Guidance: Pick a Hill and Figure out Step Two

Many years ago, I had the privilege of being managed by a truly great man named Adam Howland. When I get to bloviating, I tend to describe the year or so of our working relationship as transcendental.

Transcendental is perhaps the wrong word to describe how my working relationship with Adam was, at times, nearly spiritual. Over quite a few conversations, he helped calm my inner petulance, and showed me that it is possible to get what you want by showing people that they also want the thing you desire.

Fully recognizing the preposterous nature of aligning a good management experience with the thoughts and beliefs of transcendentalism, I set about to find a better word. But then I read more about the belief system of transcendentalism, and realized that I’d fallen ass backwards into the right word after all.

As a transcendentalism neophyte, consider me far from an expert, but here’s what sticks out. Transcendentalism is the belief that human beings, individuals, have the intuition necessary to find the right choice.

Adam did a fantastic job of validating that the gut feeling, thought, or initial reaction that I had was correct, but that my delivery was oftentimes wrong. I gained a great deal of confidence by having someone I respected tell me, “You’re not wrong.”

The follow up phrase would usually include a “but” and a short critique of my proposed delivery to someone within the organization, usually a sternly worded email.

As there are no shortage of problems in a fast moving technology company, we had ample opportunity to chat about the things that had my dander up and how I’d like to deal with them. Putting on his Socratic hat, he’d lead me down a path of self discovery and, more often than not, the right answer. Two questions always guided our conversation.

“Pick the Hill You’re Going to Die On

It’s hard to draw parallels between Khe Sanh and the sedentary life of an office drone, but bear with me.

Mankind has been charging up hills (and dying) from the word “go.” Our nature is to attack the high ground, knowing full well the deck is stacked against us. Attack the right hill, win it, and you might go down in history. But attack the wrong one, and you could similarly go down in history as the poor dumb bastard who charged up the wrong hill.

There has to be value in the hill. It has to be a hill of great importance. Damnit, you gotta know that, first, the hill is worth it and, second, that you dying on that hill is also worth it.

Each time I would bring some matter of great importance to Adam he would ask me, “Is this the hill you want to die on?”

Each time, I’d be forced to logically defend my position and come to the table with a clear rationale for why he and I needed to team up and attack whatever problem plagued me that day. More often than not, I’d realize that this hill was not worth dying on.

“What’s Step 2?”

Now and again, I would  find a suitable and noble hill for my death. We’d discuss the merits of the hill, and talk about my proposed solution for attacking it. That usually included some sort of hot headed response from me directed at some coworker. The following is my recollection of one such interaction.

TK: “Can you believe these S.O.Bs? They can’t just treat me like this. Read through this email and tell me what you think.”

AH: “Oh this is great. Truly wonderful writing. My God, really amazing stuff. Life changing. What’s Step 2?”

TK: “What do you mean?”

AH: “Well you’ve really let them have it here, no doubt. But what do you want from them?”

TK: “I want them to know how I feel.”

AH: “Well, first off, nobody cares about your feelings. So what do you want them to do?”

TK: “Fix XYZ problem.”

AH: “Do you think this helps you to that end?”

TK: “No”

On and on, we’d have these discussions. Inevitably, my leading desire would be to have my voice heard. Adam would gently remind me that, while my opinion surely mattered to him, it likely didn’t matter a lick to the party in question. So we could either find a way to turn a “me” problem into a “them” problem, or we could go searching for newer, shinier hills to die on.

A quick acid test is this. If the sole reason you want to communicate an idea to someone is to make yourself feel better, it’s shit. Assume that nobody cares.

Ask yourself what you want, and then ask how the action you’re taking furthers that goal. If you can’t show a link between the two, abandon the plan.

You Don’t Always Have to Die on a Hill

Don’t let the last few hundred words let you think that I didn’t go charging up some hills. You bet I found one or two causes worth going after, and I gave them my all, but only after vetting them with those two simple questions. On more than one occasion, I ended up prostrate, reputation in tatters. But I slept well knowing that it was worth it. I even won a couple fights.

In the years since I learned these valuable lessons, Adam moved to a different team, but we maintained a close friendship. Every now and again, a coworker comes to me with some maddening problem, their proposed solution, and a request for my opinion.

For years, I’ve asked them if this is the hill they want to die on, and if so, what their second step is. We usually go back and forth for a bit until they decide that the best plan is to take no action or they rework their original plan to better align it with their end goal. Step two is always a phone call to my friend Adam to discuss yet another career suicide avoided.


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