My First Time – Do You Remember Yours?

Apr 10, 2026 | Coaching, Leadership

(My first time being managed that is!)

I read recently, and I wish I remembered where,  that the first boss/manager/supervisor you have is significantly more influential than subsequent ones. This is because the tone and way in which they manage creates expectations for you both in terms of what you expect from a manager, and also the patterns you start to internalize when you step into that role – either copying or trying to do the opposite.

My first boss would have been when I worked a Saturday job at a local pharmacy in my last two years of school – a mortifying place for a shy teenager to work, selling contraceptives and other intimate products to my peers!  I have absolutely zero memory of who was managing me though for this two year gig so I am going to assume management was pretty much non existant. Then as a teacher, management was also pretty absent – I remember being given a classroom, a schedule and pretty much then being left to my own devices. And then, my first overseas role was in a consensus-driven small nonprofit, where again management didn’t really exist.

So I’m going to count my first boss as the person I reported to when I stepped into my first paid role in Kosovo in the late 90s, just before the NATO bombing. As I remember him, he was Texan and had a dry sense of humour and was continually wearing a cowboy hat. He was both tolerant and somewhat exasperated by my complete lack of experience at anything he deemed important. Particularly as I had been brought in to run a project that was already several months behind schedule with three months left to run and he was overseeing multiple other projects in similar predicaments. However there is one piece of advice that I still remember  30 years later.

I had a habit of coming into his office and venting/vomiting all my stress and all the problems that I had faced in the day onto him. Somehow vocalizing them allowed me to feel less responsible for them. After one such occasion he paused, and said kindly but firmly, “Anna, when you tell me this as your supervisor I then have a responsibility to do something about it. It would be much better for you and your team if you were to come to me either having tried something first OR having brainstormed possible next steps that I could help you think through”.

This has stuck with me through the years both as an invitation to stepping up to take responsibility for the challenges before trying to pass them on AND for remembering that however much we like our bosses and however much the situations may lead us into informality, there is still an accountability that lies within management. And I have tried to build this in with the teams I work with as well.

I then took an inventory of the bosses I’ve had through the years, realizing that I have been incredibly fortunate having been guided and stretched and challenged to new things by pretty much all of them. This wouldn’t feel like a particularly radical statement except that when I ask at trainings I give on management,  to think back  to a positive manager individuals have experienced, I am deeply saddened when, quite often, the whole group draws a blank. How shocking is that? I am deeply grateful to those who have managed and mentored me and hoping that our current managers are unlearning and creating new standards for management that truly supports and inspires. 

I’m sharing the questions that I have been reflecting on here as an invitation to others to think about it:

  • Who was my first ‘true’ boss and how has that first relationship influenced how I manage and have allowed myself to be managed subsequently?
  • What have I learned – intentionally or not – from the managers I have had? And is there anything I would like to shift?
  • Have I ever had a nemesis at work (I have had two over my career)? What did I learn from them? If I was to have a do-over with them, what would I do differently?
  • What is my commitment to management moving forward?

 

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