As a Manager, I Always Ask My Team This Unique Question

Only a fraction of a manager’s job is managing work. The larger (perhaps most important) aspect is managing people. And by “manage” I don’t mean “micromanage” — I mean caring for the wellbeing of one’s team so that they can do their best work.

I was the product manager and director of a customer success team at a fintech for many years. I managed seven people whose responsibilities ranged from customer onboarding to customer support. Like a good manager, I met with each team member 1:1 on a regular basis.

But it can be tempting for managers and employees to go through a list of the work that got done. That is not the purpose of a 1:1. Understanding the work and results can come through email, Slack updates, or tools dedicated to project/task management.

During a 1:1, I was trying to assess the less objective parts of the job. What challenges are being faced? What clients were being problematic? And how could I help?

I learned to ask, “Has anything weird or unusual happened to you lately?”

It may seem like an odd question, but it ended up being the most telling and often the most constructive.

Helped me understand challenges and roadblocks

At a very basic level, asking if anything unusual had come up helped me understand how employees were spending their time. And I don’t mean that in an overbearing time-tracking kind of way. I mean things out of the ordinary that might be pulling their focus from other responsibilities or causing a lot of distractions for the team.

For example, as a fintech, it was common that new product releases would cause an influx of calls and emails to the customer support line. Some of these were quick to resolve. Others were difficult and time-consuming. The support team expected this with new releases, but if a lot of strange issues were arising, it was problematic.

Some employees got stressed or frustrated when the customer support volume was high. Talking about things that detracted from day-to-day work allowed me to assure them that other responsibilities could take a backseat for a while, providing better workload balancing.

Other employees talked about strange or unusual issues with pride. They would eagerly talk about how they worked through the problem and figured it out. It was an opportunity for me to learn from them — the people working directly with customers on a day-to-day basis. I’d praise their effort… and make sure that the resolution was passed along to the rest of the team.

Gave me an opportunity to coach and mentor

Sometimes, employees would bring up client issues that gave me an opportunity to shed some light or provide solutions from my past experience.

Employees often get tunnel vision, even in the most open of organizations. They focus only on the problem at hand and don’t always think to ask, “Has anyone else dealt with this problem before?”

When employees brought up weird issues that they were facing in their roles, I was sometimes able to say, “Actually, your colleague so-and-so dealt with something similar. You might want to ask them how the issue was solved.” As the manager, I had a clearer view of all issues that the team was facing.

It was also a chance for me to help the employee find solutions. If the issue was truly unique, I would ask the employee how they would handle it. I’d also give some feedback and let them know that I might handle it differently or provide additional suggestions. I was empowering them to make decisions, but the solutions were something we discussed together.

Opened the door to commiserate and escalate

There were always instances where employees simply needed to let off steam about client-related problems. Asking about “weird things that have come up” occasionally turned into venting sessions.

At these times, I started as a listening ear. I let the employee know that I understood that the client was being difficult. But I’d also remind the employee that as a “weird issue” this would eventually pass. Or it was an opportunity to talk through how we could handle similar issues better in the future.

In other cases, the vent made me aware that the employee was completely stuck. Maybe the issue was taking too long, maybe the client was furious, maybe the employee had no idea how to solve the problem.

If I noticed that the issue had reached a boiling point, I would step in as the manager to get the employee additional help. I might ask a different employee with specific expertise to step in. Or I might tell the employee to send the client to me and I would deal with the client’s dissatisfaction.

My team knew they could come to me with issues like these and often didn’t wait for our 1:1 meetings. However, there were times when employees were trying so hard to solve the problem on their own, and it just wasn’t working. By the time we got to the 1:1, if I felt like the issue had gone on too long, I’d gently let the employee know that it was time to get someone else involved.

While I wanted my team to learn through problem-solving, I never wanted issues to reach a stage where everyone was frustrated. That didn’t serve the employees or the customers.

Provided insights into how the employee was feeling

From identifying “weird things that have come up” I got a sense, overall, about the employee’s current temperature. How the issue was described told me a lot.

Some were excited by issues they had not seen before. The issues were like mini-puzzles that needed to be solved. Others were overwhelmed and needed help or guidance. When I was onboarding new employees, a lot of issues were new or strange. Talking through them gave me a chance to point out internal resources that were available.

And there were also times when employees would bring up issues that they otherwise wouldn’t have mentioned. This sometimes indicated that something else was going on — sometimes outside of work.

I noticed this in particular at the onset of the pandemic. Many of my employees had small children that were home due to school closures. Answering non-routine support-related questions became a strain: the employee tolerance for devoting a lot of time to a single issue plummeted. That was something I heard across the board and something I needed to address: how to ease that burden.

As a manager, it was my job to have a pulse on the department. I needed to understand how each employee was doing, how well they were working as a team, and how the customers were being served.

The generic question “How are things going?” doesn’t always elicit forthright responses. Some employees would gloss over their struggles or respond in the same generic fashion with “Things are fine.”

Asking “Has anything weird come up?” gave me so many insights. After listening and assessing, I could put on one of my coach, cheerleader, or problem-solver hats.

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