What is the 'secret' to advancement?

Anonymous

October 19,2020 at 11:29PM UTC

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I have been at my current company for almost two years as a Contracts attorney, with the title Manager of Contracts. I earned my JD and passed the bar in 2010, and knocked around a few years as a Contracts Administrator, doing some litigation as a freelance, and served three years as Contracts Manager for a software company. I’m also a nontraditional attorney, in that I earned by JD when I was 40. I give this perspective as background to what I’m struggling with now.

Ultimately I’d like to be promoted given the circumstances in our department, but feel like I’m either (1 being overlooked; or 2) not being given honest feedback from my supervisor on what skills I am lacking to advance; or 3) I have the skills, just not confident enough or ‘attorney-like’ enough to command respect.

When I started, I was on a team of three attorneys, along my supervisor (also an attorney). The other two attorneys had been there longer, and were at a Director level. I was fine with my position as the greenest on the team. But since then, we’ve lost both of those team members, and we tried to hire one who was then fired for mysterious circumstances. Needless to say, my supervisor is never forthcoming about anything going on in our department. I’ve relied on rumors to understand the reasons behind this turnover. Honestly, the first firing made me nervous, since I was hoping I wasn’t going to make the same mistakes, whatever they were.

So after a year and a half, I became the ‘senior’ person on our team with enough experience now that I felt I could move up to a Director role, which was open given the recent turnover. I’m not presumptuous to think I can just jump into this role – I already do the very same work as a Director, meeting with various levels of our company’s management team, and with our customers to negotiate complex agreements. I also do a bit of my own administrative work to manage the contracts coming in, but it’s never been a job requirement. I do it because it needs to be done to organize our insane workload. This is usually the job of our administrators, but the one assigned to me is so new she is struggling as well.

My question has to do with how can I advance beyond this ‘manager’ role to the Director role – and am I my own enemy? When the second attorney left, I asked my supervisor my chances of advancement to that role and his response was so vague I don’t even think I can explain – something like “promotions are only in July” (it was March 2020) and “there’s a lot to learn here” to “I think you’re doing a fine job”. He’s not totally a bad ‘boss’ – even giving me an award for ‘making a difference’ which was a monetary boost as well.

So now our team is complete – two young male attorneys with less ‘company’ experience who are Directors and me as a ‘manager of contracts’. I also just found out that the other attorney, hired just in February, actually interviewed our newest hire, but I only met him on his first day. This made me so angry I am now writing this post.

What am I doing wrong – lots of education, years of corporate experience, but not enough confidence, skills, ‘ladder climbing savvy’, what is it? I like the money I’m earning but afraid every day that I’m not measuring up so will never advance or, at worst, my supervisor will make an excuse to let me go since I am ‘older’ and certainly not as ‘attorney-like’ as my new coworkers.

Struggling to push up that ceiling...

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AnonymousOctober 19,2020 at 11:53PM UTC
Hi,
Thank for you sharing this - it does sound frustrating.
It seems like you might be suffering from impostor syndrome, which most of us struggle with at some point. You've listed all the ways you are different from the pack (with a somewhat negative framing), but not the ways that you fit in and add value to the team. How does your life experience as an attorney later in life benefit your performance/perspective?
You've made some assumptions about how you're perceived by others - have these been validated or are you nervous about meeting expectations and being hard on yourself?
Finally, you note that you've been doing the work of a director, but don't seem to have put yourself up for that role, and instead asked your supervisor about your chances of advancement to that role. The ask was somewhat vague and was met with a somewhat vague reply.
One way to frame the ask more confidently might be to say that you are aware the role has become available and given your successful experience in performing the role, you're very interested in pursuing it. You've been doing the work, are enjoying it, and are excited to continue to grow in your contributions to the team.
Wish you all the best.
GuinOctober 20,2020 at 1:15PM UTC
Thanks so much for your quick reply. Nail on the head on my imposter syndrome. For sure, I tend to sell myself short and second guess what others perceive of my skill set. I do have a lot to offer beyond the legal background - writing, communication, tech skills. I will take the advice and be more direct with my supervisor on advancement and what I bring to the team :)
Cara HouserOctober 20,2020 at 3:50PM UTC
This may be helpful - https://ideas.ted.com/4-ways-to-quiet-imposter-syndrome-and-start-believing-in-yourself/?utm_medium=social&utm_campaign=social&utm_content=2020-10-20&utm_source=linkedin.com
GuinOctober 20,2020 at 4:38PM UTC
Thanks, this response is awesome!! I know now why I FairyGodBoss at least once a day!
AnonymousOctober 20,2020 at 4:09AM UTC
Hi,
Your explanation and questions are interesting, as was your decision to get a mid career law degree to use in contracting. I have a certification that includes contracting and I have to keep on with continuing education in the field.
So you sound aimless and needing of some strategic communication classes.
When a position opens, share with management in obvious concise wording that you'd like their support advancing to the position, your soundbites on what you add, and ask them if they are interested in developing you.
Example: Joe, I saw the Division Procurement Director position opened. You might not know this, but I have professional ties to our clients outside of work because a Board I serve on. I'm also one of very few people in the region with experience in this area along with a professional license. I'd love to add support, security, and stability to the business. Can I get your support building my career into the position over the next 2 to 5 months? I'm excited about supporting you and our mission"
FYI, many people think I'm an attorney. My response: I'd have to go to school with other aspiring lawyers, pay highway robbery for the degree, and work with even more attorneys than I already do.
Out of curiosity, do you have regrets for getting a mid career JD and will the Bar Exam, and was money not an issue?
GuinOctober 20,2020 at 1:28PM UTC
Again, thanks for the quick response - and your questions are good - what WAS my motivation? I think I took on the challenge mid-career not really knowing how it should play out in a real world.
If I had to psychoanalyze myself, I've always thought education was the key to success and security and thought that, miraculously, this advanced degree would transform me into a confident and assertive attorney. I knew I didn't want litigation which is more adversarial than I am built to be - but was more inclined to use the law and the written word to help clients. Plus I just loved learning and meeting this crazy goal.
I ended up going to a less expensive school, btw, at their night program so I kept the day job at the time. I don't want to say I regret the move (still paying for it!) because it has opened some doors. I just feel like the miraculous transformation did not happen to me, and the imposter syndrome (see above) has hampered my confidence and taking advantage of my skills to be in leadership roles.
Thanks for this - I feel like this has given me an opportunity to think about the why of my career choices...
AnonymousOctober 20,2020 at 4:14AM UTC
What you have shared sounds quite frustrating and also sounds like you have the “goods” to earn the Director seat. A couple of things jump out and that is 1) your immediate Leader appears to be a barrier rather than an advocate of your advancement. 2) The other thing is that you are a very hard worker, but
unfortunately, simply working hard isn’t enough to garner the exposure to be seen as viable for the Director seat. You know you have the “goods” but now it’s time to make the case for yourself to move up and into one of the seats. If you are interested in discussing specific strategy, let me know. I believe in what’s possible and the situation isn’t hopeless and if your team cannot see how talented you are, then maybe it’s time to take your show on the road.✨
GuinOctober 20,2020 at 1:32PM UTC
Thanks, Sheryl - seems like I do need to 'get out my seat' and make my case. Yes, interested in any advice on getting started. I do realize hard work doesn't necessarily lead to acknowledgement and advancement, and sometimes just keeps you in the same routine since 'well, you're doing fine where you are, obviously!' Anyway, I used to give myself the excuse that 'in this time of covid and remote working' I shouldn't pester my supervisor about advancement. But now we're going on 7 mos of this with no end in sight, so I will take the opportunity to start listing the successes I've had, what I've learned and applied, then make my case in our next one on one or review period. But again, any further strategy advice is most welcome!
Max PayneMarch 11,2026 at 4:59PM UTC
You’re not doing anything wrong — it sounds like you’re already handling more than your title reflects. You deserve clear feedback and a real path forward, not vague answers. And with this level of stress, even a short reset with something light like spinbetter can help clear your head.
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