Common People & HR Operation Pain Points: Lessons From A Decade in Tech Leadership
After more than a decade as a C-level executive building tech startups, I've come to recognise a universal truth: your people operations can make or break your business. At MyBento, we're focused on solving the most critical HR challenges facing growing organisations. I wanted to share some of the most significant pain points I've personally encountered throughout my career, and the lessons I've learned along the way.
Operating Without Dedicated HR Support
In the early stages of building companies, I often found myself juggling critical people matters alongside everything else required to achieve product-market fit and sustainable revenue. The harsh reality is that you tend to underestimate the complexity of people management until problems surface—and by then, the damage is often done or more costly to fix.
What became abundantly clear through experience is that your company is only as great as the people who make up your team—those who truly embody your mission, who go above and beyond to see the company succeed, and whom you can trust implicitly. While this seems obvious, it's remarkably easy to lose sight of this fundamental truth when you're consumed by the daily pressures of building a viable business.
Key Lesson: Invest in people matters from the beginning. Your team isn't just executing your vision—they are your company. When you're building a business, it's tempting to focus exclusively on product development and customer acquisition, but neglecting your people operations will eventually undermine everything else you're working toward.
Creating an Attractive Employee Value Proposition with Limited Resources
I distinctly remember dreading the question during candidate interviews: "Do you offer any benefits?" Early on, we had neither the resources nor the infrastructure to manage comprehensive benefits packages.
What I eventually discovered was both surprising and enlightening. You don't need fancy offices with expensive coffee machines and table tennis tables to create an attractive employee value proposition. What truly matters to most people is having amazing colleagues they can trust, doing meaningful work, and having flexibility in how they work.
However, we had naively assumed people would simply take care of their own benefits. The reality is that remarkably few individuals budget appropriately, save for retirement early enough, or fully understand the consequences of not having medical aid coverage. According to research from Sanlam, only 21% of South Africans don't feel stressed about their monthly personal finances. We as employers should take more responsibility in educating and guiding our teams on making important decisions that impact their financial and overall wellbeing. This isn't just good for your people—it's good for business too. According to WellRight, employees worrying about their finances cost businesses around 12.5 days of lost productivity per employee annually. Nearly half of all employees admit that financial worries directly affect their focus at work.
Key Lesson: Even with limited resources, you can create a compelling employee value proposition by focusing on building a team of exceptional people and providing the guidance your employees need to make sound financial and wellbeing decisions. This investment pays dividends in both retention and productivity.
The Recruitment Challenge
Without dedicated HR support, recruitment was one of the most overwhelming aspects of people management. Placing job advertisements, sifting through hundreds of often irrelevant CVs, conducting countless interviews, and attempting to maintain a repeatable hiring process that reliably evaluated candidates' capabilities while also exciting them about our company—all of this consumed enormous amounts of time and energy.
Perhaps the most difficult realisation was confronting an uncomfortable truth about myself: I wasn't naturally gifted at evaluating candidates! I would often see in people what I wanted to see, painting optimistic pictures of how successful they might be in the role rather than objectively assessing their actual capabilities.
What fundamentally changed our hiring success rate was implementing more objective evaluation methods and including team members with different perspectives in the interview process. I began recruiting colleagues who were particularly good at judging people, as well as those who were less invested in a particular candidate's success. Creating a test framework that allowed us to objectively compare candidates' capabilities helped keep me honest about their actual qualifications and potential fit.
Key Lesson: Create a structured, objective hiring process that doesn't rely solely on your judgment. Include multiple perspectives in the interview process, and implement skills-based assessments that allow for meaningful comparison between candidates.
The Onboarding Documentation Nightmare
By the time new joiners completed all the necessary paperwork related to FAIS, Data Security, PCI, POPIA, and other regulatory requirements, they might have thought they'd accidentally joined the CIA rather than a tech company. These processes were rarely documented properly, and different team members often relied on their own checklists because requirements kept changing and growing.
The result was that a senior executive always needed to oversee the process, making it inefficient and inconsistent. Beyond the paperwork, we struggled with ensuring that each person received the information they needed and that the onboarding journey properly reflected our company culture.
Key Lesson: Invest time in creating a well-documented, streamlined onboarding process that balances compliance requirements with your company culture. A positive onboarding experience sets the tone for an employee's entire journey with your organisation and significantly impacts retention.
Performance Management That Actually Works
When it came to KPIs, OKRs, goals, and performance reviews, I always approached the process with a sense of dread, knowing how time-consuming it would be if done properly—especially with larger teams and multiple direct reports, not to mention the complexity of 360-degree reviews.
Through experience, I observed that team members consistently valued feedback that came more frequently than standard annual or bi-annual review cycles allowed. While I'm not certain I ever fully optimised our KPI framework or the objectivity of its measures, what became clear was that people need regular feedback as their work progresses, not just during formal review periods.
Our most successful approach paired formal evaluation processes with regular check-ins and collaborative team goals that aligned individual contributions with collective success. Setting a substantial portion of goals, OKRs, or KPIs at the department or team level—where each team member shares a set of common objectives—proved particularly effective in ensuring alignment and fostering collaboration toward common goals rather than having individuals focused solely on their personal development.
Key Lesson: Growth as a team means growth for individuals. Complement your formal performance management system with continuous feedback, and consider implementing team-based goals that encourage collaboration and shared success.
Administrative Burden
The day-to-day administration of people operations consumed an inordinate amount of time and created frequent frustration:
Leave management was a constant challenge—chasing people to log their leave, planning for busy periods, remembering which team members were on leave (why wasn't this automatically displayed in calendars?), updating leave approvers, and maintaining visibility into leave balances for team managers (not just payroll administrators).
Communication around bonuses and increases created another layer of complexity. We wanted to personalise these important messages, but we also needed to ensure that no information was mixed up when transferring data from spreadsheets into emails for increase letters. The disconnect between spreadsheets, finance/payroll and HR systems created unnecessary risk and complexity for some of the most important employee touchpoints.
This begs the question: why are finance/payroll and HR systems so disjointed when it comes to some of the most critical matters affecting employees?
Key Lesson: Streamlined, integrated HR systems are not a luxury—they're a necessity for growing organisations. The administrative burden of managing people operations without proper tools diverts focus from strategic priorities and creates unnecessary risk.
Looking Forward
These challenges—operating without dedicated HR support, creating compelling value propositions with limited resources, managing recruitment and onboarding, implementing effective performance management, and handling administrative burdens—represent some of the most significant people operations pain points I've encountered throughout my career.
At MyBento, we're working to address a lot of these challenges by creating solutions that reduce administrative burden, improve employee experience, and allow growing organisations to focus on what matters most: building great teams and successful businesses.