Tackling Ambiguity — 5 Things to Do When You Don't Know What to Do

Ask Good Questions

The first step to achieving any level of clarity is usually to start asking good questions. Sometimes they don’t even need to have answers, but just the act of asking the question will help reveal where the knowledge gaps are! But what actually defines a “good” question?

In the case of ambiguity, a “good” question is anything that could help reveal hidden complexity. As a general rule of thumb, I always try to trend towards asking “bigger” questions that help define the overall context. Often times, others will just assume you have all the knowledge they do unless it directly relates to the task at hand in a very concrete way. Since this is the most likely information to get left out, I usually start broad and then work my way towards the more granular specifics.

Here are some examples of my go-to questions to ask:

• “Why?”
  (Then ask it five more times.)
• “What goals are we trying to achieve?”
• “Have we done anything similar in the past?”
• “What resources do we have at our disposal that could help?”
• “What else is there?”
  (This is a really powerful one.  Asking “Anything else?” invites an easy reply of “nope!” whereas phrasing it this way usually causes the person to think about what might be missed.)

Listen Attentively

Let’s be honest. Listening is an acquired skill. How many times have you been in a conversation and while the other person is talking you’re just thinking about what you’re going to say next and waiting for an opening? 🙋‍♂️

The second half of asking good questions is, of course, taking the time to pay attention to the answers. This will help you ask more in-depth follow-up questions.

An important part of this is maintaining a sense of curiosity as you listen as well. Sometimes it’s not enough to just settle for the answer you’ve been given. Don’t just take a quick note and leave it for future-you to dissect. Process things in the moment and pay attention to what other gaps it uncovers and what other questions you can follow-up with. The trick here is trying not to do that while the other person is still talking. Listen, absorb, then respond. And don’t be afraid of a little silence or pause in the conversation. It’s not as awkward as you think.

Sidebar: Obviously, different rules apply if this conversation is happening via slack or email. Truth be told though, you’re going to get more dense information a lot more quickly by hopping on a 10-minute call than you will by going back and forth via email for a week. Particularly with remote teams, a quick “in-person” conversation can clear things up more quickly and also help avoid miscommunication.

Take a Shot
(Sometimes in the Dark)

So you’ve successfully completed steps 1 and 2, and now you’re ready to take action. Let’s face it though, sometimes you don’t get a chance to ask questions, or maybe the answers weren’t as revealing as you like. What do we do then?

We go forth into the night!

Whether you have a little context, no context, or a lot, there comes a time where the rubber meets the road and something has to be done about it. Even if you’re not sure of exactly what the way forward is, it’s often helpful to take the first step anyway. One thing’s for sure: If you let yourself be paralyzed by fear, then you aren’t going anywhere.

In fact, there have been many, many times in my career where the path forward was only made clear because I took a step in a direction (any direction) first. Once you have something concrete to point at and observe, it can help facilitate the conversation of what should be done next with much more clarity. What’s important is that it’s no longer just something in everyone’s heads, but now it’s tangible.

A great example of this is when a client is struggling to describe their vision, so we create a design draft and now they have something to point out an provide feedback on. It helps give them a touch-point that anchors the conversation.

Don’t Be Afraid to Course-Correct

As I alluded to above, sometimes you take a swing and you miss. And that’s okay! It’s important not to see that as a “failure” so much as a step along the path to clarity. The best way to leverage these misses is by asking yourself what was learned by it. Particularly in times of ambiguity, I think you’ll be surprised by how much you can learn very quickly by making “mistakes” and then using those mistakes to stair-step your way out of the haze.

Trust Your Intuition

The final tip is hard to put in concrete terms, but essentially, sometimes you just need to trust your gut. The more times you find yourself in ambiguous situations and the more times you work your way out of them, the better your gut is going to get at reading those situations in the future.

Because of that, it’s important to get comfortable in ambiguous situations. Turns out, humans are complicated creatures, and if you spend any amount of time working with them, you’re going to run into complexity and ambiguity. The trick is trusting yourself enough to handle it. So take a deep breath, accept the ambiguous situation when it arises, and then relentlessly hustle your way to clarity (paying attention to how you got there as you do).