7 tips for a successful end of year career conversation

Appraisals shouldn’t be a yearly nasty surprise. Dr Helmut Schuster and Dr David Oxley share how to make this a much improved situation

Be honest, have you ever had a completely transparent, meaningful career conversation as part of a corporate appraisal process?

Career or ‘development’ conversations have historically been attached to appraisal processes. How do you have a genuine conversation about careers when the subtext is that you are being measured and compared? Even for those businesses that separate development conversations, the context can still be compromising.

Trust doesn’t suddenly materialise along with a calendar invitation

We consistently under-estimate the manager-employee power dynamics that seep into all workplace discussions. Plus, when orchestrated as part of a process, they run a risk of becoming check-box exercises.

The main ingredients for consequential career conversations are trust, respect, and objectivity. Trust doesn’t suddenly materialise along with a calendar invitation. Respect is earned by consistently demonstrating expertise, fairness, and wisdom. And the most difficult of all, objectivity, can only occur when the shadow of shared employment, corporate allegiances and agendas take a backseat to being a true ally, confidante, and mentor.

So, how do you have a great year-end career conversation? If the first time you think about it is when HR remind you to schedule a conversation… it may be very hard to achieve. However, it’s never too late to start. If you really want to create the right environment for extraordinary career discussions, here are seven steps you can take right now:

Step 1 – Ask yourself if you are serious

Investing in high quality career conversations requires you to segregate your own interests, and those of your organisation, with the best interests of those you advise. Consequently, it can often be much easier to provide career advice to someone not in your immediate sphere of business influence. Regardless, great career conversations require consistent and meaningful commitments of time and consciousness. It’s helpful if you find fulfilment and reward for yourself in this endeavour, rather than think of it as a chore.

Step 2 – Take a Hippo-career-cratic oath

The Golden Rule of doing no harm while doing the right thing for the individual is essential. Some people will find this easier than others. Putting aside ego, vested interests, and personal biases as much as you can. Avoid the temptation to tell, instruct, or preach. It is easy to direct and take short cuts to familiar conclusions. The goal should always be about helping someone achieve their career goals and dreams… not relive your own.

Step 3 – Think holistically about careers

All too often we limit our definition of careers to narrow corporate hierarchies. If we collapse the definition of careers into climbing a single company’s grade structure, we are perpetuating an empty charade that careers are analogous to promotions.

Take some time to think about what makes people happy and fulfilled in their lives. Think about how work fills different needs for people. There is some great literature out there, but the headline is focusing on what makes each individual unique, helping them find their purpose, the thing they care most about, and then tethering career discussions to that anchor.

Step 4 – Invest in constructive empathy

We talk about constructive empathy as the intersection of taking the time to understand how an individual is experiencing their job and related components, but in a context designed to help them move forward. You can get better at this by practicing and replacing statements with questions.

Step 5 – Make an offer

This is typically no more than a, “If you’d like to grab a coffee and talk through what you want to get from your career, I’d be happy to try to help.” If the offer is accepted, we think it wise to set boundaries creating as safe a space as possible. Great career conversations require commitment from both sides and vocalizing that can get you off to a good start.

We do not however subscribe to being too rigid. People grow, evolve, change. It’s important that career discussions also have space to adapt as things change. 

Step 6 – Be prepared and pursue the awkward truth

Take the time to understand the person’s career to date, their interests, and their broader motivations.

In our experience, many people approach conversations about careers with a superficial focus on what they want. Very often what they want has been shaped by what they believe others expect them to want. Great career conversations at their core must be prepared to challenge wants and seek to explore needs.

Step 7 – Be consistent but don’t put process ahead of need

The idea of a single ‘great’ conversation about careers is something of a misnomer. While we have certainly experienced pivotal conversations at key crossroads in our own careers, they were shared with individuals we had known for years and trusted to have our best interests at heart. The road to those moments was long but, in all cases, what bound these extraordinary mentors together was their consistent willingness to put aside their own challenges, and spend a while completely invested in what mattered to us. In those moments, we didn’t feel alone. We felt we could be at our most vulnerable, our most exposed, and rather than be judged or lectured at, we were given empathy, support… and, yes, occasionally a kick up the backside.

There is some irony or twisted humour to the observation that the world has never been more connected, and yet, many of us have never felt more alone. In our professional lives, this also plays out in the ceremonies and routines of large companies. We interact and collaborate every day. However, we perceive negative consequence if we say or behave the wrong way.  Consequently, we keep a safe distance, and are careful about how much we are prepared to confide.

If we want to help people with truly meaningful, substantive, consequential career conversations, we must find ways to liberate them from process, and unshackle them from fears of judgement, superficiality, and hidden agenda.  


Dr Helmut Schuster and Dr David Oxley are authors of A Career Carol: A Tale of Professional Nightmares and How to Navigate Them published by Austin Macauley Publishers and is available on Amazon.

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Dr Helmut Schuster and Dr David Oxley

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