Welcome to the Leadership Almanac

Gary Winters

It's All About Leadership

Creator of the Popular

Once upon a time, in an organization that was probably very much like yours, there was a guy named Dan who worked hard, day after day, month after month. He became quite good at his job and the tasks given to him, earning him an excellent performance review several years in a row. As time went on, management began to take notice of Dan, and eventually rumors began to circulate that he was being viewed as supervisory material.
One management meeting went something like this:

“Well, look at him,” one manager said. “He’s the best we’ve got in that department. It’s been a long time since we’ve had an employee that good at what he does. We should make him the supervisor!”

“Makes sense,” said another. “If he’s that good at doing what he does, imagine how good he’ll be getting other people to do it.”

After much discussion a decision was reached, and one day Dan’s boss, Suzanne, approached him about the idea of becoming a supervisor. “You should go for it,” Suzanne told him. “You’re talented, hard-working, and you’d make more money. We could always use someone with your ability and attitude to help run things around here.”

As time passed, managers continued to suggest to Dan that he consider going into supervision. Suzanne’s boss James, and even his boss, Carter, found time to encourage Dan to do it.

One day a call came from Human Resources, letting Dan know a supervisory position would be opening soon. The HR rep wanted to know: would Dan consider completing an application and being interviewed for the job?

Dan had been giving the career move some serious thought. He realized all he knew about being a supervisor came from what he’d observed working for Suzanne, whom Dan considered a “pretty good boss,” and her predecessor, Alex, whom Dan thought was a jerk.

The chance to move into supervision was compelling, if a little mysterious, and if the higher ups thought he was ready, Dan figured he should seize the opportunity.

He filled out the paperwork and sat for the interviews. Although he couldn’t be sure, he felt he’d done pretty well. But then came a few weeks of silence until he learned the position had been offered someone else. Slightly disappointed, Dan shrugged it off, returned to doing the job he did so well, and eventually put it out of his mind.

Two months later, he was caught off-guard when Suzanne called him into her office to discuss a different supervisor position that had just become available.

“I’ve got great news!” Suzanne said. “A supervisor vacancy has just surfaced in another department with which you’re pretty familiar. (It was his current department’s “customer.”) We believe you’d be simply outstanding in the position. And you did so well in your interviews, as you probably know.”

(Actually, he didn’t, but that’s another story.)

“So, let me be the first to congratulate you!” she said, as she extended her hand, giving a surprised Dan a hearty handshake. “You’ll do fine. Oh – and one more thing – you’re to start your new job a week from Monday.”

Dan returned to his cubicle full of different emotions. He was excited to have gotten the job – but anxious about it as well. Things were happening so fast. He’d have to give up his current job, of course, which he loved. He knew he’d be moving well outside his “comfort zone,” but people seemed to feel quite strongly that he’d do very well as a supervisor. One thing that was clear to Dan – it was going to be a huge change. And he’d have to be ready to go in less than two weeks.

This was going to be huge. There may no going back if it didn’t work out. Was he really ready for this? How would he know?

There is at least one thing Dan probably didn’t know. He was about to make the most significant transition in his career. He would be morphing from being an individual contributor who was responsible only for his own performance, to being a supervisor who was responsible for the performance of others. Most likely, Dan had no idea what he was getting into!


In 2011, I began delivering a workshop called S.T.A.R.T. (Supervisors Transition and Readiness Training) for people who were:

  • Considering a move into supervision
  • Being told by their organization they should consider a move into supervision
  • Newly promoted to supervisor, but not yet in the new job
  • Newly promoted to supervisor and still finding their way around

S.T.A.R.T. is unique. It’s the only pre-supervisor workshop I have found that focuses not on supervisory skill building, but on how to navigate the challenging transition from employee to boss. How to get from here to there.

S.T.A.R.T. is ideal for people who expect to be promoted to supervision within about six months, to those already promoted with fewer than six months experience on the new job. It’s been a highly successful workshop, and it now comes in two versions – one open to anyone who wants to attend, and one held in-house for a specific organization and its employees. S.T.A.R.T. is for people like Dan.

From the beginning, my book What Your Boss Never Told You was given to all S.T.A.R.T. participants as a supplement to the workbook created for the workshop.

Over time, S.T.A.R.T. has been refined and tweaked. As I worked on improvements, I began to see the need for a different companion book, which brings me to Managing Right From the Start. This book will contain all of the content of the S.T.A.R.T. program from beginning to end, except for content which would make no sense in a book, such as participant introductions.

Managing Right From the Start is being written to stand on its own. You don’t have to attend S.T.A.R.T. to have all of the content collected in one place. It will all be here. If you have the opportunity to attend a S.T.A.R.T. workshop, you’ll have additional benefits, ranging from picking the brains and hearing the experiences of fellow participants to being able to ask questions.

Whereas What Your Boss Never Told You is packed with ideas you’ll find useful once you become a supervisor or manager, Managing Right From the Start is designed specifically to help you have a successful transition from employee to boss. Think of it as a prequel. We’ll explore how to get from “individual contributor” to “boss,” ready to supervise with confidence from day one. This is a piece of professional development sadly missing in most organizations. Instead, they leave people like Dan, above, to his own devices.

Just like the S.T.A.R.T. workshop, Managing Right From the Start will have has four parts:

  1. What are you getting yourself into?
    You may be surprised, as are participants in S.T.A.R.T., that I’ll be trying my best to talk you out of taking a job in supervision. But, if you’re going to take it anyway, I want you to know exactly what you’re getting into…
  2. Getting from here to there
    You’ll learn about the difference between change (which happens to you), and transition (which happens within you). You’ll learn how people typically react to change, and why there may be some resistance to your promotion. You’ll explore how to conduct a powerful transition meeting, which can greatly accelerate your transition.
  3. Practical issues you may face (which are rarely discussed anywhere else)
    What are you going to do if you’re being asked to supervise people who are your friends and (former) peers? What if someone on the team wanted the supervisory position they gave to you? What if you’re far more (or less) technically experienced than the team? How do you get started on the right foot with your new boss?
  4. Creating a Personal Transition Action Plan
    The most successful transitions aren’t left to chance – they’re planned. Here you’ll learn a method of planning your own transition – and any others you and your team will face in the future.

Managing Right From the Start won’t be filled with academic theory. It won’t be a “textbook,” nor does it want to be. It will be an extremely practical exploration of the stuff you’ll have to tackle as you move from employee to boss. It will be as though you and I were sitting in a café, talking and sharing our experiences with one another. You won’t find any fancy talk with lots of $10 words. Supervising Right From the Start will be plain talk about the things that are going to be very important to you when you accept a promotion to supervision.

Look for Managing Right From the Start soon!

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