25 posts categorized "Project Management"

Introducing Teamwords: The Working Deck


We get asked a lot about problem solving. Not about business problems, per se, but people problems.

People seem to understand OKRs, Agile, and MVPs. Acronyms and abbreviations have specific and fixed definitions you can find on Google — and though you can get into long arguments about whether something is a tool or a process or a disruption at work, people are still, well, people. They change and then they don’t change. They’re heroic and then they’re petty. Confusing and clear, sometimes in the same meeting.

Yes, the pesky things are problems with people. No matter how sleek and refined our company needs to be, how much faster we have to get to market, or how many more hours we must be available night and day to meet the demands of customers, we’re still talking about people at work. They’re the one thing that hasn’t 100% changed about how business gets done.

So companies ask how to create better “cultures of collaboration.” Make teamwork a working norm. Rethink how cross-disciplinary talent can be best configured, how to optimize their working spaces for breakthrough innovation blah blah blah… Again, the same problem of applying jargony buzzwords to people and how they work together. Then upper management wonders why they weren’t very successful in making things better.

Words are powerful. So powerful that most of the problems we encounter are failures of vocabulary. We assume that everyone uses the same words and that they mean the same things to everyone. JIRA means JIRA, right? We see it and recognize it. But, think about the word supportive. How do you see that word in how your team works? How do your coworkers see it in your work? Have you ever sat around with your team and talked about that?

People see their values in behaviors. But when people come together in teams, they usually revert to abstract fluffy words, and leave the specifics for later.

We’re on teams that value transparency or that promise to be adaptable or disciplined, but when we feel like that isn’t happening, we rarely have particular behaviors to point to. We just have a vague feeling that someone’s not being disciplined enough. And You’re not disciplined might not be the best conversation starter at that Tuesday morning meeting. For one, it’s pretty personal. And second, even it weren’t personal, what can you do with that feedback? If someone says you aren’t being disciplined, you have to find the behaviors that go with that word — the indicators that mean disciplined to your teammates. Otherwise, the word on everyone’s mind is misaligned.

New projects come, new clients go, and the new norm is new people on new teams all the time. But the value words are still the same. Which is troubling: Everything is changing, but companies are acting like we can all sit around saying adaptable still means adaptable and that no new behaviors will emerge for us to describe it. And while corporate mandates and mission statements are great, they don’t always influence the day-to-day efforts of real people on real teams.

So, with all of those factors at play, we started thinking about how we could help teams rapidly align themselves, and most importantly, define behaviors that were unique to them. After several months of research and testing, we released a collaboration product called Teamwords: The Working Deck. It’s designed to help teams align themselves whenever they need it. Anyone can pull out the cards, find the value words they need, and list the behaviors they’re looking for from their team members.

Though we created a starting activity that’s included in the deck, we knew that the cards needed to be adaptable. We didn’t want a tool that only got used for, say, that once-a-year team offsite, so we developed a number of different ways to use the cards, both for groups and individuals. During our testing, we uncovered exercises that ranged from funny icebreakers to deep personal explorations. In other words, the deck reflected our philosophy: We turn words into actions every day, and our tools should be able to help us wherever that happens.

Bringing clarity doesn’t necessarily mean bringing rigidity — there will be plenty of new behaviors that a team will want to explore and champion on every project. And that’s fine. At least there’s a starting point. We’ve begun the conversation around what words mean, why they matter, and how we turn them into action.

If you want to reduce team misalignment in the workplace, close the gap between what people say they value and how they actually demonstrate those values. And now we’ve got a way to talk about how we’re going to work together on a team, through all of the strange stages of a project, moving past those buzzwords and unrelatable jargon.

—David and Mary Sherwin

(P.S. You can learn more here about Teamwords: The Working Deck.)

Design Business by the Numbers: Bid/Win Ratio

Bid Win Ratio of 50 percent

Numbers surround us every day. They’re woven into the fabric of our lives, part of the advice and cliched folk wisdom that we dispense to each other: Two's company, three’s a crowd. A bird in the hand is worth two in the bush. And so forth. Every one of these cliches, however, started out as a rule of them, intended to help us learn from our previous positive experiences and failures. They’re patterns we can follow that can help contribute to our future successes.

I'll be posting over the coming months numbers I heard from the design businesspeople I interviewed while writing Success by Design: The Essential Business Reference for Designers. These people had specific rules of thumb they followed as in order to ensure the health of their design business. They were either handed down to them from co-workers or mentors, or derived from hard-fought experience. I’ve added to these numbers the ones that I’ve recorded from my experience working at a range of small and large design studios.

It’s my hope that these numbers will help you establish useful guidelines that'll help you better manage your projects and operate your design studio.

Let's start things off with your business's bid/win ratio.

Anyone who runs a design business knows that if you aren't winning projects, you won't stay in business. So when you seek out new business opportunities, how do you determine which to pursue and which to turn away?

When researching Success by Design, a number that kept coming up in my interviews with studio owners was fifty. Or, to be clear, a 50% bid/win ratio for your studio's new business efforts. This is the number you should try to hit or exceed, and it correlates with how many potential projects you need to convert from proposals to paid projects every month. Otherwise, you'll be billing to much time to studio overhead (writing proposals) instead of working on paid client projects.

There are specific criteria you should use in order to try and hit that 50% number. These include gauging the following:

Dollar value of the proposal. This should be averaged over the number of staff members and hours required to fulfill the estimated scope. This assumes, of course, that you have the capacity in your studio to fulfill the work.

Level of competition. If your client won't tell you what other design businesses are in the running for the work, at least ask them how many other businesses might be in competition for the work. If you're filling out an RFP or RFI and throwing it over the wall—the odds of winning the work can be stacked against you.

Fit for the studio. Is this work that will contribute to staff happiness and morale just as much as your portfolio and pocketbook? You should determine this before you agree to write a proposal as part of your pre-qualification process. (You've got one of those, right?)

Relationship with the client. If you haven't sat down with this client and truly understood the problem they're trying to solve, you may not even be in the running at all. You also may miss nuances and politics that may be stacking the deck against you.

There are other factors to consider, but the above are mandatory considerations before you go down the path of agreeing to craft a proposal. Think about like going to a casino and choosing how to gamble your money. Say someone handed you $10,000 scot free and said, "Go bet this all on the roulette table, and if that number comes up, you get to keep the money I gave you." Would you rather put your money on a single number? Or on all odd numbers? This benchmark is intended to help you control risk and look beyond individual project possibilities to the overall impact your business development choices are having on your cash-flow. This isn't to say that you shouldn't take risks on projects that may be a great boon to your studio, per the above criteria. It's to say that your risks should be measured.

Be aware as well that when using this ratio is that you may not be winning the most valuable projects, balancing the above factors against sheer dollars and cents. If you aren't winning approximately 50% or more of the potential revenues available across the proposals in your pipeline, you may need to reassess your new business strategy.

Slides from "My Top 10 Design Business Failures"

This Thursday and Friday, I provided two lectures for SCAD's Entreprenurial Forum 2011 in Savannah, Georgia. This event was presented by SCAD's Office for Career and Alumni Success, and was designed for students across all majors to gain perspectives on how they can become successful as businesspeople in today's economic climate.

The above slide deck is from my second lecture, called "My Top 10 Design Business Failures." You could call this my greatest hits album of major business mistakes I've made over my career, both as a freelancer and while working within agencies of all shapes and sizes.

My first lecture, "Being an Agency of One," kicked off the event on Thursday night. I talked about the four primary areas that any designer or artist must master in order to create the foundation for a successful business practice and be responsible while doing what they love:

  • Understanding your business model and what sources of revenue can support it
  • Designing the appropriate touchpoints required for well-considered client service
  • Discovering how effective project management creates sustainable studio success
  • Crafting the philosophy and plan that drives both your personal practice and your business practice, via a framework that David Conrad and I created called "The Elements of Design Studio Experience"

You can see an 11-minute clip of me answering student questions after the first lecture on the SCAD eLearning site. Some of these student questions I will be readdressing on this blog in the coming weeks.

If you live in Seattle and want to dig deeper into this material, please join me for the Design Business for Breakfast Series in Seattle, which is going on right now. Registration is still open for the last three talks. The next one is this Wednesday, February 23rd.

All of this material is drawn from my current work-in-progress for HOW Books, Design Business from A to Z, which will be out in the Fall of 2012. Both presentations were deeply informed by the following collaborators, who deserve great thanks: Erica Goldsmith, Fiona Robertson-Remley, and David Conrad.

It's Not Your Fault


There comes a time in the life of every designer when things go wrong on a project or in a client relationship. Horribly wrong. The kind of epic fail written about by Greek storytellers, passed down from generation to generation, then recorded to paper to give voice to Awfulness That Shall Never Be Forgotten EVER. Fear gives way to more fear. Your heart pulses in your ears. Adrenaline drowns out words being spoken (or hollered) at you. The knowledge of things going awry makes you physically aware of your body in a way similar to, say, jumping out of a plane. Careening downwards, a constellation of past efforts glitters behind you in the darkness, while your future career in design looms closer and closer, like the factories and empty fields that pock-mark much of northern New Jersey.

Now that I've got a few major failures under my belt, and enough distance from them to have sifted through the wreckage for a few tiny wisps of insight, I've realized that in some of those awful situations, I hadn't done anything wrong at all. It was entirely out of my direct control. I'm talking specifically about ongoing politics within a client organization—the kind of politics, no matter how strong of a relationship that you hold with your day-to-day contacts, no matter how many dinners and baseball games and late-night shenanigans at the hotel bar, you just can't suss out the bitter end until the room's been turned sideways and you're hanging from the chandelier for dear life.

Continue reading "It's Not Your Fault" »

Protecting Deadlines for Interactive Projects

the great escape // throw the door away

A common mistake that marketers and executives make is in assuming that deadlines for interactive application design and development can be flexed in a similar manner to traditional marketing, advertising, branding, and visual design deliverables.

In particular, I am referring to two common scenarios that can compromise the integrity of your final deliverable—functional, stable, and bug-free code that renders properly across multiple browsers or app platforms.

Scenario 1: Heel-dragging at the initiation of a project—either in receiving a signature, payment, or critical information to start work—with the assumption that there is enough "give" in the first few weeks of the schedule to reach the provisionally agreed-upon deadline.

Scenario 2: A request is made by the client during the first few weeks of the project for the agreed-upon deadline for project delivery to be made earlier, often to accommodate a critical internal meeting or public milestone that wasn't on your direct client's radar while the scope was set.

Allowing negotiation about the boundaries of the project after you've entered into a signed contract should be a last resort for you and your team.

Here's why.

Continue reading "Protecting Deadlines for Interactive Projects" »

Using an Aging Summary

Aging Summary

When considering the most critical functions of a creative business, cashflow often falls to the bottom of the ever-present punchlist. As deadlines loom on the near horizon like Godzilla-like monsters out of J.J. Abrams films, our minds often focus most forcefully on what's right in front of us: the design work that needs to be completed. Pronto!

This isn't a strategy for sustaining your business in the long term, and can wreak havoc with your monthly finances. I've worked with both freelance designers and design firms that, at the expense of the actual day-to-day operations of the business, get the work out on time and on target, but end up causing massive havoc in the actual collection work necessary—from a bookkeeping perspective—to ensure that there's an actual flow of money allowing everyone to receive a paycheck, take care of the utilities, and maybe even cover those expenses you might have taken upon yourself (out of pocket) to take your client out to lunch. I have definitely been foolish in this department when I was doing freelance work, and I paid for it in an empty bank account. (More money in the bank = more interest = more liquidity = more safety.)

A critical tool you should make sure is part of your bookkeeping arsenal is an aging summary. This is a simple tool where you list what clients have outstanding sums of money due to you, in monthly increments. If a client hasn't paid you an invoice due after 30 days, you send them a client letter that notes what is due to you and how far it is past due. (Hopefully, you'll never get past 60 days.)

Continue reading "Using an Aging Summary" »

Making Time to Design


When talking with designers about what they enjoy most about their job, the actual task of designing the work is usually what they focus on as the highlight of each and every day—as long as they like the problem they've been tasked with solving. But most big projects today are complex enough that the percent of time spent actually designing them can be less than 30%. The rest can fall under the domain of project management: talking with clients, scheduling and planning, resource management, accounting, and if you're lucky, a little foosball.

"Oh, if only I could spend more time designing and less time doing [insert name of mundane task that doesn't seem to be design related at all]," is a constant refrain. But I'd like to ask that you refrain from saying it—at least out loud—because it's those mundane tasks that make the design work possible.

Project management is what keeps projects successful and profitable. For the sanity of both your co-workers and your clients, it can never be sacrificed. Once you do sacrifice it, you'll find that you're working two jobs—that of a designer, and that of a project manager. (And resenting the perceived overtime.) Your clients will expect this service from you. Your business will demand it.

The trick is to structure your time so that you're a designer less of the time—meaning fewer than 8 hours a day—and earmarking protected chunks of your workday that are dedicated to design, while others are for everything but design. This means check your email in the morning, respond to it, then shut it off for a set period of time. (At least two hours.) I like to get lost in the flow of doing the work, so I actually have to set myself a timer, whether in Outlook or on my phone, to force me out of delighting in the creative process and taking care of more mundane (but equally important) tasks. When those tasks are accommodated, I can then get back to work. I recently heard Scott Belsky echo this sentiment in a talk about making ideas happen, and it's an important habit to cultivate.

To protect this new behavior, be clear in your rules of engagement with clients that your response times will be 4 hours or less, so you can balance design with work time. Also, adjust your utilization so that it's clear that you don't need to be billing 85% to 90% of your time solely to design services. If you split the appropriate percentages of your time and effort between design and managing a project, you'll be able to bill all of your project time, even while taking care of what may seem like mere clerical tasks.

I'm just describing an ideal process here, however—to invest that extra little bit of quality to the design work, I do find myself verging out of the 8-hour workday. This is partly why I've been blogging a bit less. But when doing so, I'm aware of what's design and what's making the design possible.

How to Manage Going Overbudget

Bleeding Money

We went over budget on this project, and it still isn't complete. What are we supposed to do?

Projects that go 1% over budget can balloon to 50% over budget very quickly, in part because your design team (or yourself) gives up trying to hit your hours. These situations must be controlled in order to make any profit on a project. You will also risk consuming valuable staff time that could be better spent securing and servicing new projects.

Follow this simple three-step process and you'll be more likely to close out your project without blowing your margin.

Continue reading "How to Manage Going Overbudget" »

Common Pitfalls of Estimating Design Time

Estimating Actuals

As I am able to read the thoughts of design professionals, I can provide a transcript for what goes through each and every one of your minds while you're estimating a design project:

"Hmm... I think this project is only going to take me 20 hours. Last time, it took me about three days, and we only billed them for 15, so if I make it 20 then it should be approximately what it took me to design it last time."

Time passes. Your boss and/or the account manager review the estimate and think that it isn't cost-competitive. They want you to find places to cut your hours.

"Hmm... maybe I can do the concepts in 16 hours. That seems like one of the few places we might be able to cut back. Besides, I've designed a ton of web pages, so this one should be a little easier than the last time."

Sorry to break it to you, but you're going to spend at least 24 hours working on that project you just squeezed into 16. You're also going to lose money on that project, unless if you bill an astronomical hourly rate.

Why does this happen over and over again? Because of these very common estimating issues.

Continue reading "Common Pitfalls of Estimating Design Time" »

Defining the Rules of Engagement


Usually when we talk about engaging with clients, we start listing tangible deliverables they should expect from a project, from the initial draft schedule to the final product design.

When you start a project, conversations should be only about what clients require from us. It's also about what we expect from them. The best way to do this is to define the rules of engagement for your clients.

The following expectations are completely fair to request from any new client:

  • Timeliness
  • Consistency
  • Direct dialogue
  • Respect for process
  • Transparency
  • Accommodation for human error

Now, you can't just send this list to a client and say, "Hey, now you're going to respect my process!" If you don't tell your client up front about your expectations for their behavior, you're scolding them for things they never knew they needed to do.

So provide to your client in writing your rules of engagement. It only needs to be one page, which includes at least the following:

Not meeting expectations, stated or unstated, is one of the major reasons that client relationships fail. So don't let that happen—state up front what you require, and the project will always run a little more smoothly as a result.

Thanks to Erica Goldsmith for collaborating with me on this post.

Taking Apart the Org Chart: Creating a RACI Matrix

Manager of Stuff

Light from the noonday sun lit up dust motes floating in the quiet conference room—empty except for our agency portfolio case, heavy with design concepts affixed to black board.

We'd agreed to convene this quick lunch meeting, sans any actual food or drink, to discuss our agreed-upon direction for a national advertising campaign with our client's supervisor. We had worked on the project for five weeks, moving from a formal creative brief to high-level design concepts to the in-depth logistical planning required to pay off our creative approach.

The supervisor we were meeting with had been CC'd on every email that contained a critical deliverable—five, to date—and all of us, including our direct client contact, viewed this get-together as a chance for us to unpack any of the perceived nuances in those deliverables, answer questions, and receive a final blessing to roll everything into execution.

However, by the time the meeting began (a good 20 minutes late) and we walked through the introductory slides that recapped our agreed-upon approach from the creative brief, we were on much shakier ground that we'd anticipated.

Or, to be clearer, volumes were contained in the following statement from the supervisor: "I'm not sure I agree with your assertions about the audience we're trying to target. But keep going… I'd at least like to see the creative you've come up with."

At this point, we weren't walking on eggshells. We were trying to keep the yolks from gumming up our beards. Five weeks of work were at risk of evaporating, all because the most important stakeholder on the project—someone whom we'd assumed was to remain informed of project progress—hadn't reviewed a key document at the start of the project. We'd never received written feedback from them about the creative brief, and that was what was now being called into question.

These kinds of situations happen all the time to working designers. They are so common that there are specific methods that savvy design professionals use to keep them from happening. One of these methods is building a RACI matrix.

Continue reading "Taking Apart the Org Chart: Creating a RACI Matrix" »

Sign Before You Design

Before I Lift a Finger

"Before the client’s signed my contract, should I start working on that big design project?"

The simple answer: No.

The more complex answer: No. Every minute that you bill will vanish in a whiff of non-billable smoke if the client decides to back out at the eleventh hour. For some designers, it only takes one client walking away from a contract to encourage strong boundaries. Others get burned over and over again, which can be crippling for your cashflow.

As part of your pre-contact negotiations, let the client know that you won't start work until your contract is signed. Every extra day that they take to sign the contract, you should tack on that extra time to the end of your schedule, instead of trying to make up for it. This should be clear to the client, in writing, as part of your terms and conditions.

If you haven’t extended them credit, you shouldn’t work until they’ve provided you with your first payment as well.

If they say the check’s in the mail, you let them know that the project will start when you’ve received it (and cashed it). If it's "held up in accounting," then this gives them an incentive to go breathe fire down said accountant's neck.

If you have worked with your client a number of times in the past, and they have paid you promptly for services rendered, you may consider extending them credit and getting started… but only after you have a signed contract.

If you're tempted to use a letter of intent (LOI) to negotiate a big fancy contract or master services agreement, know that it's essentially tantamount to extending credit if you don't get paid up front for your time.

And if you've set up your contract so your payments are gating the work, make it clear to the client well before you get to the end of each phase that you'll be expecting payment to proceed. Otherwise, they may be quite pissed that the project is going to be behind schedule because you hadn't communicated an essential responsibility to them.

Creating a Risk Assessment

Too Many Problems

When taking on projects with hairpin-turn deadlines, high levels of technical complexity, and large cross-disciplinary teams that function across silos within a large organization, designers often have to assume a great deal of risk. This risk is often codified in a series of contingencies that serve as part of a proposal, and take on the form of laundry lists such as:

  • Our firm will receive collated feedback from client within 24 hours of each provided deliverable
  • Our firm will require access to the hosting environment for initial testing by back-end development at the start of the project
  • Our firm will hold to the specified feature set provided in this estimate; any changes in the agreed-upon scope will have an impact upon timeline, budget, or both

While these itemized lists are valuable in defining client/designer boundaries, they don't do a great job of describing what happens when said boundaries are violated—either by the designer or by the client. We rarely dive into the nitty-gritty details of how badly things can actually go wrong until we've signed the contract and started work.

But there should always be a time slotted into project kickoffs where you sit down and put together a risk assessment.

Continue reading "Creating a Risk Assessment" »

Nine Proofreading Tricks for Designers

Rare Mistakes

No one likes a typo. Especially clients.

When it's the 14th time we've made revisions on the 128-page magazine and you need to get the files off to the printer, it's inevitable that a typesetting error or grammatical mistake is still lurking somewhere in the document. The same issues apply when completing content for a website and porting it into a CMS, where gremlins always seem to lurk in the hallways of our code.

Mistakes happen, but we can catch them. Try out the following tricks from the proofreader's playbook.

Continue reading "Nine Proofreading Tricks for Designers" »

How to Mitigate Major Project Errors, Pt. 1 of 3

Crass Style Sheet

Refreshed by your first eight hours of sleep in what feels like a decade, you stroll into your office, only to be stopped cold by the message light blinking on your voicemail.

It's your client, with a three-minute description of how their new shopping cart system—which you'd been slaving over for months, and finally deployed late last night—has been balking while trying to process credit card purchases. For hours. To the tune of many thousands of dollars lost in sales.

How will you resolve this issue, and how are you going to communicate a plan of action to your client?

Where we most often fail in the client management process is when, after all that work, errors still slip through—and we can't formally explain to our clients how we'll resolve them to their benefit.

Depending on the scale of your client's business, an error in project implementation could have a major fiscal impact—not to mention the drag on your long-term customer experience. Errors like the ones I noted above happen more often than we would care to admit. Most web designers understand the value of testing protocols, debugging code, and stabilizing a build in order to deploy a website or web app. But it's how we manage the errors that slip through while testing, printing, or fulfilling your design work that forges project success. Dealing with project errors in a professional manner is what defines the longevity of designer-client relationships.

Here's a quick primer on how to maintain your professionalism and protect the integrity of your client relationships when resolving these kinds of major project errors.

Continue reading "How to Mitigate Major Project Errors, Pt. 1 of 3" »

Do or Die? Six Secrets for Managing Deadlines

Do or Die

The art director shut the door quietly behind me, waving me into a seat. Out the windows of his office, I could see snarls of traffic waiting at a traffic light. Rain sluiced off our building in rhythmic waves. The gray weather outside lulled me into a sense of serenity. I liked my new job and the people that worked there. This was my first big agency job, and so far everyone I'd met had been quite helpful. I didn't know what this meeting was about, but I assumed it regarded a new, exciting client engagement that I would soon tackle.

The first thing out of my boss's mouth?

"The most important rule here is that you don't miss a deadline."

Continue reading "Do or Die? Six Secrets for Managing Deadlines" »

How to Conduct Post-Future Project Evaluations


The website finally went live last week, and the entire staff is throwing a party to celebrate! The developers are huddled in the corner with some microbrews, plotting how they'll splice into the agency intranet to add in a virtual dartboard. Designers are mingling with the copywriters and account people, clinking wineglasses and bonding over the ads they saw during The Office--did you see that amazing CG work, where the car dissolved into a field of flowers?

Not the best time to mention that tomorrow, you're scheduling a post-future meeting (nee post-mortem) to talk about how the project really went.

Yes, the job went way over budget — and the last thing they want to think about is who needs to take responsibility for it. Was the estimate wrong to begin with? Did the designer spend too long tweaking those page comps? How come the developer pulled so many late nights, when he said he knew .NET? Besides, they'll still be nursing their hangovers. If you're the one in charge, you get to take responsibility for the result.

Or do you?

Discovering how a creative agency fails to make profit on a project usually boils down to a series of in-process decisions that, while intended to be good, lead to cost overruns and errors. Isolating and clarifying those agency decisions role by role can be painful and time-consuming if done incorrectly -- but if carried out in the right manner and in a group setting, a post-future meeting can galvanize a team and bring them closer together. By being aware of how they've behaved in the past, they'll be able to see repeated patterns and anticipate ways to stop them from happening again.

A post-future meeting affords more than just saying, "Well, next time we'll do it better." It can give your staff real visibility into how everyone's jobs are interrelated. Those dependencies are what cause true profit on a creative task. Agency professionals get budgets and hourly estimates of what it'll take to do a creative task, but those estimates can be severely influenced by staff interaction. Day-to-day miscommunications may seem like they're out of managerial control, but they aren't. Fostering dialogue and collaboration is what truly makes profit possible, especially on large, multi-phase projects that continue over a series of months.

Even if you're a solo-flight designer, answering the following questions after completing a big project will help you take a dispassionate look at how you're doing business.

Continue reading "How to Conduct Post-Future Project Evaluations" »