Five Ways to Master the Art of “Managing Up”

By Dave Wilner, CRO, Auth0

As a young sales manager I was once told that I was “virtually unmanageable” and “the most exhausting direct report” my boss had ever had. This was news to me. My team was killing it – the top-performing sales team across a $6 billion-plus business. How on earth could I have been anything other than her favorite employee?

Some two decades of experience later – nearly all of it managing teams – I have more insight into the agony I inflicted on my former boss. Here are some tips on the fine art of “managing up” and making life easier for the higher-ups.

Don’t Whine
It can be easy to get caught up in the negative – especially if, like me, you are a grump by nature. But perpetual grousing about team members, organizational shortcomings, or the negative aspects of your job in general can prove to be the proverbial death-by-a-thousand- cuts to a boss with much bigger fish to fry than your day-to-day gripes.

You will, of course, encounter roadblocks, concerns, or challenges that warrant discussion with your boss. Rather than forwarding problematic emails or dropping by their office with random, transactional beefs, aggregate those issues that require constructive conversation; then, work through these items with your boss in a regularly scheduled bimonthly or monthly one-to-one.

And, as for straight venting – which we certainly all need from time to time – save it for someone else. The same stream-of-consciousness rant you would communicate to a peer or friend will not necessarily reflect you in the best light to your boss. Save the venting for your friends, family, or the unlucky soul in line next to you at the coffee shop.

Be Concise
The telltale sign of a seasoned executive is how concise they are in their communications. New managers have a tendency to ramble, provide too much information, and neglect to set expectations on what a given conversation is meant to achieve.

Come up to your manager’s level by getting to the gist, quickly.

  • Set meeting expectations at the outset: Make the purpose of the meeting clear by outlining the topics to be covered and the outcome you are looking for.
  • Be up front with your requests: If you require more budget to advance an initiative you think is important, ask.
  • Back up your requests with data: Make sure you are prepared with solid information to back up your requests.
  • Find out what they need from you: If your boss is unable to give you the decision you need, ask what other information you can provide.
  • Stop talking: Once all the information has been laid out and your request has been communicated, stop.

Don’t Hyper Focus on People Management
This is a tough one. While people management issues are typically the most stressful matters for new people leaders, HR stuff is old hat for seasoned leaders. While you can (and should) use your boss as a source of coaching here, it’s important to give prime attention to business issues – which are more likely to resonate with your boss, given their own priorities – and relegate the people piece to a single line item in an otherwise healthy list of topics. Too often new managers over-index here.

Assign Structure
Your boss is busy and, if you sign into your one-on-ones just hoping to catch up, you will likely leave the call feeling like just another box for them to check on their calendar. By taking control of the meeting and providing structure, you will not only come off as competent and prepared, you will get more out of your meetings – and so will your manager.

When possible, take the initiative on scheduling the recurring meeting, and set the KPIs you will plan to cover in the session. When in doubt, you can structure the time together by following “The Three Ps”:

  • Performance: Review your team’s performance, with a source of objective data that can be referenced in each meeting.
  • People: Address openings, new roles, or ideas for strengthening the team.
  • Potpourri: Any other random topics worth your boss’s time not covered above.

Bring Bad News Early
At some point – whether it’s a missed quarter, a delayed ship date, or some other problem in the business – bad news will eventually come to light. For many of us, the tendency is to avoid sharing bad news until there is simply no way around it. Often the best course of action, however, is to bring the issue to our manager’s attention sooner than later. Trust me: If they find it out on their own, it looks much worse for you.

By bringing up a potential wrinkle to your boss early, and being the first to identify the issue, you show command of your business. You also display good judgment by raising the issue early – even better if you bring a solution with you – and show leadership by asking for advice while there is still time to remedy the problem.

Managing up is a critical key to career success. Otherwise-promising careers with great functional results can die by the wayside without commensurate communication skills, perspective on the bigger picture, and an ability to understand supervisors’ priorities. Avoid being the employee that managers dread having a one-on-one with. Put the same rigor you bring to your core responsibilities into your relationship with your boss.