Back in 2003, I was a young sales manager leading a small but solid team for a startup. After we were acquired by a large multinational company, I found myself reporting to an SVP of Worldwide Sales; we'll call her Marie, who was responsible for over $500MM in revenue. This was next-level for me, and my time reporting to her taught me an important lesson — how NOT to manage up.

How Did I Screw This Up?

I reported to Marie for around 12 months. During this time, my team absolutely killed it. We were the top-performing go-to-market team across the entire $6B global business. We were never at less than 120% of the plan in any quarter and were the envy of teams across the org. I was doing nothing but making life easier for my new boss.

Or so I thought.

Despite all the success, I never felt like Marie enjoyed talking to me. She canceled at least half of our weekly 1:1s, citing travel or scheduling conflicts (once her exec assistant told me she was out of town literally 20 minutes after I walked past her in the lobby — that one hurt).

When we did connect, she was brisk, all business, and very short. I wasn't expecting to be best friends. I didn't envision sipping martinis after work, grabbing dinner with our spouses, or joining her family at their Christmas party.

But I also didn't expect to be treated like I was slathered with fish entrails.

Virtually Unmanageable

After finishing my one-year earn-out period, I gave my two weeks' notice and began looking for another early-stage company to jump into. During my exit interview, the HR business partner confided in me that my boss had said I was "virtually unmanageable" and "the most exhausting direct report" she'd ever had.

Ouch.

Did I mention I crushed my numbers? Like CRUSHED my numbers? How on earth could my boss have thought of me as anything other than a beacon of light? A pillar of go-to-market excellence? A reliable watercraft on otherwise tumultuous seas?

It turns out that I was completely and utterly terrible at "managing up" or managing my relationship with my boss.

Looking back, there's a ton that I should have done differently. When I had more time under my belt managing teams of my own, I came to appreciate the art of managing up and how important it is to be intentional in how you manage your relationship with your boss.

To pack it up, here are my biggest lessons:

Lesson #1: Keep It Positive

Anyone that works closely with me knows that I'm an Eeyore. I can be a little surly and a bit of a grouch. Apparently, I tortured Marie with dozens of grumpy paper cuts each week. Any random negative thing I noticed led to a grousing, whining email (this was 20 years before Slack, mind you).

  • "It's been ten days, and I still haven't received the slide templates Marketing promised."
  • "The Solution Engineering org here is really weak."
  • "Don't you agree that our new HR business partner is an @sshat?"

I was a stream-of-consciousness communicator and communicated with my boss like I would with a colleague, a friend, or someone sitting next to me on the bus.

Venting is no problem, but don't do it to your boss. Find a peer, a friend, a spouse, a dude in line with you at Walmart, whatever — just not your boss.

Lesson #2: Pack It Up

One way to tell the difference between a relatively new manager and a seasoned exec is the efficiency of their communication. Newer managers provide too much information, too much detail, and tend not to set expectations about what they need from a given conversation. In short, they ramble or babble.

On the other hand, more seasoned executives are typically much more efficient — and effective — at quickly getting what they need.

It's tough to give this lesson the right level of detail without turning this piece into a 3,500-word essay (I appreciate the irony that I cannot pack up how to pack it up). I will save that degree of detail for another blog post; however, some quick guidelines to consider:

  • Set expectations for any 1:1 or meeting with your boss at the outset.

We have 30 minutes, yes? I have two things I need your feedback on, and two requests I hope you can approve today.

  • Layout what requests or needs you have.

I'd like your support for a new initiative to drive more page views on our site. It requires a $250,000 unbudgeted investment.

  • Share what information you have to support your request.

I shared the context and math behind the request with you by GDoc last Friday. Have you had time to review it?

  • Ask what other information they need to make a call.

What other information do you need from me to make a decision?

  • Stop talking.

→ ...

Be respectful of their time, provide context, and confirm they have what they need.

Lesson #3: Don't Over-Index on HR Stuff

This is a big one.

I focused a lot of my 1:1 time with Marie on people management issues, taking her through the minutiae of each personnel issue in my organization. Since I was a relatively new people manager, the people aspect of the job was the hardest for me, and the one most often on my mind.

Here's the thing: people issues that seem significant to an entry-level manager are par-for-the-course for executives that have managed people for much of their careers. Focusing communication on "lower-level issues", therefore, makes you seem like a "lower-level leader," and implies you're incapable of dealing with those issues.

But Dave isn't part of my boss's job to coach me and help me become a better people manager?

Of course. To be clear, this is not me telling you never to bring up people issues. It is a reminder that if you are a relatively new manager, people issues might be keeping you up at night, but that will not be the case for your boss. Lead all conversations with business issues — issues that tie to your boss's success — and save tightly-framed HR stuff for the end. Consider also leveraging a mentor, someone you can bounce ideas off of in a more relaxed environment.

Lesson #4: Set the Cadence

If your boss is overloaded, your regular weekly/monthly meetings with them may feel harried, like an afterthought or a check-box endeavor. Take control of the communication, both the cadence and the subject matter. Suggest a regular time to meet, and propose a regular set of key performance indicators (KPIs) to review. If those KPIs just happen to be metrics upon which your boss herself is measured, even better.

If you're stuck on how to structure the meetings, try something simple like "The 3 P's":

  • Performance: a review of a dashboard of some sort that objectively tracks the performance of your team.

  • People: the status of any headcount to be filled, restructuring plans, or other team-related items.

  • Potpourri: any other random odds and ends.

Taking control over the cadence and agenda shows confidence, takes an item off your boss's to-do list and ultimately makes their lives easier.

Lesson #5: Don't Hide the Gnarly

NOBODY likes delivering bad news to their boss. But if there's a problem brewing in your business, it is far wiser to bring that problem to your boss's attention than risk them discovering the issue on their own.

This runs counter to many new managers' instincts. It's often easier to convince ourselves that things will work themselves out, that the tides will turn, or engage in other acts of aggressive denial than admit dark clouds are on the horizon.

If your boss identifies a problem in your business you have not discussed with them, they are likely to assume that (1) you're not aware of the problem, or (2) you're aware but have no idea what to do about it.

Neither reflects well on you.

Bringing a potential wrinkle to your boss early, in fact, reflects positively on you as a new manager, even if the wrinkle never materializes. Consider:

  • If you identify the problem first, you're on top of your business.
  • If you bring a solution as well, then you are not only on top of your business, you know how to manage through challenges.
  • If you identify the problem but aren't quite sure what to do about it, you're displaying good judgment and striking the right balance between working independently and seeking guidance.

Some of the worst breakdowns between managers and their direct reports occur when people don't identify or take responsibility for mistakes. Identify potential problems in your business and share them early.

360 Degrees of Responsibility

My "Careful What You Wish For..." blog post looked at the difficulties of managing those on your team. But it's just as important to learn how to manage upwards if you are going to succeed. You might have the best objective results every week, but it doesn't mean a thing if you deliver those results alongside poor communications, a lack of understanding about the bigger picture, and 20 minutes of "I can't believe marketing messed that campaign up" chatter.

Like anything in leadership, be intentional about your communication strategy with your boss. Put in the time to plan, and review your progress regularly.

Also, don't call co-workers @sshats.

The End

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