Leading from the Middle: Managing Up, Down and Sideways

There’s a lack of trust in senior management, according to a survey by the human-resource firm Watson Wyatt:

  • Only 49 percent of employees have trust and confidence in their senior managers.
  • Just 55 percent say senior leaders behave consistently with core values.
  • Only 53 percent believe senior management has made the right changes to stay competitive.

Clearly, much is going wrong in the workplace, which presents middle managers with unprecedented opportunities to step forward and offer course corrections.


You see a problem. 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, and she has agreed with your way of thinking. For unexplained reasons, she hasn’t acted or given you the go-ahead. What do you do?

This could be a situation in which you take action and lead your boss. You 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. But you’ll soon discover that you need buy-in from more people, including peers and subordinates. You’ll have to become a leader without authority—an ambassador sans portfolio.


Those who succeed at leading from the middle are artful, skilled managers who:

  • Establish goals
  • Plan projects
  • Organize people
  • Execute projects on time and on budget

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.

According to John Baldoni, author of Lead Your Boss, managers who lead up demonstrate they’re aware of the bigger picture. He urges readers to ask themselves:

  1. What does the leader need? The boss is responsible for motivating people to get things right. What does she need to do her job better?
  2. What does the team need? Teams don’t always pull together because egos get in the way. What if you stepped forward and helped bring everyone together?
  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.


To lead up, you must:

  • Establish trust by following through on your commitments; be impeccable with your word; do what you say you’ll do.
  • Connect with others authentically and honestly.
  • Get out of the spotlight; share the credit with others.
  • Demonstrate that you can think and act for the boss by taking initiative and following through.
  • Use common sense; think before you act; listen to others.
  • Do what’s practical to help the organization achieve its goals.

You will also need to think and act strategically:

  • Challenge the status quo and conventionality.
  • Reframe opportunities.
  • Get out of your box and out of your cubicle.
  • Turn information into knowledge.
  • Deal with ambiguity and uncertainty.


Taking initiative requires assertiveness, confidence and decisiveness. But too much assertiveness (i.e., aggressiveness) drives people away, discourages collaboration and causes people to resist your influence.

Baldoni urges managers to practice “reflective assertiveness,” a quiet confidence and power. It emerges from experiences, including one’s trials and triumphs. You must:

  1. Listen first, showing that you value others’ ideas.
  2. Keep it low. People know where power lies. You don’t need to advertise it.
  3. Act decisively.


Those who resist your ideas will undoubtedly outnumber your supporters at first, but persistence pays off. Begin by challenging “the way we’ve always done it.”

At the same time, you may find it uncomfortable to challenge those in authority. It’s a natural feeling. The trick is to challenge assumptions, not the individuals in positions of power. Focus on ideas, not personalities.


Not all bosses want to be led. Some fear their authority will be undermined. Others are so insecure that leadership from below is a threat that must be stamped out at all cost.

These obstacles shouldn’t prevent you from trying to lead your boss, when appropriate. Observe the following guidelines:

  • Stick with the facts. Build your arguments with evidence. Make sure your research is on point.
  • Ask others to challenge your premise. Before presenting your ideas to your boss, find people who can play devil’s advocate and explore your assumptions.
  • Don’t confuse causation with correlation. Just because there’s a link between two issues doesn’t mean one provoked the other.


In some cases, all of the best data in the world won’t convince your boss that you’re right. If he’s a jerk, he’s probably insecure. He acts tough because he’s afraid of losing his job and control over others.

Jerk bosses cannot be reasoned with, so don’t even try. You can roll over, fight back or leave. Choose wisely.


Ultimately, what really matters is how we recover when things don’t go our way. Resilience gives you the strength you need when faced with rejection.


  • What happened?
  • What could I have done better?
  • What did I learn?

The resilience to bounce back from a raw deal distinguishes those who succeed from those who become stuck, bitter and angry. Remain focused on goals and engaged in the process of fulfilling them.