Management Is Hard. So Is Being an Individual Contributor.

A while ago, I was invited to a webcast about becoming a manager. The premise was reasonable enough: before moving into management, people should understand what the job actually involves rather than being seduced by the title, perceived status or career progression. But the way the message was delivered bothered me.

Management was presented almost as an act of heroic self-sacrifice. Your calendar would explode, meetings would multiply, your direct reports would consume your time and you would dedicate yourself to their wellbeing, development, problems and careers. The underlying comparison was hard to miss: managers are extremely busy people, while individual contributors apparently enjoy a comparatively relaxed existence.

At the time, I found that slightly insulting. Having since become a manager myself, my opinion has not changed very much. Management can absolutely be stressful. In a dysfunctional organisation it can be extremely stressful. But here is the important part: if the company is dysfunctional, being an individual contributor is usually stressful too. The pressure simply appears in different places.

The mythology of the overwhelmed manager

There is an entire genre of leadership content built around how difficult management is. Your diary is full. You have endless one-to-ones. People escalate problems to you. You have hiring, performance management, internal politics, reporting, forecasting, strategy, coaching and organisational responsibilities. All true.

Good managers carry significant responsibility, particularly when they genuinely care about the people working for them. But describing management as inherently more demanding than individual contribution creates a strange hierarchy of suffering. It also conveniently ignores something organisations frequently do to individual contributors: give them workloads that are mathematically incompatible with doing the job properly. Customer Success is a particularly good example.

The Customer Success workload problem

Customer Success models vary enormously between companies, industries and stages of growth, but a simplified organisation might look something like this. At the lower end of ARR, customers are often managed through digital Customer Success. The model is primarily one-to-many: automated communication, webinars, campaigns, community programmes, digital education, telemetry, surveys and targeted interventions. One CSM or digital CS team can therefore influence hundreds or even thousands of customers.

Move further up the customer-value ladder and the model changes. A commercial or inside CSM may manage perhaps 15, 20, 25 or sometimes considerably more accounts. These customers usually expect human interaction: regular calls, success planning, adoption reviews, escalations, business reviews and internal coordination.

Enterprise CSMs generally manage fewer customers because those customers are larger and more complicated. There may be multiple business units, technical teams, executives, procurement functions, security teams, partners and implementation stakeholders involved. At the very top sit strategic accounts, where a CSM may manage only a handful of customers, sometimes supported by dedicated account executives, architects, professional services resources and executives.

The ARR thresholds separating these models are not particularly important. A $200,000 customer may be strategic to one company and relatively small to another. What matters is the operating model. And somewhere in that operating model is a number that quietly determines whether Customer Success works: How many meaningful customer relationships can one person realistically maintain?

The arithmetic becomes uncomfortable

Imagine a CSM managing 20 customers. Assume a 40-hour working week. Now remove time for internal meetings, company updates, training, administration, CRM updates, forecasting, product meetings, support escalations and the dozens of other internal activities that inevitably appear. Perhaps 32 hours remain for customer-related work.

Twenty customers. That gives you 1.6 hours per customer per week. And that number includes everything:

• Preparation
• Meetings
• Follow-up
• Research
• Internal advocacy
• Escalations
• Success planning
• Adoption analysis
• Executive communication
• Documentation
• Coordinating with Sales, Support, Product and Professional Services

The arithmetic is obviously simplified, but that is precisely the point. A spreadsheet can make the workload look perfectly reasonable. Reality cannot. Some customers will barely need you for a month. Another customer may consume ten hours during a single escalation. Another will require several internal meetings before you can provide a meaningful answer to one seemingly simple question. And another will have five different stakeholders asking for five different things. Customer relationships do not divide neatly into 1.6-hour blocks.

Now compare that with management

This was the thought that occurred to me while listening to that webcast. Most managers I had worked with did not manage 20 people. They might have five, seven, eight, perhaps ten. And there is a good reason for that: managing people properly takes time. You need one-to-ones, coaching, career conversations, performance discussions, context, feedback, escalation support, planning and, occasionally, simply being available when somebody needs help.

Nobody would seriously suggest that a frontline manager could effectively coach 25 people while meeting every one of them weekly and remaining deeply involved in their development. We intuitively understand that there is a limit. Yet in Customer Success, organisations sometimes expect one person to maintain meaningful relationships with 20, 25 or even 40 customers. Each of those customers may contain several stakeholders. Each expects preparation, follow-up and action. Each represents revenue. Each can escalate. Each can churn. And each may eventually appear on a dashboard containing a very clear name next to the words CSM Owner.

Of course, managing an employee and managing a customer are not equivalent activities. A manager has responsibilities around development, performance, hiring, compensation and many other areas that simply do not exist in a customer relationship. But both are relationship-intensive activities. Both require context, preparation and time, and both become less effective when stretched too far. That is the contradiction that bothered me. We seem much more willing to acknowledge capacity limits in people management than we are in Customer Success.

The problem is not that managers have it easy

They don’t. I have now sat on both sides of the table. Management brings a different type of pressure. You become accountable not only for your own output but for the environment in which other people are expected to perform. You deal with problems that are not necessarily yours but become yours because somebody has to solve them. You sometimes know things you cannot discuss. You absorb organisational pressure from above while trying not to simply transmit that pressure downward. And occasionally you have to make decisions where there is no completely good outcome.

None of that is trivial. But that does not make the workload of individual contributors trivial either. This is where I think some management training gets the message wrong. The lesson should not be “Be careful. Managers work much harder than everyone else.” The lesson should be “Management is a different job, with different responsibilities and different sources of pressure.” Organisations should not need to diminish one role in order to demonstrate the importance of another.

When capacity planning becomes theatre

Customer Success organisations love metrics: customer health, adoption, renewal probability, engagement, executive relationships, success plans, business reviews, time to value, risk, advocacy and expansion opportunities. The problem starts when organisations require all of these activities while allocating insufficient capacity to perform them meaningfully. At that point the process becomes theatre.

The CSM updates Gainsight. The CSM updates Salesforce. The CSM attends the internal risk call. The CSM completes the success plan. The CSM marks the business review as completed. Every box turns green. And yet the customer may have received very little actual value. The organisation has successfully measured the process while simultaneously making the process almost impossible to execute properly. Then comes the inevitable question: “Why aren’t our CSMs being more strategic?” Because strategy requires time.

We are also wasting the capacity we already have

There is another side to this problem. Before asking for more CSMs, it is perfectly reasonable for leadership to ask whether the existing team is using its time efficiently. Unfortunately, in many Customer Success organisations the answer is no, and not because the CSMs themselves are inefficient. The systems around them are.

A surprising amount of Customer Success work still consists of humans moving information between systems. The CSM learns something during a customer meeting, writes notes, updates Salesforce, updates Gainsight or another CS platform, updates the success plan and perhaps updates a renewal, opportunity or escalation. Then, weeks later, the same CSM has to search through those systems to reconstruct the customer story before the next meeting. We call this digital transformation remarkably often for something involving quite so much copying and pasting.

Customer Success generates valuable intelligence

This is particularly frustrating because the information collected by Customer Success is not administrative debris. It is potentially some of the most valuable intelligence available to the business. CSMs hear why customers bought, whether their objectives are being achieved, what is preventing adoption, which projects are delayed, which competitors are appearing, what capabilities customers value or are missing, who really influences decisions, whether executive sponsorship is strengthening or disappearing, what could drive expansion and what could cause a renewal to fail.

That information should matter to Sales, Product, Marketing, Support, Professional Services and executive leadership. It should flow across the organisation. Instead, Customer Success platforms are too often designed primarily to collect information from the CSM so somebody further up the organisation can report on it. That is useful, but it is only half of what the technology should be doing.

Automation should give something back

A good Customer Success system should create a value exchange: the CSM provides intelligence, the system enriches it, the organisation benefits from it and useful intelligence comes back to the CSM. That last part matters. If I spend twenty minutes entering detailed customer context into a system but the system gives me almost nothing useful when I prepare for my next customer conversation, I quickly understand who the data entry is really for. It is not for me. It is for reporting.

That creates a motivational problem as well as a productivity problem. Notes become shorter. Fields are populated because they are mandatory. Health scores are updated because somebody created a dashboard showing which health scores have not been updated. CRM hygiene deteriorates. Management complains about data quality. The CSM complains about administration. And both sides are correct.

If data only travels upward, eventually data quality travels downward.

The information coming back to CSMs is often fragmented as well. Gainsight may know one part of the story, Salesforce another, the support platform another and product telemetry something else entirely. The CSM becomes the integration layer between systems that should already be integrated. That is a terrible use of expensive human capacity.

What useful automation should actually look like

Imagine opening a customer record before a meeting and immediately seeing that usage declined 18% over the last 30 days, three high-priority support cases were opened, the executive sponsor has not attended a meeting for 64 days, renewal is in 117 days, two success outcomes are behind schedule and adoption of another product area has increased significantly. Now the system is helping the CSM. It is taking information that already exists across the organisation and turning it into something actionable.

Compare that with: “Please update the customer health score. It has not been updated for 14 days.”

Those messages represent two completely different philosophies of Customer Success technology. One helps a CSM understand a customer. The other helps management understand whether a field has been completed. Both may sometimes be necessary, but we should be very clear about which one creates more customer value.

Why are we still building EBRs manually?

Executive Business Reviews are another obvious example. In many organisations, preparing an EBR still involves collecting information from Salesforce, Gainsight, support systems, product telemetry, success plans, previous presentations, meeting notes, spreadsheets, email and internal conversations, then manually turning all of that into PowerPoint slides.

Most of that information already exists electronically. The systems know the ARR, contract dates, purchased products, adoption trends, support history, open escalations, customer objectives, previous actions, renewal dates, expansion opportunities, stakeholders, product requests and health trends.

Most of an EBR should therefore be generated automatically. The CSM should spend time deciding what the information means. What story should we tell? What has changed? Where is the customer succeeding? Where are they struggling? What should we recommend? What should happen next? That is Customer Success work. Copying numbers from one application into another is not.

Bad automation creates another management trap

There is also a dangerous feedback loop. The team has too many customers, so leadership has less visibility into what is happening across the portfolio. To improve visibility, the organisation introduces more reporting, more fields, more health scores, more dashboards, more internal review meetings and more mandatory updates. That reporting consumes additional CSM capacity. CSMs therefore spend less time with customers, which creates less genuine customer insight, which creates more uncertainty and eventually more demand for reporting.

Too many customers → less visibility → more reporting → less customer time → worse visibility → more reporting.

Technology should break that cycle. Too often it reinforces it. Automation should not primarily exist to make CSMs cheaper or easier to supervise. It should remove low-value work so people can spend more time understanding context, building relationships, interpreting information, navigating ambiguity, advocating internally and helping customers make decisions. Management visibility should be a natural by-product of a well-designed system, not its only meaningful output.

This is not an argument for unlimited headcount

None of this means the solution is simply to hire more CSMs. Customer Success has to be economically sustainable. Companies should absolutely use automation, AI, digital Customer Success, better segmentation, integrations, product telemetry, self-service and communities to increase the number of customers a team can successfully support. But automation can increase capacity. It cannot make capacity infinite.

The problem is not necessarily having 30 customers. Thirty customers may be entirely reasonable in the right service model. The contradiction appears when somebody has 30 customers while the organisation behaves as though all 30 are entitled to high-touch, proactive and strategic Customer Success. You cannot simultaneously optimise Customer Success for maximum relationship depth and maximum portfolio size. At some point, leadership has to choose.

There is an economic argument here as well. A CSM is an expensive professional resource. If a significant percentage of their week is spent moving information between poorly integrated systems, preparing repetitive slides or entering duplicate data, the company is effectively paying professional salaries for manual integration work that software should be doing. That is not just frustrating for the CSM. It is bad business.

Caring makes the problem worse

There is another uncomfortable part of this. The people most likely to suffer under an overloaded Customer Success model are often the people who care most about doing the job properly. If you genuinely care about customers, unfinished work bothers you. You prepare after hours, answer the email in the evening, spend more time investigating the escalation, join the extra call and try to protect the customer from an internal problem they should never have experienced in the first place.

For a while, this looks like commitment. Eventually it looks like burnout. The organisation may even reward the behaviour before wondering why its best people keep leaving.

So why did that webcast make me want to become a manager?

Ironically, while the speaker was explaining all the reasons management might be undesirable, I found myself thinking: Maybe management is exactly where I should be. Not because I believed it would be easier, and certainly not because I wanted fewer meetings.

I wanted the ability to influence the environment in which people were being asked to work. I wanted to build teams where workload was treated as an engineering problem rather than a motivational problem. Where assigning another five customers required a conversation about capacity rather than another slide explaining the importance of prioritisation. Where managers were expected to push back when the team was full. Where coaching meant helping people become better at their jobs rather than teaching them increasingly sophisticated ways of surviving impossible workloads.

I wanted training, tools, processes and automation that gave people time back. I wanted the information collected by CSMs to become useful intelligence for the whole company rather than disappearing into reporting systems. And I wanted Customer Success leadership to understand that customer experience and employee experience are connected. You cannot continuously overload one and expect the other to remain excellent.

The right reason to become a manager

My original conclusion was slightly tongue-in-cheek: “I want to become a manager. The right choice for the wrong reasons.” Having actually become one, I would phrase it differently today. Management should not be an escape from individual contribution. It should be an opportunity to fix some of the conditions that make individual contribution unnecessarily difficult.

A good manager cannot eliminate pressure or magically create headcount, and sometimes the organisation itself makes good management remarkably difficult. But managers can challenge bad capacity assumptions, protect focus, remove unnecessary work, push for automation that genuinely helps the team, demand better integration between systems, coach people and escalate systemic problems rather than normalising them.

And perhaps most importantly, they can recognise when the answer to excessive workload is not another productivity workshop. Sometimes the answer really is: There is too much work. Sometimes it is: We are making people do work that software should already be doing. And quite often, it is both.

The short version

A manager should have a sensible number of people to manage because meaningful relationships require time. The same principle applies to Customer Success. If we accept that one manager cannot effectively coach 20 or 30 direct reports, perhaps we should stop assuming that one CSM can build 20 or 30 strategic customer relationships simply because the CRM allows us to assign them. Before simply adding headcount, we should also make sure we are not wasting the capacity we already have on manual reporting, disconnected systems and administration that could be automated.

Good Customer Success design is not about choosing between people and technology. It is about using technology to protect the time people need to do the work technology cannot do.

Management is hard. Individual contribution is hard. The real leadership challenge is designing an organisation where neither needs to become unnecessarily hard.