From The Straits Times    |

Do you have a professional dilemma that’s worrying you? In Work Therapy, founder of Threshold Allies Karen Tay helps working professionals navigate sticky situations. If you have a question for Karen, you can email us at or slide into our DMs at @herworldsingapore on Instagram.

Dear Karen,

As Managing Director, I lead more than a hundred people regionally, and don’t have much time to spare. I am empathetic towards my team members’ challenges, but get frustrated when their self-awareness gets in the way of their performance. For example, one of them is very capable, but defaults to blaming other teams when things aren’t going well. Another is very hardworking but often works with haste, tending to leave out important stakeholders. How do I know how much to invest in and coach them, versus simply let them go? 

Dear Managing Director, 

It’s an honour to respond to your question. First, let’s acknowledge that you’re not alone in feeling torn between empathy and frustration when team members fall short of expectations. It’s entirely natural to swing between these emotions, especially when you genuinely care for your team members’ success, which I can tell you do. 

As a senior leader, having a systematic plan can help you navigate these conflicting feelings and take actions that you can stand by. 

First, identify the facts

Start by pinpointing specific instances where team members’ lack of self-awareness hinders their performance and team dynamics. As leaders, we can get vague ‘feelings’ or ‘impressions’ about someone’s behavior, which are difficult to validate if we don’t record the facts.

Once you have the facts, give them feedback when you notice it, rather than wait for issues to boil over. For example, “hey, when I asked you why our Q2 numbers were trending downwards, you immediately said it was because the other team wasn’t pulling its weight. As a company leader, I expect you to provide a rounded assessment of what we, as a team, can do to turn things around together.” 

Second, assess their coachability over three months

While we want to give others the benefit of the doubt, we also need to assess their speed of growth over a limited time period. There are several factors that determine coachability. 

  • First, accountability: when feedback is given, do they acknowledge their role and room for improvement, even if multiple other parties/systems also have room for improvement? Do they show marked behavioral improvement in response to feedback?
  • Second, curiosity: do they seek out alternative perspectives and seek to understand the impact of their actions, or do they surround themselves only with people who agree with them? 

Note that pushing back in the moment doesn’t disqualify them from being coachable (all of us have defense mechanisms, whether to fight or flight). I suggest giving it three months because it takes time to observe patterns and responses to feedback.

If you observe that someone is not coachable over this time period, it is time to put them on an exit path. Beyond this, the amount of time you spend giving feedback exceeds the value to the team. 

What if they demonstrate coachability? How much should you invest in helping them improve? 

Third, evaluate the extent to which their skills are a good fit for the current stage of your team

In fast-growing industries, business needs change rapidly. For example, the person who was a good sales leader when the product was still nascent, might not be the right sales leader for the current stage, when there is product-market fit and scaling up is required. 

As Managing Director, you will re-evaluate your team members’ skills fit every few months. If the team member has a high skills fit for this current stage, I would allocate my time and organisational coaching resources to their growth as I believe they would be the culture and standard-setters for this stage of the business. 

If the team member’s skills fit is declining for the current stage, I would give them feedback and suggest that they invest in their personal growth such as seeking out and paying for their own coach. 

Finally, don’t hesitate to seek support from a coach or mentor yourself

Role-playing scenarios and discussing your concerns with someone outside the situation can provide valuable perspective, giving you more confidence about your decisions. 

Empathy is a valuable asset in leadership, and it’s essential to find a balance that allows you to support your team while also upholding standards and expectations. Kudos for reaching out for support and perspective! 

Best of luck, 


Karen Tay has held senior leadership and advisory roles in the Singapore Government and start-ups in Singapore and Silicon Valley. She currently runs Threshold Allies and Her Life Ally, where she supports global leaders in navigating high stakes situations and transitions. Got any questions for Karen? Email us at at or slide into our DMs at @herworldsingapore on Instagram.