Advice on how to approach my boss about a promotion

Hello Everyone!

I've been at my current company, in the same position for about a 1.5 years now. My team and boss are great, plus I get a decent amount of control over what projects I take on and can tailor it to my interests. The work-life balance and compensation (~100k) are also quite good for the level that I'm at (Product Designer). All-in-all, I really like where I'm working.

A few months ago my team announced that they're hiring a new VP for our department and are going to be restructuring. They heavily implied that this will be giving team members opportunities to move into more senior positions as we grow the team and hire more people. I'm hoping to move into a Senior Product Designer position which would be a title change and a salary increase to $110-$120k yearly. My actual responsibilities wouldn't change much as I've taken on more ownership of specific products and projects in the last year but there would be a change to start managing junior designers who join the company.

The main problem is that the company has been dragging their feet. They said we'd hear about the new team structure about a month after the VP started but it's been a full 2 months with no updates or comments whatsoever. Meanwhile, I'm getting multiple recruiter messages on LinkedIn for Sr.Design positions at different companies that would come with a pay raise and better title. The main thing making me hesitant to move is the amazing culture at my current company and the big question mark on if my future boss/co-workers would be as flexible and supportive.

I want to have a frank discussion with my boss about the situation and put a little pressure on him to follow through. He's said previously that he supports me moving up in the company to a sr role and has always been great about talking up my achievements. I want to make it clear that I'd really like to stay at the company but every month that passes by with no updates is a potential wasted opportunity for me.

Any advice on how to approach this topic in our 1:1?

Nita Singh Kaushal has lots of great resources about this kind of negotiation, and even tends to help spell out a script for these conversations. Here's one example from her library of content that talks about leveraging an offer for internal advancement:
I've been through so many similar situations (new VP, company was acquired, massive team overhaul, etc) and I will say these things ALWAYS take longer than they say they will. And usually it's never 1 reorg, but a first reorg and then another one within a year (either due to an exodus of the people who aren't happy with the new situation or because they just didn't get the team structure right the first time because they rushed it). My advice: take the conversations with recruiters (especially so you can get an idea of competitive salaries) but also have that conversation with your boss. Reiterate that you like the company/team, you're excited about opportunities, but you're ready to level up. I would NOT outright say that you are considering external offers, but just reiterate what you are looking for and perhaps he'll read between the lines.
+1 to @maggiewolff - Definitely agree you should pursue both tracks. You should not waste the opportunity to see what's out there (and even use another offer to sweeten the deal at your current company). I also agree that there is no need to say anything to your boss about the recruiters or that time is ticking. Here's why:Better to show up as a partner and leader than a thorn who is demanding they move faster bc it's costing you. You want to be in the best position possible if/when they announce the reorg. Instead: Something I always advise people to do would be to take the initiative when it comes to throwing your hat into the ring at your current company. AKA instead of waiting for them to tell you what direction the role will be going, you might start your campaign by bringing in a few ideas of what the role and department could and would look like if you were to be the one they chose for SVP. In other words, have a vision going into this 1x1 and become a thought partner to the people who are structuring the group vs the person who is urging them to move faster on your behalf. Meanwhile, take the other recruiting calls both to take the edge off the time where you're waiting and possibly court a competing offer if/when they roll out the next level role. I don't know the ins and outs of your company, but having advised women on how to get hired and promoted for a while has taught me that adding value is always the best strategy and it will also give you a sense of control to know you had a hand in shaping your role. PS: you are also able to come in with a vision for the role and dept if you're conducting a job search, in fact, if you are looking to be seen and treated as a leader, this is a real shortcut to getting there. Happy to chat more if you need more help.