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Dilanka Dilanka is a Business Development Manager at IceHrm. You can contact her at dil[at]

How to Have Great New Year Career conversations

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We always believed that the most important task for any leader is to get the next generation of employees ready for bigger tasks – and meaningful career conversations are a great way to achieve this.

There is nothing more uplifting than getting an unexpected message from a former co-worker, employee or mentee acknowledging how much their career has improved following the conversations that we had in the past.

As we embark on a new year, it’s an important time for employees to reflect on their careers and, in most companies, this is also a time when many career conversations take place.

To make these conversations as fruitful as possible, there are four principles and four rules for managers, coaches, mentees and HR to consider.

Principle 1: Encourage continuous dialogue

It trumps one-off career conversations. Career conversations have historically been attached to the appraisal process – break with this tradition! Career and performance/reward conversations are separate and follow a very different logic and choreography.

Career conversations are never one-off conversations. It is ongoing dialogue over time.

Principle 2: Prepare, prepare, prepare

Stick by this principle no matter whether the conversation is with someone working for you, someone you coach, or simply a person in your organization that seeks help or guidance.

Take at least one hour to read the CV and try to understand it. Think about what stands out and consider what you think is missing. Try to put yourself in the person’s shoes, understanding not only the professional dimension of the person but the broader context in which the person operates.

Principle 3: Listen and ask questions

We have all seen movies where the patient talks at great length and the therapist remains mostly quiet. The same principles apply to career conversations – become the therapist.

It is your role to understand what your counterpart really wants, is passionate about or dreams of.

Principle 4: Build confidence

Of all the principles, this is probably the most important and most difficult to achieve.

Most organizations are not good at telling people where they stand. Equally, they are not transparent about why people are being promoted and it’s highly likely that the person you have career conversations with will have seen promotional announcements where they would consider themselves a better candidate.

This erodes confidence. Candidates from diverse backgrounds are more typically affected by this phenomenon. Drawing out the individual’s unique ‘selling points’ and developing career scenarios that build on these strengths can be very effective.

Rule 1: Create an appealing and safe-space environment

Having a career conversation is a big deal for most employees in an organization – they prepare and have great expectations. Of course, many will be nervous, but it is your role to create a non-threatening, safe environment.

‘Fishbowl’ offices are a no-go. Sitting behind your desk is also a no-go. Oversized meeting rooms are a no-go. Restaurant or noisy coffee shops are also a no-go.

The ideal setting is a small office or meeting room that nobody can see into, with comfy chairs and refreshments at hand.

Rule 2: Have a pre-session check in, followed by a longer career conversation at least a few days apart

Conduct a brief check-in conversation before the actual discussion. This is to be clear what the individual expects but also to take out the nervousness and awkwardness of the actual conversation. It also sends a message that you take it seriously.

This can be a Zoom or phone call, or just a short pre-meeting. 10-15 minutes are normally fine.

This is also a good opportunity to ask for an updated CV, or any other information that you are lacking.

Rule 3: Structure the actual conversation in four parts

  • Re-connect and socialize
  • Let the person-talk about their career and where they think they stand
  • Explore possibilities for the coming years, discussing scenarios and possible options
  • Agree next steps and actions

Rule 4: Summarize the essence within 24 hours after the conversation

Request that the individual summarize the outcomes of your meeting within 24 hours and share them with you. You then either agree or amend and enhance. This will provide a sense of completion until the next conversation.

If you are the line manager, make sure that you agree a follow up as appropriate – which can be within the next few months if a person is proactively looking for a move.

If this is not the case, it still is advisable to have a check-in within the next 6 months.

And last but not least, you might provide one last piece of advice to finish the career conversation. Advice that one of the young entrepreneurs featured in our book ‘A Career Carol’ so eloquently articulated:

“Give someone permission to call you out. You must have someone in your life who you are 100% honest with, no gloss, no exaggeration, no spin, and outside any vested interests.”

It’s that time of the year when many look for a fresh career adventure, be that a project, promotion, secondment or a new role outside of your organization. Learn more about IceHrm.

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