Hiring for Sales: Fuzzy Math and Four Letter Words…

For the most part, people don’t know when to hire for sales in digital client services.

Truthfully many people are mostly-sorta guessing when they should hire for billable roles too... But when it comes to an unbillable position like business development, man are they guessing. Frequently recurring questions I field include “When should I hire for sales, or grow my sales team?” “What signal should I listen for amid the noise of my business to tell me to hire or grow sales?” “What number on which spreadsheet shouts ‘hire!’…?”

I’ve worked with dozens of agency owners, I’ve interviewed and spoken with approximately 100–150 more, and I’ve moderated business development conference panels and conversations with hundreds more owners. Across the board there is one consistent point in time that typically triggers most owners to hire for business development. They hire way too late.

The Money Experts…

I get asked this same vein of questions (about when and why to hire for sales) from financial advisors, consultants, and CFOs who work with agencies too. Dwell on that for second, go ahead explore the space. These are advisors who make data-based recommendations to their clients that drive their budgets and their businesses, and they don’t know the answer to “When should I hire for sales, or grow my sales team?”

They’re right to acknowledge what they don’t know. The reason is their sample size is way too small. While those advisors often make recommendations about how to staff and budget a small business (based on data and experience gathered from millions of other small businesses*) the publicly available data about small digital client services businesses specifically is simply too microscopic to be truly valuable.

*This data is deeply flawed as it relates to digital client services too. Using data from millions of small businesses to determine hiring and staffing for example, assumes that hiring and staffing in digital client services behaves much the same as hiring and staffing within that larger universe of millions of small businesses. It does not. Hiring and staffing is more competitive in digital client services than it is in most other industries. As a former recruiter in digital, I worry if these financial advisors and CFOs take the unique costs of recruiting and retention for digital client services into enough consideration, or if their recommendations are noisily clouded by bad/generic data.

Soft Algebra and Fuzzy Math

My own insight is completely anecdotal, and similarly mathematically terrible. If you prefer advice substantiated by data, then this is inherently bad advice. That’s all there is to be had. I own my mathematical terribleness however. Buyer beware.

In hundreds of conversations with owners, I’ve spoken with two (2) who intentionally hired for sales in advance of their agencies’ current needs. Two owners in hundreds who had the instinct (and capital) to invest in a sales team that represented the kind of results or growth they wanted to achieve.

Previously I urged owners to Get Ahead in Sales. What I didn’t feel comfortable doing then, was putting some math behind the message. Some hard numbers and some hard metrics. What follows is some soft algebra and fuzzy math for your consideration based on my observations from the front.

TLDR Version

8–10 employees: Getting serious with a project manager. Most agencies’ first sales hire is a PM. Never underestimate the pivotal role PMs play in client services, and by extension sales.

12–18 employees: Adding a sales support or business development lead. An owner who has led sales to this point, often hires someone junior to support their efforts (sales support), or someone more senior to replace parts of their role in sales or focus on lead generation (business development lead). The owner typically remains heavily involved in sales at this point rounding out a two person sales team.

~25 employees: An additional business development lead resource is added, or a support resource if one hasn’t already been hired. This leads to a sales team of at least three, including a dedicated owner still. This new hire depends largely on the previous hires (see basketball team analogy below), but the sales team at this point typically includes sales support, a business development lead, and fairly fully committed owner/principal. This team could include two full-time business development leads, or a sales person plus a marketer, but the lead + support + owner is the most common combo.

30–35 employees: Time to build out a sales organization. At this size a more robust sales team is required. This team can include more than one business development lead, a marketing director, sales support, and account management (in addition to, or as a part of your PM structure/role). You’re building the sales organization a larger firm will need, because agencies don’t hover at 30 people for long. They either accelerate toward the next plateau around 70+ or contract.

The Long Version

12–18 employees. Most digital client services firms hire a dedicated, unbillable resource for business development when they grow to somewhere between 12–18 staff members.

Many hire for project or account management prior to that, around 8 or so staff members. These project and account managers play an important role in sales too, but we’ll put that conversation aside for a moment. Love you PMs, mean it.

This first dedicated business development hire is often either a sales support resource, or a business development lead. Let’s unpack both a bit.

Sales Support

A sales support resource typically works with a principal who still leads sales. The support resource may manage email communication and scheduling with new leads. They sometimes have a role in documentation, everything from meeting notes to proposal framing. They might have reporting and forecasting duties. If a principal imagines their time is worth $500/hour, this support resource takes on many of the responsibilities that would bill at a lower hourly rate.

A brief word of caution: This is often referred to as “PM’ing the sales process.” That’s what I called it too in a previous life. I think this description is a bit of a disservice to good PMs though, because business development is the Tyrannosaurus Rex from Jurassic Park. It eats when it wants to eat, and shits when it wants to shit. Good PMs lead, and often there isn’t a leadership opportunity for a sales support resource in business development. Most often these support resources are administrating a principal’s role in sales, not business development itself.

This is an important distinction because often when this support role is hired, the support resource is “responsible” for the cadence and progress of sales. Respect the term PM.

Ever try to push a piece of wet spaghetti across a plate? You can’t push it from behind, you have to pull from in front, sales is often a wet piece of spaghetti (as well as a hungry dinosaur). So a business development lead might be the first dedicated sales hire.

Business Development Lead

A business development lead is most often hired for one of two reasons, for lead generation, or to free a principal of their sales (burden) responsibilities.

Lead Generation

When these leads are hired for lead generation, it may be because inbound leads have slowed, or are not growing at the same pace the agency is growing. In these cases sometimes a lead is hired for lead generation because they are perceived to bring a huge rolodex of client contacts with them. Sometimes they are hired because they scream “hustle” in everything they do, and the potential volume of activity is exciting. The short version is this lead is going to apply energy into the prospective client universe, and results will follow.

A brief word of caution: This can often lead to cold calling, email blasting, drip campaigning, and other ideas that sound like something you’d use Angie’s List to fix. Worried conversations about commissions and incentive structures spring from the fear these ideas conjure. Spoiler alert: there is no right answer about commissioning or not commissioning. Every agency is unique, and every business development lead is different, and you should plan accordingly. Anyone telling you “Always commission!” or “Never commission!” is an asshole. Generally anyone making gross generalizations about any group of people is an asshole. See? I know because I’m an asshole.

Sales Leadership

When business development leads are hired to unburden a principal of their sales responsibilities, that means the agency is a year or so away from going out of business.

Just kidding! Kind of. I wanted to make sure we’re all still paying attention.

In this role replacing aspects of a principal’s role in sales, a business development lead may assume control of closing leads, writing proposals and estimating, pitching, and nurturing sales through the sales pipeline.

Two important questions to answer in this hiring scenario are “Why does the principal want to become less burdened in sales?” and “How much oversight will they still invest in sales, once a lead resource joins the team?”

If the owner wants to become less burdened in sales because they perceive someone else would be better at it, then that’s an instinct worth pursuing. That owner is likely invested in sales to such a healthy extent, they want to improve it by getting a little bit out of the way.

A brief word of caution: Don’t go too far though. NOTHING is as impactful to a prospective client as the attention and interest of an agency owner or principal. The best sales person in the world is taking a knife to a gunfight when they’re pitted up against an owner, who has taken time away from all of their many responsibilities, to engage with a prospective client in the sales process. Additionally an owner needs to be fluent in what is occurring in sales, for forecasting, for peace of mind, for the sake of their business. Don’t go too far...

If the owner wants to become less burdened because they are bored or tired of sales, then they have already decided they don’t want to own or lead a client services company any more. They may not realize it yet. Sales is half of the equation in client services, the other half is doing the work. You can’t fall out of love with half the equation and stay in business for long.

Preventative Medicine

In each of these cases, these initial hires are often being made out of sheer exhaustion. Exhaustion from the hustle of the sales process, exhaustion from the pressure of winning sales, or the exhausting of a formerly-more-robust inbound pipeline.

Business development could be (SHOULD BE!) preventative medicine, but most often it’s not. In the cases outlined here the business development hires occurred well after symptoms presented.

As digital client services agencies grow, their business development needs and requirements continue to expand. Salary, benefits, and operating costs multiply like gremlins in a hot tub.

No sooner is a sales support resource hired, then a business development lead is needed to back fill an owner who has now focused more acutely in a specific area of business development. No sooner does a business development lead get their bearings, then a support resource is needed to free them to focus where they’re appropriately billable, rather than in the weeds of administration.

~25 employees. By the time many agencies reach a staff size of around 25, there’s room in business development for some combination of an engaged principal or owner, and up to two (or three) full time resources. One or some of these parts can be played by another owner or principal, but this means coordination and scheduling is 100x harder. The mix of these roles and responsibilities varies from agency to agency.

At this size you’re composing a basketball team in sales, not a football team. I’ll explain, because I love talking about basketball.

Basketball vs Football

A basketball team is five players on the court, and a team of fifteen active players. They play in a fluid, non-stop sport where improvisation, muscle memory, and team dynamics shape outcomes. Plays build on plays, and variables are always changing. You design a good basketball team around the abilities of the five players. You find a way to orchestrate their individual greatness, into custom-crafted team greatness.

A football team is a massive seventy plus roster with eleven players from each team on the field, four times as many total compared to a basketball game. And those players stop and start before and after each play. Players discuss strategy, line up in specific set positions, execute a play, and then regroup and repeat. Due to the intensity and violence of the sport, there is a “next player up” mentality in football too, which means roles are designed. Players and their substitutes fit into those roles. When new players join, they fit into specific buckets with specific defined roles. In football you build a great system, that individuals are organized into.

30–35 employees. When you reach north of 30 staff members, you need to start getting deadly serious about building a sales organization. At this size many agencies begin to feel the irreversible gravitational pull towards growth. Beyond a team of 35 or so staff members you need a profound investment in new business, account management, marketing, and closing sales. Read Aurimas Adomavicius’ post on Building a $20 Million Sales Organization for some wayfinding into that dense wilderness.

Buying Time

So that’s a lot of observations, but I wouldn’t leave you without some advice. I wouldn’t do you like that boo.

The conclusions I’ve drawn from these numbers (math so fuzzy it sounds like a Neutral Milk Hotel single) is that generally speaking, owners and principals reluctantly and begrudgingly hire for sales. When the pain is so acute it can no longer be remedied, or the numbers on a terrifying spreadsheet are screaming so loudly they can’t be ignored, that’s when business development hiring often happens.

Each business development hire unlocks more time for business development, and that’s what most principals really need. More time. If owners could buy another 20 hours per week for them to invest personally in business development, they’d do it 99 times out of 100. But they can’t buy more time, and HR, operations, delivery, client services, and management gobble up tons of their existing time.

Hiring for business development seems like a simple solution. The reason owners and principals often delay as long as they can though, is money.

A sales support resource is a hefty unbillable investment. They are pure cost, and they can feel like a luxury when everyone in the smaller agency to this point has been blissfully billable.

A business development lead can easily be a six-figure investment, another unbillable asset, which is tough to stomach when owners are accustomed to billing for everything. If the business development lead is commissioned and really good at their job, it only gets worse. They’ll make even more money than the owner. Did you hear that in the cheap seats? If you’re paying someone on commission, their earning more than an owner means they’re good at their job. It means they’re killing it, celebrate.

So I stand by my previous, under-read and under-Medium-applauded advice, Get Ahead in Sales. But if you can’t make that huge salary or budget leap right now, how can you hop a little?

Part-time Support

You don’t need to hire someone full-time for them to materially benefit sales. Figure out what tasks you need accomplished to serve your various sales campaign goals, and Sears Catalog Wish List of strategies. Compose a bullpen of part-time resources to service those goals. Find great writers, content strategists, freelance marketers, and designers who can offer specific support in specific areas. Hire them for projects, then deploy again and again as needed. Or better yet hire them for a project and pay attention to how they do what they do. Then internalize that process with a dedicated internal resource if it’s valuable enough.

Get ready to delegate parts of sales, the parts where you are mostly replaceable. Take Richard Banfield’s advice. If someone can do what you do 70% as capably, delegate to them.

Trust me, I’ve made a living over the last two years providing fractional business development support. And I’m doing so well I have time to wax philosophical on Medium. What a big shot! There is a model for this to work and I’ve seen the results. They are much better than not doing anything. Be careful who you hire though…

Outside Service Providers

My best advice is to vet these folks like they’re a Supreme Court nominee.

For example, there are tons of lead generation services now that guarantee meetings, guarantee leads, guarantees all the way down. They appear to offer turnkey business development hustle, that requires little to no time and support from owners or principals. Seems almost too good to be true.

I have not worked with these service providers myself, but their reputations precede many of them. What worries me specifically is they offer a foolproof system, a recipe that can’t fail, and I bump against the idea that any approach is rinse and repeatable across various digital client services teams. Each digital client services organization is inherently different, especially at smaller scale. Remember the basketball team? This feels like a football solution to a basketball problem.

Get their references, on the phone. Spend time getting to know the references and their businesses. Develop an understanding of how they sell, what they sell, who they sell to, and determine if they and their business feel analogous to you and yours. Then explore the highs and lows of the outside provider’s process and results. What were the positive outcomes? Where was there friction? What bridges were burned? What friends were won and which people were influenced? These services charge thousands of dollars per month, and they’re at their most profitable when they’re charging lots of agency clients at once. It feels super transactional to me, and I don’t think there’s one bulletproof approach out there that works for everyone.

There are other promising newfangled creative solutions out there too. I won’t name drop for fear of getting labeled an advertisement by Medium’s new content policy, but do some Googling and you’ll find them. Invest wisely, ahead of your needs when possible, fractionally when you can’t.

This isn’t some Nate Silver quantum computing. Use this fuzzy math with caution. It’s one person’s insight based on hundreds of variables. And I already told you what I thought about people who make generalizations.

2017 Under Review

Inspired by Greg Storey, who in turn was inspired by others, here is a brief overview of my 2017. Like most things in our professional lives, Greg’s is better thought out, mine is longer because I get too lazy to stop.


2017 saw some North American jesetting with work trips to Boston, Chicago, Dayton, Denver, Montreal, and Oakland. But none may have been more charming than a little trip over to Haddonfield, NJ. Adorable! That said, Montreal is pretty goddamn charming. Travel was made all the more enjoyable co-piloting with Rawle Anders on most of the trips.

In Boston my buddy Tito Botita took me to a Celtics/Sixers game, third row, right behind the pressbox. It was overwhelming and I have a whole new appreciation of the game.

The most important trip of the year was to Orlando, however, when the Rinaldi family made our inaugural trip to Disney World. Kids’ minds were blown, adults were reminded of what it was like to be a wide eyed stunned-by-awesome kid. It was a high point of the entire year, and as a parent. It felt extremely grown-up to take the family to Disney World. Mom and dad achievement unlocked.


The most important work development in 2017 was getting to work with my old “Shake and Bake” partner Rawle Anders. We’ve had more than a few opportunities to collaborate cut out from under us over the years and it was great to have the chance to saddle up again. On a few projects Rawle brought his +1 Mary van Ogtrop along to wordsmith and strategize, and the results were all the richer for it.

Clutch provided business development training, consulting, support, and prestidigitation to fantastic clients, and old friends including SparkboxUpstatement[whitepenny]PixoFour KitchensSuperfriendlyArmorAssemblePlankNeo Pangea, and Dynamo.

At Owner Summit new friends were made that led to projects with Kalamunaand Bokka Group.

And perhaps most rewarding of all has been the ongoing collaboration with/support of Eastern StandardStudio.ZeldmanChromaticKoombea, and Gistia. It’s been a year-long engagement in many of these cases and the experience has been deeply rewarding. Getting to dig in at a tactical/front lines level scratches the itch on that phantom biz-dev-guy limb.

It’s been long enough since these 2017 Clutch projects kicked off to see real results too. One Clutch client extended key accounts to the tune of over $1M, another developed an outbound sales programs that started exciting new client conversations, one repositioned themselves for better differentiation, others landed meetings, created exciting new marketing content, signed projects, renegotiated more favorable fee schedules, and in general took more ownership of their sales process and results. Thematically Clutch has delivered business development with more intentionality. That’s been fun.


In hindsight I didn’t see a ton of movies (especially in theaters) in 2017, but more than made up for that deficit with some amazing streaming series, and lots and lots of podcasts. The other thing I consumed was basketball, all of it. With a 12-year-old fellow 76ers fan riding shotgun I think we watched 90% of the Sixers’ games and most of the postseason. It’s fun to share this passion with my little blonde haired shadow. I love my sons JoJo and Ben too.

Favorite movies (ranked) include:

  • Spiderman: Homecoming (the best Marvel superhero movie to date)
  • Thor Ragnarok (the second-best Marvel superhero movie to date)
  • The Big Sick
  • Logan
  • Baby Driver
  • The Last Jedi (good but not great, fight me)

Favorite shows (ranked again, because make a decision jeez):

  • Game of Thrones season 7
  • Mindhunter
  • Stranger Things 2 (made all the more enjoyable because our 12-year-old watched it with my wife and I)
  • Godless
  • Master of None seasons 1 and 2 (I was late to this party, but now I’ve found Arnold and I’m whole again)
  • Glow
  • Big Mouth

Favorite podcasts (none 76ers-related) ranked:

  • My Brother My Brother and Me (still reigns supreme)
  • How Did This Get Made? (is so good I’m listening my way through back-episodes)
  • The Greatest Generation
  • 99% Invisible
  • Revisionist History
  • Start Up
  • Til Death Do Us Blart (This is an annual Thanksgiving Day podcast where the MBMBM boys and The Worst Idea of All Time podcast re-watch Paul Blart Mall Cop 2 every year until they die)

Favorite podcasts (76ers and basketball related) ranked:

  • The Right to Ricky Sanchez (is actually my favorite overall pod, top of the list)
  • Sixers Science (Randy Cohen is a gift)
  • The Sixers beat (Godner)
  • The Stepover Podcast
  • Cookies (the only NBA podcast I listen to, even if they’re not talking Sixers)
  • Then it’s a collection of Woj, J.J. Redick, Real GM, Game Theory, and Dunc’d On if the topics are interesting

Favorite books (many of these weren’t published in 2017, just enjoyed):

  • Warlock Holmes by G.S. Denning
  • Mortal Engines by Philip Reeve
  • Artemis by Andy Weir
  • The Art of Mondo
  • and I re-read IT by Stephen King, but yeah the ending doesn’t work at all


The two things I deleted from my life that had the most benefit in 2017 were white sugar (mostly, I’m not going crazy about it) and Bill Simmons.

By cutting white sugar out of my coffee intake and most of my snacks I’ve lost 15+ of the 20+ stress pounds I gained in my last year at Happy Cog.

By cutting Bill Simmons’ podcasts out I’ve exorcised a degenerate gambler, terrifying parent, and myopic Boston homer from my life, and opened the door to better pods.


This is a broad category, buckle up.

This is what I’m good at in many ways, matchmaking and developing connections. Most of my jobs weaponize one or both of these things. Add in “make ideas better” and those are all of the reasons to hire me, there are no other reasons.

In 2017 I found opportunities to connect lots of people to wonderful results.

I’ve been able to help folks find jobs and gigs they’re really excited about. I’ve connected clients to agencies and built projects. I’ve threaded agency teams together, and made tons of introductions. I’m a people collector in my bones and these kinds of connections are really gratifying.

I joined a 76ers Slack group that’s been fun to connect through to others around the games.

I coordinated perhaps the highlight of my 2017 social calendar, a Happy Cog alumni co-working day in December. Nearly 20 Happy Cog alumni (and Happy Cog-adjacent homies) spent a day at The Yard getting work done, not getting work done, and spending time together. It was wonderful to see all of those faces at once. Really filled a void. I’m looking forward to the sequel in a few weeks.

Last but not least I’ve made more of an effort to stay connected to my own opportunities. One of my regrets in my tenure as President at Happy Cog were missed opportunities. People I could have (and should have) worked with, but didn’t. The missed potential haunted the hell out of me.

Additionally I became aware of a bunch of opportunities I missed because I was viewed as untouchable at my old work address. This proved to not be the case of course, and in my first full year not working for Happy Cog since 2010, I vowed to make my intentions and availability better understood to the right people.

After a year of working for myself, working for someone else seems like a tall order, but there are people I’d walk through fire to work for/with (see: the aforementioned Greg Storey) and I don’t want to miss out on those opportunities. Jen Dary, Nancy Lyons, Vince Levecchia, Jay Fanelli, Ben Jordan, Dan Mall, Jon Lax, Art Adams, Joe Biden, and Oprah Winfrey all know (or know now at least if they’re reading this) that they’re on the “drop everything” list. No mo FOMO.

The last thing I want to mention in terms of connecting has been connecting with people I admire on Twitter. Twitter has become a Nazi-Trump-shitshow in many ways. I made attempts in 2017 to strike up a dialog, or at least awareness, with creators and public figures I appreciate. I was hoping to bring a little of that old fashioned engagement back to the twitters.

Whether admiring an actor’s performance:

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Or a reporter’s effort:

Screen Shot 2018-01-08 at 3.32.11 PM.png

Or an illustrator’s unmatched prowess:

Screen Shot 2018-01-08 at 3.32.30 PM.png

It’s exciting to connect, gratifying to feel like you brightened someone else’s day, and an all around hoot. I’m pledging to do this more often in 2018. I will be the guy who remarks “Wow, great job on the air conditioning temp. It’s perfect.”


I have lots of thoughts heading into 2018, not the least of which is to finally breath life into a pet project I’ve been working on or flirting with for years. I want to draw more and write more too. Not blogging per se, although I want to do more of that too, but writing fiction. I have something I’ve been circling for a decade I want to get on paper.

Per Jen Dary’s stellar advice (she is wicked smaht) I’m not building a lifestyle company called Clutch. I’m building a lifestyle with Clutch. I want Clutch to fuel and fund some of these side projects, and I’m making an effort to get to a point at the end of the year where every Friday Clutch is closed and I’m busy doing these other things. I’ll try to share as I dig further in, and I hope to have some results to share soon!

If you lasted this long you’re probably my mom. Hi mom, I love you.

Who sets the price, sales or ops?

This is not how basketball works

This is not how basketball works

When it comes to pricing, there are two schools of thought. What you’re thinking, and what everyone else is thinking. Out there it’s a wild spectrum of pricing methodologies and practices among digital client services organizations.

I remember an Owner Camp conversation where Brian Williams (from Viget) and Jon Lax (leading Teehan & Lax at the time) debated the value of tracking hours. At the heart of the time tracking debate was the impact tracking had on scoping, budgeting, and selling projects. When the dust settled, it turns out they were both right. Their respective methodologies were each powerful and successful for them, despite their differences.

Fixed-fee pricing, value based pricing, time and materials invoicing, and agile scoping all work. They’re all different flavors in the same ice cream case. There is no right answer, only the answer that’s right for you and your clients. The utility of each approach is derived from how you view pricing philosophically.

Is pricing a function of operations, or a function of sales?

Where pricing is a function of operations, there is often clarity. An arithmetic model determines a project price based on a scoped effort multiplied by a billable rate. If you scope in hours, the total hours multiplied by an hourly rate = budget. If you scope by feature/value the sum of all features’ value = budget. This method often withstands client scrutiny the most frictionlessly. “It costs what it costs” she told herself as she lay her head down for a night of sound sleep, untroubled by thoughts of “should I have charged more?!?”

Where pricing is a function of sales, there is often opportunity. When you decouple pricing from rigid operational math you can price a client with more money at a higher budget (price the client, not the project). You can cut price to make a proposal more attractive. You can price different clients, different projects, and different days of the week, in different ways. This approach often opens the door to many questions from clients, and especially from procurement departments.

In both cases though, you can successfully price the same project, from a certain point of view.

In a recent conversation with an agency, we discussed the limited profitability of a recent project.

On the one hand, one of the partners was lamenting that this project only netted $5,000 in profit. It was nearly break-even work. He felt this was not a sustainable business model, and he was right.

On the other hand the other partner was thrilled that the real win was that the work resulted in securing a Master Service Agreement (MSA) with their client’s large consumer brand parent company. She felt that if given the opportunity, they would have gladly paid $5,000 to purchase an MSA with this global brand, opening the doors to more opportunities, and she was right.

Truth be told, when I work with clients who adhere to operational pricing strategies or sales pricing strategies, they’re almost always secretly flexible within their own paradigms. An hourly pricing team isn’t opposed to raising their rates when they feel a client can afford it. Another team who prices to sell/close projects will similarly break open a spreadsheet and account for every proposed hour when the right client comes calling.

The morale of the story is that in my experience pricing is typically more alchemy than science, but it helps to determine if you think pricing is a function of operations or sales.

Are you likely to be more comforted by a reliable/transparent pricing strategy, knowing there is a ceiling to how much you can charge?

Or are you more concerned that you’re leaving money on the table by underpricing an opportunity, knowing that there is a potentially higher reward, but also increased risk?

Once you’ve made a determination about where you live philosophically, settle in, but don’t get too comfortable. Continually challenge your stance, and question whether you should introduce more formula into your thinking, or more flexibility. The only wrong answer in the long run, is getting lazy, and rigidly adhering to one camp or the other without occasionally weighing your alternatives.

Vulnerably Honest

Wes Anderson levels of transparency

Wes Anderson levels of transparency

There are so many books on negotiating tactics. So very many. Often these tactics are framed around “winning” negotiations, and it feels that way when the stakes are high. 

I’ve had to negotiate like my (work) life depended on it. I was a recruiter for 5 years. I worked in a commission-driven business model where competition from other recruiters was endless, opportunities to build relationships with clients were hard-won, and sometimes when you successfully “sold” a placement, the person you fought to place at a client changed their mind at the last moment. It was selling in a really commoditized way like selling copiers, but if the copiers could decide they didn’t want to work at Astra Zeneca thanks anyway tho. Unrelated, I have lots of grey hair.

The stakes only get higher in client services, especially if you’re selling consulting services. When you’re selling a “how” not a “what.” Winning negotiations becomes even more critical when more and more people on a team are depending on your successful sales outcomes. You negotiate with procurement, you generate consensus among large groups of stakeholders, and then if you’re really lucky you get to negotiate with legal. These are professional negotiation winners. Talk about bringing a knife to a gun fight.

With this much on the line, and this much effort invested in negotiating, you may start to employ pricing strategies, or be tempted to construct elaborate negotiating tactics, or otherwise overcomplicate an already complicated decision. You’re working to protect your interests. You’re defending against vulnerability. I know, I’ve done all of this, to positive and negative results.

I remember an agency owner telling me that when their firm suffered through layoffs, they were 100% honest with clients about what was going on, why it needed to happen, and how it would impact their relationship and work. The agency negotiated a brief pause in all client work as they reorganized, and they and their clients weathered the storm. I thought this was crazy. I’d never entertained being that transparent, but there was real power in the trust earned in that investment in honesty.

What I’ve started to experiment with (because life is too damn short) is employing a level of honesty and transparency that I found scary at first, but that I realize has become a powerful way to build trust and rapport with my own clients. 

I’m completely leveling with my clients. Not just about what I want and what I need, but about what I perceive to be their priorities, their concerns, their needs. I’ve had to disclaimer this approach at times, warning we are about to engage in some “next-level transparency” up in here. I’ve explained to them what I think they were being too polite to plainly say. I’ve been transparent with them about my business requirements and plans. 

There is real risk here. I may not be 100% accurate in my assessment of what my clients are struggling with in making their decisions. I open myself up to the risk of being wrong. There is a vulnerability in being honest with someone, and not protecting yourself by positioning or jockeying. I know I’ve rocked a client or two back on their heels a time or two as a result. But in every case, we’ve settled into a more honest and transparent conversation.

The team I’m supporting is smaller now that I’m running my own business (there are four of them and they’re all named Rinaldi and they all live in my house), but they depend on me a helluva lot more than my former coworkers ever did (boy’s size M compression pants don’t pay for themselves you know). So there are some real stakes, and a lot to lose if I can’t successfully negotiate with my clients. 

Granted, in my current line of work I began by working with people I already knew, and in many cases already trusted. Honesty is easier in those cases. But I’m well outside of that roped-off, protected little swim lane now. I’m encouraging a level of honesty with clients I barely know, and the feedback has been that they don’t feel like they’re being “sold.” In consulting services that level of trust is a valuable currency. It’ll come in handy when I need to lead my clients. So while I’m dialing up risk by employing vulnerable levels of honesty, I’m dialing up trust and positive outcomes even more. You may feel like you’re exposing yourself to vulnerability by being honest, especially when it’s an unglamorous flavor of honesty, but I’m pretty certain it’s a good policy to adhere to. Some say the best.

The Tactical Deployment of Fun

One of the challenges I face working for/by myself is "getting started." I’m a talker, and I’m at least 20% smarter when talking an idea through with someone else. 25% smarter if I can high five and walk around while talking. 

When I’m working actively, talking with a client, we cover a tremendous amount of ground really quickly. It helps that we speak a common client services language and can share ideas in a more primordial state back and forth faster. After a 45 minute call I’m often stunned by how much ground was covered, and how easy it was to plow through a bunch of topics or challenges.

Then, I sit down to do some heads down work, and time slows to a crawl. It feels like the Millenium Falcon coming out of hyperspace. It’s not that I’m procrastinating. I can watch those Joel Embiid videos later. I struggle with the frustration that my rate of progress slows so dramatically.

What I started to do to overcome this frustration, was find ways to make work fun. Well, fun may be an overstatement, but I definitely find creative ways to get rolling.

For example, I needed to rewrite a client’s proposal from soup to nuts (soup to mints? Who eats exit nuts?) and holy crap I was I getting good at staring at this document not getting anywhere. 

So I thought about Dan Mall. If I endorsed Dan Mall on LinkedIn I would obviously start by endorsing him for scarves. The brother’s scarf game is on point. But next, I’d endorse him for making work fun.

I’ve worked with Dan on a few projects now, and where he’s irreplaceably valuable is when he reconstructs a client task to be fun. Whether it’s as simple as using Mad Libs as a metaphor to get clients talking, or exploring an idea visually vs verbally, Dan is great at looking at a challenge from a slightly different angle, and making the work more enjoyable and memorable. Clients come out of his meetings humming. That spoonful of sugar is just enough.

So rather than plow through my client’s proposal, I put on some sweet sweet coffee house jazz and read other firms’ proposals. I have a wee proposal library I’ve built up over the years. I love reading them. It’s a thing. 


I started reading through other examples, and started cataloging their contents by sections, by focus, by structure. Armed with this mighty spreadsheet, I was able to run a gap analysis of where my client’s proposal has holes. Where they comparatively over-invest in content or focus. Where they stand out. Rewriting was a breeze.

I try to think like this when working directly with clients too. 

For example, when discussing business development goals with a client, I often employ a time traveler metaphor, bear with me. When you’re in biz dev, you’re a time traveler. You’re living at least part-time in your firm’s future. The projects you’re closing, the clients you’re calling, they all represent the work your team will be living with for the next six months, or the next year. You’re imagining the case studies this work will yield. The other projects it can lead to in time. You’re thinking 6–18 months ahead.

When developing these goals, I’d love to crack open the client’s Work section on their site, view source, and start to messing around swapping in new client logos and case study titles that represent their wishlist clients. It would be awesome to visually see Starbucks or the NBA or Habitat For Humanity or whatever among their client case studies, on their actual site. The reality of that would be awesome. Frankly it’s just outside my reach to pull that off live (but I know Mark Huot can do it, I’ve seen him do it in a pitch and it’s glorious, damn him).

I can’t stick the landing with my grander unconstrained goals, so I punt. Instead, I have the same kind of time travel conversation without the visual aids, and occasionally I’ll do a bit of that visual work in Photoshop offline and bring that back to the client. That’s what I’m capable of, and it still gets the job done. 

Setting the big, ambitious, fun goal at least gets me thinking in the right direction. Then I figure out how much of that vision I can execute. Ultimately though, I remain aimed at making the process more enjoyable.

It may not always be Disney World-level fun, but Action Park is still a good time. You just need to sign more waivers.

give a little bit

So I’m a small business. Kind of an accidental enterprise when I started out tbh. I was getting into consulting and I needed a shingle to tell my story. A logo sketch, some vector help from Ben Jordan, and a dusted off domain I’d owned for 8 years later, I’m suddenly Clutch. Not so suddenly if you ever creeped on my LinkedIn bio.

Lots of little decisions followed. Not the least of which was client holiday gifts. I had 8 clients at the end of 2016, and a handful of colleagues and friends I owed a drink for either sage advice, timely support, or remote high fives. I looked at DiBruno Bothers gift baskets (an old standby) and thought about sending a bottle of wine (but I live in Pennsylvania where booze is too hard).

After much introspection I settled on sending clients and friends prints from Scott Campbell. I’m an illustrator, and an illustration enthusiast, and I imagined a fellow illustrator like Scott might appreciate a little holiday business more than the larger enterprises I was considering supporting with my patronage. 

Scott has some really amazing pieces and does these great illustration series

For this year’s client gifts I settled on a tribute to America’s greatest living actor, Jeff Goldblum:


And for the folks I wanted to buy a drink for (but couldn’t because they’re all over the country) I bought his Star Wars cantina prints. Honestly, these guys look like more to raise a glass with than I am anyway:


Yeah, it’s me kind of imposing my taste on my clients, but it’s authentically something I’m passionate about, and something I sincerely think will put a smile on someone's face. 

Sorry Greg Storey, I got you a book.




I love nicknames. One time a guy I worked with in Savannah called me “Dr. J” because I’m from Philadelphia. The name did not stick, but it may have been the greatest moment in my life. Greg Storey has the cutest nickname for me. He calls me “When are you going to blog about it?” I know this is my nickname because he calls me it every time I talk to him. It’s catchy too. Dan Mall calls me “That’s a blog post.” 

With all this blog talk I began to wonder, should I be blogging?

Dan and Greg are excellent writers, and bloggers from way back. I’ve spent a long time talking about blogging with the two of them over the past few months and they’ve both taught me something valuable, again.

Yes, I should be blogging, and so should you. 

It’s a way to catalog what I'm thinking about, what I'm working on, half-baked ideas, etc. It doesn’t need to adhere to a cunningly clever editorial plan or content strategy. It doesn’t have to break the internet in half with its novelty.

It’s valuable to me to put my thoughts out there, whether it’s valuable to anyone else is almost unimportant.

My goals are:

  • To blog about my work, but remain personal
  • To blog frequently, but not kill myself if I miss a weekly schedule
  • To be honest, a little vulnerable, and a lot transparent

This is my first blog post, so I owe a little personal transparency. I do have a nickname. My family calls me Zep. It’s short for Giuseppe, and so am I.