Leadership Questions Without Easy Answers

When I was younger, I had lots of definitive and unyielding answers. As I get older, I have mostly questions. That’s been good for my clients - it’s my job as a leadership coach to ask more than to tell, and many of the questions I ask don’t have easy answers. In fact, I don’t even use the word “answers” anymore; I say “responses” instead.

If, like many leaders, you’ve been rewarded throughout your life for being smart and solving problems, you might find it discombobulating to ask hard questions.

My invitation is to keep practicing. Develop more interest in the challenging questions that face your business, your family, and the wider world.

In this blog, I’ll give examples. I’ve captured three thorny questions about leadership that come up time and again. The “answers” to all three questions are debatable, with no obvious, single solution. I share them for your consideration.

How often does change in an organization originate with the person at the top?

In leadership development circles, it has long been assumed that the CEO, president, or executive director can lead others by modeling the desired behavior, or showing that he/she has "bought into" a way of thinking or acting. The argument is that managers and staff will follow the lead of the person in charge: If that individual embraces leadership improvement, they will, too. If there’s resistance at the top to leadership development, it will not take hold in the ranks.

I used to believe that was true. But is it always accurate? Does it need to be?

I never tire of hearing about an individual living in an adverse situation who overcomes poor odds to attend a top university and become an accomplished professional. Can this apply to persevering individuals in short-sighted organizations?

If a highly motivated middle manager wants to find a way to work on her own leadership improvement, can she do this even if her bosses are disinterested or too busy to support her efforts? Can she find a way to excel at leadership even if she has poor role models?

Have you ever witnessed an individual from the "lower ranks" initiate a culturally unconventional behavior that positively impacts the organization?

What degree of “personal exposure” is appropriate for a leader to display with his or her direct reports?

In my experience, I have found evidence that a strong, personal connection with one’s direct reports gives leaders a definite advantage. One of the keys to building and maintaining any personal connection is self-exposure: allowing others to see my human side and to know me at a level that transcends work issues.

Most leaders--not just the overly reserved--need to work on openness and connection. But how far should personal sharing go?

Do my direct reports want to know that I am depressed, divorced, or financially stressed? Would they somehow feel cheated if they found out I had cancer but didn’t tell them about it? When does personal disclosure become counterproductive?

As a leader, how do I maintain the right balance in disclosing enough about myself to grow a relationship but not so much detail that my personal life becomes a distraction to the work itself?

While personal connectivity fortifies a relationship, there’s something important to be said for emotional separateness. Where’s the balance point?

How can leaders continue to work on self-improvement?

Whenever a leadership development or cultural change effort kicks off in an organization, there’s a flurry of excitement and investment.

But what happens two or three years down the road, after an initial phase of ideas, strategies, and skills have been learned and new practices have taken hold?

Too often, that’s when a company stops investing. There’s a sense of having completed something, instead of a more truthful acknowledgement: “We’ve only just begun, and we need to keep reinforcing the gains we’ve made. Progress is continual, not once and for all.”

When it comes to managing relationships – a cornerstone of leadership – it’s easy to slide backwards and lose focus without ongoing improvement efforts.

Should those efforts be built into every leader’s job description, or would that compromise the focus on other important work?

Who’s more responsible for a leader’s self-improvement: each individual or the organization?

Should forward-looking companies budget dollars for each leader to retain outside coaching of his/her choice? Or should all leaders subscribe to the same leadership development program and learn as a group? Does it have to be either or?

When we run up against tough questions, it's time to think more deeply.

It’s satisfying to produce answers to technical problems. Definitive answers offer immediate gratification. But when leaders take on the harder questions, there are two huge payoffs:

  • We become better thinkers. By shifting our focus from the simple to the complex, we expand our viewing lens. Our strategic skills take a leap forward.

  • We learn to stand with confidence on our own two feet. Whatever we come up with belongs fully to us. It fits our situation, vision, values.

Reflecting on difficult questions and crafting sound responses expands our perspective. When we share our deeper thinking with those we lead, the whole organization benefits.

Leadership Coaching, Inc.
448 Frederick Douglass Street
Rochester, NY 14608
P: 585-482-2205
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