How to Ask the Toughest Questions

We all have defining situations in our lives. The actions, emotions and outcomes of those situations shape how we act in current ones.

As a manager, you can create deeper lines of communication if you fully understand the transformative moments that have affected your employees, colleagues - even clients. But to gain a more thorough understanding of the people around you, you'll need to ask probing questions. In the end, you stand to build a more cohesive and engaged team.

Let me give you a personal example: When I was 15, I decided to make what for most high schoolers is a very difficult move: a change in social groups.

In my existing clique, the maturity levels of the guys varied wildly, and I had begun to feel awkward hanging out with them. When I walked into homeroom a few days after summer break, I went to sit with another group. (There were no assigned seats, but teenagers are creatures of habit.)

That was a tough morning.

"Dave, why aren't you sitting with us?" the leader of my group of friends called from across the room.

"I'm going to talk with these guys for a bit. I'll be over in a minute." Cold and confused stares ensued.

A member of the new group walked into the room: "Dave, you're in my seat." I told him I just wanted to stay put for a bit. "Are you staying here for good or just today?" he asked.

"For good, if I can."

"That's cool, but let me have my seat back tomorrow."

 

MAKING THE MOVE

It had all worked smoothly and easily, but there was a catch - I didn't really fit into the new group, even though I had known some of them since grade school. I had been raised in a conservative Christian home, while they had not. Our social lives didn't really fit and our conversations didn't really flow.

Meanwhile, my sudden move had burned the bridge back to my previous clique before I was sure I could get by in the new one. It left me in a social no man's land - a painful outcome I hadn't predicted.

 

LIFE LESSONS

I came out of that experience with two lessons that I carry with me to this day.

First, I am careful never to leave a situation without making it as peaceful as possible. Whether it's a natural end to a friendship or a working relationship, or even the end of an event, I always want to make sure I could call the person involved years later and know I'd be in their good graces.

Second, and perhaps more important: I learned that I had the strength to stand on my own. This confidence helps me stand strong in my beliefs and pursue goals that matter to me without worrying about whether others approve.

 

CROSSING THE ATLANTIC

A similar defining moment came when I was 23. I had grown up in England, but I was now working in Northern Illinois at a YMCA camp, working long hours that only allowed me to call home every couple of weeks.

I was nine months into an 18-month contract and was due to return home to England afterward to become a teacher. I had also been dating my girlfriend, Sarah, for nine months.

One winter's day, I called home to England - and told my mom that I was planning to propose to Sarah soon. My mother had met Sarah, but nonetheless received my announcement with a mixture of happiness, curiosity and sadness. Although she was happy that I would be getting married, this was confirmation that I would not be coming home to England. I wouldn't be coming back to move into my old room; in the future, I wouldn't be able to spontaneously drop by on a quiet Saturday afternoon.

It was a transformative decision for me personally and professionally. I was the first member of my family living in the U.S., a first-generation immigrant.

I was leaving behind a place where I had a natural support system, and I needed to survive and thrive in my new home, without a safety net to fall back on.

It gave me a strong desire to succeed at my numerous goals, and give my new family a life that provided them a substantial cushion from discomfort. It ignited my ambition - I wouldn't give up this feeling for the world.

Both of these experiences left me with clear beliefs and habits that underpin the way I operate. Yet colleagues, managers and other professionals might not know any of that, or understand my goals and motivations, without knowing my backstory.

 

TEAM BUILDING

How does this translate back to the workplace? I see a lesson for advisors who need to understand these defining moments in the lives of employees, colleagues and clients.

Start by asking thoughtful questions and engaging in responsive listening over a prolonged period of time. Try open-ended questions:

* Who would you say had the greatest influence on you when you were growing up?

* What situation from your childhood holds the most vivid memory for you?

* Is there a decision that you've made that, in hindsight, clearly defined your path?

* Do you wonder how life would have turned out if you had made a different choice?

Sit back and let people's memories come alive. They may talk about their parents, their teenage relationships, their oldest friends. Then follow up with more questions: How did those experiences change your behavior? What lessons did you take away? How did those long-ago personal relationships affect the way you communicate or interact in the professional arena?

 

PROBING QUESTIONS

These can be uncomfortable questions, but they are also meaningful and insightful - and few people are willing to ask them.

You don't have to be a trained therapist to ask. Just let people know that you'll be asking these types of questions as a way to get to know them better, both to develop your professional relationships and to enhance your work dynamic.

The information you gain will help you develop a communication style specific to each person you encounter, since your own style is largely defined by your own experiences, which naturally differ from those of the people around you.

Should your explanations be direct or exploratory? Should your interactions be oriented toward tasks or relationships? You may find it more effective to discuss things in person, or you may prefer to use email, IM or some other method.

Going through exercises like this helps you grow as a leader; it also helps develop the team that follows you. That can't be bad for business, can it?

In asking these questions, you also set yourself apart. Even if it isn't apparent that the answers have affected your relationship, your colleagues may continue thinking about the questions in greater detail.

By showing that you listen and you care, you demonstrate your commitment to those around you.

 

 

Dave Grant, a Financial Planning columnist, is the founder of Fee Only Consulting in Cary, Ill., and specializes in maximizing the potential of firms' Gen Y planners. He's also the founder of NAPFA Genesis, a networking group for young fee-only planners.

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