However, there are downsides to this as well. One is that you end up only seeing nails (hammers be hammering). To use two tech sales examples, if “your thing” is being data-driven, you risk seeing everything as a data or analytics problem. Similarly, if your claim to fame is building client relationships, then you may miss that a specific opportunity called for making a data-driven argument.

Another risk is it may become harder to accept counter arguments. If your identity gets wrapped up in a particular skill or point of view, when that skill or point of view is no the answer to a problem, it becomes hard to unwind and try something different. It becomes hard to be “dispassionate to the truth” when you can’t take in new information and re-evaluate your perspective.

So does that mean it’s not worth building an expertise or being “known” for something? Of course not. There’s immense value in expertise and having a deep set of skills. There’s value in having conviction and strong opinions which is a prerequisite to building deep expertise and skills. And there’s value in sharing your expertise and perspective with others - I mean, geez, I’m doing it right now.

But holding our convictions loosely is important. When you hold a perspective on how to approach the business, there should be an articulated set of circumstances where you would change your mind. I.E. “What would have to be true for me to no longer think this is a good idea?”

On skills, again, expertise is good, and I’m not saying be a generalist. But, instead, think of yourself as a generalist that can specialize, quickly1.

Okay, so now for the TLDR. Is it bad to have a “brand” for yourself? No. But be careful to not have it become a persistent part of who you are. You may miss opportunities to learn and build new skills and experiences.

Have several, ambiguous goals. This is critical because you want to make sure people are marching in as many fragmented directions as possible. When coming up with goals, don’t worry too much if it’s not immediately clear how it’s connected to the bottom line of the company. When asking someone on the team what success looks like for what they’re working on, hopefully it takes a good amount of time and word salad for them to pull out an answer. Even after all that verbal labor, it’s best that the goal remains little understood.

Don’t execute, and never follow up on progress. Make no effort to follow through on your work. Declare your plan, assign no owners, hint at goals (refer above on ambiguity), and hope things get done.

You don’t make mistakes so there’s nothing to learn. Why have feedback loops to check up on your plan and strategy? What’s good in theory is good in practice, so there’s no need to have processes in place to track progress and revise your plan.

The more people, the better. Have a problem? Throw people at it. Do this consistently and generously. If all goes well, org charts won’t fit on a single page. We don’t want single people to be accountable. In fact, we don’t want to work with the kind of ambitious people that want that kind of accountability. Better to distribute the blame so when things go wrong, there’s no clear person to bring a fix. Will we scare off ambitious, talented people that want to do more work and take on responsibility? Sure. But remember, building big teams strokes our egos, and big egos are the keys to success - not accomplishing our goals that, hopefully, remain a mystery.

Solve everything and do not prioritize. Pay lip service to prioritization, but never cut anything out. Never say no - solve the next problem that comes up regardless of whether it actually helps achieve your goals. This practice is easier the more ambiguous your goals are (please refer back to the top). Substance over quality is the name of the game, and make sure to create the incentives come performance time to not review impact.

Remember, principles are merely hobbies. Dump them immediately when times get tough. Set your team’s principles, post them everywhere and, when possible, virtue signal. But remember, when times get tough, dump them and chase the good vibes.

Again, this is what not to do.

Now, this is difficult to do because I’m pig-headed, but it’s something I’ve tried to work on over the years. If I can articulate some else’s point of view in a way that they agree with me, or (and this is the bullseye) make a better case for what someone is advocating it tells me two things:

1. I’ve understood their perspective clearly.

2. I can now properly identify the differences between my point of view and someone else’s.

Why is this an important exercise? Listening to a person’s line of thinking and, if necessary, doing the research to understand someone’s opinion, is a way to build trust with the people you’re working with. After all, it’s hard work to meet them where they are.

Now, if after being able to properly represent other peoples’ points of view, I still feel like I have an idea that’s worth discussing, then I know I have a point of view worth holding. How hard I hold the line on my point of view really depends on the stakes of the decision being made. This doesn’t guarantee that you’ll come to the best decision each time or come to a perfect agreement, but it improves your odds and also builds trust amongst the team.

As the title suggests, this is simply steel manning opposing points of view. I also know that folks that have worked with me reading this and thinking, “HEY HEY HEY, he doesn’t always do that!” To that I say - these posts are aspirational. Ha.

Here’s something I’ve come across while running a sales team. During times of uncertainty and stress at work there is a conversation amongst managers about the trade off between transparency and optimism. If you give teams the for realsies talk, they’ll lose focus and motivation. If you paint a picture of roses and pink unicorns, they’ll be blind sided when tough decisions are made. So optimism and transparency can feel in tension with each other. But from my experience - being forced to choose either transparency or optimism is a false dichotomy. Why?

First, it’s good to understand why we want both. Optimism keeps teams focused and motivated to do the job. It also feels good to deliver a positive message. Next, transparency means being honesty, and that’s an ethical good. Also, transparency builds trust. When you’re showing your cards to the team, you’re putting yourself in a vulnerable position, and people appreciate that.

So when we talk about optimism and transparency, we want to keep teams motivated, and we want to build trust. How do we do this during tough periods at work? When trying to strike this balance, it’s helpful to turn attention to yourself. It’s helpful to ask: Why are you showing up to work? What compels you to work hard in circumstances that may not feel great? In most cases, we’re faced with the same set of tradeoffs and bad news we’re trying to communicate to the team. When times are tough, you’re doing an implicit calculation on whether it’s worth showing up to work.

Here’s a few examples of how those calculations shake out:

• Other teams got an investment (e.g. headcount) that you feel you deserved. But the honest truth is, even without that investment, your team can manage. It hurts to not get the prize, but it’s important to remind the team that you still have what you need to succeed.

• Cost cutting has made things feel tough when compared to prior years. But when you look at your options today, where you are is actually pretty good. Painting the macro picture and laying out the trade offs can help contextualize why certain types of cost cutting might be necessary. Don’t expect anyone to be filled with joy when benefits, perks or raises are pulled, but at least they understand the need to cut costs.

• It hurts when you are on the short end of a decision that was made. But take a moment to stop and think about what decision you would have made if you were the decision maker. What are their incentives? What decision do they have to make based on what brings them success? The outcome might be tough, but it’s fair. When that’s true, you typically feel it in your bones. And when you do, it’s easier to move on.

Understanding what keeps you going and translating that for your team is a great way to be honest while still finding the silver linings to motivate your team and stay focused.

I’ve worked at Meta for 13 years, and have been running the US Financial Services advertising team for 8 of those years. While the team existed prior to me taking over, after 8 years, it feels like I’ve built this ~50 person team from the ground up. We’ve had successes and failures, and despite my bad judgement (according to my wife), the successes have managed to outnumber the failures. There’s a lot that goes into delivering good outcomes, but building a good culture is foundational. Culture is made up of values, and good values builds good, durable culture.

Looking back over the years, below are some of the values that the team has embodied to create a culture that has bred success while also having fun along the way.

• Work is Serious: Of course we want to have fun. Enjoying work and having fun comes from knowing you’re working with 1) high-caliber people, 2) on worthwhile problems, and 3) selling solutions that work. The common refrain when things get too intense is “we’re not saving lives”. Sure. But our ad solutions are helping to build the next generation economy. We give our clients tools and distribution channels to create products and services that can appeal to niche audiences. It’s important work, and we take that seriously.

• Details Matter: Details aren’t above anyone on the team (except when I play fantasy football - I’ve won 8 years in a row; just trust me, it’s true). Understanding the details is a way of building empathy for those that use our products, dashboards, and solutions.

• We Build: It may seem strange to call upon sales people to build. While strategy is important, execution is what leads to a win. When we don’t have an answer, we build. Whether it’s new solutions, go-to-market materials or thought leadership, building is how you generate value. It’s what keeps the work we do plus sum and not zero sum.

• Client Goals are our Goals: We take our clients’ goals seriously. Progress is never made unless our clients succeed. We are at the service of our clients and the industry, which sometimes means shelving short term wins to drive long term value. We build close, trusted relationships, and this is part of our competitive moat.

• Big is Not Big Enough: When we work with clients or solve industry problems, we go deep. The types of relationships we build and problems we solve take time and require rigor. That means we need to work on opportunities that yield exceptional leverage on our time and efforts. We only work on massive, ginormous opportunities. As an aside, I just discovered ginormous is an actual word.

• Stay Small: The larger the team the more organizational overhead is introduced. While sitting in dozens of alignment meetings is obvi a lot of fun, I’ve found a few exceptional and passionate people against a problem will always beat out a larger group that has those same exceptional people in it.

• Focus on Value: Everything we do drives bottom line value. This can take the shape of revenue or a second order metric tied directly to revenue. This means it’s not enough to build the “best practices” deck. It needs to explicitly drive results.

• Dispassionate to the Truth: We obsess over understanding and delivering reality. This means approaching our environment with curiosity and not fear. It means dispassionately reviewing data to better understand how we operate. It means transparent leadership, because we can handle the facts and take nuance. It means taking feedback as an opportunity to improve. My team does this every day when they tell me I’m not funny. Though, admittedly, I haven’t found a way to improve it.

• Your Win is My Win: We play plus sum games, not zero sum. A teammate’s success is one we all celebrate and share. We root for our colleagues because when they accomplish something, it’s a win for all of us. Similarly, when someone accomplishes something, they did not do it on their own. As Newton said, each of our successes “stand on the shoulder of giants”. In other words, don’t be a jerk - share the love.

I revisit these values often and anticipate revising them as times change and I learn more. If you’ve gotten this far, I’ll take some comfort knowing the planet is in just a little worse shape than it was 5 minutes ago.