Someone told me a story of a scholar, smart person, capable, who became an assistant director barely a couple years on the job. The person did poorly. Struggled to manage the team, manage bosses, and eventually got overwhelmed like 99x combo hits (marvel vs capcom throwback). Idk the person, but I highly doubt the person was that bad!
In surveys, dialogs, and complaint sessions, promotions come up here and there. Surprisingly, I haven’t encountered it much in appraisal or one-to-one chats with officers, and me as an officer. Maybe it’s the fear of getting judged or laughed at? Maybe it’s a public service thing?
Good officers who are quite senior can feel really stuck, whereas managers can also plateau before Deputy Director. So near yet so far. Sometimes it’s a genuine gap, sometimes the opportunity’s not there. Or maybe it’s both.
I guess that’s why promotions are so frustrating. Good performance matters a lot, but so do readiness, time and space (you hear that alot!), vacancies, relationships and whether somebody is willing to take a punt on you.
Disclaimer: These are my own views from what I’ve seen and experienced over the years. So this isn’t some confidential sens high HR policy document.
Before getting into management
Doing your job well still comes first
Whatever else I say below, promotions obviously start with doing your current job well. You need enough performance, competency and trust for somebody to even consider giving you more scope, a higher grade, or a different appointment.
The funny thing is that promotion can eventually move you away from the exact job you proved yourself good at. A great officer becomes a manager, then a good manager starts managing managers, and each jump introduces things you may have little experience doing.
There’s the Peter Principle that says people get promoted till they reach a job they’re incompetent at, which is perfectly logical.
Promotion can mean different things
There’s also a difference between being promoted in grade and being appointed into a bigger role. You can progress in grade while doing broadly similar work, whereas moving into management brings a much more obvious change in what you’re actually responsible for.
The criteria and mechanics also aren’t particularly transparent, and sometimes supervisors themselves don’t seem to have enough information to explain why somebody progressed or didn’t. That’s another reason promotions can feel so opaque, even to the people who are supposed to give officers useful career advice.
I’m mostly talking about moving into management
The rest of this post is therefore mainly about the jumps where the job itself changes: senior officer into management, then manager into middle management. That’s where readiness, team dynamics, managing bosses, relationships, timing and somebody being willing to take a punt become much more obvious.
Getting the opportunity
There has to be a chair
It’s just supply and demand. You need an actual job somewhere that roughly fits your seniority and experience. Sometimes there’re several good people and one chair, all competing. Sometimes one chair with no one suitable.
This is why jobs and postings are usually called a “time and space” issue. Specifically, space.
Right place, right time, right seniority
Luck definitely plays a part because you could be exactly the same person with roughly the same capability one year earlier, except the opportunity simply didn’t exist yet.
This probably matters more around the bigger jumps. Senior officer to manager is one, because somebody needs to give you that first supervisory role. Manager to DD is another, where the organization has to decide whether you can operate at a wider level and increasingly manage through other people.
Organizations also can’t conveniently manufacture a good job every time somebody becomes ready. Sometimes you wait, even when there isn’t much more you can meaningfully do in the current role.
That’s why some stories can be misleading. An officer that obviously didn’t meet the grade requirement can cover the job for some time, do very well, then get promoted to officially take the job. This wouldn’t have happened if not for the fact that it was vacant, crying out for someone to take it.
Someone needs to know enough about you
Visibility matters alot. You can be capable and hardworking, but if no one knows about it, it’s all moot. Don’t get me wrong, I don’t mean to wayang, or say nonsense at every meeting, or claim credit at every chance. It’s about letting people know (in a good way) your contributions.
Somebody eventually has to form a (positive) judgment about you. It’s much easier if the people involved have seen your work, your judgment, how you behave when things go wrong, and whether other people trust working with you.
A very good officer who has somehow remained completely invisible is harder to take a bet on because there’s simply less evidence.
Internal politics matters too
Internal politics mostly comes down to building bridges, cultivating allies, understanding how different parts of the organization work, and over time becoming embedded into its fabric as someone dependable and effective. Not the stereotype of scheming, backstabbing, sucking up.
People know your work, trust your judgment, pull you into difficult problems and are willing to work with you across teams. That matters for promotion because nobody exists as an isolated performance score.
Somebody eventually needs to put your name forward, argue for you, give you the stretch opportunity, or take the punt that you can handle the next job. The more useful you’ve been to the organization, and the more people who can credibly vouch for you, the easier that becomes.
Of course politics can turn ugly with favorites, manipulation and people undermining one another. I’d separate that from the ordinary politics of working with humans and building relationships. (Watch this if you haven’t, it’s a pretty good take.)
Somebody has to take a punt on you
For your first management job, nobody can produce five years of evidence proving you’re a great manager because you’ve literally never done it before. Someone looks at everything else and thinks, “I think this person can probably do ok”.
The same thing happens again later. A manager becoming a DD may start managing managers, deal much more frequently with senior bosses, do a bigger portfolio, and have less time to inspect every little detail.
Some of the most important parts of the next job are precisely the things you haven’t fully done yet. There’s always going to be some prediction involved.
Being stuck doesn’t necessarily mean you’re lousy
If you’re a senior officer who’s been there for a while, maybe there’re real gaps. You should want to know if that’s the case because at least there’s something concrete to work on.
But maybe there just isn’t anywhere suitable to put you yet.
Same for managers hovering below DD. Somebody else may fit the available role better, your current experience may be too narrow for a particular opening, or there may simply be no opening.
These are very different problems even if the outcome looks exactly the same on paper: no promotion.
Are you actually ready?
High achiever doesn’t automatically mean good manager
Back to the high achiever at the start. The person must have been rly good at something to progress that quickly, and I don’t think all the earlier performance suddenly became fake because the management posting went badly.
The next job simply asked for different things.
A strong officer can get very far from being sharp, technically competent, fast, reliable, hardworking and able to personally rescue something that’s going wrong.
Then management asks:
- Can you guide someone without doing everything yourself?
- Can you vet work and explain why it isn’t good enough?
- Can you prioritize across a whole bunch of people’s work?
- Can you handle someone who’s underperforming?
- Can you deal with team conflict without making it worse?
- Can you manage bosses and their expectations?
- Can you still understand what’s actually going on when you’re no longer doing most of the work yourself?
It’s a different set of requirements!
Your superpower can stop scaling
Some very good officers solve problems by personally being very good. Bad draft? Just rewrite it. Pressing deadline? Just take over and do. Something technically difficult? Much easier to just do it myself.
I’ve done plenty of this too, especially when I’m impatient and explaining the thing feels like it’ll take longer than fixing it.
This works as long as the amount of work you can personally touch remains manageable. Once you’re responsible for a whole team, you eventually become the bottleneck, where everyone waits for you to approve the approach or rescue something burning.
Your own output matters less as you go up
This was quite an adjustment for me too. You can personally produce a solid piece of work and still be doing poorly on a management job if everyone around you remains dependent on you.
The team may look good because you’re constantly rescuing everything, but take you away for a week and the weaknesses become much more obvious. (That’s why a cliche phrase some bosses say is, “My goal is to make myself dispensable.” There can be temptation to roll eyes a little but there is truth in the saying.)
As you go higher, your own output becomes a smaller fraction of what you’re accountable for. The capability of everyone around you starts mattering much more.
So how do you know you’re ready?
I don’t think you ever know for sure. Some parts of management only become learnable after you actually do the job, so at some point either you take a leap of faith or somebody takes one on you.
Sometimes circumstances force the issue anyway. Someone quits, goes on long MC, or you quietly step up because an underperforming boss isn’t holding things together. Suddenly you’re coordinating, managing upwards, fronting decisions that weren’t officially yours.
These situations are probably the best test of readiness because you’re doing the job for real, often with a bit more tolerance because everyone knows the circumstances you’re stuck with (okay, maybe not all bosses care). If it goes well, you’ve also created actual evidence that you can handle the job when the permanent opportunity comes up.
Some things just need time
There’s a reason fresh grads rarely manage teams
A fresh grad could be super smart and technically better than people with ten years of experience. I’d still be very hesitant to immediately hand them a team because they simply haven’t seen enough people in enough situations.
Over time you encounter:
- someone slowly checking out
- two people who just cannot work together
- an officer who thinks they’re ready for promotion when you really don’t
- someone who’s normally great but suddenly struggling badly
- a high performer who’s becoming increasingly difficult to everyone around them
- a quiet person doing loads of invisible glue work, underappreciated
After enough of these, you have some reference points in your head. You still get things wrong, but at least you’re no longer encountering every situation for the first time.
Different people react completely differently
Personally I feel experience is very important to managing a team.
Every team is different because they’re made up of unique individuals. Maybe someone wants to be left alone to do work, whereas another person feels lost when you don’t check in with them regularly. Someone loves detailed comments, and yet another gets demoralized from a ton of tracked changes.
There’re frameworks and courses for managing these situations, and some are useful. Then a real person turns up with a problem that’s somehow a weird combination of several things and doesn’t resemble the case study.
Years served isn’t experience by itself
Someone can also sit around for ten years and learn almost nothing new. The useful part is encountering different bosses, teams, problems, failures and people.
Sometimes you also need to screw something up yourself, realize your instinct was wrong, and remember that the next time something similar happens.
Something something school of hard knocks.
Management is its own competency
Can you actually guide someone?
I’ve written quite a lot about this in my staff work posts. A manager can take a lousy draft, rewrite everything and produce something beautiful, but if the officer keeps producing the exact same lousy first draft every month, I’m not sure we’ve developed very much.
I’m guilty of this too because sometimes I’m tired, impatient, the deadline is near, or I already know the answer in my head. Just takes too long to teach than to edit.
The harder thing is helping somebody get there.
Can you:
- explain what the problem actually is?
- give enough guidance without dictating the answer?
- recognise when someone needs more help?
- know when to back off?
- adapt to how different officers learn?
- slowly make yourself less necessary?
That’s an important part of management.
Can people get better from working under you?
As you become more senior, your own personal output becomes a smaller part of all the work you’re responsible for. Eventually it matters more whether the people around you can consistently produce good work without you personally touching everything.
I think that’s a useful question to ask of managers: do people become better from working under you?
If the answer is yes, that’s quite valuable. If everyone remains permanently dependent on you, something probably isn’t working.
Can you deal with the uncomfortable stuff?
Then there’re the conversations nobody enjoys. Someone isn’t doing well, somebody else wants an opportunity you’re giving to another person, two officers are angry with each other, or a good performer has an attitude problem that’s affecting everybody else.
These things don’t disappear because we’d rather talk about deliverables and KPIs. You eventually need to form a view, say something, and deal with whatever comes after.
Sometimes you get it wrong too. That’s part of why experience and self-awareness matter.
A huge part of management is managing bosses
You need your bosses to trust you
I feel this part is underrated. Alot of management is upwards. Your boss needs to believe you understand what they’re trying to achieve, know when something deserves escalation, can give them enough information without dumping the whole universe on them, and won’t create an unpleasant surprise every other week.
Trust gets built through lots of boring repetitions:
- you say you’ll do something and then do it
- you surface bad news early enough (don’t wait till the house burns down!)
- you know the details when they matter
- you don’t escalate every tiny problem (aka not making your boss do your job)
- you push back when there’s a good reason
- you understand the wider intent instead of blindly following the literal instruction
Eventually your boss worries about you less, which is probably one of the nicest compliments you can get.
Trust buys operating space
When your boss trusts your judgment, you get much more room to actually run. You don’t need approval for every small decision, and you can push back without every disagreement turning into some huge issue.
You can also give your own team clearer direction because you’re reasonably confident about where your boundaries are.
When the trust isn’t there, everything becomes so hard. More checking, more clarifications, more things getting second-guessed, and eventually the job’s just managing the relationship.
Your officers absolutely can tell
People sometimes behave as though the relationship between a manager and their boss is invisible to everyone below. Let’s be real, everyone can tell when their boss is trusted or not trusted.
They can also tell when the boss is constantly bypassed, overruled, contradicted, sent back to redo things, or clearly has no idea what senior management wants.
Would you respect the views of somebody whose own boss visibly doesn’t trust their judgment? If you’re charitable, maybe, especially if no one trusts that bigger boss too and your boss is really capable, but chances are no.
People figure out where the real authority sits
If every important decision eventually gets overturned upstairs, people learn from that.
They may wait before acting because they expect the direction to change. They may start going directly to the more senior person, or politely listen to the manager while mentally treating everything as provisional.
This is why undermining your own managers is so destructive. Sometimes intervention is completely necessary because the manager got something wrong, but if we keep doing it, we’ve trained the team not to treat the manager as the manager.
Then we wonder why the person can’t lead.
Yes, vibing with your bosses matters
Nobody wants a thorn in the side
I use vibe because I’m not sure a more sophisticated word would make the point more accurate.
You don’t have to be friends with your boss. You should disagree and I’d be worried if everyone agreed with me on everything, because that means there’s too little psychological safety.
But nobody wants to deliberately appoint someone where every single issue is going to become a fight.
There needs to be enough alignment around what you’re trying to achieve, what standards matter, how people should be treated, how fast to move, and roughly how much risk is okay.
Otherwise everybody gets exhausted.
The vision has to roughly connect
This becomes really obvious in middle management. Your job is partly to take a broader direction from above and turn it into something your team can actually understand and execute, while also feeding ground reality upwards when something doesn’t make sense.
If you and your boss fundamentally disagree about where the place should go, that translation becomes pretty hard.
One day the team hears one direction, then you go for a meeting, next day there’s a new direction. After enough cycles people stop believing the first one.
You need enough trust to push back too
I’ve found it much easier to disagree with bosses once there’s trust.
If somebody knows you generally understand what they’re trying to do, aren’t being difficult for sport, and will execute properly once a decision is made, pushback becomes much less threatening.
Vibe comes down to whether the working relationship and shared assumptions remain compatible enough for productive disagreement.
What promoting you tells everybody else
Promotion sends a signal
I think this has become much more explicit in recent years in service.
Imagine someone who’s an insane performer. Delivers everything, presents well, bosses love the output, probably has gets A grade every year.
But wherever the person goes:
- people burn out
- juniors don’t want to work for them
- colleagues stop trusting them
- credit somehow flows mostly one way
- conflict follows
- the team is worse off afterwards
Do you promote the person?
High performance doesn’t erase the damage
Obviously being nice while producing nothing isn’t the answer either. We’re at work and outcomes matter.
But promotion gives someone more people, authority and influence. If the existing pattern is that they leave scorched earth behind them, there’s a pretty obvious question about what happens when you increase their blast radius.
It also tells everyone watching that this behaviour apparently works.
Nobody wants to promote someone who’ll salt the earth upon taking the post.
(Just check out salary.sg forums as a fun excursion. Not my views, just interesting to read about officers who are convinced and very public about their critiques.)
Why is promotion stuff so hush hush?
Ask for the criteria and everything gets vague
Promotion is one of those topics where the conversation can become very abstract very quickly.
- Readiness
- Potential
- Competencies
- Organizational needs
- Operating at the next level
- Fit
Ok, so what do I actually need to do?
I can understand why people get annoyed when HRBP or bosses dance around the question because it feels like somebody knows the secret recipe and just refuses to tell you.
Some of it genuinely is difficult to measure
I also increasingly understand why the answer can be vague.
How do you objectively score whether:
- people will follow someone?
- they can handle a dysfunctional team?
- their bosses will trust them?
- they have enough judgment for a bigger job?
- they’re ready today or another year would make a big difference?
- they’ll fit the exact opportunity that’s available?
You can have competency frameworks and assessment criteria, and I think you should because otherwise the whole thing becomes far too arbitrary.
There’s still a lot of judgment involved.
Sometimes it’s informed gut feel
A boss may look at someone and think they’re really good, but somehow still isn’t comfortable giving them the next job.
Ask why and there may not be one massive problem. It can be an accumulation of little things over years: how the person reacted under stress, whether people wanted to work with them, how they handled disagreement, whether they exercised good judgment when nobody was supervising closely.
Eventually all of this becomes something close to gut feeling. Hopefully informed gut feeling rather than anyhow whack.
People don’t really want the subjective judgment challenged either
This is probably one reason the bureacuracy prefers keeping some of the exact criteria hush hush. The more precise the criteria become, the easier it is for somebody to say:
You said I needed X, Y and Z. I have X, Y and Z. Why wasn’t I promoted?
Fair question for real. Sometimes the answer may honestly be that another person was a better fit when everyone looked at the whole picture. That’s really difficult to turn into an Excel formula without pretending the process is more objective than it actually is.
HRBP can’t really promise an outcome
I can therefore understand why HRBPs often explain the broad framework but avoid turning it into a checklist that appears to guarantee promotion.
Once the list looks specific, people naturally expect that checking off every list item should lead to a promotion. The actual decision still includes judgment about timing, fit, relative readiness and whatever vacancy happens to exist.
But news flash, somebody’s gotta make the call.
We’ll game the criteria too
Let’s be real, if you publish the exact recipe, we’ll optimize for it.
Need two major projects? Find two.
Need people-management experience? Get somebody assigned.
Need competency X demonstrated? Somehow competency X will feature prominently in the appraisal next year.
People respond to incentives. That’s literally what performance systems are designed to make us do.
Once the measure becomes too explicit, though, people start optimizing the evidence rather than whatever the evidence was supposed to represent.
Hush hush can still become ridiculous
There still has to be enough transparency for someone to improve.
If an officer keeps missing promotion and the answer every year is “continue doing good work”, that’s quite useless. Does the person have a competency gap? Need more breadth? Need more management exposure? Difficult to work with? Or perfectly ready but there’s just no job right now?
These are v different answers.
I think people should at least understand what would make their bosses more comfortable taking the punt, even if nobody can promise an exact outcome.
The actual opportunity matters too
Some promoted jobs suck
There’s also this assumption that the next higher job is obviously something you should want.
Maybe.
You could inherit a high-performing team, fantastic boss, interesting work and decent resourcing. You could also inherit:
- a deeply unhappy team
- years of unresolved people problems
- a portfolio nobody really wants
- insane expectations with no resources
- a boss whose working style clashes badly with yours
- a predecessor who was either legendary or a complete disaster
Both extremes create their own expectations.
So yes, the promotion may be good, even if the actual job may be terrible.
Hard jobs can still be useful
Some of my best learning came from difficult situations, so I’m not suggesting everyone should look for the easiest posting possible.
A messy job can teach you a lot because you’re forced to deal with problems you would never encounter in a beautifully functioning team.
Just go in with your eyes open. A higher grade doesn’t magically make every opportunity good.
Getting promoted too early
The flaws get magnified
This is the bit that takes me back to the person at the start.
The promotion probably didn’t create all those weaknesses overnight. Maybe the person was already disorganized, struggled with people, or wasn’t particularly good at managing upwards. Those weaknesses were simply much easier to survive when the person’s main responsibility was their own work.
Once you’re the manager, everyone experiences them.
If you’re disorganized, priorities around the team become messy. If you avoid conflict, problems can sit there forever. If you can’t manage upwards, the whole team loses operating space.
If you panic, now everybody gets the 99x combo hit.
Expectations jump much faster than experience
This is why quick promotion really is double edged.
You get the title early and obviously that’s exciting. At the same time, people naturally expect more because you’re now sitting in a bigger job, and sometimes even more because you’re known as the fast-rising high achiever.
Your actual experience didn’t suddenly catch up overnight.
That’s where some people get exposed very badly.
Another year under a good boss can be worth a lot
Nobody wants to hear “wait a bit more” when other people are moving ahead. I’d probably be annoyed too.
But an extra year or two under a really good boss can give you a lot of examples to steal later. You watch how the person handles someone who’s struggling, deals with a bad situation from above, pushes back, calms everyone down, or decides something where every option has some downside.
You also get to make mistakes while somebody else still carries the ultimate accountability, which is actually quite a useful luxury.
Nobody really teaches you how to manage
I learned mostly by osmosis
Management courses have helped me here and there. There’re useful frameworks and sometimes a course gives you language for something you’ve already vaguely felt.
Most of what I do came from watching bosses, both good and bad stuff (I’ve ended up long winded… unfortunately). I also learned from bad examples.
You can practice before you get the job
Ackchyually (lul) you don’t need the formal appointment to start trying some of this. Lead a piece of work involving other people, cover your boss when they’re away, guide a newer officer, deal with a difficult stakeholder, or take on something ambiguous where you need to make the call rather than wait for instructions.
These don’t recreate the full management job, but they give you some practice and your bosses better evidence than “this person is really good at their current job”. You’ll probably also discover pretty quickly which parts you’re comfortable with and which ones you need more exposure to.
You eventually make it your own
You can’t copy another boss wholesale because their style may look totally unnatural on you.
Some people can be incredibly warm and still firm. Someone else barely changes tone and somehow everyone knows they’re serious. Another person is great at creating energy around a team.
You absorb bits, try things, screw some up, and keep the bits that work.
It’s a little like being a parent
This is where the imposter syndrome becomes very real.
You can read a book, attend a course, talk to experienced managers, then encounter some ridiculous situation nobody covered and still have no idea what the correct response is.
Ask those managers what to do and you may also get multiple answers.
Eventually you choose one and see what happens. Being promoted means somebody thought you were ready enough to try, while actually becoming good at the job carries on for a long time after.
If you’re feeling stuck
If you’re trying to get into management
I think the useful question is whether you’re already accumulating evidence that somebody can safely take the punt.
Can you:
- guide more junior officers?
- lead work involving multiple people?
- make reasonable judgment calls without escalating everything?
- manage stakeholders when things become uncomfortable?
- produce work your boss trusts?
- help people around you get better?
And if you’ve got a really good manager now, watch carefully. There’s a lot you can absorb before you’re the person carrying final accountability.
If you’re trying to get into middle management
The shift gets wider again because you need to manage through other people instead of touching everything personally. Your bosses need to trust that you understand the larger context, can translate it for your own team, manage other managers, and aren’t going to create some parallel kingdom heading in a totally different direction.
Then supply and demand comes back again. Maybe you’re ready and there still isn’t a sensible DD job for you today, which is just part of the equation.
Can you see beyond your own portfolio?
Another shift is being able to look beyond your own team’s interests. Something can be great for your portfolio and lousy for another part of the organization, or create a problem somewhere else that you don’t see if you’re only optimizing for your own work.
This is actually pretty explicit in HCS Leo Yip’s 2024 Public Service Leadership Ceremony speech. Middle managers are expected to reconcile different opinions and find opportunities to collaborate with counterparts, while leaders more broadly need to connect the work across agencies to the Government’s wider objectives.
I think breadth matters a lot more as you go up for this reason. Can you understand why another team wants something completely different, join the dots across issues, and occasionally accept that your own portfolio shouldn’t win? If you’re only ever optimizing for your own little kingdom, that’s probably going to become a bigger problem as the kingdom gets bigger.
If you’ve just been promoted super fast
Enjoy the opportunity because you obviously did something right and somebody has put real confidence in you.
Just pay attention to the things you haven’t had much time to experience yet. What does your boss keep correcting? Where are officers reacting differently from what you expected? Which situations keep overwhelming you? What are people maybe not telling you because you’re now the boss?
Fast progression means less time to accumulate some of this stuff by osmosis. That’s manageable if you’re aware of it and keep learning, and much harder if the rapid promotion itself convinces you that you’ve already mastered the level.
Personally, I’d rather arrive a bit later and do well than get there early, flop hard and spend the next few years recovering from it. There’s plenty of career left. If you flop, you might even have to leave the organization, because people remember, and rebuilding confidence after a bad stint can sadly take years.