🆙 Managing Up: 5 Surprising Questions to Ask

Diagnosing your relationship with your manager

Having trouble building a high-trust relationship with your manager or skip level? Want to brainstorm how to spend time in a 1:1 or roundtable with an executive in your management chain? Got a new manager and want to get off on the right foot?

I’ve mentored dozens of people over the past twenty years. In larger companies with a hierarchy, the topic of “managing up” is one of the most frequent mentorship topics I see, especially from early-in-career employees.

While I hope you can spend most of your time focused on driving impact with the autonomy you want, this post is for those moments in your career where you find yourself needing to work within and leverage your management hierarchy.

The following is a “virtual mentoring session” – instead of solving your problem or telling you a playbook, I’ll give you the five questions I’d ask if you were a mentee of mine and wanted to unpack your relationship with your manager. Let’s Ted Lasso this thing together!

But first, why?

There is a saying: “People don’t quit their jobs; they quit their managers.” While this is mostly a plea to managers to deliver the right culture and support, it makes another point - your relationship with your manager is too important to be ignored.

When I think about my career, my investment to develop high-trust, two-way relationships with my managers over the years has been a force multiplier because it:

• Enabled me to feel safe enough to take risks and be more creative

• Gave me the context to work on something larger than I could do on my own

• Showed me what my next job might be like, if I chose to move up the hierarchy

This post isn’t for anyone in a truly toxic situation with their manager - that’s a whole other topic. Nor should anyone be spending most of their time on “managing up” - we all joined this profession to be builders, not talkers.

Yet a little bit of self-reflection and curiosity can go a long way here - so let’s get to the five questions designed to get you to complete just the right amount of pre-work before your next conversation with your manager.

1. Can you name 3-5 ways that your manager’s job is harder than yours?

This is my first go-to question. I find people can easily name the way their own job is harder, but it’s a “think and pause” moment to put yourself in your manager’s shoes. The goal is to name specific things your manager is struggling with, activities they are doing for the first time, or painful things they are handling for you that you don’t. If you don’t know, it’s completely normal to use a 1:1 to ask - I do it at least 2-3 times/year.

I’m not asking you to solve their problems and take on your manager’s stressors yourself - but the awareness is helpful not only for the acceleration towards a high-trust relationship but because there is often a high correlation with the top problems for your company and your customers.

2. What can you help your manager learn?

When I’m at my best over the course of my career, I’ve used office hours, skip levels, and roundtables to try to share my own lived experience on the team - what I love about the team, what’s getting in the way, and what’s changing. This can be specific things - “hey, did you know it takes over 10 hours to complete this process?” - to more generic - “I used AI in this way, and I think it could help others on our team.”

It’s the reverse of the previous question - I’m asking you to do your part to help your manager walk in your own shoes.

The best managers will be curious and ask proactively about this – some organizations even have “reverse mentoring” where a more senior employee shadows a newer employee.

The other benefit of investing here is that it organizes your own thoughts – you must self-reflect about what’s easy or hard or novel in your own work life before sharing with someone else.

3. Is your quality bar higher or lower than your manager’s?

Managers are hired to be editors – but they are at their best when they function as the newsroom editor on the big picture not a copy editor fixing details.

This is my “get beyond the basics” question – and it requires some honest self-reflection and awareness. In my career, one of the best “cheat codes” I’ve found is to have a quality bar that is higher than what your manager expects and the organizational average.

This is especially important in new employee/manager relationship - as norms are being set. So it’s worth spending the extra time being typo free, rewording for clarity, and delivering high quality and polished work.

If you are unsure, it’s a great idea to ask for examples - ask your manager and your teammates: “Can you share a few examples of the best work that you’ve seen in the past month?”

4. What part of your relationship with your manager is transactional? What part is creative?

I ask this when I’m trying to diagnose if something is off with the altitude that you approach conversations with your manager. Are you bringing half-baked work to your manager when you should have worked on it with a few peers first? Conversely, did you decide something yourself that needed creative alignment with a larger system?

Every 1:1 I go to with my manager, I try to have 2-3 transactional things I’m informing them on (e.g. budget I’m spending, customers I’m closing) and 1-2 creative topics I want their equity in (e.g. a major design tradeoff, an organizational problem I’m stuck on). Classifying my conversations into these two buckets is a helpful barometer of whether I’m living up to expectations of autonomy. I’ve often discovered things that I was going to bring to my manager only to realize “Hey, I can and should figure this one out myself.”

5. What do you want your manager to know about you, right now?

Most managers will develop a mini-model of their employees in their head – what kind of tasks they like to do, what their super strengths are, and if they are bored or challenged with their current assignment. There is no need for this to be a tacit conversation filled with assumptions – so I ask this question to drive intentionality in what you are sharing with your manager.

I add the phrase “right now” to the end of the question to reduce the stress of it - you don’t need to share your 5-year career plan with your boss. It’s a trust-building gift to appropriately share how you are feeling and what you need this month.

Of course, depending on the level of trust, there may be a host of personal issues or even professional fears that you aren’t comfortable sharing. This question isn’t designed to make you an open book – it’s to get you to be intentional and drive down assumption-making from you and your boss.

Wrapping Up

If you’ve found this post helpful and want more, I have an upcoming public talk that I wanted to make folks aware of. In under two weeks, I’ll be attending the Microsoft 365 Community Conference in Las Vegas (I’m actually the executive sponsor of the conference, too) and speaking about many of the themes you’ll find in Mind The Beet:

How To Thrive In Your Tech Career: Managing Burnout and Boredom

If you are attending the conference, I hope to see you there!