Barely Treading Water – Rands in Repose Skip to content<br>Carolyn, my chief of staff, sat on the couch as I ran into my office. The Palo Alto building wasn’t built for tech; it’d been adapted to support the use case over the years. My office was in the center of the building, which had an inner atrium. Way too many windows. Maybe a salon? Great light. We arranged the furniture for 1:1s. A comfy brown couch, a captain’s chair, and a table with a plant that I enjoyed keeping alive.<br>I was running late because the prior meeting ran long, and I had a mere five minutes before the next. Her normal high energy was subdued. Her feet were crossed, and her ever-present legal notepad was nowhere to be seen.<br>This is bad news, I thought.<br>"I have bad news," she said.<br>I collapsed into the leather captain’s chair. "OK, spill. Beer bash was last night, and… someone’s in jail? Someone quit? Food poisoning in the cafeteria? Maybe it’s…"<br>"It’s you."<br>Quick readout on my professional report card before I explain how I was failing. The company was growing. We were hiring effectively. The last survey of employee sentiment highlighted a few areas where we needed to invest, but nothing was on fire. Yes, late-stage start-up, so the volatility was high, but that’s a cost of doing business. The measurable objectives were all positive.<br>"It’s me?"<br>"It’s you," she said.<br>Belief is a Funny Thing<br>Hard to earn, easy to lose. Often privately held, but publicly displayed. Belief, when it comes to your job, is the immeasurable answer to the question they ask, "Is he capable of doing this job?" They don’t judge every word or act, but every so often, they stop and ask themselves, "Is he capable of doing this job?"<br>A simpler way to understand this amorphous state: when I hand a job to another person, I instantly mentally grade them on all past tasks. How do I feel they’ve delivered on past work? Great? OK. No further questions. It’ll just happen. Wait, they did it with prodding? OK, I’ll need to nudge them a bit. They completely forgot that part that one time? Yikes. This task may not be completed. Plan appropriately. The glory of having a brain is that I make snap judgments in an instant. The problem with having a brain is that if I’ve landed on a reliable opinion for this human, it’s quite hard to change.<br>"I’m the problem?"<br>Carolyn said, "You’re the problem." And then she slid the yellow legal pad from under the couch and started reading the list.<br>It was a juicy list. She’d heard from a trusted source that there was trouble brewing for me the week before and had spent part of each day talking to trusted others she knew would speak the truth. She’d dispelled the rumors and had landed on a set of observations from the last six months that painted a picture not only of imminent failure, but of barely treading water.<br>High on Your Own Supply<br>This situation arises due to a conflict in strategy. Senior Leaders set direction. Loudly , they exclaim, "We will do the impossible. I believe we can do it." Important to note: They don’t actually know how to complete this impossible task. That’s your job. Their job is to inspire to tackle the challenge.<br>Problem is, when it comes to a failing senior leader, we attempt the same move: "I can do the impossible. I believe I can do it." Like above, I don’t actually know how to do this; I’m using the same motivational technique, except the person I’m attempting to motivate is me. And I’m barely treading water.<br>Having been in this state a few times, I can name the signs:<br>I have to-dos to fix to-dos, or, equally possible, my to-do list is becoming stale because of a lack of attention.<br>I’m adding complexity to everything I touch. Or being unnecessarily clever in order to get something done. Which creates more work.<br>The number of prequalified complex disasters showing up on my plate is increasing.<br>When someone else asks about tasks they care about on my list, I keep apologizing and inventing new deadlines.<br>People are no longer volunteering to help.<br>Inbound questions are increasingly inbound critiques.<br>And then Carolyn shows up and tells you that you are the problem.<br>Leaders Fail<br>The first fix is a prerequisite for the other three. You have to admit you are failing, and while that is easy to write, it’s close to impossible to admit because you irrationally believe, "Leaders don’t fail."<br>Of course we do. Constantly. Like, close to half the time. But the reason you irrationally believe this is that you’ve been drinking the leadership juice, which gives you the intoxicating impression that leaders must lead by example, and that means — no failure.<br>You fail. A lot. Most of the best lessons that define you as a leader came from these failures. The process of failing, learning, and improving is the example you want to see, and that means starting by telling someone you know who can help:<br>"Carolyn, I agree. I am failing, and we need to make changes."<br>Carolyn’s posture immediately relaxed because she knew what I’m telling you now:...