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Understanding and Engaging 'Millennials

Baby Boomers often complain that Millennials don't want to fit into the system, aren't dedicated to the organization, and "all expect a trophy." Millennials often see Baby Boomers as wedded to systems and processes that work for Baby Boomers but are stifling to Millennials. Here's how to get along.


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From the perspective of the generation that’s somewhat undefined ‘ Generation X (birth dates between the mid 1960s and early 1980s) ‘ we see and understand Baby Boomers (birth dates between 1946 and mid-1960s) and Millennials (birth dates between mid-1980s and early 2000s) both of which are better defined, and the sharp contrast between them. Baby Boomers often complain that Millennials don’t want to fit into the system, aren’t dedicated to the organization, and “all expect a trophy.” Millennials often see Baby Boomers as wedded to systems and processes that work for Baby Boomers but are stifling to Millennials.


Baby Boomers’ views were shaped by the fact that they’ve always had to, and still expect to, compete to succeed because there are so many of them due to the post World War II baby boom. To them, there have to be winners and losers. Their schools were over-crowded because of the baby boom, thus, competition coexisted with the need to fit into the system and share. To succeed, Baby Boomers had to stand out from the crowd and that is their lens: You win by being both “competitive and ambitious.”

Many Millennials grew up with Baby Boomer parents they barely saw because the parents were working hard to stand out. These same Baby Boomer parents raised Millennials to “get a trophy for showing up,” to be a team member. And, in college, Millennials’ sense of team was reinforced by constant team projects and consequent team grading. Baby Boomers somehow forget that the Millennial team had to win for there to be any individual trophies.

Let’s not forget that many Millennials had difficulty finding their first job. Hence the Millennial focus on a “better way” to work, structure life to enjoy it, and to succeed by their own definition as well as the desire for flexibility to accommodate that “better way.” The Millennial lens is a unique combination of “self-interest and teamwork.”

And therein lies the rub. Baby Boomers expect Millennial associates to fit into the system and to be ambitious, to compete to stand out. They had to. But, Millennials don’t always buy into “the system” and instead push for a “better way.” Rather than compete against each other as individuals, Millennials compete with each other so that the team wins. All this leads some Baby Boomers to view Millennials as disinterested in working hard, narcissistic, or entitled.

In the Law Firm

Baby Boomers disparage the “everyone gets a trophy” mentality as overly entitled rather than seeing it for what it is: an asset to be leveraged. How many times have you wished your partners would share and work together to cross-sell and develop business?

And some of the disconnect between Baby Boomers and Millennials comes from hard-wired differences in problem-solving and work style (e.g., differences in Myers-Briggs Type or DISC profiles). People often mistake differences in style ‘ whether generational or hardwiring ‘ for lack of ability, focus, or commitment because we believe that a work style that is “serious, focused, and committed to the organization” looks a certain way, our way, of course. And this is the root of the tension: The Baby Boomer “way” is about fitting into the system, which is exactly what Millennials don’t trust and believe is largely broken. Are you starting to see how these antagonistic views of how to achieve success frustrate everyone?

Given the differences in perspective on work styles, I challenge you to accept that in evaluating others: 1) your lens affects your views; and 2) you inadvertently dismiss Millennials whose work style clashes with your view of appropriateness. What to do? Use a tool for engaging Millennials so that instead of complaining, you are raving about how smart, dedicated, and creative they are.


Coaching is that tool. Coaching is the simple process wherein the coach ‘ you ‘ asks insightful open-ended questions to elicit another’s best thinking and engagement on a particular issue. Consider this: You pay associates quite a bit, don’t you want to get your money’s worth?

Coaching engages associates by fostering better understanding of the legal and business issues, forcing them to think creatively and to develop their legal skills and judgment.

The model on page 3 depicts the five steps of problem-solving process. What makes it coaching is that you use insightful, open-ended questions at each step. In practice, the lawyer-coach uses coaching skills like a surgeon with a scalpel, and in combination with a directive approach.

There are five steps of the coaching model.

In Step 1, Establish the Focus, you will most likely use a directive approach. In Steps 2 through 5, you will most likely use coaching questions to elicit the associate’s best thinking to resolve legal and business issues. For example, when giving feedback, your goal is to do so in a manner that is truly constructive, supports learning, and results in the associate getting the job done. Consider the difference in these two versions of a feedback conversation between Terry, a senior partner and Jamie, a third-year associate.

Terry: “Jamie, the memo on the regulatory and business risks of XYZ Corp’s acquisition is lacking in the depth. You’re missing several crucial nuances. My comments are noted in the margin. Get it back to me by Friday at noon; we’ve got a call that afternoon and I need you to get it done!”

Jamie: “Will do!” Thinking, but not saying: “If you had been clearer in what you were asking me to do, the memo would have been more complete. Even now, you’re telling me I’m missing crucial nuances, but not telling me what they are and I doubt you explained them in your comments. I know I’ll have questions. It’s not like you’re easy to reach between client calls.”

Does this sound familiar? Was Terry effective?

Now consider using coaching skills to help Jamie understand and think through the issues.

Terry: Jamie, the memo on the regulatory and business risks of XYZ Corp’s acquisition needs some work. I’d like to talk through the issues and make sure you understand the client’s goals and the business deal. I need you to understand my expectations so that you can succeed.” Note: Terry uses a directive approach to Step 1: Establish the Focus.

Jamie: “Great. Thank you.”

Terry: “Let’s start with your understanding of the client’s goals and the business deal. I’d like to hear, in your words, what is your understanding?” Note: Terry uses open-ended questions to elicit Jamie’s understanding of the transaction before sharing more information. Also note the more collaborative tone and language. Remember, Millennials want to be part of the team.

Jamie explains: “My understanding is that the client wants to make the acquisition to have sole access to its proprietary technology.”

Terry says, “Correct. So tell me, as a general matter, what regulatory issues might arise with such an acquisition?”


You get the picture. If you want engaged and invested associates, you must engage and invest in associates. Not only will you foster higher-quality work product in a shorter period of time, but you’ll develop a generation of lawyers worthy of running the firm some day.


Anne E. Collier, MPP, JD, is a professional certified coach with the executive coaching firm Arudia in Washington, DC. E-mail:

The views expressed in the article are those of the authors and not necessarily the views of their clients or other attorneys in their firm.

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