In my previous post, I shared the idea of ask vs guess culture, as well as some quick tips for navigating an ask culture workplace as a guess culture person.

If you haven’t already, I recommend reading that post first before continuing with this post that continues the exploration of ask vs guess culture at work.

Despite my efforts to be increasingly ask culture, it’s a bit simplistic to say ask culture is good, and guess culture is bad. The extremes are both exhausting:

• Extreme ask culture looks like people just asking for more and more, with no regard to how they are perceived, or whether it is appropriate to ask for more. It can be viewed as highly inconsiderate, like asking to order the most expensive item on the menu when you know the person who’s paying is struggling to stay afloat financially.

• Extreme guess culture is rife with passive hints and people not saying what they want. It requires expert-level context-reading, analyzing, and guessing at what people mean when they say what they want, knowing it’s not actually what they want.

Extreme ask culture and guess culture at work

In a Western corporate workplace, ask culture is more dominant, but it’s overly simplistic to just say, everyone should be more ask culture.

Extreme ask culture in the workplace might look like someone asking for raises every month, despite not meeting expectations of their current role, and frustrating their manager by their seeming entitled cluelessness. Or someone who constantly asks for time from coworkers to think through ideas live on calls, and takes up an annoying amount of time that people don’t want to give.

Extreme guess culture in the workplace might look like never asking for what you want, never getting clarity on what you want, yet hoping that opportunities that move you forward will just present themselves. Or not asking for help when you need it, because you don’t want to inconvenience all your busy-looking coworkers, leading to wasted time and frustrations on your team.

A typical ask vs guess culture clash could look like someone who leans more ask culture asking a coworker to work over the weekend to finish a presentation — they expect that the coworker will probably push back given they have weekend plans with family in town, but figure they’ll put the request out there, in case the coworker is willing. The coworker, who leans more guess culture assumes that because the request is made, it’s really important and no one else can do it. After all, their team knows their family is in town. So they begrudgingly take it on, but are later resentful to see the first coworker’s leisurely weekend photos.

We can argue in circles (and people certainly did in the comments on Hacker News) about which is better, but regardless, the reality is that we all work with people who vary widely in their communication styles. In order to work well together, we need to find ways to bridge the gap between these vastly different styles of communication.

Increasing shared context as work

One way to reduce the clashes in ask culture and guess culture at work is to increase the level of shared context. In fact, as many people pointed out, ask vs guess culture has a lot of parallels with the idea of high-context and low-context cultures.

If there are no explicit expectations of how people should behave, work with one another, etc., ask culture people may ask for too much, while guess culture people are left guessing at what’s appropriate to ask for.

A subset of things you can make explicit to help the askers ask more appropriately and keep the guessers guessing less:

• Preferred working styles – async or meetings, ad hoc vs scheduled, live feedback vs comments in docs, etc.

• Role descriptions and expectations – basic, but you’d be surprised

• Communication guidelines – when and where to communicate, level of urgency of Slack vs email, expected response times, off-hours availability

Shared expectations around asking for help

Expectations around asking for help could be bundled into the above bullet points of shared context. I broke it out, because in my experience, it’s a foundational area where people have shockingly wildly different heuristics for when to ask for help.

Some people readily ask for help in the form of a brief overview when they embark on a new project. Others only ask for help once they’ve exhausted every single idea they have about how to get unstuck.

Work culture can also differ wildly, with some teams expecting people to work things out themselves (more “RTFM” or read the fucking manual vibes). Other teams recognize that the faster someone gets unstuck, the quicker they’re back to contributing actively to team progress.

Of course, there is a healthy middle ground of learning to do some research yourself and trying a few things before raising the help flag, so that you’re not constantly bothering your coworkers.

Aligning on what exactly that middle ground ground looks like can be helpful in nudging guess culture coworkers to ask for help earlier rather than later, as well as reduce constant asks for help from over-askers. This alignment could look something like:

• While you’re onboarding, if you get stuck on something, don’t bang your head against for more than 30 minutes. Ping this onboarding slack channel to get assistance. (Assigning a specific onboarding buddy is also helpful)

• After you’re onboarded, if you’re stuck, spend at most a half day on your own before pulling in someone else or pinging the team slack channel

• As much as possible, ask for help in public channels, so that whoever is available can jump in, and the requests and responses are searchable in Slack in case someone runs into the same issue.

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Career development with guess-culture coworkers

How managers can help guess-culture teammates get clarity on what they want

Guessers tend to be less vocal in asking for what they want, and in many cases, have less clarity around what they want. They can be the most versatile and collaborative team players, but never express a strong desire for specific types of work.

But you would be amiss to overlook guessers with regards to career development. If you only focus career development efforts on the askers, you’ll end up a lot of teammates who feel quietly resentful and under-appreciated.

Go out of your way to help these teammates get clarity around what they want, and they may wow you with their energy and motivation.

As someone who grew up more in guess culture and who has managed many people with similar backgrounds, here are some general tips I’ve found for helping guess culture folks get more clarity around their career growth:

Ease off the pressure to goal-set

Let’s talk about your career goals 😬

An obvious conversation starter when you want to help someone with career development, right?

But I always felt a bit uneasy when these conversations came up, as I didn’t really have clarity around long-term plans.

Was it bad that I didn’t have a 5 year plan to work towards? Should I have one? What if I set goals that didn’t seem ambitious enough? Or if I set arbitrary goals and didn’t make enough progress towards them?

If you’re in a position to support someone’s career development, through mentorship, coaching, or sponsorship, be aware that this can be someone’s reaction to your genuine intent to help.

Ease into these conversations — make it ok for people to be figuring it out and not have a full-on plan. Offer up some options for goals that look less like “I want to be in X role within Y years” and more like “I want to explore a few different areas I haven’t touched before” or “I want to make more space for experimentation in the product.”

Let it be an ongoing conversation. It may take awhile to explore together and get clarity. Bring it up but don’t become attached to having a specific goal outlines by the end of your conversation.

Provide short-term options

Goals don’t always need to be 5-year plans. Just talking about the next two weeks or few months help you both practice talking about preferences.

Sharing options in the form of a few upcoming projects can help you both discover some preferences.

As an example, imagine a versatile generalist, always willing to pitch in on what the team needs. You might present them with these options:

• A) full-stack project working closely with product manager

• B) straightforward backend implementation project that’s well-spec’ed out

• C) experimental prototype to learn quickly from

While they may not have said, “Next, I’d love to work on something more straightforward and concrete,” they may be able to identify that option B feels most appealing for them.

Provide long-term options

If you know this person well enough to have a good grasp of possible career futures based on their strengths, let them know what you see as possible options! I once interviewed bethanye Blount, who framed it as helping people be the most bad-ass version of themselves. Share what specifics strengths you see in their abilities, and possible paths they might take.

Another effective approach is to provide options via people, though this tends to work better with earlier career people. Have them imagine what people in the company or in their broader networks have roles that feel appealing, and then dig into what about those people’s roles feels appealing. Maybe it’s how varied someone’s role is, or maybe it’s a mix of people management and project leadership, or perhaps it’s how someone built deep expertise in one area.

Reflect back what you’ve heard

You sounded really excited when I talked about that upcoming project.

I remember last quarter, you mentioned that you really enjoyed working with marketing. Are you interested in more projects closer to the business side of things?

Reflecting back what you hear, either in a single conversation, or over time, is a great way to help someone figure out what they want more or less of. Don’t get overly attached to being right. It may be that what you heard as excitement was actually nervousness with working with someone they had a bad experience with (which you weren’t aware of). But the reflection provides a conversation starter and something for them to react to positively or negatively.

If you could have your way…

I shared this hack in the previous post as a way for guess culture people to ask for what they want at work. But it’s also great as a collaborative way for a manager or mentor or coach to help someone unearth what it is they want.

• If you could have your way, how would your role be different?

• If you could have your way, what would you be doing more of?

• If you could have your way, what would you be doing less of?

The magic of if you could have your way… is that it frees guessers from the contextual information they’re constantly integrating into how they communicate. Realistically, people know that they can’t always have their way, so the fantastical framing gives them permission to dream into what they want.

Giving people space to mull over these prompts can be helpful. Ask vs guess culture aside, many people benefit from time to marinate in inquiries. You might offer it to them in a doc where they can take notes and then talk about them live in a future one-on-one.

Important tangent: when I advise leaders to having exploratory conversations with their team about what they want, a fear that often comes up—especially if you tend towards guess culture yourself—is, what if I can’t give them what they want?

As a manager, knowing what people want, even if you can’t immediately help them, is so useful. Imagine learning that someone on your team wants to step up to lead a project, but there is no immediate project for them to lead. Knowing what they want, without being able to deliver on it, creates space for conversations that deepen the relationship and let them know you are watching out for them like:

“Hey, I know you had mentioned wanting to lead a project. I want you to know I didn’t forget. Unfortunately, there’s nothing new coming up this quarter, but let’s keep an eye out in a few months as new projects get added to the roadmap.”

Or if the person isn’t actually equipped to lead a project yet, you can frame any feedback in context of what they want, which always lands better:

“I know you want to lead projects. One skillset that will really be needed once you’re leading projects is writing clearer design specs. If you’d like, we can go over your recent spec and look for ways to improve clarity.”

What are some ways you’ve found effective in creating more shared context at work, creating alignment around when to ask for help, or supporting coworkers who lean more into guess culture?

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