Builder and Maintainer: Pitfalls of Handing Off The Baton

If you make statements like: “I’d lose interest in simply keeping things moving. I’d get bored.” You’re a builder.

Alternatively, perhaps you don’t enjoy “that level of risk.” You desire to work in an established company or team with plenty of structure, doing something a tad safer — there’s nothing wrong with this — you’re a maintainer. 

It is a spectrum — few people are on either extreme, with most everyone being somewhere closer toward the middle. The point is not to put people in boxes, but employ a mental model to help us through obstacles and challenges. Risk-taking/risk-aversion is not the single contributing factor; risk, creativity, personal desires, ability to invest time, money, or other resources also factor in.

That said, for builders, I’ve noticed a trend when handing off the baton. They build like they’re handing it off to another builder. 

It goes back to the mental model. If a builder creates and passes off the package or responsibility, does the person receiving that package have the desire and know-how to keep it going at that rate?

Let’s say you build a Sales team. You develop the processes, implement all the systems, and establish the reporting. Moreover, for the sake of argument, let’s assume it’s rock-solid. Then, let’s say you pass it off as you want to pursue something new. You find a maintainer, hire him or her, and pass the baton off. You’ve succeeded, right? Maybe.

At this stage, two ingredients could spoil the handoff:

  1. The builder has all the institutional knowledge, and
  2. Training and equipping is significantly underrated as a core component

Let’s address these as a potential curse.

Creator’s Curse

It’s entirely possible (and happens every day!) that someone other than the builder can approach a broken system, triage it, and get it operational. Many clever people can approach something they’ve never seen before and understand it. It can be done, but it’s not easy.

When building, keep in mind you’ll likely be handing it off. During the planning process, think about the following criteria:

  1. Simplicity over “innovative.” If you know you will pass it off, make it simple and straightforward. Complexity is the driver of dysfunction. You may understand all the complex interwoven components, but will the majority see it that way?
  2. Documentation. You will (likely? hopefully?) document your processes a lot better. After all, who wants another person to see their messy room? Some documentation is likely better than none at all. So, at a minimum, get started early. Documentation is often seen as drudgery because it’s thought of and written as something to be stored in on a shelf, never to be read, never to be appreciated.
  3. Think things through. It’s one thing to slap together a prototype. It’s another to realize that this will be a serious investment. Building a skyscraper takes a concerted effort with immense planning. Your project will be smaller, though still requires planning ahead. It’s easy to build quickly, but you’re not just building your project; you’re also building technical debt. Even with the best of planning, you’ll procure technical debt. Choose to make it manageable. 
  4. Training. You may have thorough documentation. However, what does training look like? If you know the person, what’s the best way they learn? If you were suddenly gone, could they look at it, read/watch your training, and then execute? If so, how quickly and effectively could they take over?
  5. Coaching and development. Is it possible for you to coach and develop that person to understand the way you think, the way you design systems? Develop people to grasp how it functions.

Builder’s Blessing

Lest we ignore the other side of the coin, there is a blessing hidden within.
As a builder, you have an amazing ability: the courage to create when the status quo offers you a form of stability. Without you, the world would not have as many amazing tools, inventions, and ways of living that we have now. We must celebrate that!

So build — absolutely build. You bring incredible worth to this world. To leave a legacy you’ll be proud of, take heed of the warnings: watch out for the pitfalls and navigate the trouble spots, all to build that incredible thing in your head. Make this world a better place.

High Functioning Teams: Bland and Boring Management

From reading articles celebrating company cultures, reading various “perks” in job descriptions, and seeing how companies cite foosball tables less and less, it seems like we’re making progress on creating genuinely effective teams.

Harvard Business Review came out with an article in 2016 called The Neuroscience of Trust. In it, the author states perks are not the way forward to high productivity — neither, would I add, are carrots and sticks.

He goes after organizational trust as the keystone for what’s required. Similarly, anyone who wants to study this more in-depth should read The Seven Habits of Highly Effective People by Stephen Covey and The Five Dysfunctions of a Team by Patrick Lencioni.

Getting back to trust, it’s not about ping pong, unlimited snacks, free-flowing booze, or other amenities (of which these aren’t bad), but what is that doing? Arguably, that’s creating the distant parent mentality of “let me just buy them whatever they want as long as they get it done, but I don’t have time for or want to prioritize relationships.”

We’re human. We can go years without foosball or ping pong; we don’t need an in-house chef, or free-flowing booze (okay, some may argue with that). What we need are relationships with one another. We live in community! Happiness may come from a fun night out or some innovative perk. Joy comes from real relationships — with other humans. If we want to grow our company’s productivity, don’t focus on those things that be solved by money but lack the heart.

Here are a few ideas, with concepts taken from the HBR article:

  1. Thank your employees. Publicly, and frequently. Recognize that they are humans and could work elsewhere, could have their minds focused on other things, but instead have chosen to work with and for you.

  2. Share new challenges. We rarely say it publicly, but we often have “stay in your lane!” mentalities. Why does that employee want to focus elsewhere? Why don’t they have 100% of their focus on their current job, duty, or responsibility? Have a conversation. Maybe they need a new challenge. Perhaps they need to hear how valuable it is to you?

  3. Discretionary working. What if your employees could choose how they get their work done, when they get it done, in what order, etc.? Sometimes that’s not possible — baking a cake that’s going to be picked up at 5 pm for a birthday party requires precision of ingredients and timeliness — but are there other ways you can give your team freedom and flexibility? Humans are not robotic.

  4. Define your role. It may not be feasible to allow employees to define or create their own roles, but what if you took the popular model of allowing Fridays to be “create whatever you want” days? Alternatively, just get started with Friday afternoons. That little bit of freedom (4 hours out of a 40 hour week) is often the spark to rejuvenate a person, not just for their projects but for the other 90% of the week!

  5. Transparency. This one is a tough pill to swallow. I’ve worked for some companies where much of the information required a prybar. The funny part? The places where I knew the overall challenges and opportunities focused me on my role much more than blindly assuming things were going well, or the rumor mill spinning up ideas on how it was the end of times.

    As an employee, I learned to pose the question, “what are the top three things keeping you up at night?” Invite your employees in, find ways to share information.

  6. Socialize. No, “socialize” does not equate to happy hour. It can include it, but it’s so much more.

    What does it look like to say hi to a coworker and ask how their day is going? What about a quick video call to someone far away? A quick Slack message? Could those “little” things add up?

  7. Personal development. Similar to freedom and discretionary working, how can you help your employees in their personal and professional development? There is one new perk that I do believe in and wish to see at far more companies: company coaches. The idea is that you can work with a company coach to help your personal and professional development. Sometimes we either don’t have access to or money for hiring an external coach — though, if you can, then do that. A coach (internal or external) can help us mature, adopt a growth mindset, and see the world differently. They can also help us see the challenges and road ahead at the company, understand how to navigate it, and help us see our future there.

  8. Vulnerability. In Brené Brown’s book Daring Greatly, she goes deep into vulnerability and shame, two topics we all fear. However, as she puts it, vulnerability is a strength rather than a weakness. “Vulnerability is uncertainty, risk, and emotional exposure.” Yes, it’s fear-inducing to put yourself out there. Being vulnerable is a required ingredient for growth — as she talks about preparing to go on stage at TED, loving those around her, etc.

If you want “easy,” then go and spend lots of money going head-to-head with all the Valley VC-backed start-ups. You’ll undoubtedly lose unless you have an incredibly sexy brand and have tens of millions in the bank to entice employees to stay. However, if you want a high-functioning team, then consider what it means to relate to and know your employees. Fancy toys cannot buy trust. We build trust through relationships — real, authentic, meaningful ones.

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.