Leading the Boss: 3 Questions to Ask

I’ve been thinking a lot about the problems that arise when someone has the courage to speak up to the boss. In some cases, actions speak louder than words. If you and your boss have established a trusting relationship, you can suggest and take actions that lead your boss to better outcomes.

If you don’t have a trusting relationship, then this probably isn’t a good idea. You’ll need to figure out what’s needed to create trust before anything you say or do will be well received. This is an important issue that needs to be solved before hand. Ask your coach if you’re working with one.

Let’s imagine a situation… You see a problem and there’s a clear need for action within a certain time frame. You’ve discussed the issues and possible solutions many times with your boss, yet she hasn’t acted or given you the go-ahead. What do you do?

This could be a situation in which you take the reins and lead your boss. You could develop a plan on your own, gather data (both pro and con), suggest a course of action and ask permission to move forward.

In doing so, you’re filling a leadership void through prompt decision-making and follow-through. You’re demonstrating what it takes to “manage upward,” or lead your boss.

You’ll need buy-in from people, including peers and subordinates. To accomplish this, you must rethink what you want to achieve and how you’re going to do it. In essence, you’re not acting for yourself, but for the good of the organization.

This isn’t easy and it requires initiative, persuasion, influence, and a lot of courage and persistence.

Perhaps the most crucial element is a large dose of passion. You must care deeply and want to make a difference because such efforts can carry big risks. Michael Useem, a professor at the Wharton School at the University of Pennsylvania and author of the seminal book Leading Up: Managing Your Boss So You Both Win explains:

“Leading up requires great courage and determination. We might fear how our superior will respond, we might doubt our right to lead up, but we all carry a responsibility to do what we can when it will make a difference.”

3 Questions to Ask

According to John Baldoni, author of Lead Your Boss, managers who lead up demonstrate they’re aware of the bigger picture. They’re ready, willing and able to do whatever it takes to strengthen the organization and team.

Baldoni urges you to ask three questions if you want to lead your boss:

  1. What does the leader need? The boss is responsible for motivating her people to get things right. What does she need to do her job better? To help her, you’ll need to think more strategically and act tactically.
  2. What does the team need? Teams don’t always pull together because egos get in the way. The boss ends up spending valuable time soothing hurt feelings. What if a team member were to step forward and help bring everyone together? This would free the boss to focus on bigger issues, and the team would be more productive.
  3. What can I do to help the leader and team succeed? Perhaps you can take on more responsibility or step back and let others rally. Maybe you can sacrifice a personal need that allows the team to conquer a challenge. What will it take to help everyone push ahead?

When you can answer these questions and formulate an action plan, you’ll have a road map for leading your boss in ways that make her look good and the team succeed. You’ll  emerge as a team player who is adept at making the right things happen.

What do you think about leading the boss and managing upwards? Fantasy? Too risky? Your comments welcome.

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