Becoming a Best Boss

May 3, 2021 David Witt

Ann Phillips, a senior consulting partner with The Ken Blanchard Companies, loves conducting a Best Boss/Worst Boss exercise as a part of the SLII® leadership development program she facilitates. This fun activity not only allows participants to share stories of their experiences with great leaders, it gives Ann a chance to reminisce as well. She especially loves sharing stories about her first best boss, Jerry Nutter.

“Jerry Nutter was my first best boss,” says Phillips. “I was part of a young, inexperienced staff Jerry had working for him at the YMCA where I was a program director. He was great at giving each of us what we needed to be successful.

“Jerry was really clear with us about setting goals and performance standards. It was a collaborative process. When we needed help he would actually help us, show us how, let us try, redirect us if we were off track, and praise us along the way. He was also great at leading us to discovery when we had ideas but weren’t exactly sure what to do. And what I really loved about Jerry’s leadership was if he could see that we knew what we were doing, he would leave us alone.”

Phillips says when participants describe their best bosses, the stories may be different, the words may not be exactly the same, but similar attributes come up time and again.

“People typically describe their best boss as someone who always had their best interests at heart, set them up to win, and was caring, motivating, and empowering.”

Phillips says there is one more characteristic people ascribe to their best boss. She dips back into her own story as an example.

“Jerry, my first best boss, also challenged me. He would put me in positions that I didn’t believe I was quite ready for.”

One project Phillips recalls was a stretch project that would ultimately launch her into a career as a consultant, facilitator, trainer, and keynote speaker.

“Early in my career with the YMCA, I supervised our after-school programs. We operated a fleet of vehicles that transported children from school to the YMCA, and drivers required certification training—training that I had to learn to facilitate. I created the training design, flip charts, activities, and post-training follow up. I had some transferrable skills, but no real experience with this kind of task. Eventually, I did all this stuff that previously hadn’t been on my radar at all. Jerry knew I could handle it and was there to support me every step of the way. I watched him do presentations, we talked about desired outcomes, and we did everything together for my first presentation.

“And you know what? People liked what I did. I remember people coming out of my first session saying, ‘I never thought transportation training could be fun.’ And a light bulb went on for me. I can still remember thinking, ‘I can do this.’”

Asking for Help

“As a beginner, I got a lot of help and direction from Jerry—and I think that is missing in today’s work environment,” says Phillips. “I don’t think bosses are prepared to help people at the level they need, and I don’t think people feel safe asking for help. They’re afraid they may be seen as unskilled or needy. I’ve had that experience myself.

“I remember working on a project for another employer and asking for direction on a certain task. When I didn’t get it, I persisted. As a result, I was perceived as a problem child who wasn’t willing to figure things out on my own. Instead of being seen as a troublemaker, I should have been seen simply as someone who was trying something new and needed support and clear direction.”

Don’t Be Afraid to Provide Direction When Needed

Phillips encourages leaders to provide their people with direction and support, especially if they are new to a task.

“In every SLII® leadership development session I say, ‘Remember, direction feels supportive if direction is what a person needs—and a lack of direction can feel like abandonment.’

In Phillips’s experience, leaders often are overly concerned about micromanagement but not at all worried about under-supervising.

“Some leaders think it’s fine to assign someone a task they’ve never done before and then just say, ‘Is the assignment clear? Holler if you need help.’”

“That’s part of both the Directing and Delegating styles from our SLII® program—but what’s most needed in today’s work environment are Coaching and Supporting, the other two styles.

“A lack of support creates a downward spiral of ineffectiveness. It’s self perpetuating and people work like crazy to compensate for it. Because they don’t know any better, and the organizational culture accepts it, people who grow up in organizations like this end up treating others the same way they’ve been treated. It becomes a weird rite of passage or survival test to see if you can make it on your own.

“I understand individuals have to take accountability for their own growth, and challenges provide opportunities to develop resilience, grit, and hardiness. But when you feel neglected by your boss, it takes a toll on you. People get burned out, they feel set up to fail, and they feel lost. You should see the stuff that comes out when we ask people if they have ever been under-supervised and what the consequences were.”

The Role of L&D

Leadership, learning, and talent development professionals have a role to play in interrupting this self-perpetuating cycle, says Phillips.

“First, recognize it. I love how WD-40 Company approaches performance issues. When a leader asks to put an employee on a PIP (Performance Improvement Plan), the first questions the HR associate asks are ‘What leadership style have you been using with them? Are their goals clear? Are you working collaboratively with them to diagnose what they need from you? Are you changing your leadership based on what they need?’

“Second, model the better behavior. See performance as a partnership. Engage in frequent, high quality conversations at work. Ask for what you need. Encourage others to do the same.

“In today’s changeable work environment, we are all learning and relearning new tasks constantly. Don’t go it alone. Don’t ask others to go it alone. We need each other to succeed.”


Would you like to learn more about helping people perform at their best? Watch our on-demand webinar!

Becoming a Best Boss—the 3 Secrets of Great Leaders

All of us have experienced great bosses in our lives—people who challenged us, provided growth opportunities, and brought out the best in us. In this webinar, Blanchard senior consulting partner Ann Phillips shares three characteristics all great leaders have in common. Participants will learn how to:

  • Set motivating goals that are growth oriented and that promote accountability
  • Demonstrate caring by taking the time to accurately assess development levels
  • Serve team members by applying the right mix of directive and supportive behaviors

Don’t miss this opportunity to learn how to help leaders in your company develop the skills to create an environment where people find exceptional meaning in their work, achieve high performance faster, and, ultimately, will remember your organization as a great place to work.

Watch On-demand

About the Author

David  Witt

David Witt is a Program Director for Blanchard®. He is an award-winning researcher and host of the companies’ monthly webinar series. David has also authored or coauthored articles in Fast Company, Human Resource Development Review, Chief Learning Officer and US Business Review.

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