Be honest with yourself, how good are you at talking about the future with your team? When I say, “talking about the future”, what I really mean is: how good are you at talking to your employees about their future career goals and aspirations?

In my experience, some managers are good at it, but most are not. While some skilfully weave these types of forward-looking career conversations into their regular one-on-one’s, others only broach the subject once a year, during the annual performance review…if at all.

Are you afraid of having honest career conversations with your team members?

It’s completely understandable why so many managers don’t want to broach this topic. After all, what if one of your high-performers tells you that they’d like to get experience in an entirely different department, different industry or even different organisation altogether?
Or, perhaps you’re worried about disappointing one of your employees. For instance, if your team member were to voice to you that they’re looking for your support to progress to the next level, and, realistically, you know in your own mind that there are no progression opportunities available in the immediate future - how do you positively and proactively manage that situation? Isn’t it a given that if they don’t get the answer they’re looking for, they’ll immediately start their search for a new job as soon as they clock off for the day?

When it comes to conversations about future career ambitions and goals, there are so many ‘what ifs’ to contend with and expectations to manage. It’s not surprising then that many managers may feel it’s easier to avoid having these types of conversations at all. However, in today’s world of work where change is the only constant, being open and honest with your staff about their career ambitions and working together to achieve them can give you a strong retention advantage – so it’s worthwhile taking a deep breath and making time to sit with your staff to have this important conversation.

NOW is the time to start having more open, honest career conversations

As Lynda Gratton and Andrew Scott explain in their book, The 100-Year Life: Living and Working in an Age of Longevity, we are living in a time of seismic demographical shifts and massive advancements in technology. As a result, most of us will live longer lives than any other generation that have come before us. This all means we will have more time than ever to fill – and, for many, and for a variety of reasons, this means we’ll probably be spending more of our time working in some capacity or other.

And, with more time, comes more opportunity to do more with our careers, learn new things, and experiment, as our CEO, Alistair Cox, discussed in his LinkedIn Influencer blog post, “… so, to remain engaged and happy throughout these additional decades of working, employees will naturally crave variety, and lots of it. And what’s one of the best ways to do this? To explore new job opportunities at new companies more regularly…”

So, as a leader or manager, now is not the time to shy away from having honest career conversations with your employees. Sailing blindly into the future is never a good idea, particularly when that future is uncertain and the journey to ‘success’ potentially means navigating more and more twists and turns, some of which none of us will be able to predict.

Now is the time to start having honest, open and candid career conversations with your employees. It is, after all, your job to help your team members navigate the changing world of work, helping them reach their full potential. It is also your job to act in the best interests of your team and wider organisation.

By getting more comfortable with having forward-looking career conversations, you’re in a far better position to not only keep hold of your top talent, but also to help pre-empt and plan for any changes that may be around the corner. It really is a win-win approach, both for you and your team members.

Why future career conversations are so important

Put yourself in the shoes of your team members for a minute. If you think about it, it’s completely understandable that they’ll be keen to talk to you, their boss, about their future career ambitions and goals. After all, it’s natural to want to know what opportunities and support may be available - and, in their eyes, you are the keeper of that important information.

But, there are a few other important reasons why, as a leader or a manager, you must change your approach and start getting better at initiating forward-looking career conversations with your people:

• To drive motivation and loyalty: The more of an active interest you take in your team members’ career aspirations, the more you will be showing them that you genuinely care about and are invested in their development. This alone can be hugely motivating for employees, making it more likely that they will want to continue to work for you. As occupational psychologist, Dr Maggi Evans says in her LinkedIn blog post: “If you don’t talk to people about their future, most will assume there are no opportunities for them – and become disenchanted and leave.”
• To help your employees adopt a growth mindset: Adopting a growth mindset is crucial to secure career success in the future world work. This mindset is all about believing there is constant scope to learn and grow, no matter what your skills and knowledge may be right now. So, by actively talking to your employees about their skills development and the opportunities available to them in the years ahead, you will be subconsciously communicating that you believe in their ability to learn new skills, adapt and develop. Simultaneously, this can help overcome any skills gaps in your department, since employees can consider upskilling and developing in an area that your team currently lacks.
• To encourage future-thinking: Initiating discussions of this kind with your team members will also encourage them to actively start exploring, in their own minds, what they wish to accomplish in their professional lives in the years to come. If it’s a subject that they haven’t put much thought into previously, such conversations could focus their minds and spark more future-thinking and reflection – which can only be a good thing for both parties.
• To demonstrate your organisation’s learning culture: It has never been more vital for businesses to embed the principles of continuous, lifelong learning and development into how they operate, so that they can not only remain competitive against rivals, but also attract and retain the best people. If you’re able to consistently and naturally weave career conversations into the day-to-day functioning of your business, then you will be helping this culture to permeate.
• To aid and inform future succession planning: The moment it looks like one of your employees might leave is the time to start planning for the future. For example, if you, through career conversations, identify untapped skills in another team member which could be beneficial in the event of another team member leaving, now’s the time to help them upskill, such as by inviting them to work on stretch projects or by adding new responsibilities to their remit. Your team must continually evolve if your business is going to do the same.
• To improve your career conversation skills: Lastly, and this might sound obvious, but by initiating honest and open career conversations with your employees more regularly, both parties will start to feel more comfortable having them - which, as I’ve touched on above, is going to become more and more important in the years ahead. So, start practising now.

Eight questions to ask to get the career conversation going

However, understandably, even just the prospect of starting a discussion like this with your employee can be intimidating, especially when you open with an elevated and imposing question such as “Where do you want to be in five, 10 or 15 years’ time?” What you shouldn’t be aiming to do is catch your employee off-guard with your questioning. This could make them feel unprepared or ill-equipped.

Instead, here are a few questions that experts in this area, including Dr Maggi Evans, suggest you ask to start these types of career conversations:

1. What aspects of your current role do you enjoy or not enjoy?
2. What do you think are the key skills needed to perform your current role well? How would you rate yourself for each of them?
3. How do you see your role progressing in the coming years?
4. Do you have any skills that you think are currently being under-utilised? How do you feel these skills could be better utilised, both now and in the future?
5. Are there any skills you don’t have, that you think you need in order to get to the next step in your career? Do you think there are any specific development activities or projects you could get involved with to help you to build those skills?
6. If you had a magic wand, what work would you love to do?
7. When people think of you, what are the three qualities that you’d like to spring to their minds?
8. Are there any areas of this organisation that you’d like to learn more about?

As you can see, these questions are really designed to help your employee reflect on what they’re good at, what they want to do more of, if they have any skills gaps and how they’d like to be perceived. So, in your next one-on-one, instead of just running through the to-do list, try weaving some of these questions into the conversation.

The world of work is evolving at an unprecedented rate – and with that comes a whole lot of change. Key to navigating this change successfully is honesty, open-mindedness, courage and planning. So, as leaders and managers, we must start to feel more comfortable talking candidly and constructively with our teams about their career expectations and ambitions. After all, without that information, we’re simply ill-equipped to plan for the future, and ill-equipped to help achieve long-term success.