In this great TED talk – “The art of asking”, Amanda Palmer shares how she built a successful music career, untied herself from a record label, and even managed to enjoy the process by asking – and mastering it. When building a startup asking is your default mode – you need to ask for money, to ask users to try out your half-baked product or to ask others to share their relevant experiences. Asking might seem like a huge burden but I find it is a powerful tool and try to use it as much as possible. Asking is not about looking for help, it’s a way of interaction. It’s an incredible way to get to know people better, to create a better connection with people and by doing so – to build a better company.

I’ve noticed for quite a while now that my best meetings, those which yield the best results, are the ones that have the most balance of conversation between me and the person I’m meeting with. It doesn’t matter if it’s me trying to ‘sell’ something or if it’s the other way around. It can be an investor meeting, a meeting with customers, interviewing a candidate for a job or trying to help a fellow entrepreneur. If there’s symmetry – things click. Obviously, I can choose what to tell about myself, but in order to maintain that symmetry and understand the other side, I need to use a different tool – questions.

Stop asking numeric questions (How many years have you been working for the company? How many employees do you have?)

When trying to create a personal connection and getting to know the person I’m meeting, I try to avoid questions that can be answered with a number. The obvious reason is that these questions are usually pretty boring, but the real reason is that numbers are the easiest way to ‘measure’ others, and people may feel like they’re being judged. Every time someone asks me how old my startup is I get an insecure feeling – Takipi is only one year old – maybe they think it’s not mature enough to have a solid product, or maybe they’re thinking that after a year we should have had more customers. I always feel uncomfortable when answering this question even though it’s very technical and I’m very proud of the company. Even when you don’t mean to be judgmental (and usually you don’t) there’s a good chance the other side might think you are.

When you ask someone how long he’s been with the company, and it’s only been 3 months he might feel insecure (and if it’s the other way around, that he’s been there for too long).
Or :
How many people are there in your company?
If the company you’re asking has just gone through layoffs, they might feel understaffed or just have a negative reaction.
And the worst one: 
How much money have you raised so far?
A question I personally get asked several times each week. Even though we’ve raised exactly the amount we were looking for, I always feel I am being judged when I answer this.

People don't always hear what you really asked

People don’t always hear what you really asked

Nothing beats feelings


While asking numeric questions makes people feel they’re being ‘measured’, asking about their feelings represents the other side of the spectrum. There’s nothing good or bad about the way people feel about something, and when they share how they feel with you it’s likely to create a basic bond. Don’t get me wrong, I meet mostly with techy people and I don’t ask them about their deep feelings or early childhood experiences. But I do ask them how they feel about certain parts of their job – How did it feel to move from a technical role to the product side? How does it feel to come back to a small startup after being part of a big company? How does it feel to have your first users?

The answers may vary from very positive feelings and excitement to negative ones. Either way, this helps you move away, even if for a few seconds, from a business-like interaction to a more friendly one, from talking about facts to having people talk about and share about how they feel about them.

Let people feel proud about what they’re doing


Most of us love what we do, or at least parts of it. Getting to talk about the best parts, the highlights, allows people to share the things they’re most proud of and injects a positive and excited energy into the meeting right away. Talking about the small things people are proud of can bring as much excitement and joy as talking about their most major achievements. When I meet companies and they begin to recite their customer list I like to ask who their favorite one is. This question usually brings out beautiful stories about lovely customers who really appreciate their product, celebrities or surprising users. When I interview developers I like to ask them about the most complicated bug they’ve ever solved. It brings back their feeling of pride and accomplishment after struggling with a complex case for weeks. One other great thing about focusing on proud moments is that it gives me an opportunity to share some of mine. I can share the best part of my previous startup, a story about a great customer or tell about a complex piece of technology we’re building. By sharing the moments I’m proud of I’m able to get a bit closer to the people I’m meeting with, and to bring more positivity into the meeting.

When asking something that might cause people to feel uncomfortable – give a potential non-judgmental answer


Sometimes you can’t avoid asking questions that might cause the other side to feel some discomfort. Even if the answer does put the other person in an uncomfortable place, if they feel you’re asking without being judgemental it creates a whole different setting. I like to ‘propose’ a positive or neutral answer just to make sure the other side understands I’m not implying there’s something wrong with them. For example, last week I had to ask someone why his boss didn’t accept his recommendation to start using a new tool. If I would have just asked directly I might have implied that his boss doesn’t appreciate his opinion and recommendations. Instead, I asked whether his manager was worried about not meeting his deadlines and therefore decided to avoid testing new tools.
When I needed to ask someone why he decided to close his startup and join a large company, I ask if he was interested in understanding how large companies work or wanted to explore how it’s like working with millions of users. Your ‘suggested answer’ is probably not the correct one, but you’ll be able to give the other person a positive feeling and not push them into a corner. Once you suggest an answer there’s also a much higher chance to get an honest answer. Try it.

Explain why you’re asking, the whole truth

When I meet with people it’s usually for a good reason. I might truly believe that our product can help their company, we may be able to offer this person a great job, or I may be able to share the relevant experience with a fellow entrepreneur. In the TED talk mentioned earlier about the art of asking, Palmer explains how to ask in the most efficient way -“When we really see each other, we want to help each other”. The other side of the equation is that allowing other people to ‘really see me’ puts me in an uncomfortable place, and sharing certain facts makes me feel vulnerable. For example, I recently asked someone if he thinks there’s a good chance they’ll actually use our product. I explained that I need to know because we’re a small startup and don’t have enough resources to invest in many companies. I ask users I meet to give me all their negative feedback because we’re about to launch the product soon and we need to avoid mistakes. Asking this kind of questions and putting yourself out there is very challenging, but in a way, it represents the true essence of asking.

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