20 Professional Discussions Millennials Should Have With Their Mentors (Part 1)

Written with A. Crosser
What is the culture of your organization?
What’s more important to you corporate values, mission or vision?
If you could start your company all over again, what would you have done differently?

Were three of the thoughtfully selected questions asked by a bright young woman named Tong from The Washington Center internship program today as she ponders her career path.

The Millennial generation (born 1980 - 2000) is coming of age, and many of today’s young adults are finding themselves in their first real positions as professionals or on the cusp of starting families. As they graduate college and find jobs in their field, many younger Millennials are looking to their mentors to help guide them through this turning point in their professional lives and help them navigate the somewhat turbulent seas of the workplace.

Millennials face many struggles which are unique to their generation. They have different ambitions, and treat their professional lives differently than those who came before them. They also have Glassdoor.com, Linkedin and many tools that we didn’t have on our quest to rise through the ranks.

PURPOSE OVER PAYCHECK: According to a Deloitte study , 64 percent of Millennials say their personal values have the greatest impact on their decision-making process, and 56 percent of Millennials globally have decided against ever working for a company based on their values and standard of conduct. A second Deloitte study shows that a whopping 87 percent of Millennials believe a company’s success should be determined by more than their financial performance - namely, they believe employee satisfaction should be taken into consideration. This is a major shift in perspective, as many older professionals haven’t placed as much of a premium on where they work or at times the ethics of their company - many only see their job as a way to put food on the table for their family.

What do these statistics mean for newer members of our workforce? Simply put, they indicate lack of guidance in for today’s upcoming professionals, as they live (and drive) a new reality which older generations might not relate to in the same way. They may look at their father who worked in an unethical factory for 20 years of his life, and find no support when they say they don’t want to work there out from a moral standpoint. They might feel some skepticism toward the Baby Boomer professor who has publicly apologized in classrooms for their generation leaving the future with trillions in debt. Millennial women globally face a particularly difficult personal battle, as their mothers and other women in their family may encourage them to marry and have a family instead of pursuing a career. In 1970, only 11 percent of women with college degrees were employed by the labor force — a number which has risen to over 30 percent (in the United States) Women (with and without college degrees today make up almost 50% of the overall workforce in the US.

These statistics indicate a particular need for Millennials — the need for guidance and mentorship. We’re taking a look at the first 10 or 20 professional discussions millennials should have with their mentors in order to get the most out of their mentoring ‘sessions’. By having the discussions listed below, the next generation of young professionals can set themselves on course for great success in their fields. The answers to the questions below will help guide them in the right direction, helping them achieve their professional goals and make a difference in the world. Additionally, we encourage mentors to come up with sets of questions as well. We can all learn from each other and clear the cobwebs that often block us from seeing.

1. “What do you wish you knew at my stage?”

As we grow and develop new knowledge, we begin to find answers to questions we had during our youth. Had we known these answers earlier in our careers, we may have made smarter or more informed decisions than those we ended up making. One of the best ways to share our accumulated knowledge is with young professionals entering our field, as we can guide them as we wish someone had guided us. If you’re a professional Millennial looking for guidance, ask your mentor what they wish they knew at your age or what they wished a mentor had told them - chances are, you’ll find very useful information that could change the course of your career.

2. “What were your failures, and how did you learn from them?”

In the same boat as the discussion above, discussing past failure is an excellent way to learn what to avoid, and which paths to take. Part of making mistakes is learning lessons, and lessons should be passed on to others to help them avoid the same mistakes. As was said by Henry Ford ‘Failure is the chance to begin again more intelligently.’ and ‘Failure is neither fatal nor final.’ Here you could have a great conversation on resiliency.

3. “What would you do differently, if you could start over?”

As successful as your mentor may be, there are probably some scenarios they would do differently if they could go back in time. Ask them about situations which they believe they could have handled more efficiently, or decisions they wish they had or hadn’t made. These answers can help you avoid setbacks to your success, and make wiser decisions in the long-run.

4. “What do you struggle with?”

Everyone struggles with something, no matter who they are, their age or where they came from. After years of practice, your mentor still struggles with some aspect of their career. Take many professional women in the MENA (Middle East and North Africa) region, for example. While more than half of all University students in the Middle East and North African region are women, they make up only 21 percent of the workforce - largely due to societal demands. Many professional women struggle with raising a family and working in a career (particularly in STEM fields), despite how successful they may appear to others. These women could use their struggles to guide other young women enduring much of the same, to show them that societal demands can be overcome.

5. “What would you do in my shoes?”

When you’re faced with difficult decisions, the best question you can ask is “what would you do if you were me?” It can be difficult to objectively analyze your situation and come up with the right “next move,” and asking someone who’s faced similar decisions what they would do in your shoes can help you understand what you might consider doing next. Another way to ask this question is “Have you been in a similar situation and how did you handle it?’ We have so much to learn from each other’s stories.

6. “Describe your most rewarding accomplishment.”

Success has different meanings to different people. In our youth, success looks like fancy cars, Instagram worthy lifestyle and red carpets, but as we age it often takes on a new look. By asking mentors what they believe is their most rewarding accomplishment, you can get an idea of what they value as a result of their experience. You can get a picture of what your long-time goals might evolve into - in fact, your mentor’s answers will more than likely surprise, as they don’t often answer this question with the answers we think we’ll hear.

7. “What am I doing wrong?”

Everyone wants to be right, but in reality we’re all wrong more often than we’d like to believe. Many times, fixing one or two small aspects of our perspectives, actions, and motives can mean a world of difference for our future. However, it’s challenging to evaluate ourselves as we have a natural tendency to believe we’re always right. Your mentor’s experience will allow them to objectively look at you and tell you what you can do better - for many, this invaluable advice can mean the difference between success and failure. Another way to rephrase this question is to explain a challenging situation and ask “What am I not seeing here about my role?” Reshma Saujani really pushes in her outstanding TED Talk that we encourage girls to be brave not perfect.

8. “How can I become more productive at work?”

Even the most intelligent of people can fall victim to laziness or burnout. Some of the greatest ideas of all time may have been lost as the result of low-productivity, but even with this knowledge many of us struggle to discipline ourselves and make our dreams a reality. Your mentor has likely struggled with many of the same issues, so ask them to weigh in. It’s like being on a road trip and realizing you are out of gas or are dealing with a flat tire. Most professionals have their own set of productivity tips, so see what kind of advice your mentor has to offer to recharge your batteries. Also, please share with your old-timer (just kidding) some of the technology tools and more that make you more productive. We are big fans of reverse mentoring @Twomentor.

9. “When you were my age, what were your goals? How have they changed?”

Over time, our goals change. We begin to prioritize certain aspects of our life over others, as we trade all night parties for families and fast food for gluten-free. What once seemed valuable and important can become meaningless overnight, but the striking change can cause fear and anxiety for many as it occurs. Many times, we’re afraid to let ourselves change for the better, as we fear that we may be leaving an important part of ourselves behind. By better understanding how your mentor’s goals have changed, you might become more comfortable as you face similar changes in your own life.

10. “What traits do I need to succeed in this field?”

Every field has secrets to success - many of which you’ll never learn in a classroom. Medical professionals must be patient and empathetic, while engineers must have laser-sharp focus and an uncanny attention to detail. Artists and entrepreneurs must be both fearless and creative, while athletes must have perseverance. Your mentor can tell you exactly which traits create leaders in your field, and how you can develop them with ‘eye of the tiger’ conviction.