Layering and Being Layered
How to Hire Above Someone — and How to Handle Being Hired Over
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. If you want to learn more about how Lessons and this Substack work, you can read more here.
Layering is one of the hardest — and most essential — management skills to build inside a growing company.
By “layering,” I mean deciding that you need to add someone more senior above a person who has been owning a function or leading a team.
Sometimes the function has simply gotten too big for one person to run.
Sometimes someone is a strong individual contributor but a weak manager, and should return to an IC role.
Sometimes the company is scaling faster than the leader is, and you need someone who has seen this phase before — ideally someone the current leader can learn from.
And sometimes it’s a performance issue, and layering feels like the least-bad way to acknowledge that reality (we’ll talk about layering as avoidance below).
If you’re scaling quickly, this won’t be a one-time event. Roles change faster than people, and executive tenures are often short. In cases of true rapid scale (a business that’s 3–10×ing every year), I tell people to expect leaders to last about 18 months. Let them surprise you by lasting longer, but don’t let it surprise you if it’s shorter.
Building a leadership team inside a growing company is never “done.” It gets a bit easier as you turn into a bigger, more stable company, but when you’re 100s-1,000s of employees, it’s a constant game of whack-a-mole. My friend Max Mullen, the co-founder of Instacart, came to Glue Club a couple of years ago and said “building a leadership team is like painting the Golden Gate Bridge: by the time you finish, you need to start again.” (He said this is someone else’s quote, but I don’t know whose!)
So, that’s what layering is. It’s necessary for the long-term health of the company. And it completely sucks.
It’s painful whether you’re delivering the message or on the receiving end of it. There’s real emotion, real ego, and real uncertainty involved for everyone. It’s one of those moments that can either strengthen trust or completely break it, depending on how it’s handled. I have friends who have been layered and gone on to stay at the company and build long, successful careers — and I’ve watched situations that were handled so badly that the person rage-quit.
The difference between those two outcomes is almost never the decision itself. It’s how the decision gets made and communicated. These moments also send a strong signal to the rest of the company about how leadership treats people when things get hard.
I want to talk about both sides of this — the company side and the individual side — and what you should be thinking about in these moments. We’ll start with the company side, because that’s where the decision gets made.
If you’re the leader doing the layering
Layering itself is not a failure of leadership — it’s one of the core muscles you have to build if you’re scaling quickly.
But it’s also one of the moments where even if the decision is right, how you handle it matters enormously — it shapes trust, retention, and the story people tell themselves about working at your company.
A few principles I’ve learned the hard way:
1. Get very clear on the actual problem before you layer someone
It’s easy to be right that something isn’t working… and wrong about why.
Before you decide to layer someone, slow yourself down and do the work:
Get clear on where the real gaps are
Coach the current leader directly, making clear what the gaps are and what you need to see change
Ask uncomfortable questions until you truly understand what’s going on
At minimum, this coaching and exploration gives you a real chance to get on the same page as the current leader about the gaps you’re seeing. If you do this well, layering won’t be a surprise. That doesn’t mean it won’t hurt… but it gives them time to acclimate.
More importantly, if you skip this step, you risk hiring a more senior person and discovering six months later that you still have the same problems — just with more people involved.
This is a perfect moment to use the Waterline Model, which I talked about on Lenny’s podcast a couple weeks ago. Is this a role problem? A clarity problem? A structure problem? A skill gap? A decision-making issue?
Be precise. Make sure you’re not trying to solve a structural or dynamics issue (per the Waterline Model) at the individual level. Layering is a blunt tool if you haven’t diagnosed the disease.
2. How you handle it dramatically affects whether the person being layered will stay
You can absolutely influence whether someone wants to stay after being layered, and I see companies mess this up all the time.
A particularly bad version sounds like:
“We’re hiring above you. Here’s why…. what do you want to do?”
That puts all the emotional and strategic labor back on the person being layered. It makes them feel expendable and unimportant.
A much better version is coming with:
A clear explanation of the gaps you’ve already been discussing and why they lead you to hire above them
A concrete new role that matters to the company and aligns with how they want to grow
Areas where you genuinely want their input on how to move forward and how to set the new leader up for success
Real incentives to stay (comp, equity, opportunity to learn)
When paired with prior feedback and honest communication about gaps, this kind of thoughtful, concrete plan makes people feel seen and cared about — even in a hard moment.
Two quick notes:
1) All of the bullets above don’t need to happen in one conversation. In many cases, it’s better to start by meeting with the person to discuss the decision and a clear plan — including what their role could look like going forward — and then give them time to digest it.
Sometimes it’s worth discussing incentives in that first conversation to underscore how much you want them to stay. Other times, it’s better to save asking for input or negotiating incentives for a follow-up once the initial shock has worn off.
Thoughtful pacing here often leads to better outcomes than trying to resolve everything at once.
2) Truly, the most you can do is ask someone to give it a chance. You might want a clear, concrete decision or some kind of commitment, but you want those things because they’re good for you. At the end of the day, you made your decision by layering this person; now they get to make their decision. And particularly if they feel hurt or emotional, often the best that they can promise you is to see how it goes or to give it a chance. Don’t demand more than that if they’re not ready to give it.
3. Even if you do everything right, they might still leave — you should have a plan for that
You cannot layer someone assuming they’ll stay.
I see leaders get this wrong all the time and then act surprised when the person quits. Let’s be clear: deciding to layer someone is opening the door to them leaving. How you handle the conversations and the process makes that more or less likely — but the risk is real either way.
Choosing to layer someone is choosing to solve a problem that’s more important than retaining this specific person. You may want them to stay, but you have to be honest about the tradeoff you’re making.
That means planning for the version where they leave, not just hoping they don’t.
That plan doesn’t need to be complicated. It just needs to answer one question: what will you do if this person quits?
It might be as simple as having an interim or fractional leader ready, or temporarily folding their org under another leader while you regroup.
Planning doesn’t mean you want someone to leave. It just means you’re not scrambling if they do.
One mistake I see — and it honestly feels juvenile — is leaders getting angry when they layer someone and that person quits.
I think it often happens when the company leader still believes the opportunity is great. And maybe it is… from their perspective. But the person being layered may not experience it that way at all.
Your job as a company leader isn’t to assume they’ll see it the way you do. Your job is to clearly tell the story of why you believe staying is compelling, ask them to give it a real chance, and then be adult about the fact that layering someone opens a door.
It’s not reasonable to expect people to stay regardless of what you do to them. If you make a move that changes someone’s scope, status, or trajectory, you have to accept that leaving is a rational response — not a betrayal.
4. Don’t do this behind their back
You don’t need to have every detail figured out before you talk to the person, but once you’re confident that layering is a real possibility, honesty matters more than precision.
You can talk to your board or your manager. You can cautiously explore outside options. You can pressure-test the market. What you can’t do is pretend everything is fine with your current leader while quietly building a different future. That kind of behavior almost always blows up in your face.
Nothing demoralizes someone faster — or turns a situation that could have been constructive into an angry mess — than the feeling that leadership has been lying to them.
If you’re probing the market before talking to the person, be extremely careful. Once this starts to feel real, the conversation needs to happen before they hear it through the grapevine or infer it from your behavior.
Surprise here doesn’t just hurt; it destroys trust and removes any chance that the person stays.
Layering vs Demotion
Demotion and layering can look similar from the outside, but they’re fundamentally different conversations.
Demotion is about underperformance. The person isn’t meeting the bar for the role they’re in.
Layering is about growth. The company has changed, the role has changed, and the scope has outpaced what the current leader can reasonably handle — even if they’re strong at the work.
In a true layering situation, the person didn’t suddenly get worse. The job got bigger.
Layering can feel like a demotion because it often involves a loss of scope, status, or control — but the underlying reason is different.
One way I think about the difference is with the Legos analogy.
In a layering situation, you hired someone to handle a reasonable pile of Legos — and they did. Then the company grew. More Legos kept getting dumped on the table. Different Legos. Bigger structures. Eventually, the pile gets so large that what you really need is someone who’s seen a pile this big before and knows how to build something great out of it.
Demotion is different. That’s when you give someone a pile of Legos and realize they can’t handle the pile you gave them. The job didn’t outgrow them — it was mis-scoped from the start.
Both situations change the org chart. But they’re not the same conversation.
If you feel like you need to demote someone — meaning move them into a more junior role with meaningfully less scope — it’s important to be honest with yourself about what you’re really trying to accomplish.
In most cases, demotion is not a turnaround plan. It’s an exit-adjacent decision.
Demotions rarely work out long-term. More often, they’re a slower, more awkward way for someone to leave a company. That doesn’t mean they’re always wrong… but it does mean you should be asking yourself whether demotion is genuinely the right next step, or whether a clean exit would be healthier for everyone involved.
If you’re considering a demotion, a few additional things to think about:
Only offer a demotion if you are 100% confident the person can succeed in the lower-level role. This is the most common failure mode. Leaders demote someone, only to discover they’re still not meeting expectations.
Make the compensation match the job. Do not demote someone to a more junior role while keeping their comp or title the same. It will bite you in every possible way — their behavior, team dynamics, and perceptions across the org. Everyone will find out, and it will create real damage.
Offer a real choice. That usually means: the narrower role at lower compensation or a severance package and a clean exit.
Be genuinely prepared for either outcome. Most people will choose the package. That’s not a failure.
Demotion can be a humane way to acknowledge reality. But it’s very rarely a development strategy. Treat it as an exit-adjacent decision — a last attempt to find the right landing.
Up to this point, I’ve focused on the company side — the decision-making and the tradeoffs leaders are making. Now I want to switch perspectives and talk to the person on the other side of the table.
If you’re the person being layered
First: I’m really sorry. This can be a genuinely hard moment.
Being layered can feel like something important is being taken away. It can feel public. It can feel embarrassing. It can trigger a very loud internal story about what this “means” about you — especially if you’ve been giving a lot to the company or helped build the function from the ground up.
A few things I really want you to hear:
1. This happens to almost everyone you admire
Every great leader you respect has been layered at some point. Often more than once.
This moment isn’t a verdict on your potential. In growing companies, roles change faster than humans do. Sometimes the company simply moves into a phase that requires a different shape of leadership — not because you failed, but because the work changed.
That doesn’t make it painless. But it does make it a normal part of the leadership journey.
2. Layering is not the same thing as demotion — even if it feels that way
Layering can feel like a demotion because something visible is changing: scope, status, autonomy, reporting lines. It’s reasonable if your ego needs a good scream or a good cry.
But if this is a true layering situation, it is not a statement that you’re underperforming. It’s a statement that the company has grown rapidly and that your role has grown with it — sometimes faster than anyone could realistically keep up with.
The job got bigger. You didn’t suddenly get worse.
3. Don’t let your ego be the only decision-maker
This is a moment where ego gets very loud. Titles, reporting lines, and optics can start to feel like the whole story.
Two things I’d say from experience.
First: your ego is not the best part of you to make long-term career decisions. The questions that matter more are things like:
Am I learning?
Do I think I might be able to learn from the person coming in?
Does this new shape of the role still excite me — or could it, once the initial emotion settles?
Is my work here actually done?
Those answers will matter far more for your long-term trajectory than anything your ego is reacting to.
Second: this story is just getting started. When changes like this happen, it can feel like everyone is writing a story about you, and that story is etched in stone. But as the company keeps growing, your story will keep getting rewritten. What feels like a car crash in the moment often turns out to be a speed bump in hindsight. Not always — but often.
4. Give it a real “let’s see how this goes” window
When they explain the change and offer you a new role, if the answer isn’t immediately and clearly “this isn’t for me,” I’m a big fan of giving it a real trial period — usually 3–6 months.
That window gives you time to:
Let the initial shock wear off
Experience what the new working relationship actually feels like
See whether the role creates new learning and energy, or just resentment
You’re not obligated to stay forever. But leaving in the first emotional spike often leads to decisions people later wish they’d taken more slowly.
5. Focus on the long-term story you’re building — not the title math
Assuming the company continues to grow and has an interesting story, most future employers won’t care about the exact title you held during this chapter.
They’ll care about what you saw at scale, what you built, what you learned, and the complexity you operated in.
You can explain a layered role. Many people have. Titles are editable on LinkedIn; you can make it all make sense later. Don’t sacrifice a good opportunity because you’re worried about what other people will think.
6. If you decide to leave, leave intentionally
Sometimes layering makes it clear that this isn’t the right place or phase for you anymore — and that’s okay. If they treat you poorly in this process or show you they don’t really care about you, leaving may be the right answer.
If you do leave, try to do it from a grounded place rather than a reactive one. You’ve spent time building relationships and a reputation at this company. Don’t burn the house down on the way out.
This moment will not define your career unless you behave in a way that damages your credibility. Decide whether you want to leave or give it a real chance, then move forward with grace.
This is just a chapter in your story. And someday, you’ll be the one giving someone else advice about how to handle being layered.
Layering is one of those moments where growth, ego, and identity collide. There is no version that is painless. But when it’s handled with clarity, honesty, and care, it doesn’t have to be destructive — for the company or for the people inside it.
Most of the damage I’ve seen doesn’t come from the decision itself. It comes from avoidance, secrecy, or a failure to take responsibility for how hard this is on everyone involved.
If you’re new here, subscribe to Lessons to get new posts. And if you want to be part of the ongoing conversation about leadership, careers, and the real work of building companies, the paid tier is where those conversations happen.
I love writing things that actually help people, not just adding more noise to the internet. If you’re wrestling with something at work or curious how I’d think about a situation, paid subscribers can drop it in Subscriber Chat or reply directly to the email for this post — a lot of my best ideas come from real, honest conversations like these.
You can also find me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.
And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.