One of the first things I ask when starting a new mentoring relationship with a transitioning service member is, "What is it you're looking for out of our time together?"

It's one of my favorite questions to ask because really, the sky is the limit. As a mentor, am I helping to fill a gap? Or are we starting from scratch and putting together a full game plan to get from Point A to Point B? Maybe you already have a job, but you want to change your strategy to take your career to the next level. Whatever the need, your mentor can help you develop and implement the tools to get you where you want to go on your journey.

Some veterans know exactly what they want out of the relationship. For others, knowing what to expect and what to ask of a mentor is somewhat foreign. After all, the mentor is a stranger to you. So, what should you ask a total stranger?

When you begin working with a new mentor or advisor, the rules of engagement should be discussed upfront and openly. This includes understanding that, while your mentor/advisor will support you in helping you to meet and achieve your career goals, they will not actually find you a job. To that end, however, this relationship is primarily for you and about you, so don’t be afraid to ask for the information you need to know in order to be comfortable working together.

First, Get To Know One Another…

• Talk about what led you to join the military and what was rewarding about your military experience.

This is an opportunity for the mentor to learn who you are, and what is important to you, as well as get a sense of what some of your goals might be based on what you enjoyed doing in the military (i.e. you were responsible for logistics in the military and would really love to continue that in your civilian career.) Share as much as you feel comfortable doing so, but enough that your mentor can get a sense of who you are what you hope to, or would like to achieve/gain through the mentoring experience.

• Ask how your mentor got into mentoring, and whether or not they have a military background.

This is a great way to learn about your mentor, who they are, what's important to them, and why they do what they do. Look for commonalities - mutual love of dogs, marathon running, hunting, etc. to further the conversation.

If they don’t have a military background, decide if this is important to you in order to work together. While there is an upside to your mentor having a military background (they can walk the walk with you and you can talk with them about their own transition from the military to the civilian sector), there are also numerous benefits to working with a civilian mentor.

Civilian mentors can give you a much different perspective that’s equally as valuable, and may also include their “lessons learned” that they can pass on to you. If they’re hiring managers, they can also provide feedback on your “30 Second Elevator Speech”, resume, interviewing skills; as well as what corporate America looks for in a candidate during the either a phone and in-person interview. They can also help you work on your interviewing skills because they've sat in on numerous candidate interviews themselves and know exactly what types of questions will be asked.

Let the conversation flow naturally, but don't be afraid to ask the questions that are important to you in order for you to feel comfortable in working with this person.

Discussing and Setting Expectations…

• Identify and discuss your short-term and long-term goals.

This is an opportunity to give voice to where see your future (think 3, 5, 10 years ahead), and talk about what steps you think will be needed to get there. For example, if you want to be a Project Manager, do the companies or fields you want to work in require a PMP certification or is it optional? If you eventually want to be a Vice President in a specific field, what is the career path necessary to get there and does your skill set match that particular field? Your mentor will be able to help you flush out these answers, as well as different career paths for consideration based on your background, skill set, education, etc., and also help you determine how long it may take to hit that particular goal.

• Discuss how long you want this relationship to last (i.e., 6 months, 9 months, 12 months, etc.)

What you want to achieve and what you’re looking for in this relationship will determine, to a large extent, how long this relationship will last. In the “getting to know you” phase, you and your mentor should talk about how long you want/need to work together, and how to best achieve your short term goal(s) during that time.

You’ll want to consider if you want to work with your mentor throughout your journey, until you hit your short-term goal, or, if you just want your mentor along to help you build the foundation of your path. While you don’t need to decide right away, you should have a good idea of how long you want to have a mentoring relationship. This should be an ongoing conversation depending on how your search/transition is going and what types of challenges you may be encountering.

If the mentoring relationship is through a formal program (i.e., eMentor Program, ACP) these programs can last anywhere from 9 – 12 months. However, once they are formally terminated, you can either request that the relationship be extended or, you can ask your mentor to work with you informally outside of the program if the relationship is working well.

I want to make this point clear: There are no hard and fast rules which say that once the “formal” mentorship is over that the relationship has to end. Although many of my “formal” relationships have ended, I still continue to work with almost all of the men and women outside of the the formal mentoring programs to some degree. Again don't be afraid to ask to continue to work together if the relationship is working well and you still need some support/guidance, or just a sounding board.

• How will you connect with one another?

Will this be in person, via phone, email or Skype/FaceTime? Who will call or contact whom? This may seem like a no-brainer, but if you're both expecting a phone call and neither calls the other, you've just missed your meeting. Don’t assume anything. Make sure all of your communications are clear.

Also talk about how frequently and by what means you’ll communicate in between your formal meetings. Will you speak weekly? Will you speak every couple of weeks or monthly, but email in between? If you have questions, can you text your mentor or do they prefer phone calls or email? Make sure your mentor knows what to expect of you, as well. Do you prefer email only, or are you a texter? If it takes you a while to respond, make sure your mentor knows upfront that it may take you a couple of days to respond based on your current schedule but that it’s not personal and you will reply.

• What should the focus of your second meeting be?

After your first meeting, you should have the beginnings of a plan to take forward to begin your journey. There’s a very good chance that this will involve some homework. I’m a big fan of giving it, myself. After each call, you should expect to end up with a “To Do” list. (I usually have my own list as well). If you’re not sure what to expect for your next call/meeting, ask, “What should I have prepared or completed for our next meeting?”

During your next call/meeting, this is where you’ll begin to further discuss the steps needed to achieve your short-term goal(s). You’ll want to develop an action plan and begin setting some deadlines for your agreed upon milestones (i.e., develop a list of companies you’re interested in by the next meeting; researching roles within those companies, update your resume, develop a first draft of your LinkedIn profile by the end of the month).

• What you hope to gain from your mentorship. Know this can and may change as your relationship evolves and progresses.

Your relationship will grow and evolve the longer the two of you work together, especially if there’s good chemistry and you click with one another. When I first start working with someone, I try to be clear on what my communication style is like and what they can expect of me, (i.e. the time we spend together is theirs to focus on whatever they like; to bring to our meetings a list of questions/issues they want to work on, in addition to the items that I’ve identified for us to work on during our sessions, and above all else, I will try to make our time together as fun as possible.) And while it will be hard work, it should also be fun.

The sign of a good relationship is where you feel motivated, supported, respected, and encouraged. You see the fruits of your labor and you feel your mentor understands what you need in order for you to reach your goals. Over time, the relationship may become a partnership, and hopefully turns into a friendship. Consider what type of dynamic is comfortable for you and what you want this relationship to develop into over the course of your time together.

• Be clear on how will confidential information be handled.

Throughout the mentoring relationship, confidential information will be shared either by you and/or your mentor. You both will need to determine to what extent you want to share personal information about yourselves with one another. This is something that will occur over time once trust is developed and established, but it’s important to discuss how it will be handled. Confidential or personal information could be family-related, health issues, financial issues, etc. Be clear on your expectations for keeping your discussions confidential and between the two of you. This is something I discuss upfront when starting a relationship – anything shared between the two of us stays between us unless otherwise approved to share. I won’t even share your resume unless you give me specific approval to do so. The level of trust (on both sides) has to be there or else the relationship won’t work.

• What if the relationship doesn’t work?

If you don’t feel the relationship is a good fit, don’t be afraid to tell your mentor that while you appreciate their time, you don’t feel like this is a good fit. If it's noticeably obvious, your mentor might also bring it to your attention as well.

If you and your mentor do part ways prematurely, don’t be put off from seeking out another mentor if you don't already have a team of them.

Sometimes there may be a great personality fit but their background may not mesh with the goals you want to achieve. Or, maybe their personality is too different from yours and the communication is awkward. Whatever the difference(s), if it happens, no harm, no foul. Agree to part ways and be prepared to jump back into the pool with another mentor.

Taking the time to get to know your mentor and allowing them the opportunity to get to know you makes all the difference in developing the mentoring relationship. Setting and understanding expectations early on by the both of you during this process will also help you to determine if this is the right person to assist and support you with helping you to meet and achieve your goals, as well as set the tone for the relationship in the long term.