10 tough leadership questions to think through-01

10 Tough Leadership Questions To Think Through

If you’re like most leaders, you’re already frantically focused on kicking off your leadership plan. You’re also probably suffering from New Year Leadership Tunnel Vision Syndrome.

One major symptom of New Year Leadership Tunnel Vision Syndrome is when leaders forge forward into the new year while forgetting to reflect on what effect their leadership had in the year gone by. So let’s go back to the future and see if how you planned to lead at the beginning of last year is where you planned to be starting this year.

The Leadership Look Back Key Question Checklist


How many can you check off?

Did I make a difference? This look back question isn’t about your company, it’s about you because leadership starts with you. Don’t let yourself off easy with a “yes” or “no” answer on this one. True reflection can only be answered by “How?”

What can I do differently? It’s easy to keep wondering, “What can my people do differently?” But come on, all the blame can’t fall on them. Where did you come up short as a leader? What can you change to be a better leader?

Did my leadership happen in the conversation? The conversation is where leadership really starts. That’s where leaders can have the most impact everyday. What percent of the time during the past year was what you said and thought…the same as what your people heard and did? Be honest: Was it a year filled with lots of misinterpretation, miscommunication and misunderstanding…or opportunities, optimal outcomes and outperformance?

Was I relevant? Sure, you show up everyday. But did you show that you’re relevant? Look in the mirror and ask yourself: As a leader, was the leadership I provided a catalyst for inspiration? Growth? Winning? Change?

Where did I succeed…and fail? Every leader remembers what went right. Great leaders also remember — and learn from — what went wrong. Make a list with two columns: What Worked and What Didn’t Work. Did you learn from your successes or were you too busy patting yourself on the back to notice? Did you recover from your mistakes or were you too busy pointing fingers?

Where do I rate with Message Discipline? When you speak, do eyes open wide or start to roll? Effective message discipline translates into operational discipline. On a 1 to 10 scale, where do you rate on “Content”? How about “Context”? Finally, “Conversation Feedback Solicitation”?

Did I reach people on an emotional level? If you don’t — or can’t — no one is going to follow you. So, tap into your emotions and ask: What are my emotional triggers? Can I control them? Do I know what the right buttons to push are to motivate, diffuse, calm, spark, connect and win over different types of people and personalities…or do I talk to — and treat — everyone the same under all circumstances?

How do I handle change? If you’re not changing, you’re not growing. What change have you personally led during the past year? Are you proactively pursuing change on your own or letting change happen on its own.

What kind of leader was I? Understanding what type of leader you are will help you work on what kind of leader you aren’t. Am I strong on creating and leading new visions and strategies? Or, am I more effective when leading through a period of stability? Or, am I a Change Agent capable of leading business transformation from chaos to what’s next?

Was I willing to “Go There”? The common corporate response to almost anything new or different is, “Don’t go there.” Am I willing to “Go There”? How often do I talk about what everyone else prefers to avoid talking about because it’s too scary, emotional or controversial? Are the boundaries I set for my people preventing them from succeeding just because I personally don’t want to go there? On second thought, was there anything I declared “Off Limits” that really didn’t have to be?


Hopefully, this look back got you thinking about how you can lead more effectively this year. If you expect to win the leadership game, you can’t settle for, “There’s always next year.”

fassforward Consulting Group wishes you much success taking the lead this year.

Bio_rose2Rose is the CEO at fassforward consulting group. She blogs about Leadership, Change, Culture and Chocolate Conversations at leadingbittersweetchange.com.

You can follow her on twitter @rosefass.

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