E11: Alignment is completely overrated - with Taylor Otstot

Alignment, completely overrated.

We have to get aligned on the goal, on the plan, on whatever else. And the challenge with that is more times than not, there is hidden descent that's gonna bite us down the line.

What's one mistake that you see finance teams make over and over again?

The one they make the most often, they latch on to the idea of, okay, we have to push back on this rather than we have to help the team course correct.

Some sometimes less is more.

A hundred percent. Yeah. The the power of subtraction is amazing. More times than not, it's actually what can you take away to create the capacity, the resourcing that you need. When you're aligning on something, you go around the room and have every person say one to ten, how confident are you? But the trick to this is you say, and you're not allowed to say seven.

What's one trend in finance and accounting that you believe will shape the next five years?

I'm gonna say AI, but I'm gonna specify what I mean by that.

You're listening to the 10x Finance podcast. Quick, candid conversations with the people shaping modern finance. Hosted by Albert Ghazi.

Hello, everyone, and welcome to 10x Finance Podcast, where we dive into the real challenges and opportunities shaping modern finance teams. I'm Albert Gozi, co founder and CEO of Aleph, and today, I'm joined by Taylor Ottstott, VP of Finance at Dashlane. Taylor, great to have you here today. Are you ready to jump in?

Adi, thanks for having me.

Yeah, a pleasure. So, what's your hot take?

My hot take? Alignment? Completely overrated.

Tell me more.

So, look, more times than not, we see our role in finance of to get everyone aligned. Right? We have to get aligned on the goal, on the plan, on whatever else. But that starts to get conflated with, we're just making sure that we just need them to agree. And the challenge with that is more times than not, there is hidden descent that's gonna bite us down the line. So, my argument would be is that the goal really isn't to get everyone just nodding, it's to surface every concern, regardless if it's legitimate. Get that rooted out before you commit, because buried dissent never stays buried.

What do you think are, maybe the first thing that comes to mind as you were, like, saying your take is an advice I got that once says, you know, you should never average out advice, because, like, the advice of different people that have different opinions makes no sense, right?

Like, you actually want so, like, do you think it's related, and like, do you think it's like, you know, makes sense with what you're saying?

I think it's something like that, and the thing we have to think about, right, is it's natural for all of us to not be the one person that raises their hand and says, I'm not comfortable with this, but inevitably, like once the budget gets locked, someone goes and back channels and says, This goal's way too ambitious. We can't possibly do this. Now you're dealing with the problem, but you're dealing it with less time.

Idea here is you ultimately wanna root that out early in the process so that even if someone is still not fully comfortable, they've been heard, and there's so much power in someone at least knowing that their concerns were heard and considered before we walked the path.

How, where my mind goes is, how do you create, you know, like a lot is dealing with people and, you know, there's a lot of subjectivity. What are some techniques that you use in order to generate that?

Yeah, so I think there's a varying way you can do it, but if you're new to this or you're uncomfortable with seeking out someone to say that they're uncomfortable. One trick that I found really helpful is when you're aligning on something, you go around the room and have every person say, like very typical, one to ten, how confident are you? Ten, sure thing. One, absolutely not, right?

But the trick to this is you say, and you're not allowed to say seven. You've actually completely removed seven from the equation because seven is this line where everyone feels comfortable putting it, even if they're not comfortable, because they're saying like, oh, it's like above five, but less than ten. What that does is it actually bifurcates your population. It's almost like an NPS score, right, where it's like, hey, eight and ten, they feel reasonably committed, and no one ever says ten, by the way.

So it's really eight and nine. So eight and nine are your promoters, and then everyone else are like the neutral, the detractors, and so by doing that, you can then open up the conversation and say, oh, that's interesting that you're a sex, why are you a sex? And people can still feel comfortable saying six, because they're not saying four or three or two, right, hardly anyone ever says that, but now you're giving them an opening to talk about something, but you created a safe space where they're not undermining whoever is kind of helping to align on the plan. So that's one trick that I learned from an old CEO of just go around the room, every single person has to do it, and you make it very clear, seven is not allowed, and you create that delineating line, and then you go from there.

There's other techniques as well, but I find that one is actually the most helpful, and it's the least intrusive, it's the least combative.

I love all of those, you know, team dynamics. I think I nerd out a lot on decision making. So I'm gonna ask you one or two, like, more, you know, couple clicks on the actual method. Do you do it blind, seeing no one should know each other's ratings before they are revealed, or will you be more, okay, you know what, we go around the room and people can know where everyone else stands?

I think it depends on the situation. So more often than not, I've seen it be in the room, just because you want people to get comfortable to start bringing these things up in a group, right? The risk of constantly doing it with a pole, if you do it blind and there's only one sex, that person still has to step up, but now it feels like it should've been a secret, so you're probably not gonna get the whole thing, but also, what you wanna do is you wanna train your stakeholders, you wanna train your partners to do this naturally versus doing it prompted, what I've found is a lot of people who had other kinds of finance partners in the past, they know the game.

I just have to commit to this thing, and then I can figure it out once it launches. You wanna tell them you're playing a different game of, I don't want you to commit something that you don't believe in. I wanna be there to help you figure out how to get this to something that you believe in, whether it's more resources, more time, whatever. We can figure things out if we're not already in the midst of a plan.

So I think doing it live, as uncomfortable as it is, you may not get the full answer the first time, but you're starting to train everybody to speak up when they have a concern, and hopefully get to a point where that never comes up, because even if it does, someone says, Hey, I've already put out here that I'm a six, and here's why.

Yeah. So, you're saying is, do it a few times, you do it once, you do it twice. At some point, people are, you know, I know that Taylor's gonna do it at the end. When we all think we're done, we know Taylor's gonna ask them a comfortable question, might as well just, you know, say it upfront.

Might as well amount to it, yeah, right? Because what you're effectively saying is, look, I'm not going to accept the excuse six months from now that this was too ambitious of a plan, like this was always a stretch goal, we said, no, no, you said you were a nine. It's like, that never came up, so that's a different conversation. So you're allowing for all that stuff to get front loaded, and yeah, you're effectively training people how you want them to work with you and how free you want them to be with you. And, you know, for us, right, because we're ultimately thinking about not just this particular part of the plan, the whole portfolio of plans, what cushion we need to have. Getting that information faster allows us to think of what other things we need for optionality.

I really like the technique as a way to surface descent in some way. You started with alignment is overrated. Would you go so far as to say, even after a few rounds, if there's sixes or less, you would be okay with that? Are there some decisions for which you know, you want to do enough rounds that everyone is an eight or a nine, and some where disagree and commit is the outcome? How you think about one versus the other one?

Yeah, look, I think you have to allow for sixes and below sometimes, depending on who it is, right? So if it's your head of sales, and they're a six on their sales goal, you're like, okay, that's probably not a good answer, right? Like, we need to rethink what other levers do we need to put in the plan, because you're consistently saying you can't hit this number that we originally have, right? But if it's somewhere deeper within the org, one, that effectively is the leader of that team to kinda help figure out, right?

And two, some of the things they're concerned about, they're probably legitimate, and it may take time to overcome that, right? It could be little things where it's like, hey, I don't have enough salespeople to start the year, I can't possibly have this number, but it could be a broader, hey, we're launching a new product, we don't know how it's gonna work, and you go, yeah, I totally get that, we don't either, and then it becomes more about, I don't need to get you an eight or a nine on this aspect of the plan, but I need to get you more comfortable that there's other things going on that are gonna help compensate.

And more importantly, I want you to now, because you're a six, let us know if you're still a six three months from now, right? If you try to force everyone to an eight or nine, you're effectively just creating the same issue of you're just trying to force alignment, but you're making it seem like it's more collaborative than it is, and everyone will figure that game out quick. But if you allow everyone to be like, look, be honest where we are, we're still gonna have to disagree and commit at some point, right? Sometimes we have to take on an aspirational goal, especially if you're in the environment that we're in where it's like, you know, DCEP, you act like you gotta grow.

It's okay to be a little bit uncomfortable, but let's think about where that discomfort comes from and let's see what things we can do to help, secure it, can create more scaffolding, and again, if you're doing this multiple times with people, they start to get more comfortable with their own intentions, because they may say, Hey, I'm a six, I'm a six. If they start hitting their goals more times than not, they may start realizing, Oh, I'm just too conservative, And like, having a rating, having a score to be able to look back on and say, Where do you typically sit? Like, the inverse is true of rate too, right? Because if you're consistently eight or nine, and you miss a lot, now you can sort of say, Hold on a minute. Last three times, you said you were eight or nine, and in last three times, we missed by twenty percent. Like, talk to me about why this time is different.

You're talking a lot about the, okay, let's track the rating over time. Let's go back and say, hey, you know, why are you disagreeing? You said you were an eight or a nine. How do you do you have a Excel or Google Sheets where you are like, okay, this is decision, you know, this is what Albert said. How do you operationalize some of that? Is it like notetakers today, very popular, you know, person in every meeting?

I think in any age of today, it's probably a little bit easier. I would say realistically, when we're doing this kind of planning, it's more infrequent, so it's more things just kinda having in your head.

And again, early on, it's more about the process of creating the environment. I think this phase would be, hey, you're doing this a lot, right? If you're in an environment where it's like, hey, we're constantly re forecasting other because we're growing exponentially more than we thought we would, or we're missing our plan, these are tactics then you can introduce underneath it, and then you can start thinking about how accurately do you wanna track it. But I think the other thing to think about here is when you start asking people to score themselves, they're putting a number against it.

They're starting to think about their own judgment a little bit more than they would historically, right? Because you're drawing a line between Hey, are you sure or not? And you're actually saying, Let's actually quantify what that means. One of my absolute favorite studies I've ever seen, it was a HBR article, and they did a survey of how people interpreted language, right?

So it said, if you saw the word never, what does never mean to you as a percentage basis, right? And most people would say zero percent, but some people say ten percent, or Some people say always is eighty percent, right? And so you start to realize, oh, these words are kind of meaningless because you may say, hey, I am sure this always happens, and if it's eighty percent of the time, you feel like you're right, and I'm thinking it's one hundred percent, I'm going, no, this didn't always happen, it didn't happen this one time. So by putting it on a numerical scale that is consistent across everybody, you're kind of bringing everyone to a common language so that we're making sure that we're not misinterpreting each other.

I can see our audience that is mostly, you know, finance people, very analytical, agreeing with your preference for numbers over words, you know, to express this.

Taylor, I could keep going forever. I could ask you more questions. We want to make these short in nature. Are you ready to move to our rapid fire questions? Let's do it. All right. So, first question is, what's one mistake that you see finance teams make over and over again?

I think the one they make the most often is they latch onto the idea of, okay, we have to push back on this, rather than we have to help the team course correct. Right? I think a lot about in terms of yes and versus no, right? Which is, hey, what are we ultimately trying to solve for? And more times than not, some combination of context and guidance will help someone get to the right answer, versus trying to make yourself the point of friction.

Yeah, very, very much agree. What's one piece of advice you would give other finance leaders scaling their team?

Yeah, you know, I think the most important thing is to remember that these are humans, and they're going to do human things. They're going to make mistakes. They're going to have fears and concerns and be excited, and it's really easy for us to kind of retreat to the numbers and say, Look, we're just gonna talk in facts, right? We're just gonna be as unbiased as possible, which in certain places makes sense, but there's other times you have to look at your role and say, Hey, my role in this particular meeting is to motivate. In this particular role or in this particular meeting, my job is to make sure people feel like they're safe. And you have to realize that sometimes if you tell the numbers, even if it's the same numbers, you tell it one way, it reduces that safety, which is ultimately gonna have an impact on performance, and I just don't think we appreciate more often than not how much we can help or hurt the team simply by the way we phrase things.

Yeah, it's crazy how obvious it is that it's all people and taking that into account, and how often it gets forgotten, so I agree. What's one trend in finance and accounting that you believe will shape the next five years?

Yeah, so, I'm gonna say AI, but I'm gonna specify what I mean by that, because the thing that I'm starting to notice more and more is AI has basically shifted the constraint from the cost to produce to the cost to consume, right? So it has become easier than ever to run an analysis, to pull data, do whatever, and historically, we as finance teams would say, You know what? This particular thing, it's not super material, or it's not part of our big strategy. I just don't have the resources to do this.

Suddenly that's not true anymore, and if we're not careful, we start running a bunch of stuff and basically you have the finance equivalent of AI slot rolling through the organization, and now what you've done is you've moved all of that effort to figure out like, what do you scrutinize of what gets done to what gets reviewed? And the risk that we run then is like, we're gonna review a bunch of stuff that ultimately doesn't matter, rather than using all of this capacity power that we just gained to really leverage against the things that do matter.

Yeah, sometimes less is more, especially when it comes with.

Percent. Yeah. The power of subtraction is amazing. Right? More times than not, when we think about how to solve, we think about more people, more money, whatever. And more times than not, it's actually what can you take away to create the capacity, to create the resourcing that you need.

Taylor, it's been a pleasure to chat with.

Thank you very much for the time. I appreciate it.

That's it for this episode of the 10x Finance Podcast, bringing you sharp, real world finance conversations powered by Aleph.

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