Hilary. Career Milestones, Obstacles, Difficulties and Road Blocks

posted May 20th, 2011 by Janet Graham - Leave a Comment

I asked Hilary about the milestones which stand out when she looks back at her career and what she learned from them. She said: “There were a lot of milestones and I always took them.  I was never shy about celebrating myself.  There wasn’t necessarily someone around to give me a clap on the back and that really wasn’t what I required anyway.  So every once in a while you’d look up and both parents were gone and it’s like, well, I hope they’re up there, I hope they realize what’s gone down here. There were times when there were a couple of… I don’t want to call them sales awards… but citations for me as a sales person.  There were a couple of transactions when I was still at my old firm. One of the last things I ever did there was snatch away a transaction from a big US player. They claimed: ‘We have the mandate, her firm doesn’t have the mandate, all that stuff’ but I did it legitimately. It was all legit, that was the best part, they were lying their butts off.   We were not lying in anyway, that was the nicest part about it, we snatched it away from them.  The guy from the US firm called up the client, you would not believe the words.  We still laugh about it because I’m still close to the client. The fact that they called the client and used expletives that I would never use let alone to a client.  So that was kind of a cool thing.”


“Being an underdog; I’m not an automatic. I don’t have a university degree. I worked my way up.  So everything that I do is a milestone.  Every promotion, every title, the bigger the bonus, they’re all kind of milestones. They were all part of that big old journey.  There were transactions. There were things that I was able to do before others were able to do them. I got a kick out of that.  I was in a production-based job for 20 years but there was a ton of little stuff too. Having a client, a big client, request me for coverage, there was a lot of that.  So I don’t know if… there aren’t a couple because they’re all just kind of a series of these sort of great experiences but I don’t think the earth ever moved for me.  I’ve always viewed myself as a polar bear just plodding along.  You underestimate me at your own peril. I’m just plodding along and I love to be the master of low expectations.  You can take a look and, oh gee, we can find all kinds of faults here and then it’s like ‘what the hell happened here? how did this happen?’  So I like that part, I like that low profile.”


“I think that I’ve worked hard and to do as well as I did I’ve probably had to work harder than the average person. Because of obstacles or the fact that it’s Bay Street and when you don’t look the part, you don’t have the bio and all the rest of it, it’s challenging but I really never got hung up on that.  I remember not that long ago, someone asking me, during a gals’ discussion, talking about women being underpaid and how much more did I think the guys doing the same job were making. It was one of those negative exercises… how much more do you think the guys that are doing the same job as you are being paid and I’m like I don’t actually think they’re being paid more than me.  I think I’ve hammered it out or I’ve thrashed it out or I’ve proven myself and I don’t get the sense that there’s an issue for me there.  I may be as naïve as all get out but for quite a while now, not the whole time, I have had to work towards it and I moved around a little bit, but I was always getting better. Let’s say for the first 10 or 12 years, my formative years, I kept making more money, not necessarily on the same level as a senior guy but once I got to the same level as a senior guy that wasn’t an issue for me, I didn’t feel it was an issue.”


I asked Hilary, in terms of her career, what major obstacles, difficulties, road blocks she had faced and what she did when she faced one, where she turned for support and what she learned from these experiences. She said: “You know what’s shocking is I don’t know if I ever faced any road blocks.  I believe that I had the luckiest career, right place, right time, and people that liked helping me or liked seeing me do well.  I was at my first firm for 18 years and I started out as a sales assistant and when I left the guy that I was a sales assistant to said to me, you know, I think this is… he loved me, would have done anything for me… I think this is a lateral transfer for you, I’m not really sure why you’re doing this. For me, it was important because I moved from being support staff to professional staff.  After that, I had a series of jobs and I just kept asking for what I would like and sometimes I would have to be patient but I never, ever, went off in a huff or I never, ever, had to go to somebody and ask them to intervene on my behalf.  It has to be right place, right time. I didn’t start out with a career plan, I just bobbed along and went where the job took me, and along the way you wind up meeting critical people.  Some of them are mentors, others of them are, again, critical people that you meet along the way that look you in the eye and say I don’t think you’re being paid enough, you keep doing what you’re doing and I’m going to look after that side of it for you.”


“When I left my first firm I felt overlooked.  I was overlooked.  They thought I was yesterday’s news.  It’s like it was yesterday. I remember everything that went down. I talked to my sales manager and I asked him ‘are you sure that you’ve dealt with all the concerns of the sales people?’ He looked out at the group and said ‘yeah, I feel good, I think it’s going to be good.’ He hadn’t dealt with mine. He hadn’t even spoken to me. I had already been interviewing and I resigned later that day. He phoned me that night and he said, ‘Hilary, could you explain to me once again why you’re leaving.’ I told him you think I’m just fine with this mediocre set of accounts and I’m not.  We’ve talked about it and I know the recommendations that have been made and I’ve been sitting here biding my time. You can’t take clients away from guys where they’re already successful and I have had to wait. I said I’ve been waiting and now you don’t seem to view me in the same way so I’m leaving.  Each time along the way, even falling into the sales role, I didn’t want a sales job. I was mad, but it was the lesser of all evils. I wanted to be a trader but we had merged and they had one too many traders. The guy that was the head of trading thought that he’d work better with another guy. There was no question they liked me, so I had three or four areas I could go to and it was like, oh, I guess I’ll take sales and 20 years later it’s an automatic for me.  It’s kind of like if I had started running interference in my own career it would probably have been a disaster.  I just went along with it and worked hard and managed to meet great people along the way that got me.”


I asked Hilary to describe her impression of the difference between her experience and the experience of a male peer or colleague. She said: “Hmm.  I don’t know how much difference.  I guess the pressure, the whole bread-winner thing.  I think it’s funny that all the men that I know that lost their jobs are all working now and the three women that I know that lost their jobs, none of us are, and haven’t really looked.  So I think that’s got to be that bread-winner thing.  Now, not to say that I don’t want to work or any of that, but I haven’t felt that same pressure.  So maybe in the formative years as a result of my immigrant parents, I felt pressure, but really I didn’t.  So I can’t say that I was pressured terribly but I think the men… it maybe comes with a little less joy for the men or something.  It’s more perfunctory or it’s expected of them where the time that I came through sitting in a man’s chair doing a man’s job was really the best time for women.  The sky had just opened up, the opportunities that I had, that we had, compared to our mothers, there is no comparison.  So I think I had less pressure than the men because it was traditional that they were the men and they had to win the bread.  Me, it was kind of like gravy or something.  Wow, another raise.  Wow, look at that bonus.  Wow, look at that, look at that, sort of thing.”


What Strikes Me?


The pride which comes from beating a great competitor legitimately and celebrating your victory with the client years later


The importance of celebrating our successes


When you are the underdog, everything you achieve is a milestone


Underestimate me at your own peril!


What can be acheived being the master of low expectations!

Sometimes going along with things, working hard and being patient works out


It really helps when great people get you


Being in the right place at the right time can be a good substitute for a career plan


Knowing when enough is enough

Men feel the pressure of being the “bread-winner” more than women


When men lose their jobs they feel more pressure to find gainful employment than women who lose their jobs feel


Sitting in a man’s chair doing a man’s job was the best time for women


There is no comparison between the opportunities women of our generation had versus our mothers

What Strikes You?


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