4 Steps To Managing Up When You Have More Than One Boss

In the old days, when I walked through the driving snow uphill both ways to work, managing up to my boss was easy. I had one boss. A hierarchy was the natural order in the companies I worked in, and while that hierarchy created a lot of delegation down and up the chain, the pathway for work was pretty simple. At least compared to today, when so many of workers are in matrixed organizations and the hard and dotted lines of the organization look like a connect-the-dots page than an org chart.

What’s an individual contributor to do when she may have four, five or six bosses who may or may not get along?

4 Steps To Staying Sane While Managing Up To Multiple Bosses

1. Write everything down. You must find YOUR way of capturing everything you need to do. And even if you use Asana, Airtables, Smartsheets, Trello or another project management platform (i highly recommend that teams use one or a combination of these), writing your tasks, due dates and projects down significantly increases your memory recall of what is on your plate. You can read more scientific evidence from experts on that fact here and here.

   I have hacked my own planner by ripping up eight or nine commercially available planners and taking the bits I like from each and mashing them back together again and then tweaking everything for the last three months. If you don’t want to go to that extreme, I can recommend the Daily Greatness, the Panda, and the Ink & Volt planners to you.

2. Put All Due Dates Into Your Calendar. This way you will SEE when priorities compete and become at risk as soon as possible. You are responsible for driving clarity around your work.

3. When Priorities Compete Let Your Project Managers Know ASAP. Managing up is especially important when work for different people is due at the same time.

   When you find that priorities compete, let the managers who you’re responsible to for those activities know immediately, preferably on the same email, and detail a possible solution.  

   For example:

   Matt and Dan

   I’ve calendared Project Alpha and Project Beta, and see that both projects require my attendance at competing events on March 4th. In addition, the work flows may compete too, given when I will probably get work from Jane and Luis. Based on what I know right now, my suggestion is that I attend the Project Beta meeting on March 4th and that Jane cover for me in the Project Alpha meeting that day. Also for the competing workflows in April, I will send you each suggested tweaks to the workflow plan for each project so that I can get everything done well in time.

   What I need from you: please confirm whether the March 4th plan above works for you both. My goal is to get clarity and agreement by Friday so that I can meet everyone’s expectations.

   Thanks for your help.

   If you have a conversation instead of an email discussion, follow up the conversation with an email that details whatever agreements you’ve made. Adjust the online project management system appropriately, so that everyone on both teams can see what’s changed.

   This managing up step is even more important if Matt and Dan don’t get along. You can listen to our Millennial Minded Podcast on this topic here.

4. Be Switzerland. For each additional person you work for, the complexity of the workplace dynamic exponentializes. Since everyone is different, you will most probably be managing up to people with very different personalities, abilities, tendencies, and styles (which HBR has a plethora of info on), which brings a special level of wonderful to the work at hand.

   This is a GREAT opportunity for you to learn, to grow, to become better at your discipline. It is also a playing field that’s harder to navigate.

   It’s important for you to be a positive contributor on your teams, and NOT to favor one boss over the other. Switzerland is your best bet – staying neutral while being in great communication with everyone.

   As Duncan Lowe, the host of Millennial Minded commented in a recent AP story by Leanne Italie, confront the issues, “but do it respectfully and come with some context around the issue. Once you have that conversation, it feels really good and you feel like a weight has been lifted.”

   Take control of what you know – your workflows, your deadlines, what you know about your bosses, and you will be in a much more positive and productive place – no matter how many bosses you have.

   That is all.