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Writer's pictureKen Tan

Career Conversations That Matter: A Manager's Guide to Meaningful 1:1

Sheila is in the mid-career stage. She leads a team of 8 people after building up a track record in engineering. She wonders where her next growth is, and is interested to have a decent chat with her direct report but does not see these conversations popping up in the company. 


Tom is a young talent. He works as a Marketing Executive for a consumer goods firm.  Spending 3 years in his role, he is hoping to progress upwards and wonders if the organisation offers progression. He is keen to talk to his Head about this but cautious of asking given the unspoken cues in the team culture – fearful of being seen impatient.


Employees in the above scenarios are interested in having career conversations with their bosses.


There are many benefits – increase employee morale that will drive future performance, deepen camaraderie for closer collaboration and retain talent to save hiring cost.


However, Sheila and Tom resists the action to do so. 


Here are 3 quick ways that Line Managers should do to create the space for career conversations: 


  1. Develop a culture of career relatedness 

People love working with one another and opening their thoughts once there is a deep sense of trust. This entails the right environment for solid work relationships to flourish. 

An easy approach is to use eCards.  Encourage your staff to send informal appreciation notes with funny GIFs images (beyond just “thank you”) to one another, even for small achievements. 

Use a soft environment setting in the room to set the stage right. For example, bright-coloured tables and chairs. Ask if he/she needs a hot coffee or tea. 

Thereafter, nudge them to share anything insightful. Assure them that none of their views will be judged or graded.

Strongly highlight that anyone, regardless of seniority, can voice out but in a responsible and constructive manner. Suggest them tapping into their colleagues' expertise in a private 1:1 coaching, not necessary have to constantly turn to you. Call out their actions if anyone do so. 

Strong camaraderie leads to staff speaking up, which thereafter potentially leads to meaningful career conversations with the Line Manager during 1:1 check-ins. 


2.Use informal career tools to flesh out insights

People may feel time is wasted doing personality assessment.  Sounds too much for them.

How about using quick visuals such as “Points of You” cards during 1:1 career conversation? 

Cards are used to generate answers in an interactive way. Line Manager focuses on using the information to probe further.  The employee will feel that the Line Manager is vested in their career interests. 

Another option is to use pictures of things, equipment or even animals. Identify the image that closely resonates with the staff, and ask why they are affiliated with the object. Then discover their values or beliefs that can be related to the workplace. 

Someone who likes a Tiger because he sees the animal as a relentless predator. Does the staff uses the characteristics of a Tiger, thus exhibiting a go-getter, result-oriented attitude in work? 

What other attributes do he see in a Tiger? 

A Super Achiever in Work?

Due to the "tiger" nature -- is he often seen as using "passive-aggressive" in working style? 

Lots of valuable intelligence to frame up without telling your team member. 

The Line Manager can also share external resources in YouTube or evidence-backed articles to draw out inferences. Remember to take an unbiased view, refrain from sharing your personal experience and gently remind that he/she is in a confidential environment to share. 

While getting the information from the employee, write the key points to follow up in the next 1:1 chat -- as agreed between both parties. 


  1. Learn essential helping skills

From my observation in career conversations, I gather that Line Managers are interested to steer the right words, use the appropriate tonality and body language to get the "buy-in" from their team members.  This will intrinsically motivate them to better performance. 

Majority tells their staff or direct them what to do. What if, there is a way to empower them to see through the purpose of what they do, and align to their overarching goal?

To do this, helping skills such as paraphrasing, reflective and clarifying are excellent methods to dive deeper. Use the 5Ws 1H. (who, what, when, why, where, how) for short and punchy questions, maintaining the flow and sense-reading the employee's psychological state. 

Equip the Line Managers in these capabilities, so that they can find out the triggers in the individual and thereafter know how to motivate them. 


Ken uses his experience and knowledge in career development to help HR leaders meet a set of outcome in companies, or individuals effectively manage transition and growth. He also addresses issues faced such as burnout, change of job scope, retrenchment and many more. For a chat with Ken, reach out to ken@bluesky.net.au

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