Cory Berg

Lesson 1: Your Relationship With Your Boss

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Your Relationship With Your Boss

Managing up is not a euphemism for politics or self-promotion. It is the deliberate practice of building a productive, trust-based relationship with the people above you - primarily your direct manager - so that your team has the support, resources, and runway it needs to succeed.

A bad relationship with your manager is not just a personal problem. It affects your team. Leaders who are disconnected from their organization above them - who do not know what leadership priorities are, who do not have visibility into upcoming changes, who have to fight for everything - cannot protect and support their teams as effectively as those who have built that trust upward.

What Your Boss Is Expecting From You

Before introducing a system for managing upward, let us be clear about your function relative to your boss. Your manager is expecting some basic things. Doing these puts you in the top 5% of your peers at any organization.

  1. Help them reach their goals. Build a real understanding of what it will take to make your boss successful - their boss's goals, the organizational priorities. The best leaders are always thinking about how their work connects to what the people above them are trying to accomplish. You would want your own team thinking the same way about you.
  2. Keep them informed at the appropriate cadence and level of detail. This requires experimentation. Different managers want different frequencies and depths of update. Be open to adjusting until you land on what works for your specific manager.
  3. Have a basic level of loyalty. This means supporting their decisions and not disparaging or contradicting them in front of the team. You can disagree privately and constructively. Doing so publicly undermines both of you.
  4. Do not be a pain to manage. If you constantly seek affirmation, display a difficult personality, or need to be spoon-fed your daily list of activities, you are adding weight and effort on your boss. Self-awareness goes a long way. Do not expect to be promoted if these patterns apply to you.
  5. Do not do anything politically stupid. In the 1992 film Glengarry Glen Ross, Al Pacino’s character, Ricky Roma, yells, "You never open your mouth till you know what the shot is." Learn to read the room and know the audience before you speak. It is entirely possible to tarnish the reputation of your boss - and your own - by saying the wrong thing at the wrong time in front of the wrong audience.

What You Need From Your Boss

The relationship works both ways. You also need things from your manager, and the healthiest relationships are the ones where both people are honest about this:

  • Clarity. Clarity on organizational priorities and how your team's work fits into them
  • Feedback. Timely feedback on your performance - both what is working and what is not
  • Support. Support when your team needs resources or when you need to escalate a blocker
  • Trust. Enough trust to make decisions within your scope without needing approval for everything

Building the Relationship

Like any relationship, the one with your manager is built through repeated, consistent behavior over time. A few things that help:

  • Be prepared. Show up prepared to your one-on-ones with your manager. Know what you need to communicate, what you need help with, and what you want their perspective on.
  • Surface wins. Do not only surface problems. Surface wins too - your own and your team's. Your manager needs to know what is working, not just what is broken.
  • Be direct. State your view, even when it differs from your manager's. Leaders who only agree are not useful to their managers - they lose the ability to provide honest input, which is part of the value they are supposed to add.
  • Understand them. Invest in understanding your manager as a person - their pressures, their goals, their style. The better you understand them, the better you can communicate in a way that lands.