For several years, I've been fortunate to run coaching sessions for professionals, business leaders, and entrepreneurs. Across industries and borders, I repeatedly ask three questions to help me gain insights into what motivates an individual. The prompts also help illuminate whether someone can clearly identify and articulate his or her future goals and any specific help he or she may need. These simple questions can actually be quite handy while making new connections at conferences or even at dinner parties if that's your bag. 

1. What Are You Working On?

This question is much less invasive than the typical "What do you do?" It's purposefully open ended to invite a range of responses. Some choose to answer with their occupations, others with a current project, and yet others with a particular hobby. I'm always surprised by the variety of replies and delighted to see people's faces light up as they bare (part of) their souls. Sometimes folks may be going in for another round of funding, while others are getting serious about horticulture.

This question actually serves two functions. The first concerns the motivation equation -- why you do what you do. Is it for a paycheck, pleasure, power, fame, or something else? Unearthing this can identify some very interesting talking points. The second function is as an icebreaker. It lets people go macro or micro with their response, and is less intrusive than other archaic exercises.

2. What Will You Be Working On?

Again, the responses vary wildly here. They are usually related in some way to the first question but can sometimes deviate drastically. Many whom I've coached have, for the first time, spoken about what they yearn to do. Hearing themselves say it makes it feel real and is the beginning of public accountability.  

One Los Angeles-based brand strategist said she was working on helping agency clients with their positioning. I asked her what she will be working on, and was dazzled by her response. She was clear and convincing and explicit about how she was going to direct her energy. In the following year, she said, she would launch her organic fashion label. And sure enough, less than six months from that initial session, KENT was born.  

Sometimes, it's a very personal affirmation of what one will do. Take the instance when a very creative fellow said he was soon going on paternity leave. He was adamant about playing a more significant role in his greatest co-creation of all.

3. How Can I Help?

Everyone has an ask. The question really is whether the person can articulate it. And, if so, is the ask a compelling one? Maybe someone needs help with managing his or her time better or leading others more effectively. Often the need concerns items like raising money, finding talent, or getting introductions for new business. But sometimes all that's desired is a little support -- a laugh or an inspiring book might do the trick.

It's also possible that an individual doesn't need any help. In this case (which is really quite rare), I tell people to go away and think about it and come back to me whenever they like. Inevitably, they just need some space to percolate or determine the more ideal time to make the ask.

In group settings, these questions can help colleagues build more rapport with one another. They have helped fuel better team alchemy as well as alignment. Whoever the audience is, consider tweaking and experimenting with these questions so they fit your personality. Authenticity always wins. Go on and give it a go. I'd love to hear how you get on.

Published on: Nov 28, 2017
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