Career Compass No. 6: The Multi-generational Workplace

In this installment of Career Compass, Dr. Benest discusses the multi-generational workplace and how to balance generational dialogue.

Jul 28, 2009 | ARTICLE

I’m a Gen X professional working in local government. Many of my colleagues are Gen X and millennials who work for baby-boomer managers. My manager tends to micromanage, horde decision-making, talks about the need for me and others to ‘pay their dues,’ and is reluctant to consider occasional telecommuting or flex-scheduling. He doesn’t get it! How do I work with him so I can get more transparency and openness, and get him to respond to some of the values of my generation?

At the outset, you need to realize that there are a lot of managers who micromanage and emphasize experience over ability to produce results. One of the skills in becoming a seasoned professional is to adapt to the style of your boss and/or develop the ability to “manage your boss.”

To better manage your boss, you should follow Steven Covey’s advice: “seek first to understand, then to be understood.”  Or, as Eric Fromm suggests, you need to practice “positive regard” and get into the head of your manager in order to understand his values, hopes, concerns, and fears. Once you truly understand your manager’s motivations and fears, you can then better shape and frame your proposals for more flexibility and freedom.

So, how do you get into the head of your manager and then frame a proposal with some likelihood of success?

First, schedule several informal conversations with your manager in the office or over a casual lunch or coffee break. You are not only trying to better understand your boss but you want to also seek his advice on how you can better meet his expectations, advance over time in the organization, and generally develop your career. Remember—managers love to coach! Through these conversations, you want the manager to become invested in you and your career.

Second, focus on your top priority with respect to enhancing your relationship with your manager and achieving more flexibility. (The priority might be less micromanagement and greater trust in your ability to perform.)

Third, before you directly address the issue of micromanagement, you of course need to demonstrate that you are a committed, dependable staff person who produces results for the manager.

Fourth, after an important project is completed and put to bed, you can approach your manager and suggest a way you can lead future projects with more independence, such as:

“I was able to meet your expectations and successfully bring Project X across the finish line. If I am going to move up and become more valuable, I need to demonstrate that I can work without so much support and assistance. Therefore, for my upcoming Project Y, let’s test my ability to deliver without us checking on my progress every few days. Let’s schedule a meeting every two or three weeks or at key project milestones. I know your expectations, have demonstrated my successful performance on these kinds of projects, and am committed to achieve our project goals. And, if I get in trouble, I’ll certainly come to you for help. What do you think?”

Fifth, identify a small project or responsibility that no one else wants to take on and make the same pitch to your manager. Given your willingness to help the unit deal with the additional project or responsibility, your manager may be more open to providing more freedom in respect to that effort. You can then demonstrate your performance without the over-the-shoulder supervision.

Sixth, assuming that your manager will give you some more breathing room, you need to take the initiative to provide a thorough briefing at the agreed-upon intervals. And, if you encounter significant problems or obstacles, go to your manager and ask for help. That’s what managers are for.

Finally, as it becomes safer for the manager to give you more operating freedom, you can increase the time between check-ins.

In terms of trying to get permission for flex-scheduling or occasional telecommuting, I suggest the following:

  • Demonstrate that you are responsive to colleagues, especially the manager, even when you are away from the office. For example, when you take a day off or miss a day due to illness, respond to e-mails at the end of the day even if your message says that you look forward to discussing the issue on your next day in the office.

  • Ask the human resources director of your local government what the organization as a whole is doing in terms of flex-scheduling, telecommuting, and otherwise developing a better alignment between organizational practices and next generation values.

  • Use that information and share any organizational policies in a preliminary conversation with your manager about how flex-scheduling or telecommuting is being used elsewhere in the organization.

  • Shape your proposal given the values and concerns of the manager. Be sure to stress that the proposed schedule or very limited telecommuting will help you better complete yor work. For example, telecommuting will help you focus on a project at your home office with fewer interruptions.

  • Propose a limited telecommuting or flex schedule and ask to test it out on a pilot basis (e.g., one telecommuting day every two or three weeks or a 9/80 schedule for the next 3 months).

  • Meet after one or two months with your manager and evaluate accomplishments.

To create a state of readiness for these conversations, you can circulate an article on generational differences or the Cal-ICMA “Hiring 2.0” Best Practices Guide and discuss the material at a staff meeting. You can also discuss with the human resources director and your manager how flex-scheduling and limited telecommuting are no-cost benefits in a very tight budget situation. They are also ways for your organization to become “greener.” Again, you need to frame the issues in ways to gain support depending on the mind-set of those who have the authority to approve the proposals.

Added support can come from your union or employee association, leaders who can raise the issue at labor-management meetings.

In summary, to effectively get your manager to better respond to your values, you need to make it safe for the manager. Therefore, I suggest that you:

  1. Demonstrate your ability to produce results.

  2. Practice “positive regard” in respect to your manager.

  3. Shape proposals to respond to his or her values and concerns.

  4. Show in tangible ways that you are a safe bet and that any flexibility or additional freedom will pay off for the boss.

  5. Take incremental steps and evaluate success with your manager.


Career Compass is a monthly column from ICMA focused on career issues for local government professional staff, and appears in ICMA's JOB newsletter and online. Dr. Frank Benest is ICMA's senior advisor for Next Generation Initiatives and resides in Palo Alto, California. If you have a career question you would like addressed in a future Career Compass, e-mail or contact Frank directly at


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