Adulting 101: My friend lost her job after failing probation. Here’s how to ask your boss about your progress

SINGAPORE — When my friend told me recently that she had left her job after failing her probation at work, I couldn't understand why. After all, everything seemed to be smooth sailing in her first few months on the job.

I'd never heard her say that there was negative feedback from her bosses about her performance until her three-month probationary period was extended by a month. In the end, it didn't work out.

She, too, was surprised. She said that even though she had never checked with her supervisor about her work performance during the initial three-month probationary period, she wasn't told anything to raise concerns during the course of her work. 

"Suddenly, everything I'd been doing so far wasn't enough. They expected more.

"Maybe I should have had more frequent check-ins with my boss. Maybe my boss was too busy to tell me I needed to buck up," my friend lamented.

It got me thinking. Some might say that "no news is good news", but when your performance and livelihood are at stake, does that maxim really hold true?

And it led me to ponder other questions.

How should employees have a constructive conversation with their bosses? Should they be more proactive in doing it?

Is such a chat as simple as asking, "Is everything okay with my work so far?". Or does it have to be more thoroughly thought out, even if it's not an official performance appraisal? 

Curious, I took these questions to two human resource experts to figure out how best to navigate such conversations. 

PREPARING FOR THE CONVERSATION

Before you start the conversation, there are several things to note.

First, timing is crucial. You don't want to have such a conversation when your boss is super busy or in a bad mood. 

Mr David Blasco, country director of recruitment agency Randstad Singapore, said that choosing a moment when the boss isn’t overwhelmed or distracted ensures a more productive discussion.

It is also best to schedule a meeting in advance rather than bringing up serious matters unexpectedly.

"Additionally, discussing performance before the company’s promotion cycle can work in an employee’s favour. This allows the employee to align their performance with expectations ahead of time."

On initiating the conversation, Mr Blasco also said that the employee should politely approach their boss and request a meeting, asking something along the lines of: "Could we schedule some time to align our expectations on my performance to help me prepare for the review?"

He added: "While providing all the details in advance is unnecessary, offering a brief context, such as 'I’d like to discuss my role and future opportunities', helps set expectations." 

Mr Jonathan Lasenby, technology head at recruitment consultancy Ethos BeathChapman, said that some leaders, unfortunately, do not arrange structured and regular meetings on performance.

Sometimes, communication is inadequate, leading to employees being uncertain of how they are doing. This sounds exactly like my friend's plight.

"As employees, rather than becoming frustrated at a perceived lack of recognition, it’s important to be mindful that some leaders may have a lot on their plate or are fighting fires on other matters," Mr Lasenby said. 

"Some finesse is required to determine how often your check-ins should be. But generally speaking, many would say a quarterly or biannual check-in — whether a fixed meeting, informal catch-up or clear communication about performance — is acceptable."

Once you've set that date, some work must be done beforehand.

Mr Blasco advised young professionals to take stock of their own performance and note key achievements and areas for growth before speaking with their managers. 

This can be done by collecting data, metrics or feedback to support their performance, such as goals that they helped their team achieve, a quantifiable return of investment (ROI) for a project if that's relevant, or positive emails and testimonials from colleagues, clients and bosses.

And if you seek a raise, Mr Blasco said that employees should also prepare by researching industry salary standards, then express their request confidently but respectfully during the conversation.

STAYING PROFESSIONAL DURING THE CONVERSATION

When the conversation is underway, Mr Blasco said that a concrete way for employees to understand if they’re growing at work is to ask the boss if their performance aligns with their key performance indicators and whether their output contributes meaningfully to team objectives.

He suggested that employees may start by asking: "How do you think my performance aligns with the targets we discussed?"

This would open the door to specific feedback. 

Another important question is: "What should I focus on in the coming months to ensure I stay on track (or to get back on track)?"

As the manager responds, it is important that there be active listening and the employee should keep a positive mindset, especially when some feedback can be hard to hear, both experts emphasised.

Mr Lasenby said that employers or managers who have to provide less-than-positive feedback may also find it challenging to deliver the message directly and empathetically without hurting the employee’s confidence.  

In such cases, it is advisable to keep an emotionally balanced mind when hearing feedback, collect your thoughts and respond professionally. 

"You absolutely do not want to say something or react in a manner that may be regrettable further down the road," he added. 

Elaborating on this, Mr Blasco proposed using constructive and forward-looking language such as "I appreciate your feedback" or "I see this as an opportunity to improve".

He also said that it is best to avoid being defensive — by acknowledging areas for improvement and expressing a desire to work on them.

This may be conveyed by saying, "I see where you're coming from" or "I’m committed to making these changes".

"Ask for specific examples to clarify any feedback and suggestions for improvement, such as 'What can I do to strengthen my performance?' or 'How can I better align with the team's goals?'

"This approach keeps the conversation focused on professional growth and development." 

THE FOLLOW-UP 

After the conversation, Mr Lasenby said that the onus should be on the manager to have a clear and decisive action plan, but employees may take it upon themselves to follow up the discussion with a write-up of their understanding, action plans and mutually agreed-upon objectives.

"Locking things in, so to speak, can provide a clear record of what to track against. Lots of what is said during these conversations can 'go missing', so having a clear paper trail afterwards is important."

Then, of course, you have to walk the talk. 

Mr Blasco said that one common mistake employees make is failing to act on feedback, which could signal that they are not committed to their personal development.

"Hence, these conversations can help address issues before they become bigger problems and ensure that individuals are aligned with team goals.

"They also allow employees to discuss their progress, clarify expectations and express any concerns or ideas they may have."