Ask And Offer Culture with KWu

Ever heard these sentiments in your workplace?

  • “That was so unprofessional!”
  • “Why are they being so rude? They’re always so pushy.”
  • “Don’t they care about..?”
  • “Why won’t they just tell me if they can’t meet that deadline?”
  • “I’m so overwhelmed but everyone just keeps piling on more work.”

Different default assumptions around communications can lead to painful miscommunications and hurt feelings. “Ask and Offer Culture” (or as Ask-ers like to call it, “Guess culture”) is one way to describe these differences. KWu (@kwugirl on Twitter) is a regular speaker on the topic, and shares her extensive knowledge in Episode 28.

Show references:



JENNIFER: Welcome to Storytime with Managers, a podcast by Cohere.

Hi, I’m Jennifer Tu, and I’m here with KWu to talk about ask and guess culture. KWu, can you tell us a little about yourself?

KWU: Yeah, I am a Ruby engineer that works at Heroku currently. And before quarantine and before I had two small children, I frequently really loved attending Ruby conferences and giving talks at them as a way to meet people and broadly introduce myself and then be able to have great conversations with people after the fact. That’s how we met. I don’t remember how many Ruby conferences ago. A few, right?

JENNIFER: I think we actually met at – it was in Portland and not at a Ruby conference, but at a different conference. Yes, at AdaCamp.

KWU: Yeah, you’re totally right.

JENNIFER: That was that great conference.

KWU: Yeah. Oh, I miss living in Portland. I live in New Jersey now where we are closer to family. It’s good and all. It’s good for the kids. But Portland is kind of my heart really, I think. [Laughs] So in any case, one of the topics that I have a conference talk written about is Ask vs. Guess Culture. Because it’s an idea I learned about from the Internet, I suppose, a few years ago now. And I’m always so excited to share it with more folks and get more perspectives on whether they’ve seen the spectrum play out in their lives and experiences as well.

JENNIFER: All right. So, Ask vs. Guess Culture. What is it and how do I tell which one I am?

KWU: Yes. So the baseline description is think about it in terms of maybe default assumptions around communication. The standard way I often describe it is when you are a member of Ask Culture, you probably grew up in an environment where it was understood that it’s okay to just go forth and ask for things from other people, ask questions, ask for favors, ask for help, because if people are uncomfortable or want to refuse in some way, they can go ahead and just say no. And that’s kind of like understood as it’s not a rude thing to do in any way. And that’s how you would interact with other folks. And so similarly, you go about the world with an assumption as well that if someone hasn’t asked you for something, it’s because there’s not something that they want from you.

Guess Culture, on the other hand, very much prizes not putting people on the spot and feeling uncomfortable and having to say no to you. I’ve also heard it described lately as, I think request culture, maybe instead of guessing, even describing it as guessing is, I think, a very ask person’s orientation of like, “Oh, I don’t know what they’re saying.” But obviously there are many ways to communicate things besides saying the exact concise words for what you may be describing. I often describe it as like because for myself, I’m a very ask culture type person that I’m extremely literal. And so you may be expressing yourself just fine, but I find for me, my default is that if I’m not paying attention, if you don’t say the literal words of what you want from me, it may just completely go over my head and I will miss it and not see those signals that you’re putting forth.

So this can come up again in either asking for help, asking for favors, asking for an opinion in some way, knowing whether – oh, offer culture, I think, maybe is the other term for it as well. Because there’s this aspect as well where in this more of a guess culture environment, if people really want you to take them up on their offer, they will make sure to offer it to you several times as sort of proof of the sincerity of it versus more like offering once and you’re kind of expected to only take them up on it if you really, really need that particular help. If it’s something that you can get by with, then it would be more polite to decline that offer. Which again, for me, as an extremely literal person, I’m kind of like, “Well, if you didn’t want to do it, then why did you mentioned it in the first place?” Which again, is fine if everybody is playing under the same assumptions. But as it turns out, when you go out into the world, people are very different from each other. And we are not, in fact, robots or machines.

JENNIFER: All right. Speaking of going into the world, I can kind of take a couple of guesses, but could you give me a few examples of what ask versus offer or ask versus guess culture might look like in the work place?

KWU: In the workplace, yes. I think a very common way that this can come up is when we’re talking about kind of like softer deadlines for work that can come up in some way. Usually it’s fairly clear if there is an explicit hard deadline, like, “Oh, the client needs some proposal by some time,” like that is very obvious. But if it’s more the kind of situation where, let’s say one person at work needs to produce something that another person, if they got it earlier, it would make their lives a lot easier. That kind of softer-ish deadline, I think communication around that is ripe for this kind of communication difference, cultural difference to show up. Folks when they’re saying something like, “Oh, it would be really great if I could get that soon.” And if you’re seeing that ramp up over time, to me, they’re not saying the words, “Oh, I need it by Tuesday.” They are kind of expressing a more nuanced of, “If you really can’t get it by Tuesday, I will understand. It will be fine. But it will really make my life a lot easier if you can get it by Tuesday.” Just not saying it in quite all of those explicit words. And so, that I feel like is a frequent example of deadlines or prioritizations. Like when you’re negotiating between different teams of when you’re dependent on another team for some amount of work, that kind of thing can frequently come up.

I think it can also come up pretty often in the manager’s context in both ways. Sometimes managers, because they’re following more social rules around how they would communicate for what they’re needing from people, that can come out. It can also come out if an employee is feeling really overwhelmed and is needing help to figure out, like what they can say no to doing and stop doing certain kinds of work. I think those conversations can end up demonstrating this difference often as well.

JENNIFER: Let’s say that I’m a manager and I have two reports. One is ask culture. The other is guess culture. And neither of them really self-identify that way. But it’s really obvious because one person’s saying, “Oh, it would be really nice if this could be done soon.” And the other person takes until Friday to do it instead of bringing it in on Tuesday. What kind of things might I be hearing from these people as they talk with me about how they’re working with the other person and what should I be doing about it?

KWU: Oh, that’s such a good question. Now that you mentioned, I realized a portion of your first question was, how would you tell which one you are for yourself, which is often good to ask because people immediately want to try to categorize themselves in some way. So just to address that from earlier, because I forgot to get to it, typically with folks for myself and others I’ve met who would identify more as ask culture, you may very well identify this experience of being in the world and being like, “Wait. Did I miss something? Was I supposed to read between the lines?” And like, “I feel like I’m often really bad at that. And I miss the signals that people are sending out in some way. And I wish people would just tell me what they want from me,” is kind of often an attitude that an ask culture person gets.

The other thing I’ve noticed is that it tends to be guess culture folks that for whatever reason, feel more reluctant to fully commit to one label or another. They kind of are wanting to keep their options open more maybe or just don’t want to come down so definitively one way or the other. Whereas it tends to be that ask culture people, when I’m talking to them, seem to recognize this phenomenon I’m talking about quite quickly. So if you feel like you’re on the fence, probably you may lean a little bit more on guess culture. And also people are different in different situations, depending on the level of closeness in that relationship for communicating that you maybe one way with your family and another way at work, one way with friends, a different way with acquaintances. So that’s that part.

You asked about as a manager, how might you diagnose that this sort of situation is going on. I’m a huge fan of the Ask a Manager blog advice column. Is that something that you read regularly too? Not sure if we’ve talked about it before.

JENNIFER: I read it a little bit. Yeah.

KWU: I’ve read it for several years. And so it does seem to be a fairly common theme that comes up in some of the letters, the extent to which when you dig in, what were the words that people have been using to communicate with each other? So, it is something that you, as a manager, I’m sure good managers want to be careful not to be micromanaging. It’s not like you’re going to be asking for the emails or texts or Slack messages that your reports are sending to each other. But I think if you start hearing complaints around, “Hey, we asked them for this thing and they just keep not delivering it,” or, “It’s really hard to get what we need from this other team or this other person,” that sort of thing. I think regardless of whether ask versus guess is at the root of it, it seems really helpful to try to get a bit more information on how the communication has been happening. I mean, I know certainly for myself that I’ve gotten great advice from managers in the past for coaching me on the communication aspect of working with other people and collaboration.

This is an aside, but I was noodling on this the other day about how collaboration and teamwork are really awesome. You would rarely find someone who would say anything against it. But I feel like something we don’t talk about as much is that it actually can be quite hard to set up that environment. Because when it’s going well, it’s like you’re breathing underwater or something and you just don’t notice it in the environment if it’s been so well-designed. But when it’s not, when there’s friction, it doesn’t mean it’s a lost cause. But there’s certainly ways to smooth that out a little bit, I think.

JENNIFER: So what is it that you do when you find yourself in that situation? You’re a manager, you’ve noticed that your two reports are complaining about each other to you a lot, and you’re noticing that a lot of it seems to match up with a ask versus guess culture mismatch. What do you do? What’s the right approach to coaching the two of them around this?

KWU: I should probably also step back and mention that I have never worked as a manager before. [Laughs]

JENNIFER: That’s okay. You still know this stuff really well.

KWU: I love thinking about these topics and I’m always curious about other people’s situations, but credibility wise, I do feel like I should state that I haven’t been in exactly that situation where the power dynamics and hierarchy are at play.

JENNIFER: Let’s say that you’re not a manager, but you are office friends with these two people and they’re both coming to you and saying the same thing. And they respect your opinion and they’re looking to you for advice. What do you do?

KWU: I think in any case, when there is interpersonal conflict going on with other folks, the very first thing is to make sure that you are empathizing with the person that you are talking with right then. The one that is in front of you. And making sure that they feel heard and that you are on their side, that you understand what’s going on. That’s something I’m saying is like for me, I have a tendency to want to jump immediately into the problem solving. And definitely if I’m not careful, that can come off feeling like an interrogation of some kind. I don’t believe why the person in front of me is having the difficulty that they are. So making sure that they feel you understand where they’re coming from. A lot of active listening. Are you able to restate the conflict in a way that the person you’re talking to agrees with your summary of the situation? Because you know that you’ve been thorough about understanding their perspective. So, that’s always the very first thing before you jump in to any advice giving or trying to dig deeper.

When it’s a more casual peer-based conversation, I probably would tend to go with more potential leading questions or sort of musing out loud what the other person’s perspective might be in some way, just to help broaden my friend’s perspective of how they’re looking at the situation that they’re super frustrated by. And again, in a peer situation, when I remember it is helpful to ask as well, were you looking for advice on the situation or are we having a [vent] session? Either is totally fine by me. Obviously, it’s different when you’re in a manager position, where you do want people to be working well together and sorting things out.

JENNIFER: Not necessarily, sometimes I ask that question and the person says, “No, I just really wanted to get this off my chest. I feel much better now.” Then I’m like, “Coo. That was awesome.” And that’s it. And then they feel happy and it doesn’t come up again.

KWU: Yeah. Fair.

JENNIFER: It’s good to ask no matter what.

KWU: Totally. I feel that there are definitely situations where managers are sort of like work therapists in a way of trying to hear those things and resolve them out. But as you said, let’s say that it’s the situation where someone does want advice and is open. It’s not a situation where the manager needs to step in with their authority just yet, that there’s some room for the individuals to resolve it. I think one thing to be careful is if you don’t want to just say, “Oh, this is just an interpersonal difference. The two of you just need to sort it out. You just really need to work together and figure this out,” because that’s just not really helpful at all when you’re in the middle of being stuck with communicating with someone in some way.

I think it can be helpful to offer observations from the manager’s perspective of, “Oh, hey, you know, – as you’re talking to the employee, the one that’s in front of you, like, “Hey, look, when we work together, I’ve noticed that you seem to communicate really well. I prefer this particular style, or the way you need to get information is in this particular format, essentially. What I have found in working with this other person is that it seems to be more effective when you do such and such in some way.” So, offering observation that people may not notice themselves, I think, is one tactic to go through.

Another one that never goes wrong, I think, is encouraging the building of relationships, because regardless of where you are on the spectrum, I think everyone it’s true that when you know someone better, when you feel more comfortable with them, when you trust that they respect your skills and competence and they trust you back and that there’s a mutual understanding of that, that is so much easier to resolve potential miscommunications. I have a funny anecdote about this in the conference talk that I gave off of topic, but the example I often use is that my husband and I are like really far apart on this spectrum. And we’ve been together for over 10 years and we have two young children now. So, it can work to being a very close relationship with someone who’s very different from you on this when you’re putting the effort in and making sure to see each other’s perspectives. Does that help? Does that give some nuggets to start with if you’re facing that situation with your team?

JENNIFER: That does. One thing I’m thinking about is one of the solutions you said was to build that relationship. And I’m wondering, are there things that can help bridge the gap between ask and guess culture when you’ve got two people who want to work together, are willing to put in the time on building their relationship, but keep bumping into the communication problem?

KWU: Yeah. Self-awareness is always really helpful in these situations for each individual to be reflecting on what’s going on. And I think one of the reasons we love retros as a tool is I think that retros are such a great place for these sorts of situations to be surfaced and talked about in a hopefully blame-free kind of way where you can say, “Hey, this is what we thought we were told. These are the words that were said. This is what we heard and interpreted as.” And a retro is often a great place to examine the difference between what was broadcast and what was received in some way and then collaboratively talk about how things might be approached differently in the future. When it may not be at a team level retro or project retro or whatnot, even just on a personal level, when I noticed this happening myself, I try to be a good sport about calling it out, maybe making a couple of self-deprecating jokes about it, being totally willing to apologize for my portion of contributing to miscommunication difficulties and just not putting responsibility entirely on other people.

In general, I feel like I frequently come across articles and things like that where they seem not that helpful to me because the thrust of the article is like, “Oh, just ask.” Like ‘just whatever’ is in general not that helpful. So again, in the matter of a situation advising people on their team, having specific word formulas that you’ve come up ahead of time, wording suggestions of, “Hey, here’s something we can work out ahead of time,” so that you can phrase your request in a way that you’re comfortable with and doesn’t feel rude to you. But still, hopefully increases the likelihood of being effective at getting your point across as you needed to for the other person. So that’s sort of like role playing or talking about what words you can use ahead of time definitely helps.

On the other end of the spectrum, it is also the case sometimes that you’ve done what you can and misunderstandings still happen. I hope for folks that they are generally in environments where it’s okay to have those mistakes crop up occasionally and the relationships they can build are strong enough to withstand that. Unfortunately, obviously, there are toxic environments that when people are out there that they feel like they’re getting gas lit. And it is in fact, not entirely their fault that people can’t seem to understand or explain things in a way that makes sense to them. So for folks that may be in those situations, sometimes you do have to just get out.

JENNIFER: Okay. This has been really, really helpful. It sounds like there’s kind of three stages when you have this sort of situation where people are approaching you about conflict and you realize it might be a cultural mishap. The first is to empathize with that person, so that way, you are making sure that they feel heard and that they feel believed. And then the second is to check in if they want advice on it. And then the third part is to provide perspective on it.

KWU: Yes.

JENNIFER: Well, it sounds so easy.


KWU: I love your summary because I wouldn’t have enumerated it that way. But yeah, that is the plan. One, two, three.

JENNIFER: Wow. This has been really helpful. KWu, do you have any final words of advice for our listeners?

KWU: I guess what I would say is that I think communication is a really fascinating topic to me because I do not consider myself naturally good at it in any way. So, I really work on it and I really value it when it seems to come to be so effortless to other folks. And it’s really, really helped me in my career, in my professional and personal relationships, for sure. So, it’s just something that I guess I would encourage everyone to try to approach this arena with very much of that growth versus fixed mindset, that it’s not just like you’re either born with it or you’re not, but it is something that you can study. You can talk to people. You could think about it. You can reflect on it over time and hopefully see the benefits of that and have an easier time of it in the world. I think fundamentally people really want to feel heard and seen. And this is one of the ways that you can help with that is reaching out across this cultural gap in a way and hopefully work together that much better.

JENNIFER: Wow! Thank you. KWu, if people want to reach out and continue the conversation with you or if they want to look up this talk that you’ve done, what’s the best way for them to do that?

KWU: I’m not as active on Twitter as I used to be, but I do still occasionally. I mostly post a lot of interesting articles, most parenting related because this is what I’m reading a lot these days. But my handle is @kwugirl on Twitter. I think I also still have an active personals site at It’s actually just like a GitHub page underneath, but I’m pretty sure that my blog is linked from there and the recordings of the talks that I’ve done are linked from there as well. So, there should be a specific blog post dedicated to the Ask Vs. Guess Culture talk that I’ve done that has links to the slides, links to other relevant pieces that may be of interest to folks that want to dive into this topic more.

Yeah, I would love for more folks to share their thoughts with me. I love getting comments when people have either attended those talks or watch recordings afterwards. One of my favorite ones is something like, “I’m watching this talk with my boyfriend in the audience right now. And it’s like going to couples counseling.”



KWU: And just like if I can help others reach that light bulb moment similarly the way that I have run into it over and over again, I think that would be awesome.

JENNIFER: Super. I’ll make sure that the links are in the show notes. Thanks so much, KWu.

KWU: Yeah. Thank you. Thanks so much for having me.

JENNIFER: Thanks for listening to Storytime with Managers by Cohere. I’m Jennifer Tu. Our theme music is by Kevin MacLeod and we are edited by Mandy Moore and the DevReps crew.

If you like this episode, please think about leaving us a review on your favorite podcast listening platform. This can make a really big difference in helping other people find and start listening to Storytime with Managers. Thanks so much.

Ask And Offer Culture with KWu
Older post

Technical Leading with Edwin Mak

How do you give technical feedback and direction without inflicting unwanted help? or change direction without introducing bad feelings? In Episode 27, Ed...

Newer post

Discovering Managing with Ashish Dixit

The last episode of Season 4 is a hero's journey story! Ashish Dixit ([@tundal45 on Twitter]( shares how he found himself mana...

Ask And Offer Culture with KWu