In Marketing Strategy

rock-climber There’s one question all small business owners should ask themselves – today and everyday. No matter if you’re just starting up or if you’ve been around for decades. No matter if you’re bootstrapping or if you’ve got pans full of cash.

Even if you’re extremely successful, you need to ask yourself this.

What is the one challenge holding your business back from greater success?

You can only pick one. I know you’re facing enough challenges to fill your entire Twitter feed. But making a long list of all the things that are going wrong isn’t going to help right now. Being honest and true about the number one challenge will get you somewhere.

You can make a difference if you focus your efforts on one thing. If you try to solve a dozen challenges at once, you’ll make a little progress on each of them. But that still adds up to a lot of unsolved challenges.

So what’s it gonna be?

Focus only on what you can control. If there is something holding you back that you can’t control, I’m sorry but I left my fairy wand at the dry cleaners.

There are no such thing as wrong answers

Is your number one challenge lack of time?

That’s a bad answer because really what you’re saying is, “I’m trying to accomplish everything at once.”

What is the most important thing for you to accomplish?

What makes money?

What makes you happy (at work)?

What drives the business forward?

Do any of these challenges sound familiar?

Are you too shy to drum up new business?

Is your team carrying dead weight?

Do you routinely get caught up in distractions so that you go home feeling you’ve accomplished vey little?

Do you have cash flow issues? Let me rephrase. We all have cash flow issues. Is cash flow the No. 1 impediment to growing your business?

Is your No. 1 challenge something else entirely?

What’s the fix?


The answer is pie. (On some days). On every other day, pinpointing your top challenge and committing yourself and your team to solving it is a huge step, so go treat yourself to a latte, then come back and we’ll finish up.

With your top challenge written down in front of you, work backwards. What needs to happen to solve this challenge? How much money is it going to take? How much time? Who else needs to fully commit to make it happen?

If the challenge is a question or piece of information you need, ask yourself who has faced a similar challenge? How can you contact them? You’d be surprised how many people will help others answer a genuine question. It’s because at one time they themselves were asking the questions, relying on the expertise of already-established business owners.

If the challenge is because you’re too shy to talk about your business with others (a very common issue!!!) the answer is to practice. In the shower, driving to work, taking a walk, talk to yourself! Practice answers to these basic questions:

  • What do you do?
  • How did you get into that line of work?
  • Why do you love what you do?

Get so comfortable with your responses that answering questions when you meet new people is so easy it doesn’t make you nervous. Practice talking about your business just like you practice the piano as a child. The more you talk to others about your business, the easier it becomes. I promise!


If you have no idea what to say or how to explain your business, we can help. As a former reporter, I’m an expert at crafting stories, pulling out the interesting parts and shushing the less-interesting parts.

If the challenge is someone on your team, talk to HR about whether to let them go. If you ARE HR, ask yourself:

  • Would the person succeed in another part of the job?
  • Does the person need time away?
  • Is the performance issue constant – or temporary?
  • I’m trying to cut your deadweight a lot of slack because there may be a fantastic employee/contractor underneath the rough edges. It may be easier to work with the team member than fire and hire anew. If you must let someone go do it in a way that leaves the door open to working together again. You never know when you may need their help.

None of this applies if the person is a total stealing, lying geezerball, of course. Use your best judgement.


If your challenge is distractions, stick to this one principle and the buzz of distractions will go away. Tackle the “big rocks” first. Think of your workday as an empty glass that you have to fill it with big rocks, small pebbles, and sand. If you put the sand and pebbles in first, there won’t be enough room for the big rocks. But if you place the big rocks into the glass first, then sprinkle in the pebbles, and finally pour in the sand, everything fits neat and tidy.

The big rocks are your 1-2 hour strategy tasks, research, creative thinking stuff that you need a lot of energy and focus for.

The small pebbles are the 10-30 minute tasks that need to be taken care of but don’t require 100% capacity.

The sand is all the annoying little emails and things you have to do, like buy office supplies or fill out paperwork or send invoices. You could do it at 10pm when you’re zonked and no one would know the difference.

If you still need help, I’d love to hear more about your challenge and brainstorm what information or person you need to pin down to solve it. Sometimes, an outside person who is not emotionally connected to your business can give you the fresh and honest insight you need to hear. Being a “business therapist” is one of my favorite parts of the job!

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