

Effective orientation before orientation largely comes down to proactive, open, and consistent communication. The more all parties involved in this employment transition communicate through it and know what to expect, the better it will go. When in doubt, err on the side of over communicating plans with your Mentee, with TRP, and your team.


Chapter FourEthan Cook