being human

Two Permissions for Asking Questions

When you notice that something seems off, even slightly, then ask 'why' and keep asking until you get to the right answers. Sounds simple but it is incredibly hard to do, and most people just let things slide instead of asking questions. Here is why:

Sometimes we are afraid of sounding stupid. What if my question isn’t well informed?

While I am in discovery sessions with clients I like to start the day saying, “I need to ask for permission to ask you stupid questions, because I won't know if my question is stupid until after I've asked it and we've explored it." Maybe the question is stupid. No problem, lets move on. Maybe it is the question that uncovers the biggest piece of gold in the entire session. I have no idea. And trust me, I ask plenty of stupid questions to get to a good one.

Sometimes we are afraid of people getting defensive. Will you get tired of my incessant questioning?

I also start discovery sessions asking the client for permission to ask a lot of tough questions. Here is how I phrase it, “I’m on your side but I’m going to be asking hard questions. It doesn’t mean I don’t like you, in fact, in means the opposite. Sorry in advance if I come across as a dick." Usually the client is glad they have someone aggressively questioning them and at the end of the day the feedback is usually that they wished I had questioned more. 

The Virtue of the Long Perspective

A lost virtue in today’s world is the ability to have a long perspective. We wildly overestimate what we can get done in a week or a month and we drastically underestimate what we can get done in five or ten years. So, make five year plans. Make ten year plans. Don’t let things that aren’t connected to your long perspective demand too much attention.

Why is the long perspective hard? We intuitively know that there are thousands of unexpected things that happen in a year or two, let alone five years. That gets overwhelming so we keep our focus on a shorter horizon.

But that is exactly the point: a lot happens in 5 years. Just because you can't predict it doesn't mean you should waddle half-hazardly through it. Having a long perspective doesn't mean you have planned for everything, it just means you have long goals. When the unexpected happens adjust or capitalize.

You likely have 25, 30, 40, 50 more productive years in you. Take it five or ten years at a time, adjust as needed, and remember, you don’t have to get it right the first time, or even the second. Be flexible, stay humble, think big.


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Jonathan Collins resides in Portland, OR with his wife and two sons. He is a co-founder of EpipheoSincerely Truman and The Bible Project. He enjoys turning ideas into realities, writing, speaking and breakfast burritos.

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