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Leadership Caffeine— 11 Questions Leaders Should Ask Themselves

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December 2014
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The Leadership Caffeine series is over 200 installments strong and is dedicated to every aspiring or experienced leader and manager seeking ideas, insights or just a jolt of energy to keep pushing forward. Thanks for being along for the journey!

An early career mentor offered this comment and it has been with me in one form or another throughout my career: “If you’re sleeping through the night, you’re not thinking hard enough about your job and career and you’re definitely not asking yourself the tough questions.”

image of a foam coffee cup with brown outer sleeve

While I encourage a full night’s rest…we all need quality sleep to perform at our best, the second half of his advice on asking (and answering) the tough questions of ourselves is spot on. From CEOs to smart functional managers and senior leaders, we often get sucked into the operational vortex of our jobs and we forestall asking and answering the big questions on direction, people and about our own personal/professional well-being.

There are convenient excuses we use to keep from attacking all three of those categories.

  • People issues are sticky and they involve emotions, and when the emotions might be negative, we tend to move in the other direction.
  • Issues of direction…a change in strategy, investing in new offerings or changing long-standing processes, are by nature ambiguous and therefore perceived by us as risky. Too many managers are taught to avoid risk, and by habit, we move towards the status quo as a safe haven.
  • And issues of well-being…physical and mental health and career satisfaction are things we plan on getting to later. They take a backseat to the urgent daily activities.

Yet, no three topics are more important in helping create value (profits, market-share, efficiencies, engagement) for our firms than the decisions and actions we make and take on people, direction and on the development and maintenance of our own physical and mental well-being.

Here are just a few of the questions effective leaders hold themselves accountable to asking and answering.

At Least 11 Must Ask and Answer Questions for Leaders at All Levels:

Fair warning…compound questions ahead.

1. How am I truly doing as a leader? Am I getting the frank feedback I need from my team members and peers to help me strengthen my effectiveness? If not, how might I get this feedback?

2. Am I taking accountability for the team that I’ve put on the field? Is the best team with the right people in the right positions, or, are there clear gaps that only I can fix? Do I have a plan to fill those gaps? Do I have the courage to make the needed moves?

3. Am I a net supplier of level-up talent to the broader organization? If not, how can I strengthen my talent recruiting and development efforts?

4. How am I measuring performance and success of my team(s)? Do the measures promote the right behaviors? Do the measures promote continuous improvement? Do the measures connect to the bigger picture outcomes we are after?

5. Is the firm’s direction clear to everyone on my team? What can I do better or more of to constantly reinforce direction and ensure that our individual and team priorities support direction? Do I need to teach people about our business and how we make money and how we plan to grow?

6. Am I realistic about the need to embrace change? Are market dynamics signaling a needed change in direction and am I advocating for this change with my peers and by offering ideas?

7. Am I serving as a catalyst for productive change in my firm? Do I believe passionately in an issue that can benefit my firm and am I advocating hard for it, or, am I simply going along with consensus? If it’s the latter, how can I constructively break with the consensus and build understanding for my idea or approach?

8. Am I actively cultivating healthy relationships with my peers and colleagues in other functions? Do I recognize how dependent I truly am on the help and support of other leaders and other functional team members for my own success? Is there a rift that needs healing and am I taking the lead on making this happen?

9. Am I developing myself? What investments have I made in time, effort and money during the past year in strengthening my skills and gaining exposure to new ideas and new ways of thinking?

10. How I am doing? Is my work (my firm, my vocation) in alignment with my passion, superpower(s) and values? If any of the three are out of whack, what must I do to fix the problem? Are the issues repairable in my current environment or, must I do the hard work of making a significant change?

11. Do I understand that my physical well-being directly impacts my mental well-being and professional performance? Am I taking care of myself physically? If not, how can I adjust my lifestyle to improve my physical health? Do I need to invest the outside help of a coach or trainer help me jump-start an improvement program?

The Bottom-Line for Now:

High personal performance is an outcome of clarity and balance. From ensuring clarity for the direction of your firm, your team and your team members to gaining objective insight on your own performance, clarity in the workplace is essential for your success. Balancing your passion, capabilities and values with your daily work and backing this balance with physical well-being is essential for your satisfaction and success. The pursuit of needed clarity and healthy balance is a journey with constantly shifting terrain. Get started by asking and answering the questions noted above. And if the answers are less than ideal for you, take action.

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