Leading Up

How to lead your boss and be a boss who wants to be led.

It’s hard to believe but, bosses are people too! They are human and they can make mistakes. For the sake of this article I’m talking about good bosses. People who genuinely care about their organization and the people who work for and with them. Not bosses who are incompetent or unethical. (Check out George Reed’s book Tarnished: Toxic Leadership in the U.S. Military for those kind of bosses).

Every Boss Needs Somebody

Even good bosses will not have the right information or aren’t seeing it from someone else’s perspective. They may be tempted, for one reason or another, to make a questionable decision or miss an amazing opportunity.

This is where you have the opportunity to lead your boss! Think of yourself as your boss’s mole. You are their eyes and ears, their boots on the ground. The person who can provide them with a different perspective and insight they don’t have or simply can’t have because of their title and responsibilities.

I’m going to even take this to the next level. I believe it is your ethical obligation – to your boss, your organization, and yourself – to walk into your boss’s office, close the door and tell them when they are about to make a huge mistake or are going down a path that could lead to a major collision.

By leading your boss, you not only have a great opportunity to make an impact on your organization, you can make yourself a great asset to your boss and team. This takes courage from both sides!

Be a Boss Who Wants to Be Led

We have this cultural belief that when you have been appointed as a boss and a leader you must be the smartest person around. You are all knowing. You are always five steps ahead of everyone. That’s a lot of pressure, even for the smartest and most confident leaders!

During my career I have been part of many great organizations, and a few that could have used a little help. Those that are successful and doing great things are led by bosses who are willing to listen and be led.

How do they do it?

First, they surround themselves with smart people. You don’t want to let yourself be led by someone who could possible walk you right off a cliff!

Second, they have built a climate of strong relationships and a sense of trust with their team. The people who work for these bosses know that the boss has their back and will go to bat for them.

Lastly, these bosses welcome new ideas and ask for honest feedback from their team. This doesn’t mean they follow every idea or are pushovers. In the end they are the leader and they have the final say. But they have earned respect from their team by allowing them to be heard.

Be Brave to Lead the Boss….and Let Yourself Be Led

The idea of leading the boss and being a boss who wants to be led is not a given. It doesn’t come naturally or easily to most employees or bosses.

Employees may be afraid they are offending their boss or questioning their intelligence.

Bosses may think that creating a culture in which they seek out input makes them look weak and uninformed.

To break this stalemate both sides must be brave and find the courage to take the first step.

As an employee you must get to know your bosses comfort zone. What are his/her values? Where have they come from? Does your boss appear supported or lonely? Is he/she genuinely secure? What appears to be their failures, fears, or aspirations?

It is your goal to stay within this comfort zone and then work to expand it, slowly but surely.

Knowing HOW to present problems to your boss is critical. Don’t waltz into their office, drop a problem on their desk and walk out, wishing them good luck as you close the door. Leading your boss means you come with problems AND possible solutions. This will help you gain their trust and be in influencer in your organization. In other words, a leader!

As the boss you must create opportunities for people to share their ideas, thoughts and recommendations. Be curious about their personal and professional goals and do what you can to support them. Have a 5-minute brainstorming session at the beginning of every meeting and the only rule is that all ideas are welcome and respected. Hold post mortem meetings on activities, projects or events to discuss what went well and what could use improvement.


How have you led the boss during your career? Or, how have you created a culture where you allow yourself to be led? Share your stories with us!