If All You’re Doing Is Surviving…

Below is an example from my life about parenthood, but the principles to this story can be applied to all areas of life—work, school, volunteer, or whatever. If you’re struggling as a parent, it’s okay. We all are. Secondly, reach out for help—I do the same. We are that village that takes to raise all of our kids.

It must be a popular statement, or else it simply sticks out in my mind because I’ve begun to notice it everywhere. Here’s how the conversation usually goes:

Friend: “How old are your kids again?”
Me: “Their ages are…”
Friend: “Oh wow. Yeah. You’re just surviving. That’s all you’re doing right now.” (emphasis mine)

While I appreciate my friend’s compassion and validating my attempt at being a good parent, I’ve begun rethinking this line.

It’s not just one friend, either. It’s family. It’s many friends. It’s coworkers. The difficult thing is just that: so many people tell you this as a parent with young kids that you just accept that’s how life is.

But then what are you supposed to do? Bide your time until your kids grow up a little bit? Then you’re busy because you’re running them from school to soccer practice—oh, shoot! Then picking up the other one for ballet and then a quick bite to eat, home for homework, and finally exhausted on the couch! Then repeat the next day.

If you need to get past that period of life, then what? Teenagers? Ugh. I don’t even need to go there!

So if you’re just surviving with young kids, frazzled with being a soccer mom, and finally teenagers, then what? Wait till they’re out of the house? By then you’re in your 50s and thinking of retirement, grandkids, and if your bones weren’t hurting in their 30s (mine are) then your 40s and certainly your 50s.

There are no easy answers, only deep, soul-searching questions. But for those of you who are just surviving, I must ask the question, “what are you surviving for?” Are you surviving so that you can work to make the world a better place? Just to get by and hope bad vibes stay out of your way? So that you can live to see a concert, achieve a goal, unlock a quest, or see your kids attain _________? Is that it? Is that all?

We each have varying levels of hope for the future. Some are distraught, some are depressed, and some are optimistic—and some are in between. The purpose of this thought isn’t to be a depressant, but to awaken our souls to these questions. I’d rather go through life asking difficult questions that I may never get the answers to, than to idly sit by too afraid to open the door.

So, to those who have a family member with cancer. To those of us who are workaholics. To those of us who are in over their heads with debt. To those of us who can never seem to catch up. Who feel as if they aren’t even a half-way decent parent. Who feel like failures as parents. Who are cancer survivors. Who can’t catch a break. Who have recently lost a child, parent, spouse, or close friend. To those of us who simply feel like we’re only surviving. Here is the message: there is hope—we just spent a month sharing the Christmas story. Read it (the real version, not the fluffed up Santa version).

However, even if you’re not religious (or don’t want to discuss it), spend time with a close friend or family member. Deepen the bonds you have—or feel like once had—with that person. Shed your toxic relationships. Get away and reflect on your last year. It’s not going to be easy. But go on a walk, let it out (cry, if needed!). You can’t move forward in life if you disallow yourself to share with others and yourself. Be willing to reflect on your past, current situation, and dreams for the future. If you do that, you may find that all you’re doing is surviving, but maybe, just maybe, you’ll begin to find hints of meaning.

Reflections on Robinhood’s checking & savings fiasco

We in fintech often confuse Type 1 vs 2 decisions—reversible/not reversible. Robinhood reversed it, yes, but at high cost. As great as tech is, disrupting existing systems first requires wading through minutiae of regs + history.

It’s truly amazing to be part of companies and watch other companies move fast and do incredible things. And perhaps if I were on the Robinhood team I would have come to the same conclusion they did (our hubris will convince us we would “never have done ____________”), but these stories still illustrate to us several key principles:

1. Moving fast is high risk. If you can stomach that risk, great. But be prepared for some decisions to blow up in your face.

2. Ask for counterpoints. Groupthink is deadly. Ask counterpoints from those who agree with you will give you exactly what you expect — not much. Solicit from those who disagree or are willing to disagree.

3. Conduct pre-mortems. While not bullet-proof, when we’ve conducted a pre-mortem (assume your action will fail, and discuss why it did) to poke holes. This helped us identify many of the core issues we would inevitably face. Instead of concluding that “yes, this is awesome” we were able to comprehend, “yes, this is awesome, but _____________” to have a sober, realistic understanding of the land mines that lay ahead of us.

4. Execution is important, but pre-work is even more so. Think of it this way: if you give a presentation on a topic you’ve never spoken about before, where do you spend more time: preparing for your presentation (thinking, slide creation, rehearsing) or the actual presentation?

Sleep on it. I’ve been part of countless decisions where we did “research” (usually about 20 minutes or less). If we only had dug a little bit deeper, we would have realized some glaring issues.

5. Lastly, humility. You are human, you’re far from perfect and you are certainly not invincible. Be the leader who admits they’re wrong, don’t be the leader who is incapable of that.




You check your email. There may be a lot, or there may be a few, but tonight (and it’s Sunday night before a big week) you see one from your boss—or sometimes your boss’ boss. You click on it and see his question. It looks something like this:
Hi [your name],
Please give [name of topic] some thought so we can discuss tomorrow.
And sometimes there is the second piece:
Here are a few thoughts:
  1. We could do it _______
  2. In the meeting, we could focus on ________
  3. [something either wildly different or adding to the existing options]
Sometimes it’s harsher, sometimes it has a specific direction, and sometimes it’s about major obstacles/issues that must be addressed.
You pause. Whatever is physically going on around you at that moment just blurs out. You don’t have an immediate response and so you begin to question yourself. “Do I have what it takes? Can I do this? What if such and such happens?”

We do this to ourselves all the time. We get psyched up. We rev up our fear engine. We go a bit overboard and then our spouse, significant other, friend, or roommate pulls us back to reality. “Man, you’ve got this. You’ve seen this movie before.” And that’s when it dawns on you: your problem isn’t this issue, it’s that you’ve labeled yourself as an imposter and you’re (subconsciously) looking for evidence that you’re a fraud. Instead, when was the last time you got a challenge from a boss, customer, prospect, or project manager and instead told yourself, “I may not have the exact answer at this very moment, but I’ve got a track record of figuring out things that I never knew before. I’m excited and looking forward to this challenge.” Using “track record” and “I’m a problem-solver” aren’t just for your resume, they’re for your every day.
This isn’t some “everybody gets a trophy” BS. Yes, there are people who already think too highly of themselves and they need to come down from the clouds they’re on. And even if they think too highly of themselves, it’s likely because they don’t believe in themselves and crave outside affirmation.
So next time you get that email, phone call, text, or Slack message, stop for a moment and think about it. Even if it is outside of what you believe you’re capable of, use it as a learning experience. The best way forward is to ask questions. Gain insight.
But we get so caught up in the minutiae. There are a million reasons it would fail and the best is that we don’t even try. How many inventions would never have been invented if we, as humanity, simply gave up? I’m sure explorers such as Marco Polo or Captain James Cook had a few more concerns about traveling the unknown world with monsters, demons, and truly foreign lands than we do about our current obstacles. This isn’t self-help affirmation, but an honest question of asking ourselves whether we jump to conclusions too much? What is it that we fear?
If, upon reflection, you decide it’s truly too much, then why and what can you do to get there? What are the steps necessary to accomplish your goal? Break them out. Write them down. Sit down with a friend, spouse, colleague, and family and share your vision and ask for critique.
Because what’s often worse than attempting some major challenge is the idea of sitting alone with our own thoughts. And that, as we know, is filled with anti-affirmations.

Your Team’s Shields Are Down

A couple years ago I read an article called Shields Down describing how people don’t quit the day they resign, they resigned their post a long time ago. It’s when they became vulnerable, when their shields went down that they were open to something new, something different—perhaps where the grass appeared greener.

I was caught juxtaposing that against Customer Success. The concept of Shields Down is true with customers, too. Our customers don’t quit the day they call to cancel, they already decided they were done a long, long time ago.

It’s sometimes really hard to know when someone may be canceling. Heck, they may even be in the product every single day—but that may be just to export all the data. We tend to forget the customer’s story in which:

  1. They weren’t using your product
  2. Found your product/service
  3. Got excited
  4. Dove in—sort of
  5. Got lost, confused, or delayed
  6. Slowed toward ambivalence
  7. Told themselves they would work on it next week, and
  8. Finally decided to cut the cord

Let’s abbreviate that to four steps:

  1. Found your product or service
  2. Got excited
  3. Didn’t engage
  4. Canceled

Why? Because we don’t see where they stopped caring or became apathetic. Think about this: our CRM tell us when we get a new lead, when we’ve determined them as a qualified lead, when we have great conversations to assign a probability of closing, expected close date, sign up date, and onboarding period. But really we lack the apathy-meter. This is for two reasons, 1) there’s much less money in this process than sales and 2) it’s really, really, really difficult to measure this stuff.

The former is changing quickly. So is the second, but to a lesser degree (I invite challenges and arguments. I would love to hear your thoughts!). See, there are health scores. There are ways to quantitatively measure how much a person is using your SaaS product. Heck, that’s often a proxy for delight. Many times these approaches give us a slight early warning system on someone about to pull the ripcord. However, all of those fail because we’re looking at the psychology of people. People make decisions and many times what looks one way for one person will be similar to another. Even if we can get to the point of solving 80-90% of this for our customers there is still one unaddressed piece.

My team.

If I want to keep people on my team, I must think about what to do today to ensure they want to stay here. The decisions teammates make today are not what I may have said earlier this morning or yesterday afternoon, but a cumulation of things from months ago, weeks ago, days ago, and yesterday.

This is cultivation. I love metaphors so let us look through a farmer’s lens.

Like a garden, vineyard, or orchard, we perform actions today not to pick fruit tomorrow, but in an entirely different season. Two years ago I planted two apple trees, two peach trees, and a pomegranate tree. I may get fruit next year. But I expect five full years of growing, nurturing, water, and feeding (compost & fertilizing) before I get a return on my investment. What if I didn’t water a tree today? It would probably survive. At least, for now. But when I forget it for a few weeks (let’s say I was “busy”) I may find it either dead or severely drought-inflicted. There’s a chance I can revive it and bring it back to life, but it’ll still be scared and stunted. I’ll have to be extra careful for the next while to make sure it has plenty of water, and that it hasn’t been afflicted by disease or attacked by vermin or insects. Since it’s especially weak, it’s quite prone to attacks. In effect, shields down.

There are many parallels between cultivating plants and cultivating teammates. But one nice thing about plants and trees is that while they may wilt, they can’t exactly get up and leave. But people can. So whether you’re leading a team or in a team, keep in mind that the actions of today often bear fruit somewhere down the road. Sure, something radical may cause someone to leave today, but people have some level of patience and forgiveness. But after a while, they’ll say “enough is enough.”

Some of our favorite ways of learning about our teammates are through are one-on-ones, performance reviews, and making sure we have an environment that promotes communication, sharing, aligned goals, and a desire and ability to achieve and tackle challenges. No matter what: listen. And not the fake listen, but truly listen—we know when you’re faking it. You’re only fooling yourself.

I hope we can watch our own shields, but also remember to make time to ask about our teammates’ shields. Because otherwise we will be surprised when we get that resignation letter—from the customer or teammate—and neither is fun.




Keeping Customers at All Costs

Anti-discounts, Bad Fit Customers, and Not Doing Whatever It Takes to Retain Them

Awhile ago a few of us Customer Success professionals gathered and discussed the benefits and problems what to do under the following scenarios:
  • Something in the product goes haywire for the customer
  • They’re “going to cancel” because we don’t have such and such feature
  • We don’t have X feature and “they really really want it”
  • We don’t have X feature yet
  • Our competitor has a feature we don’t have, so we need to consider discounting our pricing
Note, the scope was limited to either product failures or missing features.
As you can imagine, this brings about a number of unintended consequences:
  • Devaluing of our product
  • Lost ARR (Annual Recurring Revenue)
  • Enabling the team to kick the metaphorical can down the road
  • Converting customers into missing feature bounty hunters
  • If we’re a pushover here, do we draw the line anywhere?
  • Not being proud of our product
There are certainly more, but, brevity. 🤷‍♂️
You may have not seen a problem with giving temporary or permanent discounts. You may see a problem, but can’t verbalize the implications. You may see the problem, but can’t convince your teammates. That last one is definitely difficult. Focusing on the last one, here are some strategies to help think through the long term implications for your company.
Loss of ARR means less engineering investment
The more discounts you give, the fewer engineers the company can hire. If you do that, you will certainly go into a spiral and will only amplify the need to give more discounts to more dissatisfied customers. That will likely mean fewer or smaller product/feature launches—the exact opposite of what you need.

Gross Margin

Freely handing out discounts also hurts your gross profit margin. If you’re a SaaS company, you need to aim for 80-90% with the higher the better. Giving out discounts lowers your revenue even though you still have to provide services to your customers.
Discounts can be good to help drive your business forward. Unnecessary ones will hurt you.
(Note: you could manipulate your gross margin to be whatever you want. Don’t play accounting tricks.)

Budgeting and forecasting

Similar to above, if you’re constantly giving discounts to many customers, not only does this make your financials look terrible, but this introduces so much ambiguity, uncertainty, and questioning into your forecasting. For instance, how many discounts should we predict for next year? If we do that, how many employees won’t we be able to hire?

“We will build such and such feature by _____”

I think everyone is aware of this, but unless there’s a contractual obligation, committing to a feature or product is a terrible idea. Things change (like roadmaps). Even if that’s the most obvious feature to build, what happens when a major customer asks/demands you to build a different feature? Or industry upheaval or a broad compliance/regulatory change happened? Could you certainly still commit to that timeline?

They’re a bad fit customer / Solving for the wrong problem

If they truly are a bad fit customer, why are you even trying to please them? They’ll always be unhappy because you’re not the product for them. Let them go before they become a major drain on you (mental energy, phone calls, social media complaints, etc.). You wouldn’t keep a toxic friend, why keep a toxic customer?
If you give the discount, you’re solving for the wrong problem and aren’t building a sustainable business. You either have a bad fit customer and need to let them go, or you need to build the product to fit your customers. If you retain bad fit customers, then they will only badmouth your company which will make it harder for sales to win future prospects.

Pareto Principle

Speaking of time, it’s limited. Bad fit customers will tend to require more time from us. So not only do we risk getting badmouthed and hampering marketing and sales, we will also find that we spend 80% of our time on 20% of our customers.

Bounty hunters

If I get one discount because one feature is missing, do I get another discount? What if I find 4 features that are missing? Do I get 4x discounts?

Does the discount hit the company, or the sales rep who sold them?

If I have to give a discount to a customer, can I then dock that sales rep’s commission? If the sales rep is suggesting we give the customer a discount, do they want that permanent discount to come from their future comp?


If you give that discount, it should count as a downgrade and go toward churn. Investors/leadership won’t like that. In fact, no one likes that. If it’s a long term discount (e.g., we likely never will ship that or won’t for X months/years), that’s really a downgrade. We can split hairs here, but it should affect your overall retention figures since the company’s revenue will be less next month than the prior month. 

Roadmap based on discounts

Right now your roadmap is likely based on the likelihood of 1) new sales, 2) retention, and/or 3) account expansion. If we’re doling out discounts for these things, does that mean our roadmap is now designed based on how much money we can get back from shipping the features where we gave discounts? 


Those are just a few reasons. Ultimately, I believe discounts are good for closing deals and a few other areas, but we should think of discounts like salt. Sprinkling some salt on our meal helps enhance the flavor, but too much will ruin it. Discount responsibly.