Want to Improve Your Decisions? Ask These 3 Questions

Decisions are hard enough to make without groupthink getting in the way. You know, that tendency for everyone to agree, even if they don’t really agree.

Maybe they don’t want to contradict the boss. Which is particularly bad if you are the boss.

It could be that they don’t want to ruffle someone else’s feathers. Or even that they don’t want to be criticized themselves. Standing out from the crowd is risky.

People in work settings also have a way of sensing the default future and just going along. It seems inevitable. Because they’ve heard lots of fancy talk that never seems to materialize.

This is the stuff getting in the way if you are trying to make an honest to goodness good decision.

So what can you do about it?

You can setup the conversation just a little bit differently and get much better results. If you focus on the three questions I’m about to share with you, you can overcome the hurdles.

Question 1: Can we agree to be uncertain?

Too many decision-making conversations start out on the wrong foot. Humans sort of default to the position where we think of any decision as being right or wrong.

As in, we are either going to be 100% right or 100% wrong.

That creates a lot of stress. And that stress starts to shut down creative thinking and any sort of disagreement. Because we don’t want to be the one who “blew it.”

But this is a totally unrealistic premise.

Decisions are about probabilities and degrees of confidence. There is no way around it.

There are just too many factors out of our control – other people, market conditions, supply chain vendors, price sensitivity, luck (good and bad), weather, the stock market, politics, etc.

Sure, we can consider many factors in our decision making, but we can’t control everything.

We are simply trying to make a good choice at this point in time based on what we know and what we think is likely to happen.

Back to the group.

If you setup the conversation in a way that recognizes uncertainty, you are going to be able to get much better information and more robust thinking.

Don’t set things up as either right or wrong. Set them up as we are trying to be more right than wrong.

A good way to do this is to show your own uncertainty at the outset. You can say, “We need to decide on a path forward and I’m not sure which is going to work best. I need your help to make sure we think this through as thoroughly as possible.”

Now, you’ve opened up the conversation. You have demonstrated that not being 100% sure is ok. You have also shown that you want input, and more importantly thinking.

This leads us to the next question.

Question 2: Can we try to find the best practical answer?

You have just opened up the conversation to thinking things through as thoroughly as possible. This means that you are inviting thinking, but also more information.

By being thorough, you need to show that you also want to be realistic.

You need honest opinions, debate, and consideration of anything and everything that will help you to make a better decision.

Here you might invite the group to embrace this by saying something like, “To find the best answer, we need to put everything on the table. Anything you can think of that might help guide us should be included.”

You don’t want people to pretend that you are all in a think tank and working with a clean slate. You need to recognize that office politics, executive personalities, and all the other stuff going on at work are in play.

By no means does being practical need to limit any creative thinking. In fact, recognizing limits and barriers and obstacles can one of the best ways to spur creative solutions.

What you want is all the information that might help make a good decision. If that information does not include practical realities, you won’t be able to make a decision that works well.

Which brings us to…

Question 3: How can we hedge our bet?

Right here at decision making time, I want you to think about implementation.

Because a good decision that can’t be implemented well isn’t really a good decision. And thinking things through means envisioning how you will roll out the change and make sure it actually works in the real world.

The reason this can work well is that it gets people thinking about the future in a way that considers the lessons of the past.

As people think about what will make the implementation successful, they will naturally reflect back on lessons learned from the past. Even if they are doing it for the first time right now in the moment.

This gives you the benefit of those lessons without needing to take the conversation down the road of explicitly discussing past mistakes. Which is a good thing to do, but can start to put people back in a defensive mode.

They won’t be defensive about the future because it hasn’t happened yet. This posture makes communication much easier but just as effective.

Here you could say something along the lines of, “If we were to play this out, what stumbling blocks might we run into?”

Or you might say something like, “What things should we put in place to give this the best chance of success?”

Using phrases like “best chance” and “might we run into” help to leave things in a discussion of possibilities and probabilities. Again, we can’t really know things for sure so it’s best not to pretend that we can.


We can never really be 100% certain about our decisions, although human nature weirdly leads us to believe that we can be.

If we shift the premise of our decision-making discussions off of that default “all or nothing” viewpoint, we can make much better decisions.

We need to start by recognizing uncertainty. Right away that sets up the discussion to be more open. Nobody is going to be judged as “right” or “wrong” for sharing information or opinions.

In fact, you desperately need that information and those opinions. Which is why you will ask for them by laying out the goal of finding a practical answer.

You want to deal in reality. Not only is that uncertain, but there are also very real limitations. You want those out on the table along with any and all other information you can gather.

Finally, you want to discuss how to hedge your bet during implementation. If you were to play out the decisions, how would it actually take shape in the world? What would you do to avoid potential problems or make success more likely?

Thinking things through into the future in very practical terms can help you better understand the full implications of the decision.

This approach to decision is messy, and maybe a little uncomfortable for a team that is new to it. But an open discussion that includes lots of practical information and contemplates real-world implementation is likely to lead to a better decision.