✍ My manager is in his late 20s (same age as me) and a first-time manager, who happened to be my closest teammate before his promotion. I’ve had a hard time navigating the professional relationship over the past year. Any advice on how to keep it personal AND professional?

P.S. I was extremely proud to see him get promoted and don’t have a problem reporting to him. But I do struggle with things being nice and casual/laid back one minute then I’ve crossed an invisible line the next…help!!!

Context: Series E Start-Up ($752.5M in funding), roughly ~350 employees, oil and gas tech company. Being a start-up, I’ve held 4 positions in the last 4 years and had 12 managers. Environment is exciting, ever-changing, but exhausting.

Cassidy Edwards, Director of People Operations at Tradeblock: 

This is a great question, because I have been here before.  First and foremost, I’d like to give you kudos for being excited and supporting your friend in this promotion.

Next, this will be all about balance + boundaries.  You’re halfway through the solution by acknowledging the change and being supportive with the transition.  Here are a few more hacks to help balance personal and professional:

  1. Open communication – define how you both are setting boundaries.  It helps to let the other person know how much you respect this great opportunity and don’t want any confusion to interfere with your work/personal relationship.
  2. Keep grace on deck – really recognize that this new position comes with some added responsibilities.  Understanding and holding grace + space for each other will strengthen the new dynamic.
  3. Flexibility is your friend – keep in mind that you both need to be open-minded to adjustments that may occur to balance personal + professional.
  4. Feedback Loops – give feedback and ask for it.  It can show that you want to grow in your role with respect to your friend being their new leader. 
  5. Continue to put your best foot forward – team work makes the dream work, right?!  Show the same dedication and affirm that you are committed to the big picture.

At times, this transition can be tricky, but keep in mind that your new manager is probably also thinking about how they can support you through accountability and continued growth. The foundation is effective communication.

Cassie Olivos, VP of Operations at Ferocious Media: 

Great question! While I haven’t been in your shoes, I have been in a situation where I became my friend’s manager.

This is certainly a two way street — especially given your comment of “I do struggle with things being nice and casual/laid back one minute then I’ve crossed an invisible line the next.” If you don’t know what this invisible line is, how can you navigate this change!

If I was in your shoes, I’d consider level setting in our next 1:1. Have an open dialogue — express your genuine support and excitement for them in this role, and discuss the challenges you’re seeing (recent examples of you crossing this invisible line) and ask for their input as well.

It could be a difference of communication styles, or if he’s reading something through slack and taking it the wrong way, or possibly even, he’s trying to navigate drawing a hard line in the sand now that he’s a manager. Use this conversation to better clarify boundaries and expectations.

Ultimately, two way feedback is important, so be open to hearing his feedback to you as well. If you approach this in a positive way, looking to move forward together as a team, I’m sure things will improve. Adjustments take time and being adaptable is such a valuable skill!

Tara Turk-Haynes, Founder of Equity Activations: 

What a great question and one that seems to becoming more and more the norm. I would say ensure that you are both very clear on structured feedback. Make sure there are agendas set up prior to meetings, that you both are clear on expectations, and that your friend/professional boundaries are very clear so you aren’t overstepping them.

Manaan Alexander, Operations Lead at CommandBar: 


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+1000 to everything Cassie and Cassidy have said, communication is key.

One thing that’s note clear to me in your message is if crossing the invisible line is a real thing that’s happened that you’ve received feedback on or if this is something you’re perceiving. I don’t want to say “it’s all in your head” but I can’t tell you the number of times I stressed about an interaction to only have the other person be like “what are you talking about” when I finally got the nerve to say something about it.

There’s a universe where you can have both the professional and personal relationship, IMO, and I wouldn’t want your own pre-conceived notions of what that should look like, especially on your manager’s behalf to impact the two of you. In that dialogue with them, I would also try and carve out specific things that might change now with this new dynamic; maybe your personal relationship doesn’t have to change much but you definitely probably shouldn’t be discussing other employees now, for example.

✍ How can I engage in a constructive conversation with your higher-level manager (CFO) about my immediate manager who may not be effectively fulfilling her job responsibilities?

Context: I do 90% of my managers job, she is slow to respond to emails and issues that are rather urgent in nature.  My counterpart who does not report to me, comes to me for my opinion and guidance.  We are in healthcare, large private practice, with over 300 employees and over 40 providers.

Alex Clermont, Director of People and Operations at TDC:

If I were the CFO and you came to me, my first question would be whether you’ve talked to your immediate manager about your concerns. Unsolicited skip-level feedback can be a big deal – which I’m not saying is right but it tends to be true. It can reflect poorly on you and damage your relationship with your immediate manager.

Absent more details, I’d be looking really hard at what else you can do without the CFO. Suggesting a different system for communication may be first on that list if emails aren’t effective.

Cassie Olivos, VP of Operations at Ferocious Media: 

I’m in a similar boat as Alex above, since there are a few details I don’t know. My thoughts are:

If you have not addressed this with your manager first, then:
Approach your manager with this feedback! Approaching it with respect, sharing the obstacles that occur when the manager is slow to respond. Asking if there is a better way to share these urgent issues for a more timely response. Could this be a communication issue — I’ve had indirect emails sent to me from my employees (I’m direct), and I did not know this was something they considered urgent based on how it was written!

Or perhaps, these are issues that the manager may expect you to handle alone — so this could be a really good conversation in revisiting expectations.

If you have addressed this with your manager multiple times, nothing has improved, then skip-level could be a good next step. If you already have skip-level meetings as standard practice in your org, then:

I’d use your next skip level meeting with your CFO to gain clarity on company/department goals — perhaps the CFO has put important/time consuming to-dos on your manager that you are unaware of? Or your manager has been told to focus in ABC vs. the work you’re doing in XYZ.

You could also use the skip level to share obstacles you’re facing, like if your manager is slow to respond to ‘urgent’ emails, you can ask for their advice on how to approach this with your direct manager so that you feel better supported. You can also offer your own solutions — perhaps your manager needs an assistant or there needs to be a level between you/your counterpart and your manager.

If you have addressed this with your manager, multiple times, nothing has improved, and you don’t typically have skip-level meetings, it could be a good opportunity to speak to your manager or other leaders about inputting skip level conversations to better understand company/department goals, professional development, and all the other perks of skip-levels.

I’ve personally had skip level meetings before and have found them so beneficial in gaining clarity, realizing where priorities lie, and as a leader myself, seeing warning signs or issues that I can help coach my managers on before they become actual problems.

Hebba Youssef
Hebba Youssef

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