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7 Tough Questions You Need to Ask to Challenge Yourself More

These questions aren't exactly fuel for the easiest, most pleasant conversations you'll ever have with yourself, but it's important to your success and development to find the courage to ask them.




Sometimes it's difficult to ask yourself the right questions--the questions that challenge you and make you a better person. It's not easy to have these conversations with yourself. Barriers like sensitive egos and time restrictions prevent some of us from being the best versions of ourselves. But it's time to change that.
I have learned that asking myself these seven tough questions (and answering them honestly) has challenged me to become better and to create more opportunity for my team and myself:
1. Am I investing enough in myself?
One of your biggest investments in life is the one you make in yourself. The knowledge, experiences, and relationships for which you expend your time and energy are the biggest contributors to your livelihood and happiness.
Many of us invest in ourselves through college or other forms of education, but it's just as important, if not more so, to continue that personal investment once you start your professional career. Whether you launch a new company or become part of someone else's venture, your brand follows you wherever you go, and a good one will make your life easier by lowering trust barriers.
Contributing content can play a critical role in fueling high-trust relationships and bolstering your personal branding efforts. A great source for creating exceptional content is this four-step guide my team put together. Map out the most important attributes that contribute to your brand, such as content, speaking events, industry awards, and other accolades, and put a plan in place to consistently invest in these--and in yourself.
2. Am I mentally strong?
I first became fascinated with mental strength after I read Amy Morin's article "13 Things Mentally Strong People Don't Do." Habits like trying to please everyone or feeling sorry for yourself can really hamstring your productivity.
I've learned to take a step back and read through the article whenever I ask myself whether I'm really being mentally strong. I sometimes realize that I'm not--that instead I'm getting caught up in thoughts that don't fortify my mind--and then I can get myself back on track.
3. Am I likable?
During the most recent Fortune Growth Summit, Mark Cuban spoke about the importance of being likable and how easy it is now for people who don't like you to become negative brand advocates--and to amplify those unfavorable opinions on social platforms.
It's very simple: We tend to deal with people we like over people we don't like. If someone likes you, it not only increases the likelihood that he'll do business with you, but it also increases your chances of recruiting a positive brand advocate. But how do you know whether you're likable?
It's easy to feel that you're likable, but it's important to seriously ask yourself whether you truly are. I came across an article by Jeff Haden that details 11 things the most charming, likable people always do, and when I took an honest look at myself, I realized I practiced fewer than half of these charismatic behaviors. Since then, I've kept this list with me and used it as a reminder to work on developing each characteristic.
4. What am I doing well that might distract me from doing even better?
When you're succeeding, it's easy to slip into a comfort zone. You're already doing something well, so you don't think of what you could be doing differently to become better at it.
I've talked with countless business leaders who boast that their companies' growth is primarily due to client or partner referrals. (And actually, I used to do the same because referrals clearly communicate that a product or service is worthwhile.) When someone thinks your service is valuable enough to refer it to someone else, it's easy to stop there with the belief that you're already doing great.
But if so much of your growth comes from referrals, you should do everything you can to stay top of mind with the clients and partners referring you. My team and I use content to nurture those clients and partners and to keep ourselves in the forefront of their minds. Content strengthens our relationships, and our referrals have increased substantially as a result. Don't let your successes blind you to the ways you could change to become even better.
5. How can I add purpose to my life?
Sometimes we confuse purpose and fulfillment with charity, but a sense of purpose doesn't have to come only from volunteering or donating to charitable causes. Purpose is more about feeling valuable and providing value to others.
A slight change or tweak in your life can add purpose, but in some cases, it takes a more significant change. Looking back on my work before starting Influence & Co.,I didn't feel that sense of purpose. But since starting the company, I've been seen it help hundreds of leaders build their brands, influence their industries, assist others, and create more opportunity for themselves and their teams. It's not a charitable cause, but it has turned into a sense of purpose that is extremely motivating, and I feel fulfilled.
6. Am I helping the people around me become better?
In my 20s, I was fairly self-centered and thought a lot about how I could make myself look better and seem like the rock star within a given group. As I've grown a little older, I've realized that the best people are those who empower others and lift them up. What are you doing to help the people around you be better versions of themselves, and how can you recognize them for the good they do, even when that spotlight could be on you?
7. What do I avoid but know I need to address?
Are there tasks or projects you consistently put off because you're scared or don't understand them well? You're not alone. A common area I see business leaders avoid is social media and social profiles.
While I completely understand why people don't want to announce on Twitter what they ate for breakfast, I do not understand how leaders can bypass social platforms entirely. Social media let you humanize your brand and connect with your audience, and lacking that presence doesn't look good for your credibility. So ask yourself whether you're procrastinating about something important, and if the answer is yes, put a plan in place to overcome it.
These questions aren't exactly fuel for the easiest, most pleasant conversations you'll ever have with yourself, but it's important to your success and development to find the courage to ask them. Take the time to think about your answers, and you'll find yourself growing as a person and as a business leader.

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