Managing Upwards Requires Real Effort

It doesn’t matter who you are, you report to someone. Even the CEO answers to the Chairman, Board of Directors, and outside investors. Besides managing people that don’t report to you, managing upwards may be the most difficult part of your job. When you hear the word “manage”, nearly everyone envisions managing direct reports, but really, you manage in four directions.

  1. Your boss (upward)
  2. Your peers (laterally)
  3. Your direct reports (downward)
  4. Your external stakeholders (outward)

It’s my estimation that most people spend 99% of their time on 2 through 4. Although 1 is the most difficult, it is also the most important. There are three main reasons people willfully ignore managing their boss. First, it can be intimidating. Second, it’s not easy. Third, it has a negative connotation. Ever heard of the phrase “sucking up to the boss”. Well, all three are 100% wrong. It’s your boss, so just embrace it. It’s not that difficult, it just requires a little thought and effort. And, who cares what others think. When done right, it will never be viewed as sucking up except by those who are jealous of your success.

When managing your boss, or anyone more senior to you in the org chart, I’ve always followed a simple three step process, and it has served me well.

  1. Understand what makes them tick.
  2. Find out how to best engage them.
  3. Discuss what matters most to them.

Now, to be successful, there is really only one skill that’s required. Emotional intelligence. What’s that? Well, I’m glad you asked…..

Emotional Intelligence, or EQ, is defined as the capacity to be aware of, control, and express one’s emotions, and to handle interpersonal relationships judiciously and empathetically.

Other than that, it’s just another process. Let’s break it down.

1. Understand what makes them tick.

This one is fairly straight-forward. I will describe it through a bunch of things you need to research. Some you can find online. Some you might need to ask your peers. Finally, you might need to ask your boss directly. So what are some things to consider? Understand their interests outside the office. Understand their bio, accomplishments, and history with the company. Understand their current role and expectations in the company. Understand the key performance metrics that guides their work. Understand their career trajectory. Understand how they are measuring your group. Understand how they measure you individually. And most of all, understand their personal interests outside of work. Now, I’m not suggesting you create a dossier on your boss, that’s creepy. Instead, have a basic understanding of them, in general terms.

2. Find out how to best engage them.

Everybody has their own style of communication. Some people prefer face-to-face meetings. Others prefer electronic communications. And still others prefer the “don’t call me, I will call you” approach to communications. And don’t forget about the frequency of the interactions. Some like engagement daily, others weekly, and some maybe quarterly. It all depends on them.  Regardless, talk to your peers to better understand your boss’ preferred style of communication. They will know. And they will provide good recommendations. So, please pay close attention.

3. Discuss what matters most to them.

A little small talk is fine, but when you have their attention, focus your time on the things that matter most to them. Tell them about your major projects, what’s working and where the challenges are (and your solutions). Give them numbers, data, and facts. They have a business to run, and you can help them appreciate how things are going. Assumptions, hearsay, and half-truths will only come back to haunt you. Don’t ever throw people under the bus. Nobody wants to be a victim of friendly fire. Don’t worry, if your boss truly cares about you, he will spend time learning more about you; however, that is their prerogative.

Short Case Study

A long time ago in a galaxy far, far away…. there was a Director of Sales that reported to me. He, along with 4 other directors, were all experienced and knowledgeable. Each were subject matter experts (SMEs), not only in transportation, but their respective industry verticals. None of them resided at our headquarters; they were spread across the continental US.

This individual was a high performer. He was crushing his numbers every quarter and he was well-respected by the rest of the organization. There was only one problem. He never built rapport with the executive team (other than me). This created several issues. First, they didn’t have a real appreciation for what he did or how exactly he contributed (except during the monthly P&L conference call). Second, the executive team never developed a genuine sense of empathy for him. Finally, whether real or perceived, it created a sense that he wouldn’t be able to advance in the company.

Now part of this was my problem because I wanted him to succeed. And if it wasn’t rectified, it was going to become a major stumbling block. So, I did two things. First, I made him schedule two days at HQ each quarter, so he had the opportunity for face time with the other execs. Second, I provided insight into each member of the executive team, essentially answering 1, 2, and 3 from above.

It definitely helped, but we never truly closed the gap. And I view that as a failure on my part. If I had to point to the root cause of the failure, it was the fact he never took it as seriously as I felt he should have. He never scheduled one-on-one time with each of them in advance (these were busy individuals). He never tried to spend time with them outside of the office. He never got to know them personally. It was business as usual. The only difference was that the execs saw he was there in-person. Unfortunately, he ended up leaving the company. And that was a huge loss to him, me, and the company.

Moral of the Story

Your ultimate success depends on a lot of factors. But I would argue that your ability to manage upwards is the most important factor. Don’t take it lightly or you will slowly get lost in the shuffle. The onus is on you. View it as personal development. The closer you get to your boss, the smoother your career trajectory will be. Do you want a strong headwind or the wind at your back? It’s your choice.

  • James Adams
  • Chief Executive Officer
  • Revolution Trucking, LLC
  • (330) 975-4145

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