I must have been involved in hundreds of career development conversations over the years.
You know the sort. Someone sits down with their manager, they talk about how things are going, what they’d like to work on and develop, and eventually the question comes up.
Where do you see yourself in three to five years?
It’s a perfectly reasonable question and I’ve asked it plenty of times myself.
However, looking back, there is something rather funny about asking someone to map out their career five years into the future when the organisation they are working for is constantly restructuring and doesn’t know what the next five years look like. But that’s okay, let’s get that development plan completed.
I’m making light of it, because I do think there’s value in thinking about where you want to go. Having a sense of direction helps you make decisions about what to learn, which opportunities to pursue and where to invest your energy.
But how much do we assume about the direction someone should take?
If someone is doing well in their role, the conversation quite naturally turns to what comes next. A bigger job, more responsibility, perhaps a move into management or if they’re already managing people maybe it’s time to think about the next level.
Before long, there's that development plan with some stretch assignments and a conversation about what they’ll need to demonstrate to be considered ready.
It’s all very sensible. I’ve spent a large part of my career helping organisations do this well. Career pathways give people something to work towards. Succession planning helps organisations prepare for the future. Having a manager who sees your potential and encourages you to grow can make an enormous difference and I don’t want to lose any of that.
I do wonder, though, how often the conversation starts with what someone actually wants, rather than what seems like the obvious next step.
I remember people who were very good at their jobs and were naturally seen as candidates for promotion. They were capable, dependable and respected by the people around them. Their managers wanted to recognise that and offering them the next opportunity seemed like a good way to do it.
Sometimes it was exactly what they wanted. Other times, I think the expectation arrived before the ambition did.
I’ve seen capable women become very good at doing what was expected of them. They delivered, took on challenges, built their reputations and earned the confidence of the people around them. They were often the people managers wanted to invest in, and because they were good at meeting expectations, they could become equally good at pursuing the opportunities that came with them.
I understand how that happens. When you’re building a career, you learn to recognise the signs that you’re doing well. Good performance reviews, more responsibility, being trusted with important work and getting noticed by senior people all matters.
It can be genuinely satisfying when you’ve worked hard to earn these. If you’re ambitious, why wouldn’t you want to keep progressing?
The interesting thing is how easily progress becomes associated with moving in one particular direction.
We talk about climbing the career ladder, moving up and getting to the next level. Even our language suggests there’s a fairly obvious route and that the aim is to keep going.
But careers don’t always work that way.
Some people want to manage large teams. Others want to become deeply knowledgeable in a particular area. Some want to influence bigger decisions without necessarily having direct reports. Others are excited by building something new, moving into a different field or taking on a challenge that doesn’t come with a more impressive title.
Those ambitions can change. What you wanted at 25 might not be what interests you at 35 or 45. You learn things about yourself along the way. You discover work you enjoy more than you expected and sometimes find that an experience changes the way you think about your future.
Yet once you’ve been identified as someone who’s going places, it can feel surprisingly difficult to question where those places are.
There were times in my own career when I knew exactly what I was working towards. I wanted the challenge, the responsibility and the opportunity to make a bigger contribution. I enjoyed being stretched, and I still think there’s something enormously satisfying about discovering you’re capable of more than you realised.
But looking back, I can also see how easy it was to assume that the next logical step was the one I should be aiming for. When you’ve spent years building your experience and doing your job well, progressing can begin to feel like the natural thing to do.
I don’t think I always stopped to question that assumption as carefully as I might have.
One of the things about career conversations is that we’re often much better at discussing readiness than desire. We can spend a lot of time identifying the experience someone needs, the capabilities they should develop and the opportunities that would help prepare them for a future role.
We’re less likely to spend the same amount of time exploring what genuinely interests them about tat future. What would they enjoy doing more of? What kind of problems would they like to solve? Where do they want to have an impact?
Those questions don’t always have an immediate answer. It’s much simpler to identify the next position on an organization chart than to work out what someone wants form the next stage of their working life, especially when that person isn’t entirely sure herself.
I think this is particularly important for women who are beginning to see themselves as leaders.
They may have spent years proving they’re capable, taking feedback seriously and making the most of opportunities. They’ve learned how to succeed within the organisation they’re part of and there’s real value that that experience. But, as they take on more responsibility, they also have more decisions to make about where they want to direct their abilities.
Sometimes the opportunities that interest them will fit neatly with what others expect. Sometimes they won’t. They may want to pursue a more senior role, move into a different area or take on work that gives them a kind of influence they haven’t had before. Sometimes they may need to explore a few possibilities before they know what they want.
There is no more authentic answer hiding in any particular choice. Wanting a senior role is just as valid as deciding you want to do something differently. What matters is whether you’ve given yourself the chance to work out what you want.
That doesn’t mean you have to know exactly how you’ll get there.
You may discover what interests you by trying something, paying attention to what happens and being willing to change course. An unexpected project or a conversation might open up an interest you didn’t know you had or a possibility you never considered.
You can have a sense of direction without knowing every step in advance. Given how much can change in an organisation between now and next Thursday, that seems like a fairly practical approach.
Organisations have an important part to play here too. We can still identify talent, offer development and encourage people towards opportunities. But perhaps we need to become a little more interested in the direction people want to take, rather than assuming the direction we’ve prepared for them is the one they’ll choose.
We should consider something in our own career decisions.
It’s possible to spend years working towards a goal, becoming more capable and successful along the way, without remembering when you decided that goal was yours.
That doesn’t mean you’ve wasted your time. The experience, relationships and capabilities you’ve built are still yours. They may be exactly what enables you to do something different next.
I think back to those career development conversations and the plans we so carefully put together. Some will have helped people achieve things they genuinely wanted. I hope a lot of them did.
I wonder, though, how many people walked away with a clearer idea of what the organisation thought they should do next, without being any clearer about what they wanted themselves.
If you’re approaching another career decision, perhaps it’s worth setting side the development plan for a moment and considering the direction you’re heading.
If nobody expected you to take the next logical step, would you still want to take it?