5 Questions Every Entrepreneur Should Ask To Improve This Year

The degree to which we thrive in life and business results seems to be directly related to the depth in which we challenge the status quo in our lives. A common ingredient amongst the most successful, happy, and fulfilled business owners on the planet is that the ability to challenge ourselves to be and do more than most.

In coaching fast-paced, visionary entrepreneurs I notice that its easy to get caught up in the doing of the day to day business and miss the signs its time to grow and evolve. Often evolution brings us more fulfillment and less stress. We lose sight of what’s important or what’s possible for the sake of just getting things done.

After coaching Susie for 2 1/2 years, her biggest breakthough occured when she realized she’d been trying to grow a business she just wasn’t all that passionate about anymore. By asking her these questions, Susie challenged her own status quo and realized she’d been trying to solve the wrong problems (no wonder her progress was way too slow for her liking!)

I always challenge my clients and mastermind members with the following five questions (and it always leads to a higher performance in their activity and profits.) Try it on for yourself and see what comes up:

1.  Is there an easier way to get there?

This question is perfect if you find yourself overwhelmed, stressed out or dealing with a lot of programs that aren’t generating enough revenues. By reflecting on all the possible ways to systemize, simplify or streamline your approach to your projects, you will probably discover that you’ve made things too complicated.

Pick one area to fix at a time. Map out a more efficient or streamlined approach and focus on implementing the changes over a 30 day period.

2. Am I really the person who should be doing this?

As an expert-preneur’s business takes off it quickly becomes apparent that you can’t do everything in your business by yourself. I’ve also noticed that many long-time business owners who have been delegating and outsourcing fall into bad habits and “hold on” to roles that someone else should be doing.

The rule of thumb is this: If someone can do it better, faster or cheaper than you, then get it off your plate so you can focus on the things ONLY you can (and want) to do.

Be brave and bold enough to let go. Figure out what you never have time for and find someone else who LOVES doing those tasks and pay them to do it for you. I know its scary at first but even if someone does it 80% as good as you, its getting done and you DID not have to do it yourself.

3. Who do I need to be to pull off my bold vision of success?

In a society that rewards action, we can forget to check in to our personal habits and thought processes. In fact, in the over 18 years I’ve mentored 7,000 entrepreneurs, the VERY first thing that has to happen is we have to BE the person who can DO what needs to be done.

If you’ve felt stuck or recognize you are playing it safe, this is a powerful question to ask yourself. You might want to get some coaching support with this one – its easy to slip into your blind spot and miss the opportunity to evolve. Typically a sign that someone is not thinking big enough is they tend to chase their next dollar (or sale) and it feels like they are spinning their wheels.

When you start thinking bigger and taking bold action towards your goal, the money follows.

4. What would need to happen so I could invest in _____________?

No matter how much money we have, the decision to invest in a growth opportunity (hiring a coach, joining a success community, growing your team, developing new marketing materials, etc.) requires diligence. But often if we don’t see the money in our bank account the opportunity gets dismissed with “I can’t afford it.”

What if that wasn’t true? What if there is a way to attain the desired opportunity but you have to be more strategic?

If every small business owner waited till the money was in the bank, we’d have 10 small businesses open on this planet.  Be willing to challenge your assumptions and ask the better question. You’ll be surprised what possibilities arise. If you feel challenged in this area, be sure to listen to episode 46 of Amplify Your Success Podcast for some helpful tips.

5. If I was spending more time doing what I really love, what could be different?

This one is a doozy. It requires that we tell ourselves a deep level of truth that can feel scary. But here’s the thing. If you aren’t spending enough tie doing what you really love and your fulfillment level is down, you are a walking time bomb. Be willing to explore what would be different if you were doing what you love.

Now, keep in mind that if you determine there is something else you want to do that you won’t just jump ship and start all over. You create a transition strategy with your coach. You want to make the shift with a purposeful roadmap that feels exciting, right?

Which of these questions brought up a shift in thinking for you? Maybe one of the questions revealed an instant opportunity to move towards THRIVING.

I’m excited to hear in the comments below.

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  • Lisa Rothstein

    September 27, 2012

    The “Who would I need to be” question is the one that gets me. I’d be going to bed earlier, drinking a little less wine and watching a lot less historical drama reruns on TV!
    The other thing would be to more proactively deal with distractions that come from having so many ideas, passions and projects. I talk a lot about this on my blog The DaVinci Dilemma – Solutions for Multi-Talented People Please stop by!

  • Jill Tooley

    September 27, 2012

    I like your first suggestion (picking one area to work on over a gradual period). As an excited, budding entrepreneur, sometimes it’s easy to become overzealous and try to tackle too many changes at once. Gradual implementation makes it less of a shock!

  • Philip Emerson

    October 3, 2012

    All questions listed here must consider by all entrepreneurs. In my case, the first question that I will ask myself before jumping in is the #5 question. Passion is an important ingredient towards success. Speak to your innermost self first to avoid hassles.

  • Lorianne Speaks

    January 7, 2019

    I loved these questions! I identify on many levels with #2 as a VirtuaL assistance company owner – I take a lot of stuff off other people’s plates – and as I grow – I need to start delegating myself!

    • Melanie Benson Team

      January 7, 2019

      @Lorianne, excellent! Now let’s grow your business so you can start delegating more!