Kevin M. Hoffman on Proposals

One of the interesting things that I've observed in working in design and process is this idea of working in the open.

My guest today is Kevin M. Hoffman. Kevin is a designer, manager, and author who has led teams of designers both inside and outside of large organizations. In the last few years, he’s turned his attention to designing better meetings. In this episode, we talk about how he’s using information to engage with prospects and clients so they can design meetings that add value to their lives.

Photo credit: Michelle Milla

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Jorge: Today on the show, we have Kevin Hoffman. Welcome Kevin!

Kevin: Hi, how are you?

Jorge: I’m doing alright.

Kevin: Good.

Jorge: I’ve known Kevin for a long time, but the folks listening to the show might not know you — so why don’t you tell us about yourself Kevin?

Kevin: Sure. My name is Kevin M. Hoffman. I go by Kevin M., just because at this point I think there’s four or five Kevin Hoffmans in the in the various platforms: email, Twitter… Anytime I speak at a conference, there are two Kevin Hoffmans that always get my replies and there’s another Kevin Hoffman that gets a lot of my emails. One time I applied for a bank account and the bank started emailing him right after I left. And I did not want to do business with that take anymore because they didn’t write my email address down correctly. So I go by Kevin M. and what I do… These days what I’m doing is taking about two decades plus of experience working in a variety of contexts, but always on a design capacity. So I’ve worked in nonprofits and in the public sector, I’ve worked in agencies, I’ve run companies, you know design consulting agencies. I started a product. And I spent the last couple of years working in a large company — in a Fortune 100 company — and I try to take all of that, and I think about specifically this one piece of everyone’s work experience which is meetings. So everybody has meetings. All of our processes — kind of a unit of measure in processes meetings — you know, if you’re a designer, and you’re part of you’ve been part of an agile transformation, or you’re undergoing that or you’re planning one — a big part of that is renaming meetings and following kind of a rigid recipe of meetings. And what I do is take all this experience I’ve had and things I learned from other people about making meetings do a job that you want them to do, and create ways for people to assess and measure meetings are doing a job for them. And if not, get rid of them. And if they are doing a job help them continue to grow and flourish. I wrote a book and published it last year about this topic. And these days what I’m doing is just talking to different kinds of clients and doing workshops and helping them develop their own meeting health indexes. Kind of a sense of how well the meetings are serving the employees of their companies.

Jorge: That’s fascinating. I’m hearing you describe this and thinking about how much our trajectories mirror each other.

Kevin: Yes.

Jorge: Like you, I was recently at a company and as of last year, I left that company, and I’m also independent. And I also have a book that came out, and I’m in the process of transitioning from working as part of a team to working on my own and being kind of more responsible for things like procuring clients and getting things done.

Kevin: Yep.

Jorge: And I’m wondering what that experience is like for you and what role information plays in that process.

Kevin: Yeah. I think the first time I was independent was about seven or eight years ago. And I was really lucky in that I had a couple of former colleagues from working at agencies that had already gone this route of going independent and then building teams of contractors to undertake design projects. And one of them — a guy named Dan Mall — he had already started working this way, and he’s worked this way for quite a long time. He has an agency called SuperFriendly. It’s named after the SuperFriends, the show from — gosh, I want to say the 80s — I think it’s the 80s — where all the DC Super Heroes would come together and the concept…

Jorge: Is that the one with the power twins?

Kevin: Yeah, where one takes the form of a bucket of water and the other one always takes the form of something else.

Jorge: Right.

Kevin: But it seems like a bucket of water is always… And they had a monkey, for some reason. I remember that. But anyway, Dan brought me into this world of SuperFriends, which is people who for whatever reason find themselves relatively senior — experienced in their craft, whatever part of the design process their craft is, whether it’s discovery and strategy or UI design or front end development or back-end development, whatever it is. And because certain people just like working together, that’s no reason that they have to necessarily form a traditional company. They can just work together when there are problems to solve together. And after spending a couple of years working with Dan and other people who worked in that way — in that context — I decided to just try it out and and learn how to really initiate a conversation with someone in any context where you learn about the problem that you might be able to help them solve and then move that conversation through into some sort of formal agreement. You know, the reason I brought up when I first started, is I remember early on a colleague of mine who I have deep respect and love for — a woman named Karen McGrane — she referred an RFP to me. Like there was an RFP for a website for a bank. A small bank — I can’t remember the name of the bank — and it was the first time I had ever written a proposal and I remember thinking to myself: I’m going to write this proposal. And I’m going to write the best proposal I can write right now.” Because I’d been writing proposals for a while in agencies… And I’m going to assume I’m not going to get this work, but this is going to become like this… What’s the word I’m looking for? I don’t want to say “cornerstone” but like this go-to document that as I write other proposals, I’ll just pull from this master proposal that I wrote.

Jorge: Like a template?

Kevin: Like a template, but it’s almost more like… I think of it this way, one of the things that I do over my career, a piece of information that I keep, is success stories or portfolio work stories where I came into a situation, I performed certain actions, and I observed certain outcomes. And trying to tell those kinds of stories at different levels of zoom, at different scale… I try to collect those. And I have a Keynote document that has like maybe between 10 and 15 stories in it that are some of the best stories I’ve collected over the years, but anytime I send that to a prospective client to say “this is what I do,” I might just pick a subset of those stories. But I had to make the master portfolio document at first, you know, and that was that master proposal thing that I made.

Jorge: Sorry. I’m just very curious about this.

Kevin: No, interrupt me at will…

Jorge: So it sounds like if…

Kevin: … somebody has to.

Jorge: [Chuckle] It sounds like it’s a like a kit of parts or like a LEGO box of sorts where you can build customized or bespoke portfolio pieces or portfolio documents based on what you get the sense is most interesting to the prospect. Is that right?

Kevin: Yeah. One of the things that I’ve learned in my work is that I think as a designer. I have a desire for the process to be clear and articulated. And in this case, we could be talking about the process of a prospective client or just a person you meet, a colleague you meet in some context. Their journey from being that to being either a regular client or at least a client that you actually help solve some problems and work with. And I think what I found is it’s better for me to think about having good collections and not worrying about the process. So I’ll give you an example of what I mean. This idea of the master proposal… I have proposals for workshops. You know, I do workshops at conferences; I do between two and four year these days, and I do corporate workshops. But anyway, I’m in the process of booking workshops. I have some master proposals for generally the kinds of content that I teach, the kind of exercises that I help my clients run, and the kind of outcomes that they can expect. But I don’t give that to anyone and I’m fortunate enough that I get some inquiries. I get a nice trickle of inquiries via my website or via conferences I’ve spoken at. People follow up when their budgets are good, whatever. I always follow up that first inquiry. However, it comes in with a 30-minute conversation. Because in that conversation I want to learn for myself if I believe that the tools that I teach and the methods and the way that I look at this problem… I want to believe that it has the capacity to solve a specific problem that that person is having. And it could be as specific as — and these are two examples from recent conversations –it could be as specific as, “we’re about to invest a large sum of money in an agile transformation at a big company, and we want to make sure people can run our daily stand-ups well or know how to facilitate a retrospective.” And it could be as general as, “one of my goals for 2019, for my team, you know, I’m a VP of design and manage between 20 and 50 designers, one of my goals is for us to set an example for what a better meeting is in this organization. I feel like our designers aren’t as present as they could be or they’re not leading the meetings that we could be having.” So it could just be like, “we just want it to be better.” And in either case, the proposal that I write has to speak to the problem is they understand it. So it’s taking that big uber-proposal and then finding out how do they describe their problem, and then identifying the methods and language in my portfolio of success stories or in my existing work that fits that problem, the way they’ve described it. And then I go through a process where I actually create a Google Doc — ideally a Google Doc, but some sort of cloud based collaborative document — where I say, “Okay. Here’s what I heard. Here’s what I think I would do. You know, this is a rough estimate of the cost. But first, tell me if this will help you evangelize this in your organization.” And I’ll give them a week to comment on it, to rewrite it, whatever they want to do. And the really interesting thing about that part of the process that I’ve learned lately is that I’ve had experiences where I’ve said things that I believe to be true — not necessarily for their company, but just universally true — like I believe that people think they’re better at meetings than they are. Right? I believe that people think of meetings as things that can be done relatively easily, and if we have to have one we have it and we get through it. And I also have the belief that most companies don’t make heavy investments in improving meetings in the organization as a serious ongoing effort of organizational change. A prospective client came to me recently. I had some language to that effect about how this isn’t a common investment, and it turns out it had recently been a big investment they had made, and what they had tried wasn’t working. And had I not known that, had I not had that step in the process for them to tell me, “Oh, this language is reminding us of the fact that we’ve already spent money on this and it didn’t work,” and re-tailor the language to say, “this is why this might work where your previous efforts didn’t work.” I might have alienated some person signing the check somewhere.

Jorge: I want to read back what I’m hearing you say with regards to the proposal, and I want to circle back afterward to the actual process of keeping track of these conversations. But for the moment, let’s stay with this proposal. It sounds like there are two parts to this. One is having the “kit of parts” that allows you to assemble a proposal for a prospect, and the other is placing those parts in a sort of sandbox — in this case, Google Docs — that allows you to collaboratively create the final thing with the prospect. Is that a fair reading?

Kevin: Yeah, absolutely. I think that one of the interesting things that I’ve observed in working in design and process is this idea of working in the open, you know. I’ve been on a couple of teams where they’ve put into their contracts with their clients that they mandate an open process either they blog the process as it happens, or they mandate an open design process meaning the process as it happens in real time is documented. These days, GitHub and obviously cloud-based things like Dropbox and Box are good for that. But via the web, there’s an evolving project story. I feel like it fundamentally… maybe not explicitly, but at a deep level implicitly, requires trust for both parties. And if I do that at the proposal stage — if I say, “Look, we’re going to work in the open… In the open as far as you and I are concerned. So I’m going to give you a document. Anyone in your organization can read it and change it, and I’m going to be reading it and changing it as well. You know, responding to your comments — not agreeing with everything you say — but just you know, helping get helping us get to know you.” The benefit of that is it gives me a sense and it gives them a sense of what it’s like to work together. So if at any point I or they feel like, “Oh, the way our dialogue is going… We’re not speaking the same language, or there aren’t really problems here that I think I’m going to be able to help you solve,” or whatever it might be. It’s a lower cost way of getting there. And fewer meetings, because all of this comes out of anything from a 15 to 30-minute initial conversation.

Jorge: That’s such an important insight. Right? The idea that these documents are not just… They don’t just exist for their own sake, but they’re also a dry run for the process of working together.

Kevin: Yeah.

Jorge: I’m curious when you say “working in the open”… That sounds very enticing to me, this notion of showing your work and co-creation is something that… something that I’ve aspired to in my work. I have not always been successful at it. And part of the reason I haven’t been as successful in some cases as I would have liked to is that I have found that the openness… So if you open something up, if you open a collaboration process up to just anybody, you might get a lot of voices that are not invested in the outcome in some ways and it could derail the conversation, right? If everyone does not have the same outcomes in mind or if you’re not working together towards the same outcomes. In the case of the proposal, it sounds like you’re working with a very specific group of people, but does this ever extend to a larger group within the organization? Or do you keep it to your prospect and perhaps a select few others?

Kevin: In my experience, for this specific process what I found over the years is that if I keep it to a smaller group and allow that group to advocate for the value they see in working with me and working together, it all also gives me a little bit of information about what their position or a capability of creating consensus is within their organization. I mean if I’m cynical, there’s always a process of finding “where am I having a conversation with someone who actually is a signer on a budget?” You know somebody who is actually making a decision about a particular budget. So it’s always a good sign… And I generally ask pretty early in the process, “do you have a specific budget that you’re thinking about for investing in this problem?” Because I have relatively predictable rates within a range, but if you have a specific budget that you’re thinking about I know what it takes for me to do the work, I can write a proposal pulling from those LEGO pieces that is more tailored to a specific budget if I have to. I don’t often find that’s the case now, but earlier when I was doing really large scale projects with teams of upwards of 9 or 10 people that I would hire, that was more often the case where I would have to be creative within usually six-figure budgets. I would say more often than not like a budget between 100k and 500k and try to really solve a problem within a constraint that somebody really had. But now if I’m talking to somebody early on as an individual consultant — I don’t build teams to do the work that I do at this point — and they say something like, “oh, we have to pause the conversation because the person who would make the decision about the budget is on vacation,” that tells me who else I need to bring into the document conversation. And I would say so far in my new consulting practice — my relatively nascent practice — I would say more than half the time I’m speaking to somebody in a position who’s managing a budget. But when I’m not it’s usually somebody who’s really motivated by the problem and has a connection. I haven’t had an experience where somebody’s playing like, “I really want to talk to you and invite you to come help my organization with this thing, but I don’t have any connection with any budget and I can’t pay you.” You know, that hasn’t happened yet.

Jorge: Yeah, but those folks are likely to not even initiate the conversation right?

Kevin: Sure.

Jorge: They’re not going to have a project.

Kevin: Yeah.

Jorge: I love this idea of the Google Document as a sort of… I don’t know if it’s fair to call it a catalyst for this conversation to happen that surfaces all this information about the team. The team for you and you for them, right? So it’s a way to get to know each other and see if the fit is right. I’m wondering what other tools you use as part of this process. In particular, it sounds like you have multiple conversations going sometimes. You talked about speaking at conferences and having folks who have read your book and reach out. How do you keep track of all these different conversations so that you know where things are at?

Kevin: So I generally… If we think of the journey of a sales lead, things generally start either via my website kevinmhoffman.com, where it says on the site pretty plainly, “if you’d like me to come to a workshop for your organization contact me,” and my email’s right there. Or I do a workshop at a conference, somebody who’s representing an organization has that experience. I explicitly say I customize this workshop if I do it for your organization, and they reach out to me within anywhere from a week to two a couple of months. Depends on where people are in their various budget cycles, and if their budget… If they’re at the beginning of a budget and they have a lot of flexibility, or they’re at the end of a budget cycle and they’re trying to spend down or whatever it may be. So anytime I think about a journey — and I know earlier I said designers like to have this clean process — the metaphor that comes to mind is this: we’re talking about SuperFriends earlier. There was also this cartoon thing called School House Rock and the one that I remember and I imagine a lot of people who know what Schoolhouse Rock is remember is, is one about a bill. “I’m Just a Bill sitting here on Capitol Hill,” and how that bill goes on a journey to become a law. So, the first thing I do to keep track of my potential clients is I try to keep a list. It’s messy but I try to keep a list in a couple of different places. So I have a big white board in my office. There is the mega list for the week that I’m constantly erasing and rewriting. And as a lead becomes viable… So here’s an example of a viable lead, I do a workshop with at a conference, somebody comes up to me and personally says, “I really enjoyed that. I would be curious about having you do this at my company. What do I do?” I say, “well, let’s set up some time to talk.” They reach out to me. We actually have a conversation. In that conversation, I’ll make a commitment to getting them a proposal pretty rapidly, usually within anywhere from 24 to 48 hours. And that proposal is just that thing that I pull you know different parts of what I’ve done for other people. I pull in what I think feels right. So the whiteboard list, that’s one place that stuff lives. Now let’s say I’m in the mode of meeting people at a conference. And if I do a workshop at a conference, I might meet all the attendees in my workshop, but I also might do something like a book signing or I might just meet people at lunch or you know over coffee at a break or whatever. I keep a running list of action items in a very messy way across a couple of different platforms. I really like Bear note. There are two things about Bear note that I like. One, I like that it’s kind of a cloud of notes. You can have no taxonomy of how you structure and organize content, but it’s very easy — like Google — to find things. So the interface of Bear note is basically a search field, and if you type into the search field and nothing comes up, it turns actually into a title field. So I can actually click on a button and start a note with that title.

Jorge: Bear note is an app, right?

Kevin: Yeah. It’s an app. It’s a macOS app but it syncs via iCloud. And I just constantly make these notes. If I’m in a meeting I transcribe my meeting notes in there; I focus on action items. They have a nice little to-do list. They use Markdown to create checkboxes. And ​if you’re comfortable writing in Markdown — which is a way of adding formatting to text — if you’re comfortable with that, Bear note does a good job of rendering it in a nice way. So I have Bear note syncing on my phone. I meet somebody from a company like IBM, they’re like,” hey, we might want to have you. Come do a lunch and learn at some point.” I’ll quickly add that to the stream of Bear note that that lives in my life. Occasionally, I might add it to use something like Google Keep. I’ve bounced back and forth between Google Keep and Apple’s Notes app for lists, but usually, those are more like grocery lists and doctor things and personal things. Most of my professional life lives in this stream of Bear notes that I had. When I was at Capital One, I basically installed Bear note on my locked down Capital One system on day one, found out that they didn’t allow iCloud synching because of regulations around large banks and had to decide, “okay, where am I going to take most of my notes and carry that device with me at all times?” So that’s how I keep track of what conversations I had with whom. Then they make their way onto the whiteboard when they become viable. Once they’re on the whiteboard, they become Google Docs. And I’m looking at: okay, what are the recent Google Docs that I’ve been editing in, watching for comments to come in, or edits to come in from prospective clients and respond you them in real-time? So those become very high priority pieces of content for me. When a proposal is in an active state or a live state. And then the next thing I do is basically establish follow-up steps. So I’m going to reach out to you by this date with these questions. You had said, “okay, the next step is when so-and-so gets back from vacation. We’re going to share this with the Executive Vice President. Get approval on this budget.” So that’s the next step in the bill becoming a law is getting it passed that approval step. Then…

Jorge: Do you do you somehow mark the next steps on the whiteboard? How do you keep track of that?

Kevin: The whiteboard is really only the next thing I have to do for the person. So the whiteboard is usually like, “write proposal – client name.” And if the proposal is in a live state, it would be like “get signed work agreement” or “send standard working agreement over” or whatever. The legalese stuff is always… I’ve found that that’s usually pretty boilerplate, but there’s always something that goes back and forth in that process of, you know… Something about intellectual property or something about work for hire or there’s some aspect of it. In some projects that I was talking about where we’ve worked in the open, that’s become an issue where if I’m doing a large-scale team size project and we say, “oh, we want to blog this process for your community. As we finish things, we’re going to put up posts and link people to the design work.” You know, some people have concerns about that being something their competitors would get a leg up on them from. And I have opinions about that. But you know, that’s not what this is about.

Jorge: This is fantastic Kevin. I’m so excited; I think I’m going to start a whiteboard of my own like the one that you’re describing because what I heard you say — and the thing that excites me about it is that it sounds like you have this process where you initiate a conversation in physical space with a person, right? You’re talking at a conference or in a workshop, and you follow up… Or the next step is moving a record of that conversation to this digital space with Bear notes. And then you follow up with those folks and eventually if they make it to the next stage, they move out of digital space again onto a physical space, to this whiteboard. And then from there, they move to another digital space, which is Google Docs.

Kevin: Yeah.

Jorge: It’s like the process goes in and out of your digital domains as it moves, like the bill going through Congress.

Kevin: Uh-huh.

Jorge: Fascinating.

Kevin: Yeah.

Jorge: T his is fabulous and it’s been really insightful. Where can folks go to follow up with you and find out more?

Kevin: Sure. So Kevin M. Hoffman is the fastest way to get a hold of me. Kevin M. as in Michael Hoffman dot com. Kevin W. Hoffman is not me on Twitter. Kevin Huffman on Twitter is not me. Kevin M. Hoffman on Twitter is me. My book is obviously out… It’s been almost been out for… It’s coming up on a year. And you can always get a hold of me through the publisher, Rosenfeld Media. The book’s called “Meeting Design: For Managers, Makers, and Everyone.” So the idea is that… The title comes from this idea that we think of meetings as either being the domain of people who are leading the meetings — usually managers — but there’s this idea that we’re all citizens of meetings. And there’s different ways, if I’m somebody who is responsible for making the thing, that there’s ways to be a citizen of a meeting, to participate. If I’m responsible for running the there are there’s ways to do it, but it’s thinking about all angles: how do you make them work?

Jorge: It’s basic literacy for anyone who has to collaborate with anyone else, basically.

Kevin: Yeah.

Jorge: It’s fantastic that you’ve written this book. And congratulations, because it’s been well received.

Kevin: Oh, thanks. Yeah, it’s the thing I wanted. Like I wanted to have this book when I graduated from graduate school and I went into the workforce. First, it was in public libraries and colleges. I was in these meetings, I didn’t know what they were for and how they connected to our mission and what my role was… And I just wish I had… I wished I’d had a manual of how to connect to this stream of information that’s happening in our work. So that’s why I wrote it. So hopefully there’s a version of me that won’t have to deal with what I had to deal with.

Jorge: Well and so many more of us will also be able to benefit from your teachings on this subject. And on that note, I want to thank you for your time today. Because we will also benefit from what you’ve told us today.

Kevin: That’s how we all figure it out. Right? We all share the ideas and hopefully, somebody avoids some mistakes.

Jorge: Fantastic. Thank you so much, Kevin.