20 Questions That Will Take Your Career to the Next Level

This article originally appeared on carenmerrick.com - helping high achievers amplify their leadership to become board ready and board worthy. Get your free copy of 11 Strategies To Prepare Yourself For Board Membership.

Questions are the secret sauce that leads to big and small successes.

They ignite new paths of thinking, challenge assumptions, and encourage us to reach beyond what we think we already know.

Questions help build and grow trust and relationships. As children we ask questions easily and often. When I was about 7, my Mom (a working mother with four children), exhausted from my constant questions, lovingly gave me a copy of what became a treasure of my childhood - a book simply called, The Curiosity Book. It was full of hundreds of questions, like, "Where do marshmallows come from?" My older sister and I spent hours reading it together.

While curiosity doesn't appear to diminish as we get older, as we become adults and work in teams, we are more cautious about asking questions.

This occurs even though surveys show two of the top skills that companies want from senior and emerging leaders are good listening and analytic skills. It's hard to be good at these sought after skills unless you become good at asking questions.

Whether you are a seasoned executive, middle manager, or new professional, your questions can set you apart. Frequently, the process of asking questions and digging for answers uncovers rich treasure that would otherwise remain buried.

Questions spark transformations in individuals, teams, projects, and whole companies.

Asking questions is also an under-appreciated and underutilized team-building skill that encourages others to ask and THINK.

Good leaders ask a lot of questions because it models that it is good to be curious, that no one is expected to know everything, and that all are welcome to ask, seek, and find.

And, if you're really concerned about the direction of a project or initiative, asking questions can be more effective (and even more subversive) than making statements.

Experts know that in conversation, the advantage goes to the one who is listening, not the one doing all the talking!

Surprisingly, there are many questions you can ask in nearly every situation.

Here are 20; cherrypick from these today and this week in your projects. And remember: the truth is, if you don’t ask enough questions, you may never achieve the potential of your opportunities or challenges.

1. Did you (or we, or they) arrive at this decision or result by logic, intuition, or both? What’s the evidence to support the decision or direction?

2. What problem are we solving for our customer? What’s in it for them? How are we adding value?

3. Where is the leverage of this idea or direction? How does it intersect with our other goals or objectives?

4. How do we measure this? In real terms, how do we quantify the effort and outcome?

5. What will it cost in terms of time, human, and financial resources?

6. Could we achieve this better with a partner? Who is (or are) the ideal partner(s)?

7. What's the risk if we don’t do this?

8. What's the risk if we fail? What is the worst thing that can happen?

9. Are we close enough to our customers? Who on our team is close to our customer, and what can they tell us? Can we collaborate?

10. What do we stand for and what do we stand against? How can this decision or project affirm this?

11. What do we need to start doing?

12. Can you or I explain this product, service, direction to my mother? (This was a favorite one we used in the early days of AOL, when the idea of connecting with people, businesses, and customers online was so new!)

13. How can we test this idea before committing more resources to it?

14. Do the managers of the team believe more in the team’s potential than the team does?

15. Are there stupid rules we need to kill? Assumptions that sounded right, but are not being proven through our experiences?

16. Have our competitors tried this? What can we learn from them?

17. Who needs to be thanked for getting us into this line of inquiry?

18. Who needs to be encouraged/persuaded to invest in this?

19. How can we quantify and communicate the benefits of this approach?

20. If we had unlimited resources, what would be possible here?

What are some of the best questions you or your team members have asked?

I believe in the power of incremental change, one idea, action, and day at a time. That's why I created the Pocket Mentor mobile app.

The Pocket Mentor app is perfect for motivated leaders who want to increase their impact, influence, and rewards. The app provides you with daily advice, tools, and action plans (right at your fingertips!) to win at work, succeed in life and enjoy it.

Good leaders know they must continually grow; and they need the advice of a variety of mentors.  

I would love for you to download the free trial of Pocket Mentor, now available in the App Store! 

You can also visit my blog and sign up to receive my free eBook with leadership and career advice, 5 Ways to Add Value and Move Ahead Now.

I’m a serial entrepreneur (startups in tech and social impact) most notably co-founder and EVP of webMethods, Inc. which I grew from my basement to a $200m global, Nasdaq company with 1,100 team members. I now serve on several public company boards, write, speak, and advise high performance leaders, particularly those who want to serve on public company boards. I’m married with two sons and our family loves to sail on our catamaran, Glad In It.

For tips on how to develop a strategic plan to join a board, visit CarenMerrick.com and get your free copy of 11 Strategies To Prepare Yourself For Board Membership.