How to Set Expectations for Yourself and for Others

Last weekend, I had a strategic planning retreat with my team, Dejah and Jenny, in Key West, Florida. It was outstanding! It was not only about the work that we accomplished (which was substantial), but the time we got to spend together on Dejah and Roby’s (her husband) boat, on the sand, on the water and during sunset — all away from all the tools that represent work.

Before I left for the trip, a close friend asked me, “Are you looking forward to the retreat?”

I responded, “I’m going in without expectations.”

“WHAT?!?”they responded. “How can you set up something like a retreat for your team and not have expectations?”

I told them that I try to be in the moment. That means not setting expectations and not looking forward toward specific events and their outcomes. It means setting a direction with intention, not trying to predict or determine every turn.

Expectations create a set of beliefs that something is going to happen or that it should happen in a particular way. Expectations also create attachments that make it harder for us to be flexible and resilient when our expectations do not align with reality. And when our expectations don’t align with reality, reality wins— every time.

So how might we go about setting and monitoring expectations, for ourselves and for others?

Identify Your Outcome Bias

Expectations help our brains navigate an increasingly complex world. They are our brain's way of predicting a particular outcome.

Most people tend to have a positive or negative outcome bias. Each can be harmful.

Negative predictions — like “This will never work” or “I’ll probably botch this up”— might help us avoid danger or anticipate a negative outcome to better cope with the emotions it brings. But they also skew the energy and effort we put into a situation before us.

Positive predictions — like “Nothing can touch us” or “Smooth sailing from here on out”— can reduce our vigilance to possible threats and create an adverse emotional outcome when things don’t go our way.

So what approach can we take instead?

Being Positive AND Realistic

Aligning your expectations with reality is the best strategy to create flexibility and resiliency.

As an avid skier, I’ve had the great fortune to attend clinics with past Olympic skiers. Beyond actual ski techniques, one of the things I’ve learned from these Olympians is how they establish expectations for themselves.

Before they start a run, they set the expectation for success while maintaining an awareness of the points of focus that will get them there. They will do a mental run-through (“Turn 3 I will do X; Turn 4 I will do Y”) to prepare for the most common occurrences that threaten their performance (based on the reality of their experience). They set a positive expectation while still looking at the reality of the possible threats to success.

How can we apply this strategy for ourselves?

When a new idea, concept or opportunity is before us, many of us feel will fall into our own outcome bias, whether positive or negative. If your tendency is a negative outcome bias, be aware of it and look for proof of others who have succeeded in a similar situation. Focus on the reality of how their skills are similar to yours and where you have skills that are more developed than theirs. If your tendency is a positive outcome bias, be aware that this is your tendency, and focus on the reality of possible threats to your success. If you can’t identify any, speak to someone else who can help you do so.

Always remember, when our expectations don’t align with reality, reality wins— every time.

I’d love to hear your questions and comments. If you would like to discuss this topic further, just drop me a note.

Until then, let’s keep cultivating our culture, together!