Gary Winters

Coach  Workshop Facilitator Author

An Open Letter From a Soon-to-Retire Employee

open-letter_1What follows is an open letter written by Craig Bronzan, the Director of Parks and Recreation for the City of Brentwood, California. He’s someone who has made public his plans to retire within the next few years. I asked him to write a letter to describe what he would want any boss of a soon-to-retire employee to understand about people in this position. The letter will be included in my forthcoming book, Managing the Soon-To-Retire Employee, which will be published soon. I did not coach Craig on what to say in his letter nor had he seen a draft of the book beforehand.  I think it’s powerful stuff. 


Dear Boss:

“What are you looking at?”

Remember that phrase we used to use when we were kids? That’s how I am feeling right now; ever since I announced my retirement date. It seems like either you want to talk to me about something but you are avoiding me, or maybe you no longer know what to do with me. As I sit here writing this letter I want you to know that while it’s true that things have changed; I haven’t left. Not yet.

I understand that I have a new classification: I’m a “sooner” – someone who’s made it public that I’m going to retire within the next few years. Yes I know I am very close to leaving this job, this desk, and this place that has grown so familiar to me. It is where I do what I do. Or should I say used to do? The world and my job, my outlook on life, and to be blunt – my life has changed so much. Not because I have announced my date; but, surprisingly, telling others the date has made me reflect on a lot of things.

I used to think my work life was the predictable part of my life. Well, not anymore. As I look back to the place I began, I wonder “how did I get to this place in my life?” When did the amount of sand in the bottom of the hour glass get larger that what is left on top?

I don’t think it matters how much you prepare for the day that you say “let the countdown begin.” Until you get there you aren’t prepared. I do not care any less these days, I just care differently. Gone are the days of my youth where outside work activities included sports, games, raising a family, weekends, and the feeling that the good times would never end. In the beginning I worked to live. And it was fun! Then one day, responsibility started to catch up with a growing family, ageing parents, fractured external family relationships, and bills, bills, and more bills. Work also become more important as I looked for growth opportunities to do more, learn more, and move up the ladder of success.  It was hectic but I managed. In fact, I believe I excelled.

As I got older and worked longer, the responsibilities didn’t stop; they seemed to become more complicated. Rising health care costs, sending kids to college, being involved in end-of-life decisions for parents created more in-depth considerations. And the responsibilities in my job increased as more was expected of me, budgets got cut, mergers happened, and the predictability of my work changed – faster and faster. I was asked to think outside of the box, do more with less, and would start hearing more often from upper management that decisions had been made in my best interest. Funny, I don’t remember being asked what my interests were.

So now you’re trying to figure out how to work with me as you wonder if I can still add value to the organization. The short answer is “yes I can.” However, before you concentrate on the details of the work you need me to perform, you need to understand what this “sooner” is going through.

I am nearly 60 years old. My body has aches and pains it didn’t have when I was younger.  My yearly physicals seem to find something new about being old each year. I don’t seem to remember things as well as I once did and my patience seems to be a little thinner. The cost of college, co-pays, prescription drugs, and life in general keeps going higher – much faster than the returns on my retirement savings. Yes, my personal life has changed a lot.  It has a carryover effect on my work life.

However, I bring years of experience, skills, and abilities that only time develops. I have been a leader, a mentor, a coach, a dedicated and loyal employee who is now trying to figure out what I will do when I leave this job and the answers to questions that now preoccupy my thoughts. Did I plan well enough for retirement? Are my kids able to make it on their own?  Will I really get a second half of life out of this old body? Decisions about what I was going to do for fun this weekend are being replaced with decisions about what the future holds for the second part of my life.

You ask: can I still add value to the job? As I said before, yes I can. Although the day I walk out of here for the last time is coming quickly, I want to be valued to the very end and add value to what I do. If you want me to add value through the last day, consider these ideas:

  • Ask me what I want to work on. I have always done better when I feel what I do is important. I know what I do best and providing me an opportunity to do that will help us both.
  • Ask me what still needs to be completed before I leave. I have been at this for a long time and I know what still needs my fingerprints before it is passed to someone else.  I know someone else will follow me and with your support, I would like to help pass the torch of what I have been working on to the next person.
  • As me what I am going to do after I leave here. It is nice to know that the person you work for has an interest in what you do outside of work. Making me feel like you care about my next adventure would be greatly appreciated.
  • Ask me for my thoughts on where the organization needs to go. I have been here a long time and have a good understanding of the strengths of the organization. Rarely are employees asked about their thoughts on the future – we usually have to adjust to changes that many times we don’t understand.
  • Say “thank you’”. As I have said, I have been here a long time, mostly because I am passionate about what I do.  I want to make a difference and be appreciated for my efforts. Saying ‘thank you” doesn’t cost anything and if it is sincere, really does add joy to people’s lives.

I appreciate the opportunity to let you know what I think.  If nothing else, maybe a part of me will live on through this letter in addition to the work I have and will do before I leave.



Craig Bronzan

“What ELSE Your Boss Never Told You” is the sequel to the very popular “What Your Boss Never Told You.” Packed inside are more tips, techniques, and insights about the challenging, but rewarding leadership position.

“What ELSE Your Boss Never Told You” is written in a conversational tone, as though you and the author were enjoying a cup of coffee and talking about the issues that emerge for new leaders. It stands alone, and/or could be read before or after the first volume, “What Your Boss Never Told You.” You can start with any chapter and read in any order you like.

if you search for a book on management, you’ll find a staggering 600,000+ books currently available. How can you narrow that down? “What Your Boss Never Told You” is the best place to start.

No textbook here – this book is short and sweet. It’s designed to help you “unpack” your new job and be effective from the first day with your new team. It contains twenty-one chapters filled with the wisdom Winters has gathered from real managers – effective, successful leaders in organizations much like yours.

Leaders make decisions every day – big and small. Most know that if they include others in the decision-making process, the quality of those decisions – and the commitment to them – will likely improve. That said, they also know it’s impractical, if not impossible, to include others in every decision they confront.

“To Do or Not To Do” tackles the question of when to make decisions on your own, and when to involve your team. It gives you a deceptively simple but proven method to determine, when you are facing a difficult decision, how to decide how to decide.

Far too many meetings are dreadful, mind-numbing, energy-draining, productivity-sapping, colossal wastes of time. As someone once said, “To kill time, a meeting is the perfect weapon.”

Here’s the deal: if you’re willing to learn and apply the techniques in “So, How Was Your Meeting?”, you’ll call fewer meetings, while vastly improving the ones you do lead. They’ll take less time, have more balanced participation, produce better decisions, and result in concrete action items for follow-up afterwards.

While there are thousands of books written for people about to retire, this may be the only book for people who manage soon-to-retire employees. Written in a casual, conversational style, “Managing the Soon To Retire Employee” will give you everything you need to know to move forward with confidence and grace.

You can be successful with Sooners. It won’t happen by chance, and it’s not a matter of pulling some management “trick” out of your hat. But you can learn how to do it, and you can apply what you’ve learned right away.

Managing friends or former peers can be awkward. When you become the boss, everything about these relationships can suddenly be uncomfortable. There’s a new set of ground rules to establish – as manager, you are going be accountable for the work performance of friends or former co-workers on the team, and they are going to have to adjust to the fact that they now report to you. Everyone involved can feel awkward and hesitant about the future. 

Have you been approached by management with an offer to promote you to supervision? Or, are you mulling over the possibility for the future? Find yourself not sure whether to accept the promotion?

If so, you’ve come to the right place. Help! They Want to Make ME a Supervisor will help you sort out a very big question: Should you accept the offer to become a supervisor? Once you’ve read this book, you’ll be confident that you’ve made the best decision for you and for your organization.