Five Questions You Can Use Today To Demolish Obstacles

Every business has obstacles where we say, “We just can’t ________.” Or, “We can’t do this now.” Or, “We don’t have the capacity or capability to do ______ now.”

We all have things we’d like to accomplish that just don’t seem possible at this moment. It might be a sales or revenue figure. It might be removing or adding some staff. It might be adding a new product line. It might be changing out an expensive system you bought several years ago that’s paid for but isn’t producing the results you want today. It might be entering a new market, etc.

But it’s something where you’re currently saying, “We just can’t do _________ now.”

So, what’s your blank? What obstacle are you currently facing where you can’t seem to find a solution today?

Once you have that in mind, you might want to consider asking the following questions to see if one of them will help you create a breakthrough.

Q1. “Who Says?”

Frequently as leaders we deal with problems because someone else has told us, “You can’t do X.” Or, “You can’t do both X and Y.” Or, “No one in our industry does X.”

But, does that make something true or right or correct? Frequently, you simply need to question convention and ask the, “Who says?” question.

Just because other people don’t do something doesn’t mean you can’t.

This question is also powerful because it causes you to reflect on who the “who’s” are—and how many of them there are.

Back in my old pastoral days, I can remember having to frequently ask this question of my board. They would hear from their friends that X was a problem. I’d have to ask, “Who says?” They’d list a couple of people (all of them their friends) and I’d say, “So, out of two thousand people we have six people who think X is a problem? Moreover, each of those six people you mentioned are old timers who prefer things the way they’ve been done. Am I missing something?” And in short fashion, the problem usually wasn’t a problem any more.

I can’t oversell how many times the “Who says?” question has broken through what others thought was a seemingly insurmountable obstacle.

Q2. “Why Do I/We Believe That?”

Whether we verbalize them or not, all of our decisions are based on assumptions/beliefs. For example, Joe may say, “If I want to grow sales, I need to hire a new sales person.” His belief/assumption is that hiring sales people always pays for itself. You hire ahead of revenue, not behind it.

On the other hand, Sally, facing a similar problem, won’t hire a new sales person because she doesn’t have enough cash to do so at this time. Her belief is that you only hire people you can afford to pay for today.

Two business owners, similar problem, different decisions. Why? Because their beliefs/assumptions are different.

So, whenever you’re facing an obstacle, one of the smartest things you can do is challenge your assumptions. And the key question to do that is, “Why do I (or we, if you’re doing this as a group or reflecting on your business/team) believe that?”

For example, let’s say you need to make a capital investment but your cash flow isn’t strong right now. There are a lot of small businesses that are completely self-funded. In fact, it’s often a matter of pride. “We never borrow. We always grow based on internally generated cash.”

But, if you want to grow rapidly, is that belief/assumption valid? Probably not. Internally generated cash has a cap on the rate of expansion. External capital can accelerate growth. Just because you haven’t used outside capital in the past, doesn’t mean you can’t use it in the future.

When I’m working with clients, I frequently find that helping them question their assumptions gets them to break through obstacles that seemed insurmountable just a few minutes earlier.

Q3. “What’s the Cost of Not Doing This?”

In general, most of the business owners and entrepreneurs I’ve met aren’t very good at calculating opportunity cost. For example, they’ll say something like this. “I can’t afford to fire Frank,” even though they know that Frank isn’t doing his job and they’d love to fire him.

Typically, I have to walk them through a scenario like this.

  • Okay, let’s calculate the cost of you keeping Frank on. First of all, how much are you paying Frank?
  • $70,000.
  • Okay. How much time do you think you’re wasting dealing with issues related to Frank each week?
  • I don’t know. Maybe five or six hours.
  • Alright. Let’s call it six because most leaders underestimate the amount of time they waste dealing with an underperforming employee. Based on your hourly rate of $100/hr, that’s 300 hours a year at $100/hr or an additional $30K you’re “paying Frank” for underperforming.
  • Next, how many opportunities do you think you’re missing because Frank isn’t meeting his quota.
  • Well, Frank missed his quota by $200K this past year.
  • Got it. Now, as far as your time goes, if you weren’t wasting your time dealing with Frank for six hours each week, how much more revenue do you think you personally could help generate for your company if you had those 300 hours back?
  • On the low-end, probably $300K.
  • Good. So, with just a few data points, we’ve just calculated that the real cost of you keeping Frank employed here isn’t just his salary, but $30K of your time, plus $500K of lost opportunities, and we haven’t even calculated the emotional toll it takes on you, as well as the morale of your people, etc.”

Once that conversation is over, typically, the business owner or entrepreneur will say, “I guess I better fire Frank.”

However, this isn’t just a firing question. Opportunity cost is involved in every decision because whenever we’re saying, “Yes” to one thing, we’re saying, “No,” to something else.

Q4. “Is There a Piece of This We Can Solve Now?”

Another major obstacle stopper is the belief that in order to solve a problem or obstacle it’s an all or nothing deal. For example, either we replace the $1M core system or we don’t. And if we don’t we just live with it.

The problem with all or nothing scenarios is that life is rarely like that. In the case of the core system, I had a client where when I asked this question, one of the answers that came back was, “Well, short of replacing the whole system I think we could hire a programming team to write a patch that would solve problems A, C, and F and it would probably only cost us $30-$40,000.” Done.

The solution didn’t solve the whole problem, but it did solve some of the biggest ones—and they were ones that could be solved quickly.

The other great thing about asking this question is that movement begets momentum. The fact that you solved a piece of the problem, empowers you and your team to believe you can solve the bigger problem.

So, looking at your problem, is there a piece of your current obstacle that you can solve now?

Q5. “If ______ Were In My Shoes, How Would He/She Solve It?”

One of the keys to solving any problem is to get a different perspective. Well, one way to do that is to imagine that you’re someone else and then ask how you think you (being that person) would solve this problem. For example, if you were

  • Tim Cook or
  • Bill Gates or
  • Thomas Edison or
  • Elon Musk or
  • Marissa Mayer or
  • Jeffrey Bezos or
  • Howard Shultz or
  • Sheryl Sandberg or
  • Larry Page

You pick the person. But how would you solve the problem you’re facing if you were that person?

The fun part about this question is that it gets you to think outside your normal ways of thinking. For example, if Richard Branson were in your shoes, how would he solve your problem? Well, whatever his solution might be, you could probably guess it would have to be big/global, it would have to challenge the status quo, it would have to be fun, it would have to be scalable, it would have to be able to run without direct oversight, etc.

You might not come up with the final solution right away, but just by asking this question you’ll start looking at your obstacle more creatively and objectively—and that might put you on the path to the right solution.

So, there you have it. Five questions you can ask anytime you’re facing an obstacle or a potential problem that you want to demolish

  1. “Who says?”
  2. “Why do I/we believe that?”
  3. “What’s the cost of not doing this?”
  4. “Is there a piece of this we can solve now?”
  5. “If ___________ were in my shoes, how would he/she solve it?”

Ask these five questions on a regular basis and you’ll be surprised at how frequently they help you break through the obstacles you’re currently facing.

To your accelerated success!

P.S. If you have some other questions you’d like to add to this list, make sure you add them in the comments section below (or click here >> if you’re reading this by RSS feed or email)