How I've learned to deal with ambiguity and open-endedness at work
Lessons from the past six years of tackling big questions and "putting a stake in the ground"
At Bain, one of the items on our professional development skill tracker was “putting a stake in the ground.” I remember very distinctly being told that this was one of my development areas when I was about a year into full time work. I was really stressed out by this feedback, because it came with this overwhelming fear and sense of responsibility. I worried about making the wrong assertion or having the wrong hypothesis. In my mind, putting stakes in the ground felt like an inevitable path to getting in trouble – or at minimum, getting publicly embarrassed for having done something wrong.
Now, fast forward many years, I’ve realized that the complement to “putting a stake in the ground” is actually “not being afraid to make the wrong assertion.” Perhaps, had I been given more concrete instructions on how to make an assertion and present it even if I wasn’t 100% certain, I would have embraced putting a stake in the ground much more easily.
Before I understood the two parts of this equation, I often felt like I was being asked to make bold declarative statements without having all the information I needed. I didn’t really appreciate the bigger picture of what I was being asked to do, which is to stand with a hypothesis and make forwards progress to test the hypothesis further.
Over the years, I learned a combination of skills that led me to be less afraid of making assertions even in the face of uncertainty. Once I figured that out, putting a stake in the ground suddenly felt easy.
Amidst uncertainty and ambiguity at my new job, I reflected on the moments where I started to crack the equation:
The first was when I was given an assignment at work that was truly open-ended, instead of one where everyone around me already had a sense of what the right answer was. (In those scenarios, it’s just one big guessing game of getting to the right answer to make sure you’re aligned with everyone else. I will say that for better or for worse, a lot of consulting is like this…)
I worked on a few cases at Bain where the work was less strategic and more operational, and we were clearly aligned on an end outcome but not how to get there. One example was helping the firm roll out new software to employees during the pandemic: my job was to manage the change and educate everyone. No one had an explicit playbook on how to do this and thus no one had strong convictions on how it should be done. I was allowed to chart my own path on how to get there.
This was very empowering – for the first time, I could actually craft an answer to an open ended task without feeling like I had to answer seek it to someone’s existing idea. I learned for the first time that my common sense was worth something in the workplace! It was kind of crazy to have gotten so far in my career before finding that I could just use my brain…intuitively…instead of always trying to conjure up some framework or some existing way of doing things.
Later on, at TestBox, I built several programs from the ground up, including our approach to product, marketing, and customer success. I didn’t have firsthand experience in any of these domains, and had to go off of best practices in the industry, thought leadership I could find, and wisdom that more experienced leaders could share with me. I learned very quickly that I was never going to know if something new would work – instead, I figured out how to best propose new experiments where I was uncertain about what outcomes they’d yield. I started sharing the same context for each new proposal I made:
My rationale for the hypothesis
How this approach aligns with the organization's broader goals and values
The metrics I plan to track as signs of success and how long I plan to track each metric for (i.e., how long I plan to experiment for)
Any potential risks or issues associated with the path I am suggesting
As I also started to coach others on the team to do the same, I really realized firsthand that no one ever knows with full confidence and certainty what the outcome of a given path forward will be. At the end of the day, moving quickly exists in direct tension with taking on risk. And what matters the most in a workplace, for one to be successful in the face of uncertainty, is being able to align on making the right tradeoffs between forwards progress and taking risks.
So, if you’re early career (or later) and asked to handle ambiguity, open-ended tasks, and craft answers where there isn’t an obvious answer, here’s my advice:
Start with doing your research on if someone else has strong hypotheses; if they do, the task at hand may not actually be as open-ended as it sounds
Barring the scenario above, think about the problem from a risk mitigation perspective to get started; what are the most likely things? What are the 50% certainty things? Which of those can you experiment with to possibly drive results and progress?
Trust your own common sense and don’t hesitate to approach problems in an intuitive way if there isn’t an existing framework you have to follow
When sharing your plan with your team, use the format I’ve laid out above