Why Middle Managers Struggle—And How to Set Them Up for Success

Navigating the Shift to Senior Management [11:35]

As managers move up, their role becomes less visible and harder for others to understand.
Employees often question what higher-level managers actually do.
Senior managers should communicate openly with broader teams about strategic goals and challenges.
Explaining how different teams contribute to larger initiatives builds understanding and respect.
Vulnerability and honesty in communication are key to maintaining credibility and trust.

Moving Beyond Generational Stereotypes [14:00]

Treat employees as individuals, not based on generational stereotypes.
People have different communication preferences (email, phone, text, etc.) and feedback needs.
Age does not determine technological ability; people from all generations can struggle or excel with tech.
Work preferences vary; some prefer working from home, others thrive in an office setting.
The key is to understand each person’s unique needs and adjust management accordingly.
Generational stereotypes are limiting and undermine effective management and relationships.

Importance of Cross-Functional Relationships [17:53]

Cross-functional relationships are critical for building influence and credibility.
People often get labeled as underperformers because they aren’t well-known within the organization.
Managers should proactively build connections across departments, even if the culture doesn’t fully support cross-functional work.
Asking genuine, curious questions about others’ roles can help build meaningful relationships.
These relationships can provide support during tough times, like layoffs or performance reviews.
Personal connections make it harder for negative perceptions to form about colleagues or teams.

Navigating Return to Office Orders [22:31]

The push for return-to-office orders is often a reaction to deeper issues, not the solution.
Problems like long meetings and poor communication existed both remotely and in-office.
Businesses facing struggles may revert to old habits, like in-office work, but this doesn’t address underlying issues.
Leaders should focus on results and work quality, not where or how the work is done.
Effective managers track performance and outcomes, not the physical presence or actions of employees.
Return-to-office policies may mask poor management practices and won’t necessarily improve performance.
Chris helped redesign Microsoft’s compensation system for 33,000 employees.
The challenge in compensation systems is ensuring the right outcomes are monitored, not just the expected ones.
In sales, commission-based systems can lead to undesirable behavior, like selling unwanted products or rushing orders to meet targets.
Compensation systems often encourage employees to game the system, so objectives must be clear and aligned with business goals.
It’s important to avoid superficial metrics like “mouse movers” or “key twiddles” that only make employees appear busy without driving real results.

Interview Highlights