8 Questions I Ask During Tough Decisions

I got stuck with a hard decision that I needed to make on a quick deadline last week.

Often, when I’m faced with decisions, my process is pretty straight-forward: I try to write down the crux of the issue in the simplest, barest-bones manner and then I write down what bigger values I’m concerned about with this decision. Those values can run the gamut—everything from helping end poverty worldwide to upholding my personal integrity to not wanting to embarrass myself.

So a simple decision might look something like this:

Decision: Go out tonight v. stay in and work

Values:  Take care of myself, uphold my commitments, maintain relationships with friends, end mass surveillance.

Often, identifying the heart of the conflict and figuring out the values I’m solving for will make the answer obvious.

Except when it doesn’t. Sometimes, the values themselves are in conflict, the facts are murky, the outcomes of various choices are unknown, there are political and personal relationships in the mix, and the more I dig into the issue, the more complicated things seem to get. Worse, these complicated choices sometimes have to be made on a tight deadline and come with huge consequences.

I think I hit a version of these super sticky decisions once every few months, and I get lesser versions—still complicated and with a range of uncertainties, but with fewer ramifications—weekly.

Whenever I’m stuck, I write. Writing makes it easier for me to lay out facts, thoughts, and emotions as honestly as possible. I can read things over with fresh eyes after taking a break, which helps me notice things I may have overlooked before. Writing also forces me to slow down.

I’ve tried writing facts on sticky notes and moving them around on a big pad of paper, and that’s useful. I’ve also tried making lists of pros and cons and journaling, and that helps. One thing I find is not useful is attempting to create a matrix of all the parties involved, their perspectives and the impact decisions will have on them. I thought this process would be very helpful in moving toward a decision, but my experience has been the opposite: this exercise tends to make situations more complicated, brings few if any new insights, and delays clarity.

What I’ve found to be most helpful is answering a series of 8 questions. I try to write a long paragraph for each, and I tend to answer them in this order. Sometimes I’ll work at these questions on and off for a day or more, tweaking my answers and adding additional data. The last question is the hardest, and sometimes doesn’t have a good answer so much as a few bullet points and vague ideas.

Here are my 8 questions:

  1. What assumptions are you making? (Try to start every sentence with “I’m assuming…”)
  2. What don’t you know? (Try to start every sentence with “I don’t know…”)
  3. What is your deepest fear about this decision?
  4. How connected to reality is your biggest fear?  If it happens, what will you do?
  5. Is there a silver lining to this situation that you haven’t considered?
  6. What’s the best outcome you could imagine?
  7. How much are you weighing short term v. long term outcomes? Is that the right ratio?
  8. Is there a way forward that you haven’t considered, that might address all concerns?

These 8 questions are a way that I can step away from politics and personalities, face my own fears and assumptions, and focus on positive outcomes. This process works for me, but it won’t necessarily work for everyone or work in every decision. I also believe that over time, this list of questions will grow and change. So I think of it as my working draft of decisionmaking questions.

One last thought about decisions: there are decisions that have sweeping ramifications on my life and the lives of others. But most decisions aren’t that. Most decisions are actually somewhat mundane, easily reversed, and with few consequences for choosing wrong. I try to always be aware of how and when I’m making a low-consequence, easily-reversible decision, and try to assess whether the amount of time I’m putting into my decisionmaking is appropriate for the seriousness of the given decision, especially when the outcomes of choices are fairly uncertain. I think there’s a tendency to treat all decisions as life-or-death choices, when most choices are a bit closer to an experiment, i.e. we aren’t sure what will happen so let’s try this, if it doesn’t work, we’ll try something else.

There are negative connotations associated with changing your mind—she’s fickle, she’s indecisive, she’s unreliable—but truthfully, a small decision made quickly and then efficiently reversed is not such a bad thing.  In fact, sticking with a poor decision can be so much worse. In 1999, I decided to go see Runaway Bride in theaters (what was I thinking?), then walked out and switched to another movie after watching for 20 minutes (20 minutes of my life I will never get back). In 2010, I rented my first apartment in San Francisco–where rent prices exceeded anything I’d imagined before–and soon found myself accruing significant debt. I broke my lease to move to a single room in the Mission, even though I’d never imagined breaking a lease in my life. This year, during a month-long backpacking trip, my partner and I were scheduled to tackle a section of the Colorado Trail above treeline in the middle of a ferocious storm. We abandoned our plan when we got to the top of the ridge and the wind hit us with full force, even though it seriously complicated our resupply plan for the rest of the trip. We hustled down the mountain, found a road, and eventually hitched into the nearest town.

These are all decisions from my personal life, but I actually find this rule applies even more to my professional experiences: expect that some of your decisions will be wrong, so try to notice and adapt quickly.

For the really crucial decisions, when the stakes are higher and ramifications are serious, the cost of a failed experiment can be more significant. And in those cases, answering those 8 questions can be one way of stepping back and getting perspective.

What questions do you ask during tough decisions? Feel free to leave a note in the comments or send me an email to share your thoughts.

Groundwork offers management training and leadership coaching to nonprofit professionals. Learn more.

One thought on “8 Questions I Ask During Tough Decisions

  1. Really good stuff! A keeper. The only thing I would say is that it is never too late to back down from a bad decision. That is the best piece of knowledge I got from a book called, “Deep Survival. Who Lives, Who Dies and Why.” Applicable to so many things.


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