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253. Why We Question Things: What the Enneagram Reveals About Skepticism at Work
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Why do some coworkers question everything? And why can their questions sometimes feel like criticism, resistance, or a lack of trust?
Inspired by a recent conversation between Adam Grant and Brené Brown about the Enneagram, we're exploring skepticism through a different lens.
What if three people questioned the exact same idea, but for three completely different reasons?
In this episode of Enneagram at Work, we're looking at how Enneagram Types 1, 5, and 6 might approach skepticism, what's potentially motivating their questions, and how understanding those differences can help us communicate and collaborate more effectively.
We'll use a common workplace scenario (introducing a new process) to explore how questioning can be driven by a desire for improvement, a need for information, or a concern for trust and security.
And while any Enneagram type can be skeptical, these three examples give us a useful starting point for getting curious about what's underneath someone's pushback.
In this episode, we explore:
Type 1: Questioning to improve: Why a coworker's attention to errors, inconsistencies, or standards can sound like criticism when their intention may be to make something better.
Type 5: Questioning to understand: Why asking for more information, evidence, or processing time doesn't necessarily mean someone disagrees.
Type 6: Questioning to establish trust: How anticipating risks, questioning assumptions, and wanting contingency plans can strengthen a team's decisions.
Why we often mistake skepticism for negativity, resistance, or someone questioning our authority.
What each of these coworkers might need before feeling ready to move forward.
Three simple questions that can help you respond to skepticism with curiosity instead of defensiveness.
Three questions to try with your team:
What about this doesn't feel right yet?
What additional information would be helpful?
What concerns do you have that we haven't addressed?
You don't have to know someone's Enneagram type to start asking better questions.
The takeaway: Skepticism isn't always resistance. Sometimes it's someone noticing something important that the rest of the team has overlooked.
The next time someone challenges an idea, try asking one question to better understand their concern before jumping in to defend your position.
At Enneagram MBA, we help teams turn personality insights into practical conversations about communication, collaboration, and workplace relationships through facilitated workshops, leadership retreats, and team development programs.
Welcome back to another episode here on the Enneagram at Work Podcast. I'm your host, Sarah Wallace, founder and managing director here at Enneagram MBA, which is a team training company where we get to bring the Enneagram into the workplace through various standalone workshop experiences. This time of year, we do a lot of off-site retreat Enneagram experiences as well as team development programs that extend over a specific amount of time. And if you are new to the Enneagram at Work podcast, welcome. I don't want to say this is definitely a standalone episode. But if you haven't yet caught the episode from Monday where we talked about Adam Grant's skepticism of the Enneagram and if it is warranted or not, um, that episode inspired this episode today. So that might be a good one to go back and listen to after this one. Kind of see where it where it came from. But if you are a returning listener, welcome back. And we're gonna pick back up from where we were on Monday. And regardless of where you are, quick refresher on a recent Curiosity Shop podcast with Adam Grant and Bernee Brown. They were talking about Adam's skepticism of the Enneagram. He has agreed to take the assessment. Um, they're going to be showing sharing his results in a future, it sounds like 2027 podcast episode of his podcast, Rethinking, um, where he'll be having Bernie Brown join him as a special guest on that one. So I'm I'm excited to see what comes of that. Keep an eye out for that one. Um, today, though, we're going to talk about uh skepticism specifically. So I thought Adam had shared, he was willing to take the assessment. Brene had said she had some ideas, I had some ideas too, based on the little I know about Adam from that podcast and some other podcast interviews. I follow him on LinkedIn. So by no means is this necessarily a fair or accurate uh guess at Adam's type, but I thought, okay, this could be a fun um channel, fun inspiration uh for this topic around skepticism. Now, of course, all types can be skeptical for a variety of reasons, and any person can be skeptical outside of an Enneagram description. Um, but because this is the Enneagram at Work podcast, we're gonna look at this through an Enneagram lens and we're going to play to the stereotypes just a little bit, um, not to label anybody, not to be able to predict anybody's behavior, but just to kind of give a couple different examples of where skepticism might come from so that we can better understand our teammates. And instead of trying to convince them when they're feeling skeptical, get a again here. This this uh theme of getting curious comes up yet again. Um, and by by sharing it kind of in this way, we have some um some prompts, some some containers to kind of think about why might why someone might be skeptical. Again, this is not a if you are type one, you're gonna be skeptical for this reason, you're gonna be skeptical for a lot of reasons. Um, but yet again, we're just offering some Enneagram theory here to prompt some curiosity to go back and question, uh, start a question with a coworker, maybe even self-reflect on your own skepticism. And um, I'm using the three types that I think Adam could be. Now, he could be something that's not this because I don't know Adam well enough. He could end up being a type eight, he could end up being um a type two, you could, you know, any type you could end up being. Um, so I I don't know. Um, but just like I said, based on that little, the little that I know about him, I thought, you know, um, I think this there, I think there is some validity to him being potentially a type one, striving to feel perfect. We're gonna talk about the skepticism around there. Uh, potentially a type five, striving to feel detached and and what that might mean. And then uh potentially a type six, which I think is has a reputation stereotypically for being skeptical, uh, but they by no means have a monopoly on skepticism. So um I thought let's let's use that hypothesis and talk about skepticism in the workplace and imagine for a moment that you're in a meeting presenting a new process to your team. Uh, three people are pushing back and start asking you questions from the outside, they all might look a little skeptical. You might even experience them as a little difficult. Uh, but what if they're questioning your idea for three completely different reasons? And so that's what we're gonna look at today. We're gonna look at three hypothetical coworkers. The first one is gonna be your type one, who might be concerned that the process isn't being done correctly. I'm also gonna introduce to you coworker number five, who doesn't have enough information yet to evaluate it. And then your third hypothetical coworker is type six, who wants to know what could go wrong and whether this plan is dependable. Does it have a backup plan? Do we have some sort of contingency plan? And so uh we're gonna look at this. And the I don't think that the most interesting question here is what type is Adam Grant, but um, just to start to get an idea of the different reasons people might question things in the first place. Okay. Um, so our type ones, according to the awareness to action framework, they are the strategy they use most often is striving to feel perfect. So they're questioning maybe to improve something, to improve the process, to improve maybe the thought process, the decision-making process here. So they might ask something like, is this the right way to do it? So possibly underneath that question, their underlying motivation um is probably gonna be a pretty strong sense of integrity, um, improvement, very improvement-oriented. We always talk about how the ethos of the type one a lot of times is that good to great book. Uh, and um, what else might be under that motivation is the wanting to be in alignment with their own values and internal standards. So this questioning, this type of questioning and skepticism might show up in the workplace, and it might look like this person notices inconsistencies and errors. They might push back on shortcuts or poorly defined standards. Uh, they might look to um improve things, even if something's already working. This is I just need to, it's good, but it could be great, it could be even better. And they could sound a little critical, even though I think most of them would say their intention is to be helpful and not to be critical. Um, I think a lot of times the intention is good for most of us, and then just how it gets delivered or what the other person hears based on their own lens of the world, um, they can hear something different sometimes. So, a workplace example of this might be you have the leadership who introduces a new onboarding process, let's say the type one immediately notices there are three inconsistencies between the proposed procedures and company policies. So, what your coworkers might hear in this situation is they are finding fault with everything. But what might actually be happening is the type one thinking, hey, I I just want this to go well. I want us to do this well, and I can see so clearly where we are falling short. So in this situation, I think a a useful takeaway is to ask, okay, what um, okay, type one coworker here, um, what standard or principle do you think is being compromised? And as much as you can as the the leader, um, make room for those improvement suggestions. They they might have a really great idea. Um, there might be something in all of those suggestions that is helpful and needed and a good catch and something that the team needs to know about. Now, again, type one does not have the monopoly on asking these types of questions. They do not have the monopoly on integrity and um standards and values, but this tends to be a strong focus for somebody who is looking at the world through a type one lens of striving to feel perfect. And this makes sense. Someone who is striving to feel perfect, well, they're going to notice the imperfections in themselves, um, in processes like this, in the group, and you know, what the company, the direction of the company at times. And again, it's not necessarily from a place of negativity. It's I'm being skeptical or I'm questioning because I want to get this right. I want it to be good, I want it to be perfect. Okay. Um, the other type, I thought, oh, uh, potential skepticism coming out here might be the type five, who, according to Awareness to Action framework, is striving to feel detached. And this person might be um, with their lens of the world, might be questioning to be able to better understand. So listen, I just, I'm just I have a few questions. I'm not saying you're right or wrong. I just don't have enough information yet to even know that. So um they they might be asking themselves, well, well, do we even do we even have enough information to make a decision if this is the right or wrong way to go? So potential um underlying motivations here might be around um wanting to acquire more knowledge, wanting to be make sure that they um and the team and the leadership team and the organization is capable and competent. Um, and they are also adequate adequately prepared based on having all of this research and information and then having the time to process it and look at it, analyze it, and kind of make a decision then based on all the information and analysis. So um, questioning for the type five here might show up as they want to understand how something works before committing to it. Okay, you're saying we're gonna do this new process. Again, not disagreeing, even though it might sound like it. Um, I'm just trying to understand before I'm before I say yes or no here, that yes, I agree with this or yes, I'm in. Um, they might ask detailed or highly specific questions to get more information, to be able to get more information. Um they might be a little uncomfortable making decisions without what they feel like is enough information. Um, we were talking in an episode last week about the type five specifically, um, and how sometimes people might think that they are aloof or not paying attention in a meeting, but so much is happening up in their heads. They're not gonna typically be super emotive or have a lot of expression, facial expressions. Um, but so much is happening in their head, and they would say, Oh no, I'm I'm very, I'm very engaged. Um, I'm just taking it all in. And then I might need some time to process it. So one of the tips that we talked about last in that episode last week was around if you're going to expect some sort of answer or people to share their opinion as much as possible, give people a heads up ahead of time. Um, I guess that's what that means, a heads up ahead of time to um think about what they might say. And that's gonna be really beneficial for someone like a type five. Um, the same onboarding process, let's say, is presented to the type five. And the five, though, may want to know how the technology is gonna work, uh, how these proposed changes are going to impact what is currently there, what's the what's the current system being used? Um, and then what data supports the recommendation? Are we just going off a gut feeling here? Are we going off you you're excited about this? We're we're get we get to try a new technology. This is exciting. So we just want to change something for the sake of changing. Um, they're really gonna want to understand not just details about what is being changed, but why? Why do we think that this is a good idea? So a coworker, you know, might hear these questions from a type five and think they're overcomplicating this. It's not that difficult. It doesn't have to be this complex. Um, but the type five might be thinking, or maybe they say, you know, I I just want to understand what we're getting into before we make a decision. I mean, I think that's that's really fair. Um, I know that there are some of us on the Enneagram that have a tendency to kind of jump into it and figure it out along the way or figure it out on the way down. And that absolutely has a purpose and can be a huge benefit. And then other times we need some of this, like let's slow down, let's understand what's the data behind it. Um, why do we think this is a good idea? Is it just because we're excited today or what what's behind it? Um, and so a practical takeaway here for better understanding this type five, striving to feel detached teammate might be what we what we typically talk about is share context in advance when you can. Um, to give them time to process and to be able to show up, you know, with a little bit more confidence, with a little bit more understanding. Um, as much as you can answer the their questions directly and give them time to process the information. You know, you can say this is kind of where we're headed, we're gonna talk about it more next week, but wanted to plant the seed or wanted to give you guys time to think it through, come up with questions, share your thoughts and opinions. We'll be talking about that next. You know, do what you can um to give them that space. And then the last type, I thought, oh, maybe um, maybe Adam is maybe Adam could be this type. And I the this type has the reputation for being skeptical anyway. Um, is the type six striving to feel secure? Again, that makes sense. Somebody who's striving to feel safe and secure, it makes sense that you would be a little uh skeptical. Um, it makes sense that you would be looking to establish trust. And so the question here from our type sixes might be have we thought through what could go wrong? And then I also think that they're going to ask something about who is recommending this? Who is telling us to do to change this process? Who's saying that we need a new process? Can can they be trusted? Do they have our best interests at heart? Um, is this a person that I can trust, that I can feel safe and secure around? Um, and so some things that are might be potentially underneath that question, some underlying motivations is the need for the need and want for security, um, the the need and want for certainty as much as possible. And then just trying to understand who and what to trust. So, some examples for how this questioning might show up from a type six, striving to feel secure. Um they might want to test those assumptions and be on the lookout for vulnerabilities. One of their superpowers is their ability to see and assess potential risks. And again, my gosh, we absolutely need this person on our team. Um, we need we need everybody. Uh, we need a mix of people who are gonna push forward. And then we also need a mix of people who are going to ask the questions that might slow us down a little bit in the moment, but might actually be able to help us move faster because we're removing the roadblocks and obstacles now. Um, they might raise questions around contingency planning. Do we have a backup plan? What happens if this doesn't go well? What happens if this doesn't go like we thought it might? Um, they want to understand who is accountable if the plan fails. And then they may challenge authority um or seek reassurance from authority, uh, depending on the situation. So they have uh kind of uh, we joke sometimes about sixes saying, Don't you dare tell me what to do, but could you also just tell me what to do? So it's uh it's very much a push-pool. I can relate to that as well, but uh that sometimes we'll just we'll give our sixes a hard time on that. Um a workplace example here is we're you know, we're talking about this new onboarding process. Let's say the six is going to ask or might ask, you know, what happens if the onboarding timelines slip? Who is going to be responsible when something goes wrong? Um, do we have, do do the, does the team in place that is responsible for this project do they have adequate support? Um, do we have, you know, a backup plan if the if this does uh start to get behind schedule? What does that mean for for other things? Um a coworker might hear, oh, you're being so negative. All these questions, you're such a Debbie Downer, such a negative Nancy. Um, but you know, internally they might be actually thinking, well, I just want to know that we're prepared before we move forward. Again, very fair, makes sense. I like this energy. I I also was uh would appreciate this. Um, so a practical takeaway here for better understanding this person might be to treat their uh risk assessment as a valuable contribution and not resist it so much. I know sometimes, especially when we feel like, okay, we're in charge of this project or this is, you know, we're leading this team, it can feel like they are questioning my authority. And, you know, our egos can kind of get in that a little bit. And I, you know, I absolutely uh can can relate to that. That has happened to me before. So I, so I understand that reaction. Um, but ultimately when we really start to understand this teammate, we find out, oh my gosh, they care. They actually really care, not just about their own safety and security, but for the team's safety and security and and want the team to be okay. Um, and so we want to look at how can we make responsibilities and contingencies and decision making processes more clear. And when they're not, to be open to, or when they're not for. A person such as a type six, um, to be open to answering those questions again, like the five, as directly as possible and and being patient and making the time to answer those questions, um, to get them on board, to help them build up that trust so that they're able to come along and we can all kind of move forward in it a little bit more smoothly, maybe with less friction. Uh, so you know, here we have again three potential types that might be skeptical in the workplace, and three potential types that might be fueling Adam Grant's skepticism of the Enneagram. Um, and and his skepticism and questioning of a lot of things. You know, it's just not, it's not just the Enneagram that he's kind of poking holes in. This is this is, I think, a pillar of his work is to question, uh, is to question things. And so uh, you know, what what is behind that? I don't know. We'll see with that specifically. But um for our specific type one, type five, and type six teammates, um we just might be open to uh questioning where we think that they're coming from and and get more curious. So for our type one, um if we think, okay, we know this person, they said that they have a type one, or we're we're picking up on some of those type one tendencies about getting it perfect, right, good, and high integrity, making things better. Um, they might need from us before moving forward confidence that this new approach, this new process is going to meet important standards. It's going to be an alignment with our company values, um, whatever that might be. For a type five, what they might need before moving forward might be just sufficient information and time to understand the decision process behind the decision. What is the data? What's the information? What's the research? What's the analysis behind why we are doing what we're doing? Again, not disagreeing with it necessarily. I just want to understand a little bit more. And then for our type sixes, they might need a little bit more um confidence that the any risks that might come up have been thought through and that contingency plans are in place if something goes off the rails, something doesn't go well. Um, and so as much as you're talking about the plan and the new process, also mentioning, oh, this is our backup plan or this is what might happen. So obviously, all of these are just tendencies, and I am being very stereotypical with these specific types. Um, these are not tried, you know, tried and true characteristics of everyone, five, and six. Any type can care about accuracy, any type can care about information, any type can care about risk. Um, but it's meant just to kind of zoom out on our skeptical teammates or the moments when they are skeptical. So um, teams, you know, teams can get into trouble here when they see someone's behavior and then we kind of assign our own meaning to it, like they're being difficult, like they're questioning my authority, like they're being negative, like they're being critical. Um, and so it can seem we can experience those their questioning as resistance, um, as negativity, um, as you know, a way to derail the process. Um, but potentially what could happen if we got a little bit more curious about what's underneath those questions and that skepticism and what the person is actually needing to hear or see. So I think I'll leave you with three questions that we can use with our colleagues who might identify as a one of five or a six, or who might um have a tendency to be more skeptical. Um, you could ask them something like, what about this doesn't feel right yet? What what doesn't feel right yet? Uh what additional information would be helpful? And the third one is what concerns do you have that we haven't addressed? And that's a great one because there's probably going to be something. And so that's a way to um just enhance your thoroughness of this process that much more. Um, it's a way to have all of these are a great way for people to feel heard and cared about. Um, even if they might disagree, I think you taking their questions, taking the time to answer their questions and taking their skepticism and concerns seriously is going to mean a lot. And you're gonna build that much trust. And, you know, maybe you disagree, but that doesn't mean that you still can't respect each other, that you still can't trust one another, that you can't work together for the future. So uh you don't have to know as a leader, as a teammate looking to be supportive, you don't have to know everyone's Enneagram type to start asking better questions. So, you know, even if you're listening to this and your team hasn't been through a workshop or nobody knows uh anything about the Enneagram, how to pronounce it, what the heck it is. Um, that's okay. You you can still kind of start to notice maybe some patterns and then just get curious, just start to get curious. We always quote Ted Lasso at the end of every workshop, get curious, not judgmental. And it is really difficult to do in the moment. And I have had some personal experiences recently where I wish I could say, oh, I just I remembered everything that I talk about with the Enneagram. And I was just so non-judgmental and just really curious. Um, I think in in a moment where it is really emotional and kind of heated. So, you know, depending on how heated this questioning exchange is, could determine whether you're kind of using this in real time or whether, you know, motion emotions got the better of you, which it happens to us all, and you're kind of going backwards and having some sort of repair conversation about your perspective, trying to understand their perspective, and then trying to minimize um that type of friction in the future. So I still do not know if Adam Grant is a type one, a five, a six, or something other than one of those three numbers. Uh, obviously, we cannot, and I am not going to attempt to, you know, type him uh just from a podcast interview, from a couple of LinkedIn posts over the years. But what is interesting is that that skepticism was just kind of a fun prompt to look more closely um at something I use all the time, the Enneagram. And, you know, uh maybe that is the opportunity when somebody questions us at work too, um, is to just get kind of curious about it instead of immediately, immediately trying to change their mind. What would happen if we just got curious about what's motivating that question? And I am curious. Uh, I think I have some ideas, and he has shared some of what's behind his skepticism. Um, but there are other things where people do not have podcasts and are publicly speaking about why they're skeptical about something. And so we have an opportunity to get curious to try and learn a little bit more. So um, I guess the final kind of thought takeaway here is a little challenge that the next time someone pushes back an ide on an idea of yours or that you're supposed to be communicating um on behalf of the company, you know, do as best as you can to not immediately start defending it and ask one question to better understand what's under that concern. So uh with that, I would be curious if you happen to have listened to that same episode that I did with Adam and Brene Brown, or you've been a fan of Adam. Um, I'm curious if you have any takes or guesses on his uh Enneagram type that you would want to share, feel free to chit-chat with me over at Enneagram NBA.com forward slash contact. Um, if you have experience, either you're the one that's typically labeled a skepticisse skeptical, or you have found uh best practices for dealing with the skeptics on your team. I also always love to hear from your real world experiences. So please share those over at Enneagram MBA.com forward slash contact as well. Thank you for being here. And these are the types of conversations and insights that we bring to our Enneagram workshops, off-site retreats, um, developmental programs. And if that is something you are interested in bringing to your team, especially as the year ends, maybe a um an end-of-year company retreat, maybe a new year kickoff uh retreat, even potentially, you know, spring summer retreats. We're already starting to plan for those. Um, I'm gonna invite you to check out the options over at Enneagram NBA.com. Thank you for being here, and I hope to see you in the next one.