12 Difficult Moments I Navigated as a Manager

Businessman in the middle of a maze

Anyone who has spent any amount of time in a role managing and developing others understands the need to face up to the tough issues. How we handle these issues defines our character as a manager and our growth as a leader.

Here are some of the major hurdles, challenges, goofs, gaffes and dilemmas I’ve navigated in a few decades of managing and leading. Take the lessons to heart and learn from my experiences.

12 Difficult Moments I’ve Navigated as a Manager:

1. Admitting to my team that I was wrong. And it wasn't just a small mistake, it was a whopper! The team members respected me for my admission and rallied to save the day. It turns out, It pays to get over yourself!

2. Telling my boss he was wrong. Speaking up saved us from making a major strategic blunder. I thought he was going to fire me. He didn’t, and he eventually thanked me. There’s often a great deal of pressure to remain silent. Bad things happen if no one raises their voice.

3. Firing a friend. Hiring the friend was one of the dumbest things I ever did. It’s true: friendships typically don’t survive these incidents.

4. Saying goodbye to a team and ​job I loved. I’ve done this twice in pursuit of my own growth and development. It doesn’t get easier with repetition. I would do it all over again.

5. Standing down in a protracted battle with an internal adversary. I extended the olive branch to this character and after awhile, we ended up doing some good work together.

The whole process was humbling. I worried that I would be perceived as capitulating to this character. It turns out that I was perceived as a diplomat and peacemaker. I learned that it’s healthy to be humbled once in awhile.

6. Remaining on the side of goodness for what was truly an ethical dilemma. By avoiding the gray-zone, we gave up a big opportunity, but no one ended up in the papers or wearing prison stripes.

It’s your job to choose between right and wrong, even when the issues are fuzzy.

7. Throwing conventional wisdom out the window. Against the advice of just about everyone around me, I made a counter-offer for a rising star who had accepted an outside opportunity. She stayed and helped transform our future. Be your own person: the conventional wisdom isn't always right. 

8. Selecting and owning a controversial strategic direction for the firm. If the choice had been wrong, a lot of good people and their families would have been hurt. It was right and we prospered. However, I didn’t sleep well for two years while we were figuring it out.

9. Standing up and fighting for someone I believed in. For a variety of reasons, this individual ended up on the wrong side of some politically powerful characters in my firm. They did everything they could to bully her around and then out. Ultimately, she left, but for an opportunity, not because she had been bullied. I am glad to this day that I expended my political capital and personal energy in supporting her. It was the right thing to do.

10. Tolerating the existence of a toxic character in the organization. Initially, I didn’t have the political heft to solve the problem.

I eventually developed the political heft and fired the individual. If you're trying to build a great culture and great firm, you cannot tolerate toxic team members. It’s a good day when you get some toxicity out of your culture.

11. Admitting that I needed help to solve a problem. I’ve always been confident in my abilities to figure most situations out without too much trouble. When faced with a particularly complex challenge, I recognized the right thing to do was admit, “I don’t know,” and go get help. The help was priceless and once again, I learned that it pays to be humble on occasion.

12. Adjusting my leadership style from command and control to servant. As I let go of the dictatorial style and focused on helping others succeed the results improved, as did my love of my work. 

The Bottom-Line for Now:

There’s nothing about sleepless nights in the job description or employee handbook, however, they come free-of-charge and built-in with your job as a manager.

Some people are masters of dodging the big and sticky issues and ultimately they do more damage in their firms and to their teams than good.

The next time you come face-to-face with one of these vexing challenges, smile internally and remember that these issues are what define you as a manager and leader. And then tackle them head-on without hesitating.