How to Lead Up

Most of us have a boss – if not multiple bosses. And it seems the higher in a company you go, the more bosses you have, and the more important those bosses become. But no matter what level in an organization you’re at, a critical skill to both your career success and success as a leader is that of “leading up.” 

My word choice here is very deliberate. It’s not managing up. In its most simplistic form, management is about controlling things. It’s closely tied to titles and positions on an org chart. Leadership is about influence and winning the hearts and minds of followers, irrespective of title. You need a title to be a manager. You don’t need a title to be a leader. So, you can’t “manage” your boss, they manage you. But you can lead them. You can build a meaningful work relationship that benefits both of you by learning some specific skills. But first, I’ll share a story… 

A few years ago I worked for one of the most intelligent and hardworking managers and leaders I’ve ever met. She was always the smartest person in the room and was always a few steps ahead of everyone else. She was also kind and people-focused. But truth be told, I was a little intimidated by her. So, when she promoted me to manage a small team, I was eager to both prove myself and also to reward the trust she placed in me. 

My first few tasks were to create the team strategy with my team, prepare a presentation to our SVP, and co-present it with my boss. I worked with my team over a few weeks, and we had what we thought was both a solid strategy as well as a decent presentation. We were scheduled to present it to the SVP on a Tuesday, so the Thursday before the meeting my boss scheduled a meeting with my entire team to hear the strategy, review the deck, and prepare for the upcoming meeting. It was our moment to shine. But shine, we did not. 

We jumped on the call, got through the pleasantries, then dove into the heart of the meeting. We shared our strategy, showed our deck, and then waited to hear the feedback. The seconds that ticked away after we finished stretched on for what felt like hours. Finally, my boss was able to compose the thoughts that she needed to convey: we missed the mark. And now we only had a weekend to fix the situation. I was devastated. And, I was embarrassed. I put my team in a position to take some pretty brutal feedback, and there was nothing I could do to protect them. 

After the call we regrouped as a team and tried to figure out how to move forward. Later that day I received a call out of the blue from my boss. I was hesitant to pick it up as I didn’t want more “feedback,” but knew I couldn’t ignore it. When I finally picked up, her first question was “how are you doing?” Not a “how’s it going,” but a very clear, probing question. She wanted to know how I was feeling after the “feedback” earlier in the day. I was honest in that I wasn’t great, but that I was fine. She asked how the team was doing, and I shared an equally lame answer. She saw through my “brave face” and did her best to let me know this was not the end of my career, but she was honest we had a lot of work to do to salvage the situation before Tuesday. We jointly came up with a plan that included her and I working on Saturday to refine the strategy, greatly improve the deck, and prepare for Tuesday. 

Somewhere through the weekend she gave me some additional feedback, but this time it was on me as a leader. Where I had gone wrong is that I had not involved her from the start. I tried to simply do it all on my own, and she had trusted me to do so. But when I didn’t live up to that trust, she needed to step in and fix the situation. The worst part of it all: I thought I was doing exactly what she wanted me to do. I thought she wanted me to show her what I was made of, I thought I was building a strategy that was in line with her thinking, and I thought I was building a deck that looked like other decks she had created. I was wrong on all three counts. 

In the end, our work over the weekend paid off. We created a strategy that was well received by our SVP and that set our team up for success for years to come. And maybe more importantly, this along with a few other experiences taught me how to “lead up.” 

Here’s what I learned: 

1. Learn your boss’s style, then adjust yours to meet theirs

In that case, my boss appreciated being involved in the details. She often had insight to share based on her experience and on conversations she was in that we were not. Not every boss will be like that, some will only want to know the high level direction of projects. Either way, knowing their style and adjusting yours to match theirs will build their confidence in you, which in turn will make you more influential to them. 

2. You can either treat your boss like a client, or a team member

In my example above, I treated my boss like a client. And she did not like what I delivered. My team and I did all the work without her involvement, then presented it to her for her consumption. However, if you take this approach, you better be 100% sure you know exactly what your client/boss wants and how to deliver it for them. If not, see point #3. 

3. Until you can read your boss’s mind, involve them early and often in your projects

Make your boss a part of your team and let them iterate with you. This may mean you have to go slow to go fast. The last thing you want is for your boss to swoop in at the end of a project with completely different ideas of how it should be accomplished or what results it should deliver. So early in the project, get them involved, get their input, iterate with them. It’s much easier to make course corrections early rather than having to scrap something at the last minute and start all over. But also set the expectation with your boss that at some point the iterations need to stop and the project needs to proceed. 

4. Stakeholdering and coalition building are underrated yet necessary leadership skills

Every one of us has people we trust and listen to. Learn who those people are for your boss (their stakeholders) and get those people on your side. If your project or idea requires your boss’s buy-in but they seem reluctant to get on board, target those who they trust and get them onboard. Then have them work on your behalf to influence your boss. 

Bonus learning: Micromanagement is most often a “you” problem, not a “them” problem

Nobody likes to be micromanaged, but often we simply blame the boss for being a bad manager when we feel micromanaged. However, the brutal reality is that often our boss’s micromanage us because they don’t trust us. My boss had to micromanage me until she could trust me. But once I won her trust, and once I learned how to “lead up” to her, I enjoyed an incredible amount of freedom and flexibility with my projects and ideas. So, if you feel you are being micromanaged, start by looking inward. What are you doing that may be prompting your boss to micromanage you? What could you do differently to win their trust? How could you better align your approach with theirs?