Read the full article here

Similar to an earlier post, this is a summary of a presentation- let me know what you think of this alternative format.

Types of difficult customer situations

• Incomplete onboarding
• Low user engagement and feature usage
• Feature request
• Disengaged point of contact
• Weak relationship
• Unrealistic expectations
• Pricing conversation
• Cancellation threat

Incomplete Onboarding

Possible Reasons

• Disengaged point of contact
• Poor success planning
• Lack of internal alignment and prioritization
• Low attendance during kickoff call and onboarding
• Unfinished implementation

Suggested Tactics

Poor success planning

• Create a Sales handoff process to better capture knowledge shared during the sales process
• Work with the customer to establish and agree on a success plan within the first 30 days

Lack of internal alignment and prioritization

• Highlight customer’s original buying reason
• Assign tasks and hold people accountable

Low attendance during kick off call and onboarding

• Define everyone’s roles and responsibilities
• Bring issue to the attention of Management/ Executive teams

Unfinished implementation

• Confirm appropriate resources have been allocated within both organizations

Low user engagement and feature usage

Possible reasons

Low user engagement

• Incomplete onboarding
• Absence of processes that encourage long-term engagement

Low feature usage

• Unclear value proposition
• Insufficient knowledge of new features

Suggested tactics

Low user engagement

• Absence of processes that encourage long-term engagement
• Work with point of contact to create and enforce new processes
• Leverage buy-in and support from Management/ Executive teams

Low feature usage

• Unclear value proposition
• Present new features from the perspective of what goals they will enable end-users to accomplish
• Insufficient knowledge of new features
• Announce new features through multiple channels-trainings, emails, in-app messages, etc.

Feature request

Possible reasons

• Incorrect expectations set during Sales process
• Issues with product quality
• Customer’s needs have changed or will in the future

Suggested tactics

Incorrect expectations set during Sales process

• Collaborate with Product to uncover underlying use case/ need and identify possible solutions or work-arounds
• Clarify what value the customer can expect to receive from current features

Issues with product quality

• Provide feedback to Product around high-priority bugs or features customers find it difficult to use
• Work with Support to address any outstanding issues

Customer’s needs have changed or will in the future

• Explain feature request process
• Assess how feature request might impact renewal or possible cancellation

Disengaged point of contact

Possible reasons

• Incomplete onboarding
• Low user engagement and feature usage
• Main point of contact leaves
• Unresponsive

Suggested tactics

Main point of contact leaves

• Build relationships with multiple contacts
• Do research internally (Sales, Support)

Unresponsive

• Ensure every interaction provides value
• Review usage metrics to assess cancellation risk level
• Reach out to active end-users across multiple channels
• Get creative with outreach strategies

Weak relationship

Possible reasons

• Disengaged point of contact
• Poor relationship with CSM
• Weak relationship with Management/ Executive teams

Suggested tactics

Poor relationship with CSM

• Escalate internally
• Reset relationship by restating roles and responsibilities and establishing a mutually agreed upon success plan
• Build a check-in and escalation path should any further issues develop

Weak relationship with Management/ Executive teams

• Engage through succinct updates on progress of success plan
• Connect success plan to higher-level company goals
• Provide materials that support advocacy and budget approval

Unrealistic expectations

Possible reasons

• Incorrect expectations set during Sales process
• Request an unsustainably high level of service
• Misunderstand product value

Suggested tactics

Incorrect expectations set during Sales process

• Work with Sales to ensure they are conveying a reasonable value proposition to prospective clients
• Identify misalignment on customer goals and expectations early in the onboarding process

Request an unsustainably high level of service

• Define roles and responsibilities
• Agree on customer’s roles and responsibilities as part of a shared success plan
• Be specific about what resources can be committed

Misunderstand product value

• Review customer’s original buying reason
• Reset expectations and establish a success plan that will allow them to see value
• Collaborate with Product to uncover underlying use case/ need and identify possible solutions or work-arounds

Pricing conversation

Possible reasons

• Change in customer’s business
• Need to negotiate upsell or expansion terms
• Issues with pricing

Suggested tactics

Change in customer’s business

• Revenue concerns — propose reduction in seats and associated costs
• New ownership — provide material that supports advocacy and budget approval
• Shift in strategic initiatives — suggest ways customer can continue to find value

Need to negotiate upsell or expansion terms

• Connect future usage with value currently derived from product

Issues with pricing

• Know legacy pricing plans
• Work with Accounting/ Finance to understand basic billing processes

Cancellation threat

Possible reasons

• Low user engagement and feature usage
• Feature request
• Pricing conversation
• Lack of value
• General dissatisfaction

Suggested tactics

Lack of value

• Define value and illustrate with data
• Review success plan deliverables, feature usage, engagement data from onboarding, QBRs, etc. to demonstrate value over time
• Provide material that allows point of contact to make a strong case for renewal

General dissatisfaction

• Reassess product fit
• Explore recovery options to ‘reset’ the relationship
• Manage any ongoing issues
• Avoid getting backed into a corner by an aggressive customer

It’s a typical Thursday at 2pm, which means you’re dialing in to your standing client call with ABC Corp. The call kicks off with the expected pleasantries, and you suggest diving into the agreed upon agenda. Your contact at ABC Corp cuts you off- “I think there’s something more pressing we need to discuss. We won’t be renewing when our current contract ends in September.” You’re blindsided by the cancellation and left flabbergasted as to where things went wrong.

Cut to your quarterly review 2 months later. Your performance has been solid by your assessment, and you expect the conversation to be a bit routine. Your manager clears her throat. “While you excelled in Q2, we really saw a drop in your performance this quarter. In particular, it was concerning that you didn’t anticipate ABC Corp’s intention to cancel.” This is the first you’ve heard about this cancellation reflecting poorly on you. When it happened back in August it didn’t seem like a big deal. Your manager has never directly broached the topic outside of asking you to complete a cancellation feedback template. You’re taken aback and realize your manager has been sitting on this feedback for months- why didn’t she say something sooner?

Unfortunately both of these scenarios are based on my personal experiences and I’ve been on both the giving and receiving end in each. I’ve been cancelled on and cancelled; I’ve received delayed feedback and given it. It truthfully sucks to be on either side of the table- the singular feeling you’re left with is one of disappointment. As a CSM you wish you could have proactively addressed issues that led to a customer wanting to cancel; as the customer you just want a product and service that works and would prefer to not have to look elsewhere to find it. The individual contributor feels hurt and slightly betrayed that they didn’t receive negative feedback until it had grown into a more serious performance concern; the manager has to consider if the core issue is the CSM or their own lack of coaching. Feedback is the solution to all sides of this equation.

Customer Feedback

One of the key ways to get ahead of unexpected cancellations is gather honest feedback from customers. Receiving negative feedback is hard, but so is giving it. Customer Success teams need to create situations and environments where customers feel comfortable giving an honest assessment of their product and the relationship.

Ways Customer Success teams can solicit feedback:

Business Reviews

• Formal business reviews should be collaborative and dynamic. In addition to your day to day contacts, the customer’s executive stakeholder should also be in attendance. Reviews always include a look at the state of the business to date, but the majority of the meeting should focus on what’s next- including honest feedback on what it’s going to take to achieve those goals together

Customer advisory boards

• Getting your customers together creates dialogue across departments, as well as among customers themselves. These conversations are a chance to establish broader alignment on pain points, opportunities, and priorities across your customer base

Surveys

• People often have an easier time being honest responding when responding to a survey than they would filling in a blank feedback form. While NPS, everyone’s go-to survey, can provide high-level insights, it lacks specific details around the state of the partnership. Good surveys challenge the recipient- done well they’re a chance to ask questions you wouldn’t normally get an honest response to on say a weekly call

Manager Feedback

It makes sense why our customers shy away from giving feedback- it can feel awkward, like they’re overstepping, or that it won’t be acted on. We can’t allow our internal teams to be blocked by these same barriers. Why is it that providing consistent feedback can sometimes feel harder than giving someone a bad review, or even worse, letting them go? Managers of Customer Success teams need to learn to give immediate, clear, and consistent feedback.

Ways Managers of Customer Success teams can solicit feedback:

Impromptu feedback

• The quarterly performance review setting described in the scenario above is familiar to most people, but feedback doesn’t have to be so formal. Don’t discount the value of quick, but specific feedback. Impromptu feedback is something you can squeeze in between meetings in 3 minutes or less, using one of these easy tactics

Formal reviews

• That being said, setting aside dedicated time for reviews can be a helpful way to give structured evaluations. Reviews should ideally be used to as a chance to start a dialogue, not a one-way conversation led by the manager. Managers should be prepared and receptive to a response

Skip level meetings

• A skip level meeting is one where a manager’s manager meets with employees to discuss department concerns, obstacles, opportunities for improvement, etc. with a focus on maintaining and/or improving overall communication. These can be helpful to get feedback on the manager that employees aren’t comfortable delivering directly

Surveys

• Surveys are valuable tools for internal feedback for the same reasons they work with customers. They can be team specific, or part of a broader company-wide effort to gauge happiness and engagement

The best way to get good at giving feedback is to start by soliciting it from others. If you’re interested in diving deeper into the world of feedback, I recommend reading Radical Candor, which changed the way I think about the topic.

Most companies still think about marketing in terms of a funnel- a bunch of leads go in the top, and a few customers come out the bottom. But leading SaaS companies have starting thinking about Marketing as less of a funnel and more of flywheel.

“Whereas funnels lose their momentum at the bottom, flywheels leverage their momentum to keep spinning. Also, because they preserve momentum so well, all of the additional energy you add to spin it faster adds to the capacity of the whole.”- HubSpot

In a flywheel marketing model customers are at the core of your strategy and messaging, which makes Customer Success an integral partner in crafting and influencing your marketing plan. Here’s a few tactics to incorporate Customer Success teams into your marketing strategy.

Ideal customer profile

Customer Success can define the characteristics that make a good customer to ensure marketing is attracting people and companies that are more likely to find value in your products and become long-term, satisfied customers.

Case studies

Current customers help articulate the value your product and services bring customers. This is your chance to share your differentiators and give prospects a sense of what it’s like to work with you. Compelling case studies and testimonials attract leads and increase sign-ups.

User marketing

Getting users to sign-up is just the beginning! Customer Success and Marketing need to work together closely to create a consistent customer experience. These two teams should collaborate on identifying key actions that increase the likelihood of a customer being successful, and to use this data to create campaigns that engage customers through a blend automation and human touch.

Referrals

Customer loyalty and advocacy are cultivated by a Customer Success team that is focused on delivering value and delight. Satisfied current customers are a great lead source for referrals- don’t underestimate how much positive word of mouth can amplify your marketing efforts.

An infinite loop

Hyper-growth SaaS companies have pricing models that allow them to capture additional revenue as customers receive incremental value from their product and services, or to upsell/cross sell products to grow ARR. Customer Success teams directly impact this process by assisting customers in achieving their goals and influencing expansion and retention. This makes Customer Success an integral part of your company’s marketing engine- by attracting interest from current customers in complementary products or services, engaging them through mechanisms that deliver value, and sufficiently delighting them to repeat the process over and over again.

While there’s been a lot written (and debated on) the topic of how many accounts or how much revenue a Customer Success Manager should own, there’s been relatively little discussion on how many CSMs a Manager of Customer Success should oversee.

Startups grow organically and remain flat as long as they can

Startups struggle to balance the desire to remain a flat organization with the realities of effective management. What’s the appropriate number of direct reports per manager? One study showed that across seniority levels, managers and their direct reports agreed seven was the ideal number of employees for a manager to oversee. That being said, many respondents cautioned that such a “magic number” lacked nuance. What works for one manager within the same org may not work for everyone, especially when you try to draw comparisons across teams and seniority levels. Management roles might include some component of individual contributor work, especially at the lower levels and early in the company’s lifespan. This certainly limits the size of the team you can oversee. As the company grows, you will likely have more experienced and tenured employees who might require less time, or they could require more hands on coaching if you’re providing guidance around their next career move. For this reason, it’s helpful to look at the maturity of the company to provide insight into the appropriate CSM to manager ratio.

Ratios depend on company maturity

Founders have certainly heeded Jason Lemkin’s advice that Customer Success is a single-digit hire. In those early days it’s common to have more senior team members act as leads for smaller 1–2 person teams before bringing on a dedicated manager. Fast forward a few years and those startups that invested early in Customer Success are now growth stage companies with expanded resources across all teams- including Customer Success. At the same time, Customer Success is being adopted by enterprise companies that have larger workforces that require more structure. Due to these two factors, the size of the average Customer Success team has grown- with nearly 55% of Customer Success teams consisting of more than 10 members.

And this growth appears enduring even in the face of uncertainty- 30% of Customer Success organizations still plan to hire additional CSMs in spite of challenges presented by the COVID-19 pandemic.

With so much growth, it’s safe to assume gaps are opening up in Customer Success leadership roles. Additional research shows the ratio of CSM to manager increases as ARR grows- starting at an average of 2:1 from $0-$5M ARR and peaking at 5:1 from $50M-$100M ARR, before dropping down to 4.2:1 at $100M+. If we assume a flat rate of 5 CSMs for every 1 Manager of Customer Success, and a ratio of 4 Managers for every 1 Director, 31% of companies with Customer Success teams have a need for a mid-level Customer Success leader. The data supports this assessment, with the same study cited above showing companies hire a Director or VP of Customer Success at around $5M in ARR. Is the Customer Success discipline and its leaders mature enough meet this demand and ready to take a seat at the leadership table?

Customer Success investment at the C-level remains rare

Tomasz Tunguz recently released interesting data comparing the stages and prevalence of leaderships titles across startup GTM functions. Across Customer Success, Sales, and Marketing, Sales usually gets the first VP opening at between $1M-5M in ARR. Reaching $5M-20M in ARR, things even out with each team having a dedicated VP. However, the Chief Customer Officer title, remains the rarest of the C-level titles- appearing in less than 10% of companies at $20M in ARR or higher.

While there’s no “magic number” of direct reports a Manager of Customer Success should oversee, 7 is generally considered the maximum, with most teams averaging a ratio of 2–3 CSMs per Manager. This number increases as a company’s ARR grows, and creates opportunities for more senior titles in the Customer Success organization.

“Great by Choice” is a bestselling work by the popular writer Jim Collins, whose other business books include: “Good to Great”, and “Built to Last”. I’ve skimmed Jim Collins’ books in the past, but what drove me to finally sit down and read this one was the core question Collins and his researchers sought to answer: why do some companies thrive in uncertainty, even chaos, and others do not? Collins sought to identify the qualities that allowed companies to prosper in situations where their peers failed. “We labeled our high-performing study cases with the moniker ‘10X’ because they… beat [their] industry index by at least 10 times.” Needless to say the topic seemed appropriate given the current health, economic, and social climates we find ourselves in.

Business (and life) is full of uncertainty, and yet Collins finds that some companies and leaders navigate this type of environment exceptionally well. “They don’t merely react; they create. They don’t merely survive; they prevail. They don’t merely succeed; they thrive. They build great enterprises that can endure.”

This book helped me realize that by accepting the inevitably of struggle and anticipating future challenges, we can reduce feeling so helpless in our current situation. Yes, so much of life is outside of our control, but it’s how we as managers react to the circumstances we find ourselves in, and how we prepare for the next unexpected turn of events, that defines us. “On the one hand, 10Xers understand that they face continuous uncertainty and that they cannot control, and cannot accurately predict, significant aspects of the world around them. On the other hand, 10Xers reject the idea that forces outside their control or chance events will determine their results, they accept full responsibility for their own fate.”

Below are the main leadership lessons startups execs, managers, and individuals can take away from “Great by Choice” during this time of crisis.

Fast yet rigorous decision making, fast yet superb execution

• Defined in the book as: fantastic discipline
• Application in everyday life: take time to evaluate your options- don’t rush into making huge decisions. You often have more time to weigh your options than you might think, and even if you don’t, rushing into change is often worse than doing nothing and staying the course. Once you make a decision, embrace if fully and focus on execution

“Rapid change does not call for abandoning disciplined thought and disciplined action. Rather, it calls for upping the intensity to zoom out for fast yet rigorous decision making and zoom in for fast yet superb execution.”

Break ambitious goals into smaller milestones

• Defined in the book as: the 20 Mile March
• Application in everyday life: ambitious goals are more attainable when they’re scaled down into more milestones you can reasonably and dependably hit. These milestones can feel overly easy on good days, and insurmountable on bad days, but consistency over time leads to compounding results

“The 20 Mile March is… about having concrete, clear, intelligent, and rigorously pursued performance mechanisms that keep you on track. The 20 Mile March creates two types of self-imposed discomfort: (1) the discomfort of unwavering commitment to high performance in difficult conditions, and (2) the discomfort of holding back in good conditions.”

Re-invest in your team

• Defined in the book as: inspired motivation; empirical creativity
• Application in everyday life: people are your single greatest asset. Once you have the right team, encourage them to make small bets and invest further if these experiments pay off

“The environment doesn’t determine why some companies thrive in chaos and why others don’t. People do… Of all the luck we can get, people luck- the luck of finding the right mentor, partner, teammate, leader, friend- is one of the most important.”

“The great task, rarely achieved, is to blend creative intensity with relentless discipline so as to amplify the creativity rather than destroy it. When you marry operating excellence with innovation, you multiply the value of your creativity.”

Resilience, not luck

• Defined in the book as: luck is not a strategy
• Application in everyday life: we can’t control luck, but we can control how we respond to it. In moments of crisis consider how much stronger you’ll be when you get past this

“10Xers shine when clobbered by setbacks and misfortune, turning bad luck into good results. 10Xers use difficulty as a catalyst to deepen purpose, recommit to values, increase discipline, respond with creativity, and heighten productive paranoia. Resilience, not luck, is the signature of greatness.”

We all know the current situation we find ourselves in is unprecedented, and that many people’s lives and livelihoods have been fundamentally altered. Those of us fortunate enough to still have a job are grappling with uncertainty and insecurity- especially those of us interacting with customers on a daily basis. Before we pick up the phone or draft an email to our customers we need to pause and ask ourselves: how can we rise to meet this moment? Companies will be forced to answer to the pandemic (even operating with a “business as usual” mindset is a deliberate choice), and Customer Success teams need to think about how to shape their response to COVID-19.

Re-think your customer lifecycle

The customer lifecycle isn’t linear under normal conditions, and it will look even more erratic under current conditions. Customer Success Managers should be ready to adapt.

Start by auditing automated touch points to avoid appearing tone deaf during this difficult time. From onboarding (hey you haven’t logged in lately!), to payment failure (your credit card was denied, try another!), to NPS surveys (how would you rate your experience with our product that took 3x as long as usual to ship?) you’ll likely find more than a few messages that come off as cringe-worthy in this climate.

Hitting pause on some 1-to-many communications means CSMs will spend more time talking directly to customers. Now isn’t the time to adhere to rigid tiers or segmentation criteria around service levels, or tech-touch versus human-touch workflows. Being accessible and responsive to customers is critical as we adjust to this new environment. Be prepared for customers who were relatively low touch and self-sufficient to need more hands on support.

People don’t want a canned response. They don’t want you to measure their happiness after they’ve waited for a month for a product that normally takes three days to arrive. What they want is a drop of humanity, a bit of truth and honesty in the face of something genuinely terrifying and unprecedented for all of us. Make sure you give it to them. — Help Scout

Provide value

Companies are being asked to do more with less. In this environment it’s never been more crucial to demonstrate and provide value to customers. Where do you start when your health score is no longer reliable, your customer champion has been laid off, and the upsell opportunity you were discussing has been put on hold?

A recent survey from Gainsight showed 65–80% of companies have frozen hiring for the next few months and 30–45% have frozen hiring and backfills indefinitely. In addition, 60–70% of sales leaders polled are reporting delayed sales cycles (source).

Go back to the basics- make a human connection with your customers and seek to gain a deep understanding of their business. Ask how they’re doing personally and how their company has been impacted. Once you have a better lay of the land, come to them with solutions. Manage champion churn or layoffs/ furloughs the same way you normally would- build relationships across different teams and seniority levels and rest the partnership. Changes in your customer’s business (good or bad) mean big projects are likely to be put on hold or changed in scope. This could be the time to try something radically different to reshape your partnership. Or, it could be the time to double down on what has worked in the past if customers need to mitigate risk or cut costs.

Uncertainty has people looking for guidance and answers and Customer Success teams are naturally poised to fill this void. Despite the fact that we all feel a bit unmoored, you have access to insights that can be presented as meaningful thought leadership. What shifts are you seeing across your customer base? Can usage data be anonymized to show directional trends- see examples from ChurnZero and Chargebee. Can you conduct industry surveys or generate interesting content?

Finally, value is linked with cost. If customers are no longer able to extract as much value from your solution during these times, consider ways to lower costs to mitigate the risk of permanent churn, such as: downgrading their plan or reducing seats; pausing their account for a period of time; offering them a price reduction or discount.

Invest in the long term

None of us know what the future holds. But thinking long term keeps us from being too overwhelmed by the situation we’re in, and it also helps us avoid making decisions in the moment that could sacrifice our eventual success. A points to leave you with:

• Be human, be kind
• Remember people have long memories- your actions today will impact your customer relationships long after this pandemic
• Take care of yourself and avoid burn out

If you’ve made it past the headline, I probably don’t need to tell you burnout is a serious concern for individuals and employers. While burnout isn’t a new phenomenon (I was surprised to find the arguments in this 2016 post remain very relevant), the potential for burnout is exacerbated by elevated stress and anxiety stemming from the COVID-19 pandemic. Customer Success burnout in particular is tied to two factors: unrealistic expectations and an inability to imagine a time when things will improve. What can Customer Success teams and companies do to decrease the chances of burnout during this pandemic, and lay the groundwork for lasting change?

Manage customer expectations

I would argue that burnout is more common in service roles such as Customer Success because our work includes an element of emotional stress that comes from working closely with other people. To limit the strain these interpersonal dynamics have on our mental state we have to manage expectations and set boundaries.

Set work hours

Schedule regular working hours and share them with your customers. This is especially important if you cover multiple timezone- nothing’s worse than waking up in Los Angeles to 3 urgent emails from a customer based in New York. Without a defined schedule you risk letting your working hours span the majority of your day in a misguided effort to cover 9am EST- 5pm PST. Throw in the occasional weekend issue and you won’t be left with much time to unplug.

Design after-hours escalation protocols

Customers often ask us to work around their schedules. While we need to be responsive when a truly urgent request comes in, it’s draining to be in a constant state of vigilance. Escalation protocols define expectations around after-hours assistance in a way that improves the experience for external and internal teams. These protocols can either be part of a formal SLA framework, or fall into more informal expectation setting. Take the time to map out the process of tackling after-hours requests- how customers can get in touch, who will troubleshoot internally, and what kind of updates will be provided. I also recommend creating a protocol for how to communicate with customers during a crisis- such as when your product is down. Having an escalation framework in place reduces stress that results from uncertainty, and helps speed up resolution time.

Ask for help

Now that we’ve set our customer’s expectations around what we can deliver, it’s time to challenge internal assumptions around workload.

Communicate with your manager

If you’re feeling overwhelmed by a never ending list of tasks and responsibilities, you need to immediately raise these issues with your manager. As someone who manages a team of 7 CSMs, I know firsthand how hard it is to be attuned to people’s individual workloads and personal situations. This challenge is amplified when people’s personal and professional lives have been disrupted by a pandemic. When CSMs on my team say they’re struggling I don’t view it as a sign of weakness- quite the opposite. Asking for help requires enough maturity to speak up when you’re worried about letting your customers and team down.

Find resources

If you feel like your manager isn’t receptive to this type of feedback, escalate it up to leadership or HR. Support doesn’t necessarily need to come from the top, connecting with a peer can go a long way. Talking to a fellow CSM can provide a safe space to vent, brainstorm solutions, or validate that others share your concerns. Don’t suffer in silence- people can’t help if they’re not aware of your circumstances.

Get out of the weeds

When we’re overwhelmed in the day to day it’s challenging to plan for the future. But when we’re too busy to think about our goals and what lies ahead, we’re unable to imagine an end to our current crisis- don’t let yourself get stuck in this self perpetuating cycle.

Think big picture

What do you like about your job and what would you change about it? If the parts of your job you hated disappeared tomorrow, how would you spend the time you’ve gained? What else would you want to accomplish in this idealized version of your job you’ve created? Admittedly it’s unlikely you’ll be able to get rid of every aspect of your job you don’t like. However, it’s helpful to think about this future end state and tie your day to day back to big picture questions such as what do you want and what can you change to get close to that goal?

Block off time

Set aside time to make progress on your goals by working on special projects and investing in professional development. People pushed to their breaking point can produce amazing innovation. That’s not to say it’s entirely on you to fix the situation (see “Ask for help” above), but you should look for even small opportunities to improve your situation. It’s especially important to look for opportunities to better scale and create efficiencies.

Walk away

At a certain point after you’ve tried to manage expectations, asked for help, and gotten out of the weeds- you have to be willing to just walk away.

Take control by setting boundaries and sticking to them

In a time of less concrete commitments it’s easy to spend an unsustainable amount of time working. When you don’t have a workout class that starts in 30 minutes, or a happy hour planned with friends, what’s the harm in sending one more email, or two, or three. Sometimes I find myself working because “there’s nothing better to do”. When I stop and reflect, I realize how silly that sounds. There is always something equally or more worthwhile than work to occupy your time! With fewer external accountability it’s on you to set boundaries and stick to them. If you don’t usually work past 6pm, then don’t start doing so now. If you usually take a half day one Friday a month, keep it up. Not only are these habits unsustainable over the duration of the lockdown, they’ll make it harder to transition back to normal life when the pandemic ends.

Change how you think about your free time

Your free time is just that- yours and free for you to use however you like. But perhaps even more impactful than what you do with your free time is how you think about it. For instance, a recent study found that people who had treated their weekend like a vacation were significantly happier than those who had treated it like a regular weekend. “Research shows that slowing down and paying more attention to your surroundings, the activity at hand, and the people who are involved allows you to enjoy the activity more. Without ruminating on the past or getting distracted by anxieties or fantasies about the future, increasing your attention to the present moment makes you more sensitive to the pleasures that are already in the environment. It helps you savor experiences and life a bit more.”

Be well and stay safe.

Product workflows have a major impact on customer experience. They’re scalable, touch every user, and are measurable and data-driven. But customers often dismiss our best attempts at self-navigated trainings or in-app tooltips because they feel disruptive or irrelevant. Customer Success Managers (CSMs) bridge the gap between templatized product onboarding and a customer’s goals. This post will demonstrate how CSMs can translate well thought out and well intentioned product workflows to language and actions customers can understand.

Onboarding impacts churn and expansion

Des Traynor of Intercom argues that retention is more important than conversion, and high customer retention is built on great product onboarding. The data backs him up — research by ProfitWell found that customers with a positive perception of their onboarding experience are far less likely to churn within the first 21 days of using a new product. This is crucial because churn not only hurts your short term profits, it also puts future grow in jeopardy since 80% of a company’s future profits come from 20% of their existing customers (source). With the median B2B SaaS company losing about 5% of their customers annually (source), it’s clear that investing in a high-impact retention strategy like onboarding is worth your time.

User onboarding is imperative to customer retention and, by extension, building and growing your company.

Connect customer goals to onboarding

Use insights captured during the sales process

Before you can onboard users, you need to acquire new customers, which means Sales is often the first human touch in the onboarding process. Some SaaS companies are able to operate without a dedicated Sales team, but most have found that adding sales teams improves the buying experience. This is even true among Product-Led Growth companies like as Atlassian and Slack that once prided themselves on not having dedicated Sales teams. These sales reps don’t operate in the old ‘boiler room’ mentality of doing anything to get a deal- they work to understand the customer’s needs and validate whether or not your product can deliver on their expected outcome. Don’t let these hard earned insights disappear with the sales rep after the ink has dried, instead share this knowledge to Customer Success in a clearly defined transfer process. Heading into onboarding with an advanced understanding of your customer’s goals allows you to narrow your time to value.

Communicate benefits, not features

Customers might say they bought your product because you have a certain set of features, but in reality they care about the outcome. What can your product help them achieve? Customer Success teams help translate a list of product features to customer goals and outcomes.

Customize the onboarding experience

There is no one-sized-fits-all version of onboarding

Now that you’ve identified the customer’s goals, you should tailor the onboarding experience to meet their needs. Customer Success teams use this information to customize the onboarding process- from setup and implementation, to training programs, and even laying the foundation for future performance reviews. Personalized onboarding should also trickle down to the user since the company’s goals will be achieved by individuals using the product in different ways. Below is an example of how QuickBooks presents users with the option to customize their onboarding experience- they ask users what they want to accomplish and then adjust the experience to match:

Incorporate behavior-based messaging

PC users from the 90s will easily recall Clippy, Microsoft Word’s overzealous tool tip helper. People’s experience with Clippy usually started off positive enough. For instance, if you started a document with “Dear X,” Clippy figured out that you were writing a letter, and offered to help with formatting, etc. However, Clippy quickly became a nuisance to most of us. What changed? More like what didn’t. In a postmortem Microsoft conceded that Clippy was “optimized for first use.”

“What has happened is that the usability test showed that people who have never seen a feature before have trouble with it in the first hour of using it. So the designer makes the feature hold your hand through the process. That improves the results in the test, but ruins the feature for people who know what they are doing.”

Don’t fall into the same trap as Clippy- adapt your onboarding to reflect the behaviors your users have (or haven’t) taken in your product. Triggers such as time since sign up are usually meaningless. During an arbitrary 3 day timeframe one user could be a pro who’s spent 20 hours in your product, and another hasn’t logged in since they started a trial. Consider which actions successful users do that average ones don’t- these activities are likely to be what drives long-term value for both you and your signups. Then use behavior based messages to drive users towards taking those actions.

Iteration and incrementality

Onboarding is not something that you do once and forget about it. It’s not a feature that is included in a sprint and then moved to the “Done” column of your Trello board. Onboarding experiences need to be iterative based on feedback from customers and Customer Success. As new features are released, teams need to roll out new onboarding campaigns and materials. For every feature release there needs to be a complementary plan for how to appropriately notify your users of this change. If you don’t pair incremental deployment with Customer Success and Education frameworks that support incremental onboarding, even expert users will start to fall behind.

We’re confronted with change in a hundred different ways on a daily basis. A street on your morning commute is closed so you take a detour, your manager assigns you to a newly closed account, or your flight is delayed. And of course change don’t just happen to us, we also volunteer for change. Big changes are usually accompanied by optimism- you’re going to start going to the gym 5x week, sign up for an online course, or save more money for a house. Unfortunately we’re often unsuccessful in making these transformations stick. Why? Because change is hard.

The dynamics of change in our personal lives are often mirrored in our work- with the added complication that it’s usually not just one person undergoing a transition, but an entire team or organization. Companies identify a problem or an opportunity, such as improving the expense report process, and as part of the change process, buy a product to help facilitate the shift. Knowing change is hard, how can we as Customer Success Managers overcome the hurdles standing between us and sustained, long-term change? How can we help our customers make the switch?

The inspiration for this post is the book Switch: How to Change Things When Change Is Hard by Chip and Dan Heath. The concepts below are drawn from the framework and case studies outlined in the book.

What makes change so hard?

Chip and Dan Heath argue that the brain has two independent systems at work at all times. First, there’s the emotional side. It’s the part of you that is instinctive, that feels pain and pleasure. Second, there’s the rational side, also known as the reflective or conscious system. It’s the part of you that deliberates and analyzes and looks into the future. The authors use the analogy of our emotional side as an Elephant and our rational side as its Rider.

“When people try to change things, they’re usually tinkering with behaviors that have become automatic, and changing those behaviors requires careful supervision by the Rider. The bigger the change you’re suggesting, the more it will sap people’s self-control. And when people exhaust their self-control, what they’re exhausting are the mental muscles needed to think creatively, to focus, to inhibit their impulses, and to persist in the face of frustration or failure. In other words, they’re exhausting precisely the mental muscles needed to make a big change.” — Switch

To achieve change, you’ve got to appeal to both Rider and Elephant. The Rider provides planning and direction, while the Elephant supplies the necessary energy. When Rider and Elephant aren’t in sync, change is all but impossible.

How these concepts apply to Customer Success:

1. Direct the Rider. Streamline the process and provide clear directions
2. Motivate the Elephant. Don’t focus on failures, look for ‘bright spots’
3. Build habits. Put the Rider and Elephant on auto-pilot

Script the critical moves and shrink the change

Any successful change requires a translation of broad goals into specific behaviors. Customer Success Managers need to script the critical moves by providing crystal-clear directions. Collaboration with the customer is key to ensure you intimately understand their needs and how their organization works. From there, look for opportunities to customize their implementation and onboarding, highlight aspects of the product they’re more likely to find valuable, and speak in their language to remove barriers. Finally, secure buy in from the customer’s leadership team to ensure you won’t be a solitary advocate.

Once you’ve scripted the critical moves, try to shrink the change as much as possible. This doesn’t mean diminishing the task ahead of you, but making it more approachable to people who might resist a major 13 step implementation plan. Two strategies for shrinking the change: 1) limit the investment you’re asking for; 2) identify small wins that are within reach.

Find the bright spots

The authors found that people are often so focused on what’s not working that they overlook critical examples of where change is working. Ask yourself, “what’s working and how can we do more of it?” Let’s say you’re having trouble driving usage or product adoption across an organization- are there teams or individual users who are logging in regularly? What about their use case, role, or environment can be replicated on a broader scale?

Build habits

Habits let our emotional and rational systems default to auto-pilot. Creating users habits is a highly desirable but somewhat lofty goal. How can we become so engrained our customers’ lives that they don’t even stop to think about when and where they should use?

Nir Eyal, a thought leader on habit formation, argues habits are comprised of a trigger, an action, a reward, and an investment. Consider what motivates your users to use a product. Do they want to stay in touch with their customers, easily accept mobile payments, rent a bike on the go, etc? Now what kind of trigger could motivate them to use your product, or stick with your product instead of using a competitor? According to BJ Fogg successful triggers have three characteristics: “First, we notice the trigger. Second, we associate the trigger with a target behavior. Third, the trigger happens when we are both motivated and able to perform the behavior.”

Product features to help drive habit formation

Progress bars are most effective at motivating users when they show a substantial percentage of the bar filled out. Starting with a partially completed progress bar helps a user feel like they’ve already accomplished something, instead of starting from scratch. This sense of progress increases a person’s desire to complete the task at hand.

Checklists can turn complex, multistep processes — like scheduling out a month of social media content or centralizing your financial accounts — into simple, achievable tasks. Checklists work best when they live alongside your product as a present reminder of that tasks that still need to be completed.

Do you feel like you’re more prepared to help your customers make the switch?

Additional resources on the Switch book by Agile Lean Life and Sam Thomas Davies’ book summary page.