"Why" and Other Questions to Ask Yourself When You're in a Rut

Anyone that worked with me when I was in sales knows what my favorite question is.

"Why?"

Whether it was during a sales call with a lead or a goal-setting conversation with a training client, it was my go-to. My bread and butter. The one thing that I really enjoyed. Heck, I would argue my tendency to ask why is what sets me apart as a coach.

There was many a sales meeting at the gym I used to work for when my manager would ask: "What are some of the best questions you can ask a potential client?" There would be an awkward pause (because who likes talking in mandatory meetings). I'd chuckle. Smile. Make eye contact with my manager. "Why?" I would say—every single time, for weeks on end.

Was I being cheeky, expressing my displeasure at being required to attend a meeting that wasn't serving me? Definitely yes. I also intended to do a service - to drill in the importance of that question to everyone who was newer than me or hadn't quite got it yet. 

I would be remiss if I went any further without thanking Simon Sinek for bringing this ultra-powerful word back into the corporate lexicon. So thanks. It's good stuff.

The problem, though?

We're not using it to its fullest potential. I argue that we've barely scratched the surface.

"Why?" you may ask. (See, told you. Favorite word.)

Because we spend hours asking it of other people. Clients. Prospects. Maybe if you love it (and are really brave), you even ask your boss from time to time.

But when was the last time you asked yourself? 

• "Why am I eating this even though I'm trying to be healthy?"
• "Why am I staying up late watching TV when I need to sleep?"
• "Why haven't I taken a vacation in two years?"
• "Why aren't I doing the job I wanted to do in college?"

These are powerful questions to ask. They can also get uncomfortable fast. You might have felt it reading them or thinking about some of your own "Whys?" That discomfort - it's the growing edge. The place that you move towards to improve yourself, learn more about yourself, level up.

One thing I've learned as I've grown as a coach: "Why" is only the tip of the iceberg when we're talking about powerful questions to ask ourselves.

Here are some others for those brave enough to dive deeper and reflect.

"What happens when...?": This is a favorite of mine when looking towards the future. It has two great uses. The first is when figuring out how a current decision affects the future. By treating it as if it has already happened, you can move beyond what decision to make and start to imagine the outcome. 

The second use, and my favorite, is in giving yourself a reality check. We tend to catastrophize. 

• "What if I fail." 
• "What if they say no." 
• "What if I can't do it." 

These are gut-wrenching, stress-inducing what-if scenarios. It is easy to get stuck there, to get trapped in panic and anxiety. Sometimes, it feels a little bit like we're going to die.

Instead, try asking:

• "What happens WHEN I fail." 
• "What happens WHEN they say no." 
• "What happens WHEN I can't do it." 

It still isn't a great feeling, but it helps look at the results and plan for the future. In almost every situation, the worst possible outcome isn't actually that bad.

"What about this ...?": This is like asking "Why," but better. "Why" and "why not" result in vague, nebulous responses ("Why? Just because"). This is especially true when you're asking it of yourself. Instead, get specific. 

• "What about this appeals to me?" 
• "What about this do I like/dislike?" 

Instead of working with obscure, emotional answers, you can start getting the facts down on paper.

"How...?": We've talked about getting beyond "Why" to get specific. Now let's talk about taking action. "Why" is excellent for understanding the reason behind our actions. It doesn't help us jump into action, though. Motivation is garbage without a plan to go along with it. 

Instead, try asking this:

• "How do I accomplish this?"

This question allows you to begin to build a plan. You know why you want something, how it serves you. It will enable you to start to understand how to get there.

"What's the goal?": I love this question for anyone that gets caught acting 'just because.' I had a conversation with a friend recently, and he was telling me about this new project he got saddled with at work. It wasn't what he wanted to be doing. He didn't pick it. He didn't know where to start. So I asked him: "what's the goal?"

His eyes lit up. Not because he knew - in fact, he didn't know what the project's goal was. That was what was holding him back. He couldn't take the first step because he didn't have direction. Suddenly, instead of feeling stuck, the gears were churning. He was moving again.

If we don't know where we're going with a project, a workout, or in our free time, how are we ever going to get there? Goal first, then action.

With each of these questions, the point isn't to be right. Nobody knows everything. The goal of asking is in the reflection. By reflecting, you gain clarity on your own internal process. In understanding the process, you can make better, cleaner, clearer decisions that serve you better.

If you're struggling to do this yourself, find a coach, a mentor, or a friend who can call you out. Sometimes all you need is a sounding board.

About me: Owner of Behavior by Design Coaching and self-proclaimed Workplace Pirate. I'm here to help high-performing tech professionals achieve a balance between work, health, and passion. I started out startup obsessed, in love with the speed of growth, the go-go-go mentality, and the "move fast, break things" mantra. I didn't realize that sometimes when you move too fast, the thing that breaks is you.

I left my job in tech to pursue my other passion: fitness. There, I regained control of my health and committed to helping others achieve their peak fitness. I also saw countless others experiencing the same problem I had. Pushups and protein shakes don't cut it when you spend every other hour working or thinking about work. I pivoted again, combining my abilities as a coach and my love of the tech world. Now, I help talented tech pros reach the next level by developing the skills you need to improve your health, mindset, and productivity while succeeding at work.

When I'm not coaching, writing, or reading, I'm spending time with my partner by the beach outside of Boston, skiing in the mountains, or kicking back and playing games.