Helping a co-worker to prepare their future

The future, in a company, is sometimes a taboo subject or is quickly swept aside by managers. Do we think that the short term is the priority? Do we fear giving "false hopes" when nothing is sure? Nevertheless, our work does carry in it a future, one that the manager can help to sketch out!
Speak of the future... that's all
We sometimes tend to think that professional trajectories, advancement, career paths are in the domain of Human Resources... However, each manager might ask himself, "what is my role in the professional development of my co-workers? What is it important for me to know? With what aim? When do I need to hand things off to HR? ..."       
Abolish judgement
To listen to aspirations, dreams, hopes, doubts, implies a posture of unconditional benevolence. There is neither judgement nor censure ("that won't be possible!", "you don't have the background"...) You may of course offer an opinion, once the door is open. And in particular a door that opens onto the present: what can your co-worker do, today, in his current position, to prepare for the future he wishes?       
Assist reflection
You can help a co-worker to project himself into the future, to clarify his wishes, to refine his projects: "What interests you in this direction? What are your assets...? What is lacking? How can you work on that? What obstacles do you see? How can I help you? ..." These questions do not constitute a promise from the manager regarding particular opportunities, but they have two virtues: they encourage your co-worker to deepen his reflections, to measure them against what is "possible", and they reinforce the quality of the relationship.       
Each question has only one correct response, but be careful: among the possible responses there is one that is "almost correct" and might make the choice harder!
1 / 3   A collaborator doesn't have any plans
Elliot tells you: " I've been in the same position for the past 25 years, what else do you want me to do? ".What do you say to him?
You can do many other things ...what would you be interested in?
This answer could make Elliot think he has no other option than to change! There is a risk he closes up.
The aim is not necessarily that you change, but that you reflect on what is needed in order to stay competent, or to adapt, for future needs.
You open the conversation on the possible opportunities of the job and the skills needed for this position.
I am asking you the question because it is at the heart of the professional review, but if you don't wish to do something else, that's fine, I will just note it down.
You give up too quickly. Delving into, questioning the collaborator's response could help identify some areas of development in his current position.
These days, we expect employees to take responsibility for their career. It is important to look towards the future.
You are warning Elliot, showing him he is not "as he should be". It would be better to help him to reflect.
2 / 3   The question of employability
Should you talk about employability to Elliot?
Yes,Elliot should know he won't stay in the same job all his life.
The purpose is not to scare him! Just to make him reflect on how he should manage his career.
No, this is a word which will scare Elliot and it isn't the manager's role to prepare him for the changes.
On the contrary, speaking with an open mind of the possible opportunities is part of the relationship manager-collaborator and causes less anxiety than things unsaid.
Yes, this is a subject which concerns him, as it does all of us. But you must help him reflect on what it specifically means to him.
Absolutely, the objective is to demystify the term and to address it as a topic of debate, just like the others.
3 / 3   Having a project by any means?
Zoe tells you "you never know what the future holds; I prefer not to have projects but to adapt» What do you say to him?
Absolutely, but times change and professional life is more and more demanding. You can't always act as you did in the past. I would rather help you reflect.
The remark will cause anxiety and the help offered is too premature
Of course and I guess you have always managed this way. The word project may give the impression that we absolutely want to look far into the future ...but you can look ahead short term. Do you already have any ideas on what you will soon have to adapt?
You reassure Zoe: it is her right not to have project! And you open the conversation by steering him towards the short term. If she doesn't' have any specific ideas, then insisting would be counter-productive.
But this could be seen as not being proactive which could possibly be held against you...
This is judgmental! Zoe can only defend and justify herself.
Of course, it is difficult to look towards the future, how can I help you?
Too early. The collaborator doesn't see the benefit of looking ahead, you can't help him.  
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