How To Manage Up

Leadership

May 30

One of them most impactful bits of feedback I ever got was when I was interviewing for a VP of Product role at a startup. I didn’t get the job. I was about 32 at the time, and full of vim and vigor, as they say. I was so sure that I was perfect for the job. I had run a business with a dozen engineers for nearly a decade.

I made it through countless hours of interviews with all of the senior people in the organization. At the end, when I was gently let down, the reason that stuck in my head to this day was something like this: “You’re smart and tenacious. You just need a little more gray hair, kid.”

I paraphrase, of course. But the phrase “gray hair” was actually used. I was so pissed at the time. How dare they underestimate me, I thought?!

Well, here is what I didn’t realize at the time about the reality of being an executive, or what “gray hair” really meant to the CFO who said it to me.

They think differently than you do

The world at the top is very different from the world at the bottom, and both are nothing like the middle. The decisions are bigger, and information is less available and more coarse grained. There is very little time to have any meaningful conversations with peers or direct reports about each of those decisions.

Due to the difficulty in measuring outcomes from past decisions directly, executives tend to go with their gut. Collaborations happen with very lightweight conversations with other executives, over a series of quick exchanges, sometimes in meetings but just as often in the hallway, over lunch, or on the phone.

Many decisions are based on the personal ambition of individual leaders, in terms of their own position in the company relative to their peers. Their biggest concern is recruiting capable people like you to whom they can delegate goals and objectives. That way they can ignore the details, and move on to the next decision.

Remember whom you’re dealing with

If you have never read William Whyte’s amazing 1956 classic, The Organization Man, I strongly suggest you do. Over 60 years since its original publication, the message in that book is a true as ever today. Here’s a nice interview with Whyte, which might whet your appetite. https://www.pbs.org/video/the-open-mind-the-organization-man/

In short, the higher you go in an organization, the more the collective will of the organization fuses with that of the executive. They see their futures inextricably linked, and work ceases to be just another job. This trend, of course, appears to be counteracted by the trend of people in general staying in jobs for shorter and shorter times. But where they converge is in that aspect of those at higher levels being more tied to the fortunes of the organization than those at the lower levels.

Keep it simple

From the executive point of view, the decisions are bigger, and information from the front lines is less available and more coarse grained. It has been filtered up through various management layers before it gets to them. At their scale of responsibility, your ask is one of a hundred others just like it.

There is no time for long slide presentations or sheets of data. To make your case, you’ll need to be able to summarize what you want to say into an extremely small number of words. Oh, 25 or less should do it. Can’t get it down to that few? Try harder.

Ask questions, then shut up, and listen

People tend to be guarded against requests and opinions by default, often without even knowing it. You can’t mount a full frontal assault of “persuasion” on an exec and expect to get anywhere. Instead, use the fact that people — especially those in power — like to be asked what they think. Frame your request not as a direct ask, but rather as a set of simple questions that lead them toward the subject matter you want to discuss.

Their objectives are bigger and more vague than most people are comfortable with. So, they tend to go with their intuition a lot. If you can build empathy with the challenges that they are dealing with, and frame your request in a way that fits into their strategy, you’ll be much more likely to win their support.

Leverage their relationship with their colleagues

It’s likely that what you are trying to accomplish will require support from more than one executive. Remember that they are not alone up there. There is a whole “Game of Thrones” going on in the executive suite, and they have likely formed allies and enemies in their attempts to get their projects through the usual budgetary and decision processes. Don’t ask about their relations with other execs directly. But you can inquire if there is a colleague of theirs that they can connect you to for next steps.

Make it easy for them to support you

Along the lines of fitting your request into their master plan, it’s best if you can work out how to make it very easy for them to actually support you. In other words, what are you actually asking practically for them to do? Talk to someone? Sign something? Send an email on your behalf? Advocate for you in a meeting?

Make sure that you have a very clear and easy “call to action” to share with them. The more complicated the ask, the more likely they will put it off and gradually “forget” to help you at all.