The Subtle Art of the Ask: Unveiling Opportunities You Never Knew Existed

I’ve found all the opportunities in my own network. Looking back it’s a simple formula:

Give Value + Expect nothing in return = Opportunities

No, not every time you add value it rewards you with opportunity. But still, it probably gave you a great learning experience.

In networking, finding and meeting hidden needs in your circle can turn weak ties into close ones.

The art of the ask—a nuanced skill in posing the right questions—plays a pivotal role in unveiling these concealed challenges and aspirations. Or put in simple terms: Learn to ask the right questions to find the struggles within your network. Then match those struggles with. solutions you can offer.

This article delves into crafting inquiries. They reveal hidden needs and set the stage for you to provide impactful support.

The Power of Inquiry

Asking the right questions is like peeling an onion. They reveal the core concerns and desires hidden beneath the surface.

This process is not about prying or being intrusive. It is about showing real interest and empathy to your connections.

The right questions can show the challenges people face. They reveal their unfulfilled aspirations and where they seek support. This often happens before they’ve fully seen these needs.

Crafting the Right Questions

Effective questioning’s essence lies in its ability to encourage open responses that reflect. Here are some strategies for formulating such questions:

Open-Ended Questions: Encourage deep thinking by asking open-ended questions, not yes/no. For example, “What’s been occupying your thoughts lately?” or “What challenges are you currently facing in your projects?”

Follow-Up Questions: Show active listening and interest by asking follow-up questions based on the information shared. This demonstrates your engagement and encourages deeper exploration of the topic.

Empathetic Tone: Frame your questions in a way that conveys empathy and understanding. Phrases like “I can imagine that’s quite challenging. How are you planning to tackle it?” can make the other person feel supported and understood.

Asking for Opinions: People love to share their expertise and insights. Ask for their opinions on relevant topics or decisions you’re facing. This gives you valuable perspectives. It also helps you understand their interests and skills.

Example questions:

Open-Ended Questions

1. “Can you walk me through a recent project that you’re particularly proud of?”

2. “How do you envision the future of your role/industry in the next few years?”

3. “What’s one thing you wish you could change about your current work situation?”

4. “In what areas are you looking to grow professionally right now?”

Follow-Up Questions

1. “You mentioned feeling overwhelmed with your current project load. What aspects are particularly challenging?”

2. “Earlier, you spoke about wanting to learn new skills. Which skills are at the top of your list, and why?”

3. “You said you’re excited about the upcoming changes in your company. What impact do you think these will have on your team?”

4. “You mentioned a successful project you recently completed. What do you think was the key factor in its success?”

Questions with an Empathetic Tone

1. “It sounds like you’re juggling a lot right now. How are you managing everything?”

2. “Dealing with that situation seems like it was quite stressful. How did you navigate through it?”

3. “I can only imagine how rewarding that achievement was for you. What did it teach you?”

4. “Facing such a challenge must have been tough. What support did you find most helpful?”

Asking for Opinions

1. “I’m curious about your take on the new software update. How do you think it will affect our workflow?”

2. “I’ve been pondering over a couple of strategies for our next campaign. Could I get your insights on them?”

3. “You have a lot of experience with remote team management. What best practices can you share?”

4. “Given your expertise in [area], how do you think we should approach this upcoming project?”

The Context of the Ask

The setting and timing of your questions are as crucial as their content.

A casual coffee meeting might be more relaxed. It is better for open sharing than a formal business setting. Similarly, timing your questions when the other person seems more open to dialogue can lead to more fruitful conversations.

Here are some examples of “in-between” moments you could use:

1. Immediately After a Meeting: Utilize the brief window when a meeting ends, and people are gathering their things but haven’t yet moved on to their next commitment.

2. During a Shared Meal: Breakfasts, lunches, or coffee breaks offer a more relaxed atmosphere conducive to open conversation.

3. While Commuting: If you share a ride to an event or meeting, use this time to engage in a focused yet casual dialogue.

4. Pre or Post-Event Networking: The moments before or after a scheduled event can provide a chance for brief, meaningful exchanges.

5. During a Group Activity: Team-building activities or group workshops can present moments to engage in side conversations.

6. In the Elevator: Elevator rides can be an unexpected yet effective time for a quick check-in.

7. Waiting Areas: Times spent waiting before a presentation or conference session can be ideal for sparking a brief conversation.

8. Virtual Meeting Early Joiners: A few minutes before a virtual meeting officially starts when early joiners are waiting.

9. End-of-Day Wind Down: The time when the official workday is ending, and people are more reflective about the day’s challenges.

10. During Unscheduled Office Encounters: Casual run-ins in the office, like at the printer or coffee machine, can be opportune moments for a quick chat.

In every situation, keep it short, on point, and caring. Make sure your message feels helpful, not intrusive.

Don’t go full stalk mode on your boss, manager, or the local store owner. Try to find the sweet spot, whether it’s showing up early for work or just asking for a perfect time to grab a coffee.

Listening with Intent

The counterpart to asking insightful questions is active listening. This means fully concentrating on what is said. It’s not just passively ‘hearing’ it. Listening can help you catch nuances and hidden messages. They will guide your understanding of how to add value.

If you notice how certain situations stress your boss out, consider it useful info. I’ve crafted solutions purely based on triggers like this. We’ve turned a whole store into a webshop. The issue was that the owner was very introverted and couldn’t deal with annoying customers. So we created a business perfect for introverts, a webshop.

Acting on the Information

Finding hidden needs is just the first step. The real impact comes from how you act on this info.

You can connect people with someone in your network who can help. Or, you can offer your own expertise. Or, you can simply listen. Your response can greatly strengthen your relationship.

Don’t overthink the “value” part. Even recommending a good book, course, or article could help the person you talk to. It could also position you as an expert.


To master asking, be genuinely curious, empathetic, and engage meaningfully. Navigate talks well to unveil hidden needs, and offer meaningful support. Enhance relationships, become a valued network member, fostering collaboration.

Leave a Comment