Thrive in Ambiguity

Or how to effectively frame and approach ambiguity at work

Matt Kandler
7 min readJan 25, 2016

If you live & work in Silicon Valley, the following phrase is practically a requirement on your resumé:

Thrives in ambiguity.

For good reason too: in a fast-paced, startup environment you’ll often find yourself being the first to solve compelling problems. You’ll be joining a small team where you take command of many unexpected aspects of the business. You’ll be learning about the problems just as much as the solutions.

Remember grade school math? The easy problems gave you equations, but “story problems” were dreaded by the entire class. In the corporate world you’re more likely to get a prompt like these:

  • “Design a safer airbag without adding cost.”
  • “Go find us a new office in SF.”
  • “Make sure our financials are all set for tax filing.”

Those story problems don’t seem so bad anymore, do they?

It doesn’t matter if you are an engineer, a designer, an office manager, or a CFO — you will have to solve problems that no one on your team has ever dealt with. Unless, perhaps, you plan to toil away at monotonous tasks that may soon be taken over by an army of robot workers.

Lathe work could become ‘robot’ work as 3D-printing takes off

The ability to deal with ambiguity is a powerful skill.

The problem is that even for people with the perfect growth mindset — people who thrive on opportunities to challenge themselves and grow their intelligence — ambiguity can be daunting, even downright scary.

Where do I get started? What if I mess this up? Am I good enough to do this? Will I get fired? Should I even be in this role?

Not all ambiguity is created equal. Some is bigger, scarier, and more challenging than the rest, but some of it may actually be bad. My goal is to help you frame ambiguity in a way that makes it approachable and a better opportunity to learn and create value.

Good Ambiguity

I was introduced to ambiguity during my senior year of college, while writing graduate school applications. My advisor mentioned that schools would put emphasis on your ability to handle ambiguity, especially in a research setting. Doctoral students are breaking new ground and making their “dent in the universe,” NOT solving solved problems.

Perfect! I had been working in a robotics research lab for years. We had created robots completely from scratch. I could handle ambiguity.

What I didn’t realize is that this was the perfect kind of ambiguity. Each project started with a prompt from a research partner or professor:

We need a robotic ‘head’ for a walking robot that will be able to provide the xyz robot with stable vision (not shaky) during operation. The head must connect to the xyz torso, be controllable by a user, fit within a given size, and weigh less than 2 pounds.

- Thanks!

Over the next summer we created a robot ‘head’ that was far under the required weight and size, would mount on its parent robot, and even allowed for control via joystick. Mission accomplished. High-fives for the interns.

There was plenty of ambiguity — we could have used different motors, a different design, or even different materials. So then, what are some qualities that gave this project a sense of good ambiguity?

  • Well-defined constraints (size, weight, functionality)
  • A clear, known goal (to give vision to another robot)
  • Could be measured as effective or ineffective (stability etc.)

Now, you might be thinking, “but Matt, each of the items in this list would reduce the ambiguity of a task.”


The best way to approach ambiguity is to reduce the amount of unknowns, making it LESS ambiguous.

Imagine your manager asked you to “go build something.” That’s certainly ambiguous, but there’s no goal here except to perform any building task. I’m guessing a balloon animal is not what your manager had in mind…

All businesses have goals, and thus each task should have some lesser goal along the lines of larger goals. This could be anything from making profit to reducing inequity.

Which leads us to my next point: what’s all this about bad ambiguity?

Bad Ambiguity

There are some conversations you never forget. Certain phrases are burned into the folds of your brain. There’s something about the timing and pointedness of the words that never leaves you.

“Maybe you just aren’t cut out to handle the ambiguity.”

I bit my tongue, not knowing exactly how to articulate my thoughts. A simple nod. Maybe I do struggle with ambiguity.

But this wasn’t the sort of ambiguity I had dealt with before.

The most harmful ambiguity is the kind where you are blind to some piece of the big picture. Maybe there was a conversation about the project goals in which you were not present. Maybe your manager forgot some details when describing the task. Maybe you just didn’t ask the right questions. There’s rarely a clear reason

Let’s try an example:

Your boss tells you they want a delivery device. This device needs to be able to deliver 2lb. boxes of Jolly Ranchers to elementary schools in Nashville.

You decide that, in order to reduce costs, you can piggy-back on existing truck delivery routes in Kentucky. It turns out that xyz company already delivers notebook paper to the elementary schools in Nashville. You call up their delivery specialist, strike a deal and eagerly prepare a PowerPoint to show off your solution.

During your team’s meeting the following Monday, you present your solution. The presentation goes perfectly. You deliver each bullet point like a pro, show the monumental fiscal impact of truck-sharing and reach your final slide.

Your boss chimes in as you expect to hear a round of applause:

I was really hoping we could use a newer technology. Did you hear about Amazon and their drone deliveries? Now, that’s a genius idea. Matt, as an engineer I was hoping you’d be able to impress me with something more, well, novel.

Your face goes red, holding back the pressure to scream:


What can I do?

The wonderful thing about ambiguity is that it can be framed, molded, put in relation to other goals, and made into something useful for your organization. Many people actually thrive when presented with ambiguity. It can create a greater sense of autonomy, provide more learning opportunities, and lead to greater job satisfaction.

Let’s try and create some of that.

As an employee

Alright. So your boss, co-worker, or whoever has presented you with an ambiguous situation that makes you uncomfortable.

First off, don’t be a victim. Employees are not helpless: there’s always something you can do (even if that something might inevitably mean quitting).

Here are a few things you could try to turn this bad ambiguity into good.

  • Frame the problem — The first thing I would suggest with any ambiguous problem is to start sketching out what you know.
  • Ask questions — If you have a question, try asking! Even if there isn’t a response available, you’ll help create a culture where it’s OK to ask.
  • Just get started — Sometimes the best solution is to just start something. You’ll learn more quickly once you start executing and you’ll have something from which to gather feedback.
  • Solicit feedback — It can be hard to welcome criticism in the early stages of a project, but if you can muster up the courage, you’ll be rewarded with less iteration in later stages.

Practice a little empathy when needed. Your manager is human just like you, so naturally, they will make mistakes. At the end of the day, if you just can’t get on the same page, maybe it’s time to clean up your LinkedIn profile.

As a manager

Guess what? People cannot read your mind. It doesn’t matter how well you write your memos, emails, Slack messages, and check-in remarks. Even the perfect message can always be misread.

You want to give your employees room to thrive, but you also want to do your best to make sure they have all the knowledge and tools they need. This can be incredibly difficult because the feedback loop for managers has so many flaws. Many employees will just take a task and do it — never asking you questions, expressing their struggles, or explaining their decisions.

Here are some tricks to make sure your employees are dealing with bad ambiguity:

  • Discuss the project — Have a thoughtful discussion about the project from the beginning. The bigger the picture you share, the more your employees will be able to handle ambiguous tasks moving forward.
  • Check in often — Frequent check-ins are an obvious solution to ensuring work is going in the right direction. Just don’t start micromanaging.
  • Reflect on mistakes — When something goes wrong, take the time to reflect on it. Schedule a post mortem without any finger pointing.

If employees seems to struggle with this process, it could be worth taking a deeper look at your own management style and company culture. Is it common for employees to collaborate on projects? Do your employees see you as competent and approachable? What do your project timelines usually look like? Are you spending enough time helping to frame problems?


Ambiguity is a necessary and oftentimes difficult part of any career. It’s important to realize that it can come in many forms, good or bad. Employees and managers are both responsible for managing ambiguity, and doing so will ultimately save you hours, days, or months of frustration.

If you have any good stories about ambiguity, I’d love to see them in the comments; just type them in below!

All photos were found on Unsplash — it’s this oh-so-cool not-so-secret-anymore use-for-anything photo sharing web app.



Matt Kandler

Builder of many internet things & founder of @happyfeed — an app to help you appreciate the little things.