Grace For First Impressions

“Nope, that one has a spelling error.”

“That one just doesn’t look great.”

“Really? Two spelling/grammar errors?”

Scanning resumes is difficult. 

Scanning through several hundred in an afternoon can be a headache, especially when you’re already behind on other projects. Our brains seek shortcuts. How can I quickly cut out 90% of these resumes and be left with only a few? 


They missed a comma, nix this one! They were inconsistent on using periods on their bullet list, g’bye!

I lacked grace when I would read resumes. It was easy to justify that attitude. 

  1. I don’t have time,
  2. I have other “more important” priorities, and 
  3. I needed an easy way to sort through them.

Classy. Gracious. Considerate.

Now, that the tables are turned and I am the one trying to get an interview, it feels a bit different. There’s the proverb: Pride comes before the fall. Meaning, your arrogance is gonna trip you up — you’ll fall flat on your face. Peeps will likely laugh at you, too.

It gets better. After reading, re-reading, and re-re-reading my resume several times, printing it to read with red pen in hand, and reformulating it far too many times, I thought to read it one more time. What did I find? A spelling error in the first sentence. The. First. Sentence. 

Pride comes before the fall. There were other edits, too, albeit not true errors.

I apologized to my wife. “If recruiters are like me, the places I’ve already applied will nix my resume right off the bat!” It was a sobering realization. An epiphany which wiser people have already had — these people are further along on their journey of grace. As I reflected, I knew I am a solid candidate, great with people, have thorough organizational skills…but I slipped. I had at least one spelling error in my resume. 

Hey, if you would still hire yourself even with a couple errors on a resume, what about all those candidates you never interviewed because of just one error?

We learn through failures and oftentimes we have no recourse but to learn from errors we commit ourselves. Spelling mistakes could be a sign to avoid a candidate…Or it may be a case to extend grace and take the risk that they’re really great, but just like everyone else, they’re also human. Certainly we must wisely steward the recruiting roles we hold and ensure our product (and people) are high quality — there’s no doubt about that! — but maybe, just maybe a perfectly polished resume is not the best indicator of the talent you need? Perhaps getting to know the person is the way? Maybe it’s best to learn to swallow our pride, realize behind these resumes are real human beings, and that there are better ways of reviewing resumes than the easy way out. 

Perhaps there’s grace. Or perhaps there’s a shortcut to save you time.

Which do you choose?

Active vs. Passive: Wording Matters

Photo by Anna Auza on Unsplash

For many, passive attitudes are a heck of a lot easier. Avoid stirring the pot. Refrain from creating conflict. Allow the other person to make up their own mind on their own time. 

Confusion is created. Goals become unclear. In fact, these sentences are written in the passive voice!

We sometimes don’t even realize when we write in the passive voice — it can be so natural. The passive voice is often misleading. One way that we see that play out is when we’re indirectly asking for something — a call to action. The root of passivity leads to a flourishment of poor effects.

If you build it, they will come. 

We all dream of easy solutions; we don’t aspire to hard work. What if what we think of as a straightforward request is actually a lax, unconfident ask? 

  • “Buy now”
  • “Learn more”

There isn’t anything wrong about learning about a company, however, does our email drip campaign, website, and other collateral unintentionally connote confidence you’re the right solution? Alternatively, does passive selling result in passive purchasing? Put another way, to an audience reading your content, what’s the difference between shying away from what you offer (the “buy now” option) and you not being sure of how to phrase what you offer? 

As a seller, if I’m confused about what I offer, my wording will be vague — not by my choice, but because I lack the refinement of my ideas — and customers won’t know how to proceed. Effectively, they move because of my vagueness.

So, two things to consider when you think you might want to be more direct. Wait! That’s weak and passive language there. “Consider.” “Might want.” 

Employ these messaging core principles:

  1. Know thyself. What do you offer? Why would anyone want to talk with you?
  2. Be direct. Do not gamble away opportunities. Employ active language.

We’ve used Marketing and Sales examples as backdrops, however, this can easily apply to any arena: Customer Service teams, Operations, Leadership, Customer Success, Customer Onboarding, pizza delivery, grocery store clerk, and on. 

The point is this: know what you want and communicate that. Many people want to help. However, how can they help if you don’t see what you want and if you don’t tell them?

Distinguishing Support, Customer Success, and Customer Onboarding

This article is a work in progress. I was sharing this with several people so I figured I might as well make it public.

Customer Support, Customer Success, Customer Onboarding, and Customer Experience are often conflated terms. For one company, it’s the same thing. In another company, it’s different. I may use “Customer Success,” and you may use “Customer Experience.” Our industry will continue to refine the language we use to describe each role, and to help, here are a few ways of thinking about it. 

Note: I’m excluding Customer Experience for two reasons: 1) brevity and 2) because it can be quite complex. Is it Product-focused? Does it oversee Support and Customer Success? Other?

No matter what, here are guiding principles that all customer-facing teams should find agreement. Just like any other principle, one held onto too tightly and not held in tension by something else can go too far. A maniacal focus on the customer experience sounds good, but pursued to its logical end is not a good plan.

Guiding Principles

  1. Best for the customer, not for us.
  2. Leverage your expertise, not weakness.
  3. Everyone is busy. Don’t adopt a victim mentality.
  4. Teamwork.

Examples of Guiding Principles

  1. Best for the customer: if you’re on the phone/email with the customer and know the answer, help them.
  2. Leverage your expertise: each of us develops specializations, we should play to our strengths. If my weakness is sales, I should support others in selling. If my strength is technical, then I should utilize that and help others.
  3. Everyone is busy: helping customers is our job, and yet many things can get in the way. It’s common in fast-paced environments to adopt a victim mentality. At the same time, voice your concerns—don’t bottle them up!
  4. Teamwork: let’s honor our teammates, help them out, and make sure we ask for help.

Departmental keywords

These are examples of descriptive (not prescriptive) terms for each team. There will — and should be! — overlap.

TransactionalTimeline: first X daysNo endpoint
Product expertiseImplementation expertiseRenewal expertise
Break/fixEngage usersBest practices
Cases (problem & incident management)Develop habitsProjects

Team Objectives


  • Reactive. Respond to customers (live chat, email, phone).
  • Product experts.
  • Problem/Incident management (manage bugs and coordinate with engineering).


  • Proactive/reactive. Reach out and respond to customer needs (email and phone).
  • Present high-level business case of the product to new customers. 
  • Generate revenue. Through hitting customer success milestones, generate referrals and upsells.
  • Share resources, best practices, tips with customers.
  • Not product experts. 

Customer Success

  • Long term care team for customers exceeding $X ARR.
  • Proactive. Reach out before the customer is thinking of it.
  • Renewal manager. They are the primary owners of renewals (this is sometimes its own team).
  • Upsells. After the customer has surpassed onboarding, the CS team will take over.

Note: sometimes it makes more sense and is more efficient to combine Onboarding and Customer Success. As they say, mileage may vary.

Product Knowledge Goals

While each industry, company, and manager may see it differently, here’s a framework to think about the level of knowledge for a CSM (note: I fully expect plenty of disagreement on the percentages applied to each category, that there should be more/fewer categories, and the definitions.

Let’s assume this is about Acme, Inc., which sells an AI tool to help inbound Support reps understand if a customer is likely to be agreeable, scream/cuss at them, cancel their account, etc.

Customer Success Product Knowledge Goals

  • Know 100% of the internal processes
    • Examples: how to sell, upsell, cancel, downgrade, pass customers to appropriate sales reps
  • Know 100% of product functionality
    • Examples: How the product functions, navigation, best practices, selling points
    • Metric: should know almost everything in the Help Center, but NOT necessarily [internal wiki] or institutional knowledge
  • Know 20% of product methodology
    • Examples: fundamental methodology, assumptions, calculations
    • Does NOT include: in-depth knowledge on the algorithms at play
  • Know 40% of industry knowledge
    • Examples: understand broad terminology
      • The typical tooling of a Support rep, their average day, and the structure and handoffs between teams
    • Does NOT include: nitty-gritty detail about the Support industry (helpful, but not required for  — can be learned on the job)
      • Specific tooling in, say, Zendesk, or how the phone system connects to XYZ

The lines between these teams are blurred and will continue to be so. For instance, when a customer has a need, who helps them? Below are general guidelines. If a customer needs help, we should help them.

Straightforwardness Delivers Results

Simple, straightforward language. 

That’s the most powerful, effective way to communicate value propositions to prospects. Anything more can get confused or lost in translation.

Taking a cue from the FinTech industry, let’s examine the life of a financial advisor for a moment. Clarity helps thousands of advisors communicate their proposal. Two essential means to differentiate your firm are: 

  1. Simplify your message
  2. Explain your (often niche) value proposition without gimmicks

 As an advisor, having the knowledge, skills, and capabilities to tailor a financial plan, establish and follow a rigorous investment strategy, and maintain a solid set of books and records are vital — no doubt about that. However, on a first date would we ever talk about having kids, where we want to be buried, and where we’d like to spend our retirement together? Probably not — unless you want to scare off your date! In other news, you kept your dating message simple and didn’t go into detail — yet. Same is true for your business, find a way to simplify your message. Life (and working relationships) is a journey; it will take some time to get to a level of comfort. 

Many websites and proposals lay out an unfathomable amount of information. How often have investors been scared off by 100 pages of “light reading” or didn’t click “contact us!” on a website because they got overwhelmed with options? Boil it down to one or two takeaways for the investor. It’s not about convincing them all of the ways you can serve them, but something short, something memorable.  

As a thought exercise, pick a field you’re not very familiar with—dentists, contractors, plumbers, or a family practice doctor. Look up local websites and act as if you were vetting them because you were interested in switching. Is their message clear? Do you know what they do or their specialization? Do they give you a convincing reason for why they are the answer? If you are convinced to get in touch, do they have a smooth, quick way to get hold of them without losing you as a prospect? Are you looking to solve 5-10 things all at once, or just get started with the first thing? 

In the same way, demonstrate a simple, easy-to-grasp message to explain your firm in light of your niche. Many investors want your services, but they want to vet their choices. A significant component is ensuring you’re the clearest — not the loudest or flashiest. They need you, not a fancy website. They may want to know the technical components later in your relationship. Right now, they want clarity instead of enough information to make their eyes glaze over, just like our dating analogy up above. A few concrete examples of how you can improve your presentations:

  • Common ground. Start by focusing on what matters to your client. Ever try to win an argument by starting from the point of disagreement? Instead, find your common ground. Discuss why you agree there. Then realize you agree on 90%, and then with that as a reference point, discuss the remaining 10%.
  • Brevity is king. Shorten your client reports. Do they need to be thatlong? What can you cut out that isn’t absolutely necessary? Alternatively, what could you cut out that you could merely mention, “I reviewed XYZ too, but I just wanted to focus on this for now. If you’re interested in XYZ, just let me know a good time to discuss it.”
  • Client-centricity. Similar to the reports, prepare your meetings for what matters to your client. It may make sense to prepare ten different analyses, but if your client isn’t ready for it, slow down. When I was a practicing CPA, I once gave a client their “management recommendations” list which encompassed well over 15 items they needed to “fix.” While I naively thought this was perfectly helpful, it was overwhelming and defeating to them. All they saw were how terrible I thought their processes were. I could have proposed a solution in a more straightforward, more step-by-step manner to get to the same conclusion of helping them become a better version.

 As you’re thinking about who you are and how to serve your clients and future clients, remember to keep it simple. They should walk away with that single, memorable line. In a word: clarity.

Need an elevator pitch? Try one of these: 

  • A lot of people know how much they have, but they don’t know if that is enough. I help investors learn their chances for success, discover any potholes in their future, and find ways over, under, around, and through.
  • Many good people want to do the right thing and provide for their future self, but they don’t know how. They want to avoid the costly mistakes they read about in the paper. I help guide people to make the right decisions so they get that future they want.

Thinking Evergreen

Earlier this year I read a book that was written in 1989, 30 years ago.

It’s made me realize how much of my thinking, writing, philosophy is developed for the here and now. It’ll will only be relevant for a couple years. How much knowledge am I amassing that’s irrelevant in three weeks?

On one hand, we’re on the cutting edge of a lot of cool things in technology such as AI, machine learning, autonomous cars, and 5G, but it’s also a reminder that a lot of what I do and how I think will be obsolete pretty soon. Remember when taking photos with your phone was radically new? Remember when you first started using a computer NOT connected with multiple cords — you had this thing called wireless.

Compare that to the book I’m starting — written 30 years ago — it’s still extremely relevant today. In fact, you could call at Evergreen. It was valuable 30 years ago, it is valuable today, and it will be valuable 30 years from now. 

What are you doing today that will be valuable 30 years from now?

What are the contributions that I want to make? Sure, I want to make contributions that affect the here and now. However, I also want to make long lasting contributions. Leave a legacy, is what they call it. They want something that will last far beyond their own short life. They realize life is short and want to be remembered. And I guess, in a way, I want the same thing. I want to create something that has a long half-life. I don’t need to become Albert Einstein, Mohammed, Buddha, Alexander the Great…but I want my work to be meaningful. 

I believe part of this is when I think about the “here and now,” I should not only find the specific momentary relevance , but define the underlying principles. An old Jewish proverb says there’s nothing new under the sun. On one hand, that’s honestly a little depressing because that means there’s really nothing new in life (sure we can make discoveries like whether there was water on Mars, a different type of frog in the Amazon rain forest, or something else. But it’s not like I can reinvent the second law of thermodynamics. That just is.). But there are certain underlying principles that can be rediscovered, explored in new ways, or taught to the next generation. Too often we put aside what is true and established for what is new and fleeting.

So as the memories of this book fade but the truths remain, I want to reflect upon the underlying principles I’m learning in my day-to-day life and how they relate to other fields, industries, and the future. Some things are evergreen, they were with your grandparents, your parents, you, and will be around for a long time. Don’t you want to know those truths too?