10 Things I’ve learned from my bosses

I’ve been reflecting on my experience of being managed; looking back at the different bosses I worked for back when I was an employee, and what I’ve learned from them. Some lessons I apply more frequently and rigorously than others. The process of doing this has helped me reconnect with lessons I need to apply more often.

Quite a mix of lessons, some may seem to contradict one another, but taken together they’re principles that have stayed with me over the years.

Of course, there have been some ‘what NOT to’ lessons along the way too, when bosses (sometimes the same people) have inadvertently delivered a lesson in how not to go about something – but that’s for another time. For now, here are my top lessons learned from bosses.

  1. Be ruthless with time and gracious with people
  2. When we’re rushing round, always on, ‘crazy busy’, etc., etc., it can be all too easy to get those words the wrong way round. We’re being too gracious – or extravagant – with our time and that can result in us being ruthless with people. Rick always seemed to have time for people: to answer a question, offer advice, give his opinion or check in on how things were going. Yet he usually did this with a caveat, “Sure – I’ve got 5 minutes”. And 5 minutes was what you got. This focused the mind somewhat, requiring us to get to the point. And we also got the point that the guy’s time was very valuable, yet he still had time for us.

  3. How can this be better?
  4. At the other end of the time management spectrum was Ian, who was always obsessed with how things could be better or improved. Perfect was what he was after. This could be disruptive to say the least. But it made a huge difference.

  5. Explain your rules
  6. If you’re the boss, you can make life a lot easier for those who report to you if you’re crystal clear about how you like – and don’t like – things to be done on your patch. That’s exactly what Sam did on my first day of working for her. It wasn’t a lecture; it was a very simple, matter of fact explanation that set the tone for how we’d operate.

  7. Go home dammit
  8. “Why are you still here?” asked Eddie one night as he appeared unexpectedly in our team’s office. “Go home!” We started to protest: deadlines, demands, etc. We probably expected sympathy. What we got was, “If you can’t get your job done by now either you’re not doing it properly or there’s something we need to know”. Ouch.

  9. Decide
  10. We may not always agree with a boss’s decision, but I learned it was preferable to no decision at all. Rod was very decisive and when he stepped into the role he unleashed a whole new phase in our performance and results.

  11. Marshall evidence for sound decisions
  12. I once put forward an opinion in Simon’s presence and was silenced by his response: “I think you’ll find that’s not actually true” – he was probably right (as usual). He was great at giving people autonomy and letting us get on with it but very tough when it came to making decisions. Evidence had to be gathered, examined and weighed up; cause and effect assessed. “What are the facts here?”

  13. Family matters
  14. Derek had the top job, so heaps of demands on his time. But his kids’ school plays were non-negotiable. This can be a tough one: we may feel guilt, internal conflict and the disapproval of peers. It comes to down to being clear about our boundaries – with others and ourselves.

  15. Give people autonomy
  16. Robert was a great believer in letting people act on their suggestions. Got a burning issue? Give him your suggestion and he’d invariably let you get on with the job of making it real. That’s what happened when I complained about the lack of training at the company. Robert said, “Hey Dawn, you got yourself a night job”, which turned into a career I’ll always thank him for.

  17. Have fun doing it
  18. Mary was full of fun, laughter and mischief. No matter how heavy the workload and unreasonable the demands clients made on her and her team, she always seemed to be able to find some element of comedy or nonsense in it. Sure she could get tense, but she was very skilled at defusing that with a joke – often at her expense.

  19. Don’t wait for clients to call
  20. On Friday afternoons, Colin would always ask us “have you put your clients to bed?”, or “tucked ’em up for the weekend?” Now this seemed rather quaint to us junior members of the team, but the underlying sentiment is as sound now as it was back then. We learned that when we made contact with clients on a Friday afternoon, made sure they were happy with the work done that week and we were all set for the week to come, we seldom had an unhappy client to deal with on a Monday.


Dawn is the author of ‘How to be Zoomly at work’, available on Amazon.

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