Mentoring Transitioning Veterans – Story of ‘The Chicago Six-Step’

Black Diamond Charities (BDC) offers a mentoring program to complement the project management training they provide to transitioning veterans.  I have the honor of managing this program.  I recently received debrief on an especially successful mentoring engagement.

The BDC mentoring engagement consists of six sessions.  Mentors are successful senior level project managers who volunteer their time, and they need to know that they’re signing up for a time-boxed commitment.  With only six sessions, there is no time to waste, which is why capturing an effective flow is valuable.

One of my mentors, Paul Conley, came up with the flow illustrated below.

The receptiveness of the veteran mentee was critical, but this flow devised by Paul seemed effective, so I wanted to give it a name (The Chicago Six Step), and summarize it here.

In the kick-off meeting (step 1) I personally introduce the mentor and mentee, tee-up the engagement, and then get out of the way.

Paul then ‘interviewed’ the mentee using a ‘story’ approach.  By asking for the mentee to tell his or her ‘story’ information flows freely and naturally without the undue influence of specific questions that might tend to steer the conversation into false (less relevant) directions.  Paul brought sticky notes and asked the mentee to jot down key points surfaced during the storytelling (aka ‘interview’).  The mentor is looking to flush-out items in the quadrants of the SWOT framework throughout the interview, but keeps this focus largely to him or herself.


This first interview is about much more than just a SWOT analysis though — all sorts of history and thinking patterns are being explored as well.  At the end of the session the mentor assigns homework to be performed by the mentee prior to the next session.  That first homework assignment (step 2a) is to categorize and prioritize the various key items that were flushed-out during the story-telling ‘interview’.


In the second meeting session (step 2b) those key items from the SWOT analysis are discussed further, along with their categorizations and prioritization.  At the end of the session the next homework assignment is given (step 3a).  Typically the goal of the mentee will be to improve their civilian career profile.  Hence the assignment to search through job listing and find some that are appealing.  Job listings could be internal to the mentee’s current organization, or external.  The purpose is to explore ambitions, not to suggest or prompt a job change.


In the third session (step 3b) the selected job listings are discussed and a gap analysis is performed together, to identify areas where the mentee needs to do some development in order to strategically position him or herself to have a better shot at obtaining those jobs.

At the end of this session, the homework assignment (step 4a) is for the mentee to diligently map their time usage for a week.


In the fourth session (step 4b), the time usage patterns are reviewed, and any needed adjustments are discussed.  In Paul’s recent engagement, this led to a huge ‘ah ha’ moment for the mentee.  Often there is a large disparity between our ambitions and the quality time we set aside to work on advancing those ambitions -- hence the value of this step.  This completes the discovery phase of the engagement.  The homework assignment (step 5a) is for the mentee to draft a project plan to achieve some particular achievable near-term ‘win’. 


In the fifth session (step 5b) the plan and goal are reviewed and discussed.  The homework assignment in preparation for the last session (step 6a) is for the mentee to design the agenda for that final session, so as to best support the mentee’s efforts to achieve the ‘win’. 


In the sixth session (step 6b) the mentor and mentee plan together to position the mentee as effectively as possible to achieve the near-term ‘win’.  With this ‘win’ (whatever it is), we have begun a cycle of accomplishment that will hopefully continue over time, and about which we will hopefully hear many glorious updates through the various BDC social media channels.