Leading with optimism.
Janice, what a moron.
Janice wakes up every morning, dyes her hair green, buttons her purple vest, and heads into work with the explicit goal of ruining your roll-out of a new accounts payable system. “Janice,” you tell yourself, “just wants to watch the world burn.”
Probably not, right.
Unless you’re some kind of cubicle Jesus, at some point in your career you’ve looked at a colleague across the org. chart and thought “what a $%&^ing idiot.” They’re lazy, they’re negligent, they’re jeopardizing the business. The only reason they show up to work is to try to sabotage you and only you in your quest to do some super important thing. And so when Janice asks if you can change the footer format on your TPS reports so that AP Gorilla™ can ingest them without having to buy a separate AP Gorilla™ add-on you drag your feet. You skip meetings. You write “per my last email” emails.
The problem with this kind of cynical thinking, especially in growth companies, is that it’s really unhelpful. After all, startups are nothing if not faith-based initiatives wherein you believe that where many have failed you and your team will succeed. It is a fundamentally optimistic endeavor where everyone - you, your boss, your team - needs to believe that something better is possible and then work together in that direction.
Put simply, where cynical leaders believe that humans are default “bad” and, left to their own devices will bias toward their own narrow self interests, optimistic leaders believe that humans are default “good” and will bias toward doing what’s right for those around them. Just ask yourself:
Do you lead by clarity of goal or precision of instruction?
Do you structure incentives as rewards for success or consequences for failure?
Do you give feedback to help your people succeed or record their errors?
Do you find win-wins with partners or try to overpower the Janices in your way?
Do you distribute praise to your team or seek recognition for yourself?
Do you build products to delight your customers or squeeze them for revenue?
Now I’m sure many of you are reading this thinking “yeah, of course, this is obvious.” First, per the #1 rule of Substack, at least you’re still reading it, which is great for me. But second it’s actually nuts how frequently we encounter cynical leadership and management structures in the wild.
There’s a reason it’s called a North Star objective
To paraphrase Steve Jobs, you don’t hire great people and tell them what to do.
While a cynic might think that their team depends on their unmatched intuition, strategic brilliance and direct instruction, in reality the best leaders leverage the talents of their team to get where they need to go. They set a single, clearly defined objective and then empower their people to go achieve it, bringing to bear the best of their unique skills, creativity, and drive.
And while simple-sounding, taking this approach as a leader isn’t always easy (hence why it’s often not taken). It requires having a great team around you, the confidence to allow them to deploy solutions you might not have picked, and to fail-and-iterate without you immediately intervening.
I remember at DoorDash we were trying to figure out how to get our 1,000s of front-line customer service agents to deliver a uniformly great experience. We tried everything. Scripts. Flow charts. Scorecards. Policies. All totally unsuccessful. There was too much complexity, too many random situations, too many clunky, stilted interactions. What ended up working? We stopped treating our teammates like robots and started treating them like the intelligent, creative, empathetic problem solvers they were. We gave them a very short list of clear North Star principles on which to rely, as basic as effectively “just listen, apologize, and solve the problem,” and it turned out that not only did our CSAT scores go up and costs go down, but we started seeing agents hack together brilliant solutions for edge cases we’d never anticipated.
The much-celebrated “$%^& sandwich” is still a sandwich full of $%^&
The entire history of performance reviews is more or less just 1,001 ways to tell someone they suck.
I joke, sort of, but even thinking back to my consulting days, your weekly, monthly and quarterly performance conversations were always effectively just a run-down of all your $%^& ups (reader, the list was long). And even going in, you always knew the mistakes you’d made, it wasn’t like you needed reminding.
I would call this cynical management. That to get the best from people you must find and stamp out their errors. And only by this repeated wrist slapping will people finally be good, and help you accomplish whatever goal you need to hit.
In contrast, I would suggest there’s a more optimistic and effective way to lead people. And that’s by focusing them on a clear objective and then giving regular feedback and coaching on explicitly how to get there. After all, what’s more motivating, being told all the ways you’ve failed or how you’re going to reach the pinnacle of awesomeness?
First, structure your regular performance conversations around where you’d suggest that person invest to get to the next level and how you’ll help them do it. Maybe they need to work on their hiring, maybe they need to be more data-driven, maybe they need to improve their cross-functional collaboration. Whatever it is, it’s all based on the premise that you see in them great potential and you’re going to work together to bring it out. And by the way this works for the superstar that’s gunning for your job (you should help them get it!) all the way to the C student who’s not quite found their groove (nothing keeps a C student a C student like treating them like a C student).
Second, when you start seeing the person putting your feedback into action call it out immediately. I think there’s some study or something somewhere that says positive reinforcement is like a whole bunch more impactful on changing behaviors than the alternative (there will not be a link or a footnote, this isn’t that kind of blog).
Now, of course, there are times you might have a D student. Those situations are not always terminal but they require a slightly different conversation, still based on the premise of helping get that person where they need to go (it’s sometimes into a different company). It’s usually something like: “Listen Doug, I know that your performance isn’t where either you or I want it to be [there is usually nodding here]. At the end of the day we’re in this together, your success is my success, and I have your back as we right this ship. But for us to keep moving forward together I need a substantial increase in effort/ diligence/ attention to detail/ hustle/ etc. over the next [time period] and a significant improvement in [metric].” It presumes they have high standards for themselves, gives them the security that you’re in their corner, and sets the explicit results needed for that support to continue. I tell you this as someone who’s had this message delivered to me; it very often lights the white hot fire needed for the person to turn things around.
Everyone is the hero of their own story
DoorDash was - and remains - a really difficult and customer service-intensive business. So much so that in my time there we referred to CX as “the end of the river of garbage”. This meant that the lion’s share of my job in leading CX was trying to get my peers in growth, logistics, selection - people who definitely did not have to listen to me - to help me hit my goals, often at the expense of their own. There was, you can believe, some friction.
The cynic looks at this situation and tries to figure out how to overpower the person blocking them. Can you yell, stomp your feet, and intimidate. Can you escalate to a more senior decision maker. Can you throw up blockers of your own to try to extort concessions. In short, these don’t really work. I know because I tried them all.
The optimistic approach, in contrast, starts from the belief that your partner is good and has fundamentally good intentions. A playbook:
Assume the most favorable interpretation (MFI): In a world where true psychos are less than 1% of the population, it’s most likely that the person doing a thing you don’t like is doing so based on their own learnings from prior experiences, the best information they have, and their own current incentives and goals. Once you can view your partner’s actions through their own eyes it’ll be much easier to cut a path to a solution.
Recognize that anger is simply externalized fear: Anger rarely manifests because someone’s a lunatic and just loves being angry. It’s because they’re deeply fearful that your actions will result in a bad outcome for them. After all, every great keyboard battle begins with two people who think the other is standing in their way. Use anger as a map; follow it down to the underlying fear that’s at the root of the problem.
Demonstrate strength through vulnerability: In conflict don’t hesitate to make your own fear explicit. “Hey look, I have a manager who is on me to make this happen, and if we can’t find a solution I am genuinely concerned I’m missing my goal.” People generally want to help others out of a jam; you’ll be surprised how quickly the discussion turns to helping get you what you need.
Reject false trade-offs, seek a win-win: While on the surface it may seem like a professional conflict is zero-sum, in reality, once you dig deeper, there are almost always ways to ensure both parties get the outcomes they need. Simple example: I remember fighting with our growth team to move $5M from customer acquisition to improve our customer service response times. In short we ended up figuring out that we could deploy that money to improve response times and VIP customer retention such that we ended up hitting both goals. But that was only possible by working together and understanding the mechanics of both problems at their root.
Salesforce tower is a giant middle finger
Salesforce, as a software product, might as well punch you square in the face every morning. Write your letters, I could give a shit.
Nothing says “we’re basically the only game in town, we’ll cash your checks forever” like the Salesforce interface. It’s ugly, it’s counterintuitive, it’s unhelpful. You can immediately tell that Joe Salesforce is pretty sure that you’re gonna keep using that trash pile until the lizard people have overrun all our major cities and put Lizard President in the White House. Just keep coming to our basecamp, summer camp, camp camp conference every year, post your #slayforce TikToks with Flubble the Salesforce swamp rat or whatever mascot they’ve got this quarter, and hit the road.
That’s a cynical product. And cynical products - products that ignore their customers in service of revenue - eventually, eventually, get beat. Just take Blockbuster, everyone’s favorite business punching bag. A cynical business doesn’t stock enough Talladega Nights and then charges a late fee when you forget to return their only copy of Green Lantern. Fast forward, I can’t get my 4 year old daughter’s attention away from Netflix long enough to explain what a Blockbuster even was.
Whenever launching a new product or feature, just ask yourself this one question: “Why is this better for the customer, not just us?”
After a couple years of reflection I’ve come to think that Tony Xu, DoorDash’s co-founder, is arguably one of the best CEOs of all-time. And among Tony’s many superpowers - not a sponsored post - is that he is a deeply optimistic leader.
And it’s not surprising. The man decided to build a business squarely on the premise that every day hundreds of thousands of non-employees, absent of 100% perfect information and incentives, would generally take the right actions to successfully deliver many millions of other peoples’ take-out orders. Turns out he was right.
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