askST Jobs: Am I being ‘difficult’ if I speak up at work?

In this series, business journalist Timothy Goh offers practical answers to candid questions on navigating workplace challenges and getting ahead in your career. Get more tips by signing up to The Straits Times’ Headstart newsletter.

Q: Will speaking up about what I dislike at work affect my career? Does likeability trump hard work?

Speaking up at work can strengthen a career or quietly stall it. It often depends on how the message is delivered.

Many organisations publicly encourage openness and even hold townhall meetings for staff across different levels of the hierarchy to speak up. Yet in practice, workplaces are still social systems shaped by perception, trust and interpersonal comfort, said David Leong, chairman of PeopleWorldwide Consulting.

“A highly competent employee who is consistently perceived as combative, dismissive or perpetually dissatisfied may gradually be labelled ‘difficult’,” said Leong.

“Such a label is hard to erase and people will repeat it like a chorus in a song, even if the substance of the concerns raised is valid.”

This is why likeability can sometimes appear to trump hard work, said Leong.

In reality, what often matters is not superficial popularity, but relational capital – in other words, whether colleagues and leaders trust you.

“People promote individuals they trust to manage complexity without creating unnecessary friction – career progression is therefore influenced not only by output, but by emotional regulation, communication style and the ability to disagree constructively,” said Leong.

But silence is not necessarily safer.

Employees who never speak up may preserve short-term harmony, but risk long-term disengagement, ethical compromise or invisibility.

They may also come to be seen as overly passive, or labelled as people there is “no point asking” because they rarely offer constructive views.

“In such cases, self-preservation can slowly turn someone into an inconsequential cog in the organisation,” said Leong.

Jack Chong, director of Emerge Consulting, said employees should, where possible, raise concerns privately first.

One-on-one conversations give others space to process feedback without feeling exposed or defensive, helping to keep the focus on resolving the issue rather than reacting emotionally.

When speaking up in meetings, it can also help to lead with the shared goal rather than the problem itself.

Instead of saying, “That won’t work”, employees can try phrases such as “I want this to succeed. Can we pressure-test one assumption?”

“The message may be similar, but the tone becomes more constructive and collaborative,” said Chong.

Employees should also try to suggest solutions or offer support when raising concerns.

Even phrases such as “I’m not sure yet, but I’m happy to look into it” can shift how someone is perceived, from a colleague who only critiques to someone who contributes, said Chong.

“Pairing concerns with ownership signals that you are invested not just in identifying issues, but in helping improve outcomes,” he added.

Leong said that ultimately, organisations do need constructive challengers, particularly in environments facing rapid change, governance risks or innovation pressures.

Many major corporate failures occurred not because no one saw the problem, but because nobody felt safe enough to voice it, and groupthink sets in, he noted.

“In workplaces, especially under economic uncertainty, employers increasingly value employees who can combine candour with collaboration,” said Leong.

“The best way is to put up a problem accompanied by probable solutions, not to act like a complainant but with no answers.

“The most respected professionals are often not the quietest people in the room, but those who can disagree without destabilising trust.”