Seven Questions Leaders Ask Themselves Daily

I’m going on seven years being an entrepreneur. During this time, I’ve had some great highs, low lows, and ultimately many lessons, both good and bad.

During this journey, I’ve had the wonderful opportunity to meet some great people who have changed my life. From my business partners, friends, colleagues, mentors, clients, and even competitors, I’ve always found that by surrounding yourself with people that push you positively, you can end up in places you would never have thought possible (albeit, the inverse can be said if you surround yourself with negative people).

During this time, I’ve also had the opportunity to learn lessons from some amazing global leaders (some we can even call clients like GE’s Beth Comstock or Raising Canes’ Todd Graves) on what has made them successful. The thing is, it’s not specific tips I’ve learned that makes these leaders successful. Instead, it’s the answers to questions they ask themselves daily, in spite of the demand of public pressure, market change, and professional/personal obstacles in their lives. These leaders reflect on these questions daily and their answers help dictate their results.

Seven Questions Leaders Ask Themselves Daily

1: If I were hired as the new leader of my current organization, would the work I do today reflect what the organization needs the most?

Try to imagine regularly what your first day as your team’s new leader would be like. What would your most important goals look like? Identify the key actions that need to happen to meet said goals.

Work your daily OPA (outcome, purpose, actions) toward these goals and remain focused. Trust your gut when things need to change.

For more info on OPA’s, check out:

2: Is the organization currently taking enough shots today to keep giving us the opportunity to grow? 

While you never want to take too many crazy shots to take you out of the game, it’s important to still manage the risks that might take your company to great heights.I learned from Ryan Williams of Cadre that growth and comfortability can’t coexist. However, it’s easy to get sidetracked with too many ideas.

Learning the balance of taking on too many crazy ideas requires listening to your gut, your team, and your priorities. All three have to be onboard to make sure your crazy ideas have the best chance of success.

3: Am I too far away from my work and people? 

Keep learning about your craft by surrounding yourself with experts. Listen to front-line employees for suggestions on how to improve and hold specific individuals accountable on implementing changes. Always remember that change starts with you, and that you need to live what you preach.

My partner and Chief Strategy Officer Jeremy Beyt does this well by sharing lessons at our weekly Monday morning meeting. He calls them “Weekly Whys”, and the lessons always reflect our values. He holds himself accountable for a new challenge every week, and it motivates the team to follow.

4: Am I limiting my best people? 

Don’t hold your best people back by micromanaging and making too many decisions for them. If you hire right and everyone has bought into your organization’s vision and values, you should be the one listening to them on how to get things done.

It’s also critical to empower them with authority to make certain calls within their best judgment, especially when you are not there. Be supportive if they don’t make the right call and learn together what should be done next time. You should also invite your best people to challenge you with Radical Candor.

(Extra: Here’s more info on how our agency lives Radical Candor:

5: Am I living urgently with my passions?

I learned this lesson from Bozoma Saint John, Chief Brand Officer of Uber. Life is short; if you are passionate about something, make the time. Ultimately, are you taking small steps in order to accomplish all the things you want on a daily basis?

You need to bring your whole self to work, and fulfilling your passions will make you a more productive and happy person. This pursuit also reflects upon your team and helps encourage them to be fulfilled as well. Fulfilled team members equals better work!

6: Did I say no enough today? 

Resist temptation. The more successful you are, the more opportunities will be thrown your way. The counter way to see it is that the more successful you become, the more clear your goals should be.

The trick is to learn to listen to your gut. It will tell you if any new opportunities or “fires to be put out” are critical to your goals. If they are, then you can deal with it immediately.

(Extra: Watch Kenny’s TEDxLSU talk on the Art of Saying No and why Big Fish Presentations turned down Shark Tank here:

7: Am I building the organization I want to read about? 

We all want to be remembered when we are gone. Same thing goes for an organization.

  • Are we making the right decisions to make key improvements in people’s lives?
  • Are we taking enough bets that grow our team and company with new opportunities?
  • Are we creating a great diverse culture that empowers everyone to succeed?
  • Are we giving back enough to the community?
  • Are we thinking too local and not thinking bigger?

Guide yourself in a direction where, if the company ever dies, your decisions will give the company a wonderful eulogy, rather than just a resume piece.

(Extra: Watch here on Kenny’s talk on how to focus on your eulogy rather than your resume at Hubspot’s Inbound conference –

I know I am writing this post on a strategic marketing blog, I believe everyone can learn from lessons like these, no matter what industry you are in. I have to remind myself of these questions every day at TSE and work it into my actions. While some of these leaders make it a habit to answer these questions correctly as a reflex, young entrepreneurs like myself benefit from having these questions written down and reflected upon regularly.

I hope this post can help you become the best leader you can be and please let me know of any other questions you think great leaders ask themselves daily at We love learning from our readers!

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