Tips for handling the career progression conversation (for First-time people managers)

I still remember the first time a team member sat across from me and asked, "So... when am I getting promoted?" I'd been managing people at my agency for maybe six months at that point, and I had absolutely no idea what to say. I fumbled through some vague answer about "performance" and "timing" and walked away thinking, well, that was terrible :P

After 18 years in advertising and managing teams across Singapore and now the US, I've had this conversation more times than I can count. Career progression is universal across cultures, and sooner or later, your team will bring it up. You're probably more familiar with being on the other side of this conversation (asking about your progression), so I think it's worth preparing for it well in advance. The prospect of career progression can be incredibly motivating, and the lack of it can absolutely tank morale.

A few things I've learned the hard way:

• People compare themselves against others in the office — especially those they see as peers. When one person gets promoted and others don't, you can quickly get a sense of favoritism and unhappiness brewing. I've seen candid collaboration just evaporate overnight because of a poorly managed promotion cycle.
• Promoting someone without clear evidence of achievement, or doing it too quickly, sets dangerous precedents. I once saw a graduate get promoted after nine months. The next batch of graduates who didn't get promoted within a year started questioning everything. That's a mess you don't want to clean up.
• One of the trickiest situations (and I might be wrong, but from my experience, this is the hardest one) is explaining to someone that while they're performing at the next level, there's simply no business need or headcount for the promotion right now. That conversation is painful T.T

So as a first-time people manager, what should you do?

Know your company's process

Every company handles this differently. In my experience, the larger the corporation, the more complex the promotion process tends to be. Some have annual reviews, others have multiple cycles. There may be training programs and resources you can sign up for — take advantage of them. The more you understand the mechanics, the better you can advocate for your people.

Plan six to nine months ahead

Promotions do not happen overnight, and the groundwork takes longer than you think. You need real time to:

• Delegate meaningful work and evaluate whether your team member is truly performing at the next level
• Build a business case and get buy-in from your line manager, finance director, or even the managing director
• Assess the knock-on effects on the rest of your team

Invest in goal setting

I know, I know — this sounds simple but it's genuinely hard to practice well. It is awfully easy to skip or rush through goal-setting exercises when there's a client deadline screaming at you. (Ask me how I know.) Go for quality over speed in these conversations.

Recognize performance beyond promotions

If someone is working hard but not yet at the next level, a spot bonus or public acknowledgment can go a long way. I've found this especially useful in agency life where budgets are tight. Promotion isn't the only way to show someone their work matters.

Manage expectations honestly

Give your team member a realistic picture and don't over-promise. If the promotion comes sooner, it'll be a pleasant surprise. Under-promising and over-delivering works much better than the reverse.

Handle team transitions carefully

If someone moves between teams, make sure the progression conversation carries over. I'd recommend:

• A discussion between you and the new manager about performance and any ongoing progression conversations
• A three-way meeting to align on progress and expectations
• Clear documentation so nothing falls through the cracks

When someone threatens to quit over progression

This one deserves its own section because it's one of the most stressful situations you'll face as a new manager.

Occasionally, you'll have a team member who's unhappy with the speed of their progression and is thinking about leaving. If this is your first time dealing with it, get your line manager or HR involved for guidance — do not try to handle it solo.

The critical question is whether they're genuinely performing at the next level. If they are, and you want to keep them, you still don't want to create the perception that threatening to quit is a fast track to promotion. That sets a precedent that will come back to haunt you.

From my experience, an experienced manager — after consulting with HR and finance — will be able to articulate how far they're willing to go to retain someone, and what the right message should be. The goal is to retain good people without rewarding ultimatums.

What's been your biggest challenge with career progression conversations? I'm still learning myself, honestly.

Cheers,

Chandler