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The Subtle Art of Asking for Things


As a part of the Developer Relations industry, Kurt constantly collaborates with people and stresses on having a system to get consistent results when asking folks for things.

He believes we must rethink the nature of relationships. When we ask people for things, it falls into two buckets: transactional or relationships. Negative engagements are associated with transactions while positive engagements are associated with relationships. Kurt challenges this sentiment and emphasizes that all relationships are inherently transactional. Positive relationships are consistently ongoing transactions where both parties are receiving value. It’s more about what happens in that transaction that defines whether it is positive or negative.

For successful collaborations, Kurt suggests the 3Rs:

  • Recognition: Recognize that we are asking someone to exert effort to help us. Let them know why they were sought out specifically. It shows you put in the effort to pick the right person for the task.
  • Request: Once the consent of the person(s) involved has been gained, share the actual task as descriptively as possible. Avoid preemptively thanking someone. It makes the assumption they will say yes and can turn a positive transaction into a negative one.
  • Reward: Make sure the person helping out receives something of value. It’s hard to reward someone properly if you don’t know what they value as an individual.


Hey everyone how's it going? I'm excited to talk to you today about the subtle art of asking for things. So real quick, I just want to start off by saying. Hi, how many times have you received a DM like this? I know for me, I probably get a decent amount of them each week. I won't go into specific numbers, but it's pretty high.

It's some form of pretty actually that's funny high and it's some form of hi. Hey, how's it going? How are you? What's or even sometimes it'd be like, Hey, I have a question I would like to ask you. And that's honestly a little bit better because at least they're leading me into what it is that they would like to engage with me about.

When we're asking for things is essentially what we're doing. We're starting in engagement. And so another question I'd actually ask is better yet. Have you ever since the one like this, have you ever wanted to ask somebody for something and you led off just by greeting yourself by saying. How's it going, it's not inherently bad to do that to greet, but a lot of times, especially the further away we are from a connection, a long-term relationship with this person, the li the less effect a greeting, a standalone greeting is going to have when it comes to fostering some sort of.

Incidentally like 5 million high messages are sent daily on Twitter. If you see there, there's a little aspect. I actually have no idea if that's true, but by the amount I get and other folks get, and there's 330 million Twitter users, I find it hard to believe that this number is actually, this is probably low.

Plenty of times. People want to start a conversation, a collaboration and engagement with. And most times, like it's never out of ill intention, right? It could be out of nervousness, not sure how to approach the situation. Thinking a greeting is the better than diving in and out. And all of these are true, but I think what is lacking from high is something that we value a lot, which is context.

Context is honestly, it's everything. It's one of the most important things that we can have available to us, right? When we make decisions, which is when we're asking somebody something, that's what we're doing. We're saying, Hey, I want you to make a decision about this. The more context we provide, the easier.

I want to take a quick second and pause right there. I got a awesome introduced introduction. So thank y'all for that, but I just wanted to dive a little bit deeper into who I am, why we're here and why I'm giving this talk. Hey, I'm for couple again, a founder and principal advisor at Forthright. I'm also the worst dev on Twitter.

So you can find me there. Actually. That's probably the easiest place to engage with me. I am a multi disciplinary tech leader, engineer teacher. I've worn many hats throughout my career over the last little over a decade in tech. I'm also the creator of developer advocates guide series, DX audits, and the developer advocacy value cycle.

The reason I mentioned a lot of these things is because a lot of the work that I've done over the last four or five. Has been in the business of asking folks for things I've been working in developer relations and as is implied by the title of relations, there was a large socio aspect to the job. I was constantly collaborating with people, both in the community, as well as internally at the company.

I even do this today through my consulting work with. All of this to say is that after years and years of asking people, if they'd like to collaborate or give a talk or coming alive stream or participate in some thing or some thing, or help out in some way, I've really honed my skill set or built a system, a framework that I use every time I ask somebody for anything it's been wildly successful, the amount of not just willingness to participate and engage in and help, but the wanting to do it again and again, because at the end, that's what we want to do.

We want to build a lasting relationship. So we don't. Ask people for things and then walk away, which we'll talk a little bit about too in a minute. But all that to say is, uh, that's where my experience comes from and why this talk is happening. Actually started with a tweet actually, technically it started with a DM, somebody me real quick.

Hey, how are you? Here's the job description. Would you mind either passing it around or passing on some names to me, of people who might. Be interested. It seems innocuous enough. And it's somebody who I know respects me. And so there was no ill intentions, but I had to be honest, I hadn't talked to him in a while and it hit me quick and it was out of left field and there was more words in the actual job description that was.

Crystal clear. I had all the contexts on what the role was, but there was more words than that. Then there was an asking me to do the thing or even just saying, Hey, and sometimes we might do things, which I know that they did that in order to save time, they were trying to be respectful of my time, but the problem was.

They didn't understand what I valued and we'll talk a little bit more on that. And it wasn't my time that I valued it was actually having enough upfront information to make an informed decision, and then having them recognize that they're asking for it and showing appreciation. If I chose to help them, I love to help people out, but at the same time from nobody wants to help others and then feel completely unappreciated for doing that.

Helping it takes a lot of effort. Time recruitment is literally a career path that you can do. So, you know, or talent acquisition, right. When we make these asks, even when they seem small, we always have to remember who's on the other side. And so that's what we're going to be talking about today. We're going to be talking about really two things.

We're going to be talking about the proper way. I take that back. Let's not use absolute, we're talking about a way, a structured way of asking for things so that we can teach it, repeat it. And if we were for work report on it, but essentially what we want to be able to do is have a system that we can rely on to get consistent results, to have a system to improve upon because you can't get better at communicating and asking for things.

If you don't have some sort of base system to work off of. The first part of this is actually rethinking the nature of relationship. So largely when we think of asking for things, it falls into two buckets, it's either transactional or it's a relationship. This is often what we hear. And often times negative engagements are associated with transactional and positive engagements are associated with relationship challenge.

The idea that transactional is necessarily negative and that relationship is necessarily. I don't think that that's correct. I think the proof of that exists in the world and that you might go get a tattoo. Right? I've got plenty of those. I might go get a tattoo and I'm going to sit down, get my artwork.

Hopefully I love it. And I'm going to pay my tattoo artists, but they have requested for that. Now that's a transaction, right? I've given them something of value money. And they gave me of something value artwork that I get to wear with me for the rest of my life. But it's still a transaction. Now what's interesting enough is if I returned to this tattoo artist for a couple more times, right now, we start to say, this is a relationship, right?

I might even start recommending my tattoo artists to other people. Oh, Hey, I've got a great relationship with this tattoo artist. You should check them out. But if we circle roll it back, you're hurt to that first moment. There was no relationship, it was a transaction. I got a tattoo and they received money.

So I've had some, so I always like to think of like, why is the term transaction so poorly received? Like, why do we say, oh, don't be transactional strive for relationships. And I think it's because when we don't really understand the nature of asking for things we might do so in a manner where. Is often realized entirely or largely on one site.

And so what happens is in situations where the value transfer is skewed in a transaction, it starts to get bucketed, right? I believe firmly that all relationships are inherently transactional. And what matters is the distribution of value? I see positive relationships. Consistently ongoing transactions of varying sizes, either spoken or unspoken where both parties are receiving the value where they feel like they received value from that transaction.

That's a healthy relationship. Whether that's with somebody you're a partner with, or somebody who you're working with. And so I think we want to first, before we can have a system understanding. All relationships are inherently transactional, but it's more about what happens in those transactions that defines whether or not it's positive.

So moving on to that, what does this mean in a transaction where essentially somebody, it could be by directional in the case of a tattoo I'm asking for a tattoo and they're asking me for the money, right. In most situations where we want to collaborate with some on or something like that, it's not a commercial transaction.

It's more of a, it can be commercial at times, but it's more of like a personal transaction. Anybody can go walk into that tattoo shop and if they pay the money, they can get a tattoo. I'm talking about the type of transactions and relationships with folks who you want to build a more personal connection, who it's not their job to do the thing maybe that they're doing, or even if.

You just don't want to foster a good relationship with them so that when you ask you're more likely to get positive results. And so the way that we do that is with the three RS.

So the three RS basket, the first one is recognized. All right. And honestly, it's the most crucial part of this. And we're recognizing two things. The first is essentially that we're asking, right? Recognizing that we are asking for them to exert effort in some form or fashion to help us, like we have a goal we're trying to achieve and we want them to help us.

Let's let them know that we recognize we're asking them to do something for us. And we don't think it's easy. We don't want to minimize their time effort or. But the second thing that we want to recognize is why me? Why are you asking this person? What is it about them specifically that made you seek them out?

This helps people understand I've put in the effort, like I've got this project I'm very serious about it or this thing I need to get it done. I know you are the person because of X, Y, and Z. We've done two things now already with just this, just a couple lines of recognition. We have set the expectation that we understand.

We're asking them to do something that is going to be essentially work on their end and we'll be appreciative of it. And the second is that we took the time. To make sure that they were in fact, the right person before we even asked them, we're not wasting time. Like you might ask someone to do a talk, but if they've literally said a bunch of times though, I don't like doing talks.

I'm, I'm not a public speaker. I prefer written content and things. Then you're showing that you have not put in the work to recognize, uh, that they don't even do that type of content. It's a pretty negative experience. So always be asking why them, right. Or they should be able to answer, why me? Why did they ask me?

That should be apparent from your first message. All right. So we've recognized, right? So that is one, what is next? The actual request. And so let me roll those back. We started from high and I know it can feel like a lot to jump from high to. A couple of paragraphs, but I would like to say that if we really want to respect people's times a time, then the best thing that we can do is provide them all of the contexts that we possibly can up front so that they can make as informed of a decision as possible with as minimal effort as possible.

So we've got our recognition and it may look something like, Hey person, I'm working on. And event actually, Hey, let's use this. I'm working on coming conference and I'm trying to fill some of the talk slots. Okay. So what we've done is we're setting the stage a rough stage of what we're asking next. We get into recognition.

I know that doing talks is a lot of work and I've seen that you've done a couple this year, but I wanted to see if you could, if you would possibly be interested in speaking at this event on this. So now we're starting to set the tone. So we know one, they understand we actually dug in and figure it out.

How, how roughly busy is this person? How many talks are they doing? Are they even doing talks? You could talk about how they're in alignment for a particular topic. It's not unlike how I ended up talking to you today. It was a great example of the way. For things and you want to lay out all that information and then also let them know that you understand it's work, but that we're not done there.

That's just the second step. So then is the question, right? So we want to know if you'll be able to do this. How long is the talk? Is there a Q and a, what date is it? If roughly, what time is it? Th you can show them again, recognition. There are times zone. Hey, I know you're in west coast time zones in California.

Uh, happy to have you come on. These. It shouldn't be too early or too late for you. And so we're building up to that request, right? And so we make our ask and then as descriptive as possible as you can about the actual, and we'll get to the third part in a sec. But before I do, I just want to say this.

Thanks in advance. Avoid preemptively, thanking someone. It makes. Assumptions about what they're going to say and how they respond. And it actually puts them in a position where now they have to counter your banks if they didn't have the bandwidth or were interested in the engagement, but you've put them in an interesting situation.

It can quickly turn a positive transaction into a negative one. Just adding that one line. Thanks in advance. Can throw it off. Even if you put in all this work, because it makes the assumption that they're going to do it right. And we can't do that. Next is the. Right. So we want to make sure that we are letting them know what they will get.

So we're back to the nature of relationships and the transfer of value between a transaction. What value will they get? What are, what is the reward for them? If it's a talk, maybe it's monetary, maybe. You worked for a company as a large platform. And not only can we give you money, but we're going to try to promote your content on our blog, social media, whatever, for the next few months, right?

Like you have to be creative, but also you have to know what they value because if you offer something that they don't value, then there is a not an equal exchange. Value has gone more to you than it has to them. And we want honestly, to capture less value than we create in transactions as a general rule, because that means the person walks away feeling like they got a lot of value from it even more than you did.

So that's what we want. Show me the money. When in doubt, it's not always possible to know somebody well enough to know exactly what they value. Most people value money because we need it. When all else fails. Money is always a great option. Now, this is a little something extra. I'm going to try to breeze through this a little bit.

I know we're coming pretty close up on time. I believe couple more minutes, but I wanted to talk about something I've added in here and it wasn't in the blog post. I wrote about this either, which is really the four pillars of positive relationships. So whenever I'm on like a devrel team or DX or anything, that's very socio unrelated, or honestly just how I try to treat relationships as a person, as a whole.

I try to do it off these four pillars and. I talked about the system to outline it. When I didn't give you as a lot of examples about what those messages might look like in practice. And that's because it's all very situational and hard to do. But if you use these four pillars and the three RS, I think you'll find that your requests will go a lot further.

So the first one is be authentic. I don't know how important, um, or how much I could stress this, but this one I would say is definitely the most important. You never want to misrepresent yourself or others, meaning you don't want people sending messages on your. The half, right? If it's saying it's coming from you, you don't want to use the likeness of other people without their permission.

It means being transparent about why you're asking for things or what you will benefit from that situation. If they decide to help you so that they can understand the true value distribution. And so we have to be authentic, it's critical. And the second is getting. It is never okay to use anyone's content, likeness ideas, or even ask them for their help without first getting their consent.

And so that's very important, right. Just to make sure that they're willing to help the. Be empathetic. As I was saying before, we can't have a equal distribution of value if we don't know what people value and we can't know what people value, unless we're being empathetic. What goals is this person working towards?

What current needs do they have? What things are they interested in? And you should know these things. If you have enough about someone that you want to ask them to help you with something. You should be willing to put in the extra effort to know enough about them, to know what they would value from, uh, getting back from helping you, who has a lot of words, but you get what I'm saying there.

You got to know what they value to provide value, right? And then lastly, create more value than you capture. It's not always. It might be that you maybe made some open source project or trying to get on a podcast and you want to talk about it a little bit and share it with some folks. And so you might reach out to the podcast person to get on there.

Now there's still ways you could possibly provide value, but it's probably not going to be more valued than the value of having that large audience and getting your reach out. That's okay. Cause we're still setting, we're still letting them know that we recognize what we're asking of them and we recognize how valuable it would be to us to be on that and how you know, so I think it still shows people that you care you've put in the effort and if it were.

Capability to provide more value. You absolutely would. But again, be creative value can take on many forms. Maybe you're good at editing. You can help out edit a couple of podcast episodes, maybe somebody else who would make a good guest of the list goes on. But now I will say this. If you are asking on behalf of a company, I say this because I was a developer advocate for a long time and worked in REL for quite some time.

If you are asking on behalf of a company, I'm going to find it extremely hard to believe that you are not capable of finding a way to create more value in that transaction. Then you capture from somebody. If you're asking someone to do a talk, they should be paid, right? You should promote their content on companies, platforms, things like.

And that is essentially the four pillars there. And if you keep these in mind, when you're following the three RS, hopefully you'll get a lot better results from your asks. If nothing else, maybe it'll just help you have a little bit more positive engagement in relationships. But with that go forth and ask respectfully, thank you so much for joining me today on I had an absolute blast.

I am excited to get into this Q and a and answer any questions and.