Questions to Get Unstuck in Strategy Workshops
By Levina Kusumadjaja
It’s easy to feel stuck in strategy workshops.
You are trying to dig deep and trying to uncover golden nuggets from your client in the strategy workshop. You ask them about their passion and their heart behind their business. You ask them about their customers and how they want other people to see their brand. And after 2-hour conversation that seems to be going well, you can feel the energy dropping in the room. And suddenly the momentum is lost. You feel like you are getting surface level answers and you don’t know how to spark a fresh perspective on the same topics—topics that have been discussed in the workshop but still need to be dug deeper.
What do you do now? Many friends from the Brand Strategy Bootcamp have shared their experiences over their learning journey on facilitating strategy workshops. And from those stories, I’ve curated 5 questions that have helped me and my friends keep the momentum going in workshops:
#1: That’s interesting. Could you tell more about what you mean by ________?
This question is especially useful to explore specific words, phrases, or illustrations. If you catch your client using generic words like “successful” or “growing”, perhaps you can invite them to go deeper by asking them what they meant about the specific terms they used in the conversation. This helps make sure that we are all at the same page too.
#2: What brought this question to mind?
Usually, the questions people ask don’t reflect the things that they are really trying to find out. The questions often show a surface of what they really mean. Asking them the reason behind the question invites them to give you context and to fill in the details that you perhaps won’t uncover without knowing these reasons.
#3: If it were you, what would you do in that situation?
So many people ask you what you would do not because they don’t have any ideas in mind, but because they probably want a confirmation that they are heading towards the right direction. Letting them share their opinion first and diving deeper into their thinking helps us understand where they are coming from. Being listened to first communicates value to other people, and that’s always a good thing.
#4: I’d love to know your thoughts on ________! Do you mind sharing?
People want to be heard. When you affirm that you are interested to hear about their opinion, you are inviting them to more transparency in the conversation. If they feel uncomfortable sharing, let it go and move on to the next subject. But if they are comfortable, you are opening a new window of conversation where you can dig deeper from.
#5: How might we ________?
This is a great question to ask when you spot a problem or challenge. Instead of hammering down the problem or challenge as a negative thing, this question invites you and your client to look at the problem from a place of possibility. Instead of seeing it as a dead end, it invites hope and answers to overcome the problem.
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Have you ever used the questions above? Are there other questions that you have used previously that have helped you get unstuck during your workshops? Let me know what you think and I would love to hear about your experiences in facilitating strategy workshops.
Cheers!
Levina
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About the author:
Levina is a writer based in Indonesia. Because of Melinda Livsey, she recognized the power of brand strategy for every creative. She is sharing about her learnings as she goes to help creatives have fun in their growth and journey of building brands. Connect with her on LinkedIn and say hi!