Arrogance v. Confidence

Arrogance v. Confidence

By JT Benton, of the Tempe Bentons

First off, long post alert about arrogance. Like, 1,140 words long (10 minute read). And even though our VP of Marketing Rob Stevenson keeps telling me that short form is better, this piece just came out this way. So read at your own discretion.


Last year, I wrote about curiosity as a defining characteristic of great sales and business development people. In that piece, I pointed to the trait as the one most present in highly successful people I’ve met in this line of work.

Today, I’m writing about a different trait, which I think can have the most destructive effect on the work we do: arrogance.

Among those character traits we must endure, I’d argue there’s nothing worse. Compulsive lying, negativity, insincerity, laziness can all make their case for being worse – but we largely remove these behaviors from our lives.

Good people and good companies can just decide not to associate with dishonest, nasty, insincere or lazy people for very long. But, we all have to manage relationships with arrogant people. Could be your boss, your employee or peer. Or your counterpart on a deal that’s really important to you.

Worse yet, it could be you.

And since arrogance in business isn’t going anywhere, I thought maybe we should talk about it. Read on (unless, of course, you’re too busy or important or already know all about this)…

Defining arrogance

Webster’s Dictionary defines arrogance as ‘an attitude of superiority manifested in an overbearing manner or in presumptuous claims or assumptions.’ For interpersonal, non-commercial relationships, this definition works. We see it when we meet a person who acts as a know-it-all, or comes off as smarter, wiser, cooler or better.

But I think there’s another kind of arrogance that we often see in business development. This one is far more innocent and totally avoidable. I call it cover-up arrogance. Cover-up arrogance happens when we try to cover up our deficiencies. It’s the imitation of confidence when we’re not really confident about something.

This plays out when we feel ‘less than’ and we feel bad about it. This can be because we’re incorrect, don’t know the answer to a question or just aren’t completely prepared – and we feel guilty. Instead of fessing up, we beat our chest or make larger claims than we should.

Confidence vs. Arrogance

Given how negatively we experience arrogance, one would think we’d all be constantly worried about being perceived this way. You’d think we’d avoid it at all costs in our own behavior, and that it would largely go away.

But that’s not the case. In fact, the ugliest truth on this topic is that we’re all arrogant at least some of the time. It’s unavoidable. I think this is because arrogance and confidence keep very close company, and because our behavior is ultimately decided through the way others experience it.

For business development folks, confident communication is a must, but too much confidence or insincere confidence will likely be perceived as arrogance. Think of confidence like it was a product you use to enhance something. Like mayonnaise on a sandwich. Without it, you’ve got yourself dry, plain food. Add too much of it, though, you’re left with an unpalatable and offensive mess.

For anyone who has to persuade others as part of their job, arrogance can be an occupational hazard. And because everyone has a different threshold for what they think is arrogant behavior, it doesn’t seem possible to avoid ever being seen or experienced as arrogant and still do our job. Here, folks, we have a bummer.

How to avoid being arrogant while remaining confident

I’m terrified of coming across as arrogant, and yet, I know I can be guilty of it. When I receive feedback that I’ve been too brash or come off too strong, I reel back and I question everything. To me, this is the worst kind of feedback. So, I’ve got a vested interest in figuring out the very best ways to avoid this.

This applies to WorkBook6’s team, too – our work demands that we communicate influentially on behalf of our clients. We make a lot of assertions and recommendations, and we are asked to appropriately justify these perspectives. This is fertile ground for arrogant behavior, were we not paying attention to it.

So, we talk about this a lot. How do we stay aggressive without overdoing it? While the answers are constantly evolving, we’ve made it a cultural imperative to acknowledge it.

And we’ve made a point of enforcing the traits that soften our edge, without lessening our position. These efforts have formed a sort of behavior map for us to follow and leverage when we find ourselves at risk. I’ve posted it, below:

  • Be curious. A sub-trait of arrogance is an overt focus on one’s own self or one’s own purpose. It’s a red flag. To avoid it, we can work hard to develop our curiosity. One is far less likely to come across as arrogant if they demonstrate a sincere interest in their counterpart.
  • Be relevant. This is curiosity’s partner. Once you’ve learned all you can about your counterpart, tailor your own contribution to tie into what they’ve shared. If you’ve listened well, you’ll be far more prepared to provide relevant content.
  • Be vulnerable. This is, like, major. If you buy that ‘cover-up arrogance’ is a real thing and you want to avoid it, just be vulnerable. Say (and, mean) stuff like, ‘whoa – you stumped me; I don’t know the answer to that.’ and ‘I’m not sure I understand; can you help me better grasp this? Another great one when things get tense: “I think I made a mistake. Can we reset?” Most importantly, if you caught yourself (or someone else caught you) being arrogant, acknowledge it and apologize. If you’re dealing with a good person, the vulnerability should help you get back on track and build a great relationship.
  • Soften the blow. When it is time to make a recommendation, you can still do so with conviction without being overbearing. Just soften the blow a bit. Try this: “I have a suggestion that I think might work. But if it doesn’t, I’d love your feedback…”
  • Ask for criticism and be grateful for it. You care about doing a great job, right? Then find out if you’ve done that by asking. And if you learn you haven’t been your best or that you were off target, be grateful for the lesson. You’re better for it and you’ve demonstrated your willingness to invest in the relationship.

These are our best practices for doing great work and not being arrogant. But, we’d love our readers’ feedback.

Did we miss something?

Are there other great ways to mitigate this? Let us know – we’ll take any advice on this we can get!

Leadscon is coming!

Leadscon is coming | From Likes to Leads Session

It’s absolutely crazy when you think about it, but Leadscon 2018 is only six weeks (and counting) away! We’ve been hard at work as we plot and plan the second Strategic Partnership Workshop, which is being held in conjunction with Leadscon again this year, and the lineup looks amazing!

Do you have your tickets yet? Pro tip: use the promo code: LCLVSPKR and get a $150 discount off your total event registration. And remember – prices go up February 8!

For example – the WorkBook6 team has collaborated with our friends at Facebook, Active Prospect and WD Social to present “From Likes to Leads: Leveraging Facebook Lead Ads for Customer Acquisition”.

Facebook changed the way companies reach and engage customers. Like, forever. This isn’t just true for awareness and branding efforts; Facebook’s lead ads product has also helped many direct response brands win big. Join Sona Parikh from Facebook and Active Prospect’s CEO, Steve Rafferty, for an overview of the lead ads product and a deep dive into how brands and agencies are profitably deploying it. 

This session will cover not only the medium, but also technology components which help marketers get the most out of their investment. We will also include key advertiser insights from Sam Bhatt of WD Social. This first-party knowledge and best practice content will help ease the learning curve for those new to this product as well as provide new perspectives for anyone already active in the channel.

And that’s just one of the five amazing sessions we’ve got planned – will we see you there this year?

Anna Lewis Leadership Team

WorkBook6 Adds Two to Leadership Team

Anna Lewis, Rob Stevenson latest additions to Phoenix-based strategic partnership hub, part of continued growth plans as firm expands to meet client needs

Phoenix, AZ – January 16, 2018 – Leading strategic partnership marketing firm WorkBook6 today announced the additions of Anna Lewis and Rob Stevenson to their Senior Leadership Team as the firm expands it’s national footprint.

With more than a decade’s experience in senior leadership positions across the customer acquisition and lead qualification ecosystem, Lewis brings leadership, experience and a deep network cultivated to the Partnership Development team at WorkBook6.

“Anna is a dedicated, motivated, and trusted business development professional with proven team building, leadership, growth and sales success,” said JT Benton, founder and CEO of WorkBok6. “At this stage in our organization’s growth, being able to attract a top talent like Anna speaks volumes about what we are trying to accomplish. I am thrilled to welcome her to our team.”

Lewis will commence her role as Vice President, Partnership Development, effective January 16, 2018. Previously, Lewis served in progressively senior customer acquisition roles at Invoca.

“I have a passion for creating, building and motivating teams of A-players, and executing on growth initiatives, which has served me very well in my career,” said Lewis.  “I have known and worked with both JT Benton and Brett Kaufman for years, and being able to join the team at WorkBook6 is very exciting.”

WorkBook6 also announced the appointment of Rob Stevenson as Vice President, Marketing at the firm. Stevenson had previously specialized in B2B marketing and client success roles during his nearly 20-year career.

“Adding someone the caliber of Rob to our marketing team offers WorkBook6 a critical in-house resource as we work to build and strengthen our client network,” said Benton. “His combination of experience and expertise allows WorkBook6 to truly put our best foot forward, while simultaneously looking ahead to the opportunities on the horizon.”

Stevenson officially assumed his role at WorkBook6 effective November 1, 2017.


About WorkBook6

We Power Partnerships. Uniquely positioned across four primary service areas, WorkBook6 combines strategic leadership with unparalleled experience across all facets of Strategic Partnership Development, Marketing Program Management, Media Monetization and Affinity Organization & Membership Group engagement. WorkBook6’s technology leverages the efforts of a diverse team to power dozens of partnerships throughout a wide range of industry categories, building sustainable revenue for our partners across the customer acquisition and customer retention ecosystems.

For more information, please visit


Annual Letter

The Annual Letter

One of our clients has an end-of-year New Year’s tradition I really like – the Annual Letter.

Once a year, the firm’s Chairman and the CEO sit down and write an annual letter addressed to the company’s shareholders and employees, and they post it on the company’s website.

In the letter, the two executives give a transparent and detailed review of the year behind them, as well as a look to what’s ahead. This company is exponentially larger than we are, but I love the idea – so, we decided to do it, too.

Our clients and partners will have a hard copy of this, but for broader distribution, I’m posting it on our blog. Hope you enjoy!

The Annual Letter: Looking Back – and Ahead

Dear Reader,

Greetings and Happy New Year! I’ve decided that this year, as we end WorkBook6’s first full year as a business, we’ll begin a new tradition – our annual letter. I’ve written this as a ‘thank you’ of sorts; it’s intended for clients, partners and the many great folks who have supported us along the way. Doing this over the holidays and the turn of the year had an unexpected effect for me: it was a central part of my own process as I reconcile the year behind us, and plan for what’s ahead.

While we started in earnest in 2016, 2017 was our first full commercial year. To put it mildly, we’ve been busy. Looking back, it’s hard to imagine having grown or expanded more than we have over these past 12 months. We’ve accomplished a lot, but I found the below highlights most notable:

  1. We grew from a founder and one part-time contributor to a team of eight talented professionals. We’ve grown both in our primary location (Tempe, AZ) and outside; WorkBook6 now has boots on the ground in Boston, metro Los Angeles and Denver.
  2. We’ve grown our client roster by more than 500%, and broadly expanded our reach within the customer acquisition and engagement ecosystem. Today, WorkBook6’s engagements touch many of the US’s largest direct response categories, as well as leading media, technology and services solutions that help to plumb and power these industries. We’ve also become very active in several not-for profit and affinity categories.
  3. We’ve moved offices – twice! We’ve been fortunate to grow more quickly than I expected, and our space needs have ballooned as a result. The new digs are beautiful and they’ll give us room to grow plenty without having to move again.
  4. We’ve found our operational stride; we’ve learned a great deal about our clients in this past year, and we’ve leveraged their feedback to create accountable, trackable programs. This learning will serve us well for many years to come.
  5. We’ve begun to build products where and when it makes sense. We learned early on that because our business model is new to the market, we would occasionally need to build our own solutions. Our own, custom CRM program,, is a great example of this. We evaluated every commercially available product, but nothing let us fly as fast and freely as we wanted. So, Max Richardson built the industry’s first many-to-many partnership development relationship management platform, and it has been an amazing addition to the WorkBook6 team.
  6. Most importantly, we’ve written our own rules, and we’ve had a lot of fun along the way. A little over a year into this, WorkBook6 has grown in most measurable ways – we’ve powered many proprietary partnerships on behalf of some of the largest and most innovative enterprises in the world. We’ve done it on our own terms – and without outside capital.

Just reading through the above, it’s a lot. This team worked incredibly hard to help us become a real company, and I’m immensely grateful to that gritty effort – and for the many long hours. To put it another way: whoa.

So Much to Be Proud of

There’s much to be proud of, but there’s so little time for pride. Everything we accomplished in 2017 has the effect of elevating our expectations for our production in 2018. So, game on, so to speak.

I’m a big fan of good advice from great thinkers, and one piece I’ve clung to this year is very simple: our output is the sum of all our vectors.

This point, explained through linear algebra, is that to succeed, you need to point every effort toward the right outcome.  As we transition into 2018, nothing could be more relevant to our work.

To me, it’s critical, brilliant stuff: it’s not good enough for everyone in a company to just work on stuff. It’s not even good enough for everyone in a company to do great work on stuff.

To do the best you can, the trick is to get everyone to do great work on the right stuff

This is what we will do in 2018. Here’s how I hope that plays out:

  1. We power partnerships. We will own this. This is what we do and it is who we are. WorkBook6 will continue building a better, faster and more cost-efficient way for companies to grow profitably. This forms our strategic direction.
  2. We will operationalize rapid growth. We will continue to make improvements to the way that we onboard new clients, engage their new partners and track the progress. This operational vector will include the work of a newly-formed client success team, which will grow significantly in the coming year. It will also involve the deployment of new products and platforms from our technology team.
  3. We’ll do it the one best way we can. When this means leveraging great existing technology, we’ll do that. When it means building from scratch, we’ll jump right in.
  4. We will go to market more efficiently than the marketplace has ever seen. Our proprietary process will provide tremendous leverage to our clients and create efficiencies for them.
  5. We will spread the word on our clients’ behalf. Our brand will be their growth – and every dollar we spend on marketing WorkBook6 will carry the intention of helping our clients grow.
  6. We will continue to have fun doing this our way, and without external capital support. We love the accountability that comes with being bootstrapped, and we know that we can control the direction – and sum – of our vectors better by doing it this way.

That’s it, folks. We had an amazing year. And we want to make our company bigger, faster and more efficient in 2018. It’s been an amazing opening chapter for us at WorkBook6. For all those who helped us get to this point, we’re grateful beyond measure. And we’re thrilled to take on the hard hustling that remains ahead of us.

Happy Holidays and Happy New Year!


JT Benton
Founder, CEO


Affiliate Summit

Affiliate Summit 2018, and Conferences In General

By THE Brett Kaufman

It always seems that no matter what industry I am in, January is Vegas conference month to start the year off. When I first began my career, it was coming for the PPAI Expo, then it was CES for a number of years and lately it has been for Affiliate Summit West.

Vegas seems to have this mythical power over conference attendees. Maybe it is the lights, the food, the gambling, the drinking or whatever temptation you’re in to. I’ve been coming to Vegas for 20+ years, this is where we would come as kids on vacation. Living only four hours away meant a lot of quick weekend trips and having a father that lived right on the strip for three years made it my second home.

As Affiliate Summit rolls around, I’m reminded of why the long 18 hour days are worth it. We represent some of the best brands in the world and helping them build strategic partnerships is a fun adventure for all of us at WorkBook6.

If you’re going to be in Vegas, let our team know, we’d love to meet up and say hi or better yet, come join us at Marshemello on Sunday night at XS (because if you know me, then you know that’s where I’ll be).

The Annual Letter 2018


In continuation of a tradition we began at the end of 2017, we recently sent out our annual letter to a number of our clients, partners and old friends. And, as we did last year, we’ve decided to post the letter on our blog, as well. There’s a lot, here – some might argue it’s too much. And while it’s true that I’m particularly open and candid in my remarks, here, there’s nothing in this letter that I’d censor our team from discussing with a client or partner.

I hope you enjoy reading it!

Happy New Year, JT

For the second year, I sat down in early December to compose this Annual Letter. This is a new tradition for a young business, but it has become one of my favorite projects. Taking time to reflect on the year we’re now wrapping up – and being thoughtful about communicating our plans for the coming year – has helped me, tremendously. If you don’t do this or something like it in your own business, I urge you to try it, yourself. In fact, my own inspiration for this comes from a client of ours, whose Chairman and President have been jointly-authoring one for over 30 years. While our mentors lead a much larger company, I immediately saw good reason to do something similar, albeit on a smaller scale. I hope you enjoy reading this as much as I have enjoyed composing it.

While WorkBook6 began to assemble in 2016, 2018 is actually just our second full commercial year. This is important to note, as I believe our accomplishments over the past twelve months resonate just a touch more meaningfully when one considers the truly nascent maturity of this business. As a parent of young children, it’s hard not to see the parallels between starting and growing a company and raising children. In that sense, I like to think of WorkBook6 as a promising adolescent. We are at once proud of our progress and mindful of how we can continue to grow. Among other milestones, we’ve accomplished the following, this year:

  • Our team has doubled the company’s topline revenue for the second consecutive year. While this may be ‘table stakes’ for a young firm, I can assure you that we don’t take it lightly. Growth like that is the product of the entire team’s tireless work, as well as the trust our clients and partners have invested in us.
  • Our partnership development team has increased performance-based revenues by over 250%, Year-over-Year. This figure, which refers only to those fees that the firm earns through our clients’ execution and performance in new partnerships, is perhaps the single most important indicator of WorkBook6’s health. 2018 was a year of tremendous progress in this area.
  • To meet this growth, we have expanded our team. WorkBook6 is a technology enabled service business. To provide great service, we’ve added great people. This year, we welcomed Anna Lewis, Chris Cox, Justin Guido, Savannah Day and Kyle Casaccio. We also announced the acquisition of Maszi, Inc, which brought Kara Hutcheson into the firm on a full-time basis. Each of these people have made material contributions to our work and to our clients’ growth.
  • We have developed a fully-functional and entirely proprietary technology platform. This system, which we call, is the backbone of the entire operation. Today, our team leverages this technology across many disciplines, including relationship management, sales and marketing automation, task management, business intelligence and even billing. In fact, we believe to be the first many-to-many business and relationship management platform. This, as I will point to later on in this letter, is critical to our business’s identity. We’re particularly thankful to Max Richardson and Savannah Day’s work in this area.
  • Through the hard work of our client success leaders, we have successfully launched and incubated our full-service partner management program. This effort, which involves full scale partner program management, came at the request of an ambitious client, to whom we’re deeply grateful for the trust and resources they’ve committed.
  • We’ve continued to build out our workshop series as a marketing and partnership development mechanism. In 2018, WorkBook6’s workshops at LeadsCon and InsureTech Connect attracted over 300 attendees.

As I think through these accomplishments, I’m left with what might best be described as a ‘dumb grin.’ That’s because throughout the process of building this momentum, it didn’t always feel as if we were making such progress. As I’m sure many entrepreneurs will tell you, it’s hard, sometimes, to see the business’s progress while it’s happening. I spent much of my time this past year thinking through new kinds of challenges and evaluating new types of opportunities. This, I’ve learned, is what growth feels like in this business. I once listened to a keynote given by Brian Halligan and Dharmesh Shah (who co-founded and continue to lead HubSpot). While I recall many useful lessons from that talk, perhaps the assertion that best applies to the year behind us is this: “companies are more likely to die of over-eating than starvation.” I don’t think there are more useful words of advice for a young business that’s lucky enough to be growing, quickly. The message, which speaks to focus and discipline, could have been better applied to some of our work this past year, and will certainly influence what we decide to do – and not to do – in 2019.

In this sense, I’m most excited about all the things we can still refine, here. I think the holidays are a fine time for candor and for vulnerability, so I hope you can find some value in reading about a few of our hard-earned lessons, too. Key learnings for our business this year include the following:

  • We have a sweet spot, and we also have the opposite. In 2018, we sometimes stretched ourselves too far to meet demand that didn’t actually align with what we do best. Good growth takes time, and sometimes it’s actually best to pass up immediately available revenues until more befitting opportunities emerge.
  • Doing what you’re told to do and doing things right aren’t always the same. On a couple occasions, we deferred to external direction despite a ‘gut feeling’ that the strategy might be off-target. We’d have been better off pushing back in those cases, or even walking away.
  • Finally, there may be CEO’s out there who are great at account management, but ours isn’t one of them. In 2018, I learned that the most respectful thing that I can do as a leader is actually to avail our best resources to our clients. And, when it comes to account management, that ain’t me!

These lessons have informed our plans for growth in the new year, which will differ somewhat from the past. As we begin our third full year in business, we’ll do so with a few important themes guiding our strategy. These themes, which have been drafted with input from our entire team, are designed to help us focus on quality growth and revenue diversification while taking a deeper approach to serving our clients. Each of these themes are outlined, below:

  • We will stay independent. Our business has not raised outside capital. We plan to remain on this path, because we feel that having the autonomy to operate this business and apply the learnings we’ve worked so hard for is paramount.
  • We will focus on deepening our relationships with our existing clients, and also limiting the number of new clients we agree to take on. Two consecutive years of rapid growth is fun, but we feel we can continue on this trajectory without taking on business that doesn’t ideally suit us. More importantly, we plan to expand several existing relationships to include our full-service management offering, and we’d like to focus more of everyone’s time on client growth than we do on our own.
  • We will continue to invest in technology and systems. Through continuing our work on, we believe we are building a company that can mature far beyond being perceived as a mere ‘relationship’ business.

As you can see, we’ve got a lot to be thankful for. For both the growth we’ve accomplished and the opportunities to continue improving, we are grateful. In this light, it only makes sense to end this letter with a sincere note of thanks. Because so many people and companies impacted our successes and our lessons this year, we must stay general here. To each of our clients and partners, as well as our friends and families, we offer a very heartfelt and earnest ‘thank you.’ It’s been an incredible year, and we’re brimming with optimism for 2019. We wish each of you a happy, healthy holiday season and a new year filled with accomplishment.

JT Benton
Founder, CEO

Let’s Connect!