A friend resigned last week. Her boss found out at 10am. By noon, she had cleared her desk and started her one-month notice by taking one month of accumulated leave. She never returned.
Good employees often leave before they tell you how unhappy they are
This is every leader’s nightmare. You lose someone good with no warning. Their work gets redistributed overnight. Projects slow down. Team morale drops. Recruitment takes months. Replacing a mid-level analyst costs between six and nine months of their salary. But the real cost is invisible. You lose institutional memory. You lose the glue that holds teams together.
Informal conversations reveal things formal check-ins missMost organisations shrug and say there is nothing they could have done. The truth is, much of this is preventable. And it does not require expensive benefits or grand HR programmes. It requires $10 per employee and 30 minutes of a leader’s time each month.
These are three things I have seen work in practice, across government, Fortune 500 companies, and even Nvidia.
1. A $10 coffee can create more honesty than another survey
Early in my career, I hit a wall. I had reached management but was relatively young in that tier. The unspoken rule was to wait our turn. Promotions went to those who were more senior and had a bigger work scope. It was disappointing to do good work, get good grades but had to stay where I was. I was frustrated enough to consider leaving.
Then I met a director from another unit at the gym. Between sets of squats and pull-ups, we talked about work. He saw how much I was trying. Three months later, he offered me a lateral move. It wasn’t a promotion, but it gave me space to grow and a boss who believed in me. That kept me for another year.
Most employees never get this chance. They do not know leaders outside their chain of command. So when they feel stuck, they immediately look outside because they cannot see any internal path.
One organisation solved this with something very simple. Every employee received a $10 Starbucks card with a single rule. Use it with a boss from a different department. That tiny gesture created conversations that would never happen naturally. People learnt about roles they did not know existed. They built relationships across the organisation. And when someone felt stuck, they had someone new to ask, “Is there space in your team?”
That $10 breaks the single-boss bottleneck. Employees stop feeling trapped by one person’s view of them. Leaders get early warning signs of employees leaving. And organisations buy time to fix the real issue before resignation becomes the only option.
2. Informal conversations at skip-level reveal things formal check-ins miss
A friend joined an organisation on the promise of a promotion to a better pay scheme. Within three months, it was clear HR would not approve it. He also clashed with his immediate boss. She thought he was too blunt. He thought she was too defensive. Their relationship deteriorated fast. He wanted to quit within the first quarter.
What kept him was a skip-level boss who quietly stepped in. He checked in casually. He asked what my friend was working on. He brought his work up in leadership meetings. He tried to get the promotion approved. My friend still left in the end, but he left on good terms. And the skip-level boss was not blindsided and felt he had done his best to keep my friend.
One leader I know does this systematically. Every month, he meets a group ten officers from across his directorate. It takes him just 30 minutes a month, 6 hours a year. That time surfaces problems early. It makes people feel seen. And it reduces the number of “I had no idea she was about to quit” moments.
If you feel too busy for this, consider what Jensen Huang does at NVIDIA.
To cut through layers of filtered reporting, Huang created the “Top Five” emails. Every week, every employee writes an email to their team, their manager, and distribution lists that Huang can access. They list the top five things they are working on or observing. Customer pain points. Competitor activity. New technologies. Delays. Every Sunday, Huang reads these emails with a glass of Highland Park whisky. He asks follow-up questions. People know the CEO sees their work directly. What began as a way for him to spot process problems and market trends became a way for employees to feel connected to leadership. This costs nothing except an hour of a leader’s time each week. And the impact shows up in retention. Nvidia has some of the longest work hours in tech. On weekends, they are expected to respond to emails within two hours. On weekdays, people work 60 hour work week. Yet Nvidia’s turnover is 2.7 percent, way better than the semiconductor industry average of 17.7 percent and Singapore’s national average of 7.6 percent. High pay alone does not explain why they stay. Plenty of companies offer good pay and still lose talent. We should not discount the power of people staying because they feel seen.
3. Let people test other roles before they test other companies
At MasterCard, we have a programme called Unlocked. Employees can spend 10-20 percent of their time working on projects in a completely different department. Any directorate can list opportunities. Anyone can explore them. This creates optionality. And optionality creates retention.
I know someone using this now instead of quitting. She is feeling unsatisfied in her current role because she gets little direction from her boss based overseas. She has no close colleagues locally. She once told me, “If I die tomorrow, nobody in the office would know.”
But instead of resigning, she is using Unlocked to explore new opportunities with the business development team. She is discovering roles inside the company that may fit her better. If she still feels stuck after six months, she can move laterally. She will not need to leave entirely. The receiving teams get free help. My friend finds a place where she feels fulfilled. Our company avoids the cost of attrition. It is rare to find a retention strategy that costs nothing and benefits everyone involved. This is one of them.
Do you want to build your personal brand on LinkedIn?
I work full time, so if I only wrote when I have an uninterrupted hour every evening, I probably wouldn’t have built much of a LinkedIn presence.
What I do is that I collect my stories while I’m walking, cooking or tidying the house in a “story bank”, then sit down and edit them into articles later.
I’ve tested a few dictation tools over the years, including including ChatGPT and Wispr, but Typeless is my favourite because it understands my Singaporean accent. It’s also smart enough to edit our my “em’s”, “ah’s”, copyedit out my rambling, and use numbered bullets whenever I start making a list.
If you’ve always wanted to build a LinkedIn presence but felt you didn’t have the time to write, try this out: https://www.typeless.com/?via=eileen
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