I’m going to experience brain drain, but I’m also patting myself on the back because I know I set a good example for how to work cross-functionally, acknowledged the strengths of my team, and pushed them to expand their abilities beyond their direct role. I think that makes me a decent manager, or at least I’m good at hiring.

Informally, it’s been recognized in passing, like ‘Wow, you’re sending great people everywhere,’ but nothing formal in reviews yet. I have a good relationship with our C-Suite, and there’s been some laughs about the fact that they're taking all my best employees.

But this leads me to two questions:

1. How do I market this ability to develop talent, without taking away from the innate abilities of my employees?

2. In a performance review or compensation discussions, I need to be able to leverage this in a tasteful and thoughtful way: how?

- Colin F

I’m back on Truth, Lies & Work to help them celebrate their 300th episode!

Jake: The paradox of being a talent magnet is that you make your own life harder when you frequently graduate great people!

Your first question raises a subtle point, which is that in practice, it can be hard to distinguish how much of an accomplishment is a product of innate talent or developed capability. But frankly, so long as you’re focused solely on the specifics of what you did to hire and then develop talent, I wouldn’t worry too much about your self-advocacy coming across as egotistic. And that specificity is the difference-maker. Focus on how you hired well, enumerate the discrete actions you take in small moments that grow talent, etc. If you’re genuinely talking about actions attributable to you, it won’t feel like you’re taking credit for your employee’s talent. Because you aren’t.

And the specifics also relate to your second question. The more (specifics) you can muster, the more you can credibly leverage your talent development skills. I would think about preparing for your performance review in two ways.

First, think of your review as an exercise in arming your own manager with the data points to back up what has already been loosely acknowledged. What bullets can you hand them on a silver platter that make the case for your advancement without having to allude to purely anecdotal or ethereal notions of “being a good manager”?

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Second, make the formal performance conversation into an aggressive request for more resources (people). Try pre-empting the conversation with your own version of something like this: “It’s been a highlight that so many of the people I’ve hired and developed have moved up elsewhere in the organization. But the result is that my team is under-resourced to accomplish our goals going forward. I want to make sure that we are given enough resources to both meet our goals and also account for our team being a developmental hub for the organization.”

I would also start marketing yourself as someone who has a track record of developing talent. On your LinkedIn ‘About Me’ section (yes, I know, ugh), highlight stats that showcase your managerial capabilities. Emphasize your passion for developing people throughout your bio. As painful as the idea of having a ‘brand’ may be, everyone has one (like it or not), so lean into it with grace and honesty.

In general, it sounds like the brain drain you’ll experience from losing your people puts you on defense. So play offense. Rather than just trying to get back to “neutral”, advocate for getting further ahead. Ask for more responsibility and more talent to grow. Right now, you’re experiencing a deficit, but it’s because of your strengths as a manager. Lean into those and insist the organization catapults you further ahead in the coming months.

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- Sarah J

Jake: This is an uncomfortable spot! You don’t want to be wrong in either direction. If she’s interviewing elsewhere, it might make her uncomfortable. If she isn’t, your assumption will almost definitely make her uncomfortable (although, maybe just flattered).

Let me cut to the chase and be blunt: whether or not she’s interviewing, the conversation you seem to be afraid to have is one you should probably be having anyway. Ambitious people who feel unseen will eventually leave. The only question is whether you’ll have a chance to change the outcome.

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The minimum you should do is schedule a straightforward career conversation. Not a performance check-in, not a one-on-one with a buried agenda item — a dedicated conversation about her goals. Write “Career Development” as name of the meeting. Ask what she wants to be doing in a few years, what she feels is missing from her current role, and what she needs to grow. If you genuinely see a future for her at the organization, say so! But avoid coming anywhere near a commitment you can’t keep. “I see a real future for you here and I want to help make that happen” is meaningful. “I think you should be up for a promotion soon” is a commitment you may not be able to honor, and broken promises to ambitious people tend to accelerate exactly the exit you’re trying to prevent. Aim to spend 85%+ of the conversation listening.

Then, if you want to probe a little further, try something like: “I’d like to help you advance. Have you come across any roles — here or elsewhere — that you’ve been drawn to?” It’s a low-pressure invitation. She can take it or leave it. But it signals that you’re paying attention and that you’re a manager she can be honest with — which, more often than not, is exactly the kind of manager people choose to stay for.

Go talk to her.

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I read through her previous annual reviews and was shocked to find that her prior managers rated her as either ‘meets’ or ‘exceeds expectations’ every year. I know both of her previous managers and they complained about her repeatedly. They completely avoided managing her and now the burden has fallen to me.

How do I fairly assess and manage someone who carries a lot of informal baggage but technically has a spotless record?

- Name Withheld

Jake: This is an all-too-common problem. Managers are not given the training and support needed to give accurate feedback, and so they demur when it comes time for hard conversations. Instead, they complain about their employees in private and turn performance management into an HR checkbox activity, rather than an opportunity to get the most out of their people and create a culture of supportive excellence.

Side note: In my experience, this avoidance is particularly commonplace in workplace cultures where people are generally “nice”. There’s a desire to just sweep problematic behaviors (and people) under the rug and hope they go away... or wait until they become someone else’s problem.

In allowing this underperformance to go unchecked for years, your colleagues have let you and the organization down. And they’ve also let down your new team member, whose had their organizational death warrant signed for years. No one should be operating in the dark with respect to how they’re actually perceived by others, especially when managers have a duty to… well… manage.

Charitably, I doubt that your colleagues felt they had any choice. They likely did not feel equipped to give tough feedback. Or perhaps they felt unsupported by the organization and opted to just pass the buck. It’s possible to be empathetic toward everyone involved. (Almost) nobody wakes up in the morning wanting to underperform. Their prior managers probably did the best they could; this employee likely doesn’t know they’ve been screwing up; and your boss might reasonably see handing this employee to you (as you are evidently more capable in these aspects of management) as the best solution.

As you think about what to do, I’d ask you to keep this question front and center: How would you handle this if you were just hired from outside the organization and given this information? In other words, what would you do without any of your current institutional knowledge and relationships?

Struggling with something at work and want some advice?
Tell me what’s going on (anonymously) and I’ll respond in a ‘Reader’s Ask’ column:

Reader's Ask

Specifically, I’d recommend scheduling a meeting with your boss and HR to discuss the gap between this person’s reputation and the formal feedback they’ve received to date. Make them aware of the disconnect and ensure the three of you are on the same page.

Then, you have the option of talking to their former managers to get more context. When you do, I’d advise approaching the conversation with a spirit of curiosity rather than frustration. They will probably feel self-conscious about not managing them appropriately, and it doesn’t do you any good to remind them of this. Frame it in the positive: “I want to capitalize on [person]’s strengths — what do they do well that’s earned them positive reviews over the years?”

Finally, when it comes to this employee, start with a blank slate and approach the future as entirely unwritten. Set clear goals and expectations, ask them what support they need to achieve them, and try to spend some time connecting with them on a human level and understanding what motivates them about the job. Maybe they’ll welcome this change of scenery (and hints of more competent management!) and rise to the occasion. Looking forward, as if they themselves were an outside hire, is probably the fairest and most productive path for you both.

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- Name Withheld

Jake: Fair timing, reader.

For those who missed it: shortly after last week’s newsletter argued that AI adoption would lag well behind AI capability, Jack Dorsey announced that Block was laying off 40% of its workforce (4,000 employees) and attributed the cuts directly to AI. My friend, this week’s anonymous reader whom we’ll call “Matt”, forwarded me the news with the subject line “lol.”

I’ll give you the honest answer, which is: this is precisely what I’d expect, and it doesn’t move my thesis much. But it does raise something I find genuinely interesting and now I have a bit of a hot take!

As a quick aside, there’s also a version of this story worth asking about even if I can’t answer it definitively: how much of Block’s headcount reduction is genuinely AI-driven, and how much is AI-as-narrative? At least one former employee raises the possibility that this is just a convenient framing for pandemic-era overhiring. Cost-cutting rounds have always needed a frame. Automation, outsourcing, restructuring — each era produces one. I’m not accusing Dorsey of bad faith; I genuinely don’t know the internal calculus. But “we’re cutting because of AI” is a hard claim to verify from the outside, and some epistemic humility seems warranted.

But let’s charitably assume that these cuts are largely AI driven. Last week’s piece argued that AI adoption would follow a bell curve — early movers at one end, regulatory and culture-bound laggards at the other, with the organizational mass of the economy clustered somewhere in the slow middle. Block is sitting at the far right of that curve. They’re an AI-native-adjacent company led by someone who has been openly aggressive about restructuring around AI for years. They’re not the median firm. One well-publicized data point is exactly what you’d expect from a distribution with a long right tail.

So Block’s “AI is coming for your job” announcement is completely consistent with my thesis, just funny timing. But it also got me thinking…

Maybe massive layoffs are the best way to quickly implement AI.

Last week I argued that embedded resistance is a primary reason AI adoption will be slower than capability forecasts suggest. The resistance isn’t usually deliberate — it arrives dressed as prudence, operational readiness, data quality concerns. But it’s real, and it compounds across every layer of an organization.

Which raises an uncomfortable implication: if you actually want to implement AI at scale, you may need to cut headcount not after you’ve seen the benefits, but before.

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- Name Withheld

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Jake: I’m sorry that your boss ignored your email. Sending those emails takes a bit of courage and to have it ignored is frustrating. But avoiding the topic amidst other conversations throughout the week? That’s just immature. Even if your boss has a busy week or isn’t sure how to respond, a quick “just letting you know that I read your email and am not ignoring it” is not just thoughtful, it’s basic management.

After 4-5 days, you should absolutely follow-up. I’m not sure that even qualifies as additional self-advocacy so much as basic interaction hygiene, but either way you should feel more than secure that an additional mention is not overstepping boundaries. If you’re in-office together, first try popping by and prompting them to schedule time to speak about it. Try: “I sent an email last week about career advancement—I know this moment isn’t the right time to chat about it—when would be best?” By deferring to a future conversation, they aren’t put on the spot, and you still have momentum. This approach also works as an email if you’re not in-person (you might also want to shift to a different modality for this reminder—such as Slack or text, depending on what your team’s norms are).

You are always welcome to ask your manager about promotion timelines and career advancement. Sure, one can overdo it, but I get the sense this is not a repeated request of yours. Just don’t be thrown if they give you some version of “I don’t think you’re ready for a promotion”. They have to be able to justify their thinking, of course. But just as you should ask directly about your promotion, you should also permit them to respond in kind. That’s healthy!

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I don’t know if I should say something to them, mention it to someone in leadership, or just accept that this is how people operate now. But I’m genuinely bothered by it.

Jake: Over-embellishing on LinkedIn… say it ain’t so!?

Sorry, I’m being too sarcastic. The truth is, I can relate a little too well to this predicament, and sarcasm is my main defense mechanism. (Whenever I read a post that starts, “I was speaking with several senior leaders…,” my first reaction is: a) you maaaybeee spoke to one person, and b) you are probably just making this up and invoking authority + social proof to sound credible.) So I’m with you, but let’s break this down a bit, because you’re framing this as a principled stance about truth and accuracy, and I think there’s more going on here.

I suspect that you’re “genuinely bothered” by their LinkedIn self-promotion in a way that goes beyond the casual annoyance we have when friends post over-curated vacation photos on Instagram. Social media exaggeration on friend-based networks is mostly costless—annoying, but contained.

What your colleague is doing feels fundamentally different because professional credibility has currency. Their misrepresentations can potentially create real opportunities—promotions, external offers, and more—based on a distorted record. And while professional opportunity is not a fixed pie, it is somewhat fixed (especially for internal opportunities), and your colleague might benefit at the expense of others who are actually more deserving.

So no, you’re not being unreasonable for finding this (a little) troubling. The question is what, if anything, you should do about it.

Saying something directly to your colleague is unlikely to go well. They’ve already rationalized this behavior, so I doubt there’s some magic phrase that would cause them to change while keeping your relationship intact. (Though I suppose if you don’t care about maintaining your relationship, go for it! In that case, a simple “these LinkedIn posts are complete exaggerations—what gives?” would probably suffice.)

You could try to frame it as though you’re their savior, telling them that they’re the talk of the office. But going with the (Trump voice) “many people are saying…” approach is dishonest, and dishonesty is the very thing you’re complaining about here.

Mentioning it to leadership is tricky. If you say, “So-and-so is exaggerating their LinkedIn posts,” you risk sounding petty. Same goes for socializing this among peers just to create animosity.

Now, if their misrepresentation has created real confusion, such as colleagues thinking they’re the point person or external clients making decisions based on incorrect information, then you have standing to raise it. But frame it around quantifiable organizational impact, not the principle of the thing.

In an ideal world, I’d advise you to treat it just like any other cringey bullshit Instagram post: just roll your eyes and let it go. But it’s clearly bothering you enough that letting it fester will breed resentment. So here’s my two-fold recommendation:

First, unfollow them on LinkedIn. You simply must attempt to control what is privileged to command your attention. You’d advise a friend to do that, wouldn’t you? So do it.

Second, try to dig in on precisely why this particular person’s LinkedIn behavior is eating at you so much…. because there’s no way this is the only exaggeration you’re seeing on LinkedIn! So what makes this different? Maybe it triggers a reminder that your own work contributions are not getting the affirmation that you want. Maybe it’s a deep-seated wish that you could self-promote more. Maybe I’m overstating the psychological impact and it’s far simpler.

But either way, do some digging. This behavior is absolutely annoying and absolutely ubiquitous. In fact, it reminds me of a discussion I was leading with several Fortune 100 CEOs at Davos last week…

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Here’s my problem: His boss has zero visibility into these issues, so if I give honest feedback about these specific gaps, it will be blindingly obvious it came from me — I’m literally the only person who would know. Tom and I have a decent working relationship, and I don’t want to destroy that. But I also don’t want to lie when directly asked. How do I handle this?

Jake: If the dilemma were solely about whether to give honest feedback or preserve your relationship with Tom, I think there’d be a fairly straightforward path here: Be honest without being comprehensively honest.

Since you can’t guarantee anonymity given that you’re uniquely positioned to provide this feedback, take advantage of the beautifully vague request to simply provide “some thoughts” and use that ambiguity to your advantage. The best way to handle this is to keep your input forward-looking rather than simply retrospective (a best practice for most feedback).

For example, you might say something like “Tom might benefit from additional technology or resources to manage the heavy load of details he’s entrusted with.” Or something like “Tom’s generally helpful tone and intentions don’t always come through in client emails.”

What I wouldn’t recommend is skipping any constructive input. That may feel like the safe move or even kindness, but it actually misleads the organization. You’d be misrepresenting the situation for Tom’s boss, Tom, and for yourself. It could also backfire.

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You don’t mention whether or not Tom seems to be aware of his shortcomings. Suppose he’s already received feedback that he’s struggling, and when asked, you don’t flag any problems. At best, that might encourage Tom’s boss to think Tom has everything under control. At worst, that makes you seem unobservant and out of touch. So you definitely want to mention something.

Importantly, I think there’s a larger piece here that’s missing from your question. You’ve framed this dilemma purely as a tradeoff between being honest and preserving a positive dynamic between you and Tom. But there’s a third variable that anyone in your position has to confront: You don’t want to keep working with someone who’s underperforming!

Perhaps you haven’t realized that this is a key motivator for you, or you’re omitting it here, but either way you have to confront that there must be a real desire to ensure that Tom is held accountable. And that’s entirely valid.

So go ahead and be strategic with the feedback you give, keeping it forward-focused and thinking about ways to help empower Tom rather than just venting frustrations or speaking in broad generalities about your perception of his general lack of intellect. Where this gets particularly tricky is if you’re pressed for more insights or specifics. If you trust Tom’s boss to handle the information deftly, then I think you should take the risk so long as you can be specific and actionable.

But speak up: while it’s not your job to assess Tom, you do share responsibility for making sure that your team is getting the right inputs (in this case, honest feedback) to achieve its goals.

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Reader: I have a talented 24-year-old on my team. She’s been in her role for 10 months and doing good work, but she keeps bringing up ‘next steps’ and wanting to map out a path forward. I really want to encourage her to be ambitious and advocate for herself, but she needs more skills and experience before she’d be ready to handle more senior positions.

When I mention this, she seems a bit deflated. I wouldn’t say she acts entitled, but she believes she could handle more, and she’s just not ready. How do I validate her ambition and keep her engaged without either giving her false hope or making her feel like she’s stuck? I also can’t help feeling like I’m just another manager complaining about Gen Z... but it’s extremely real.

Jake: You’re not “just another manager complaining about Gen Z”—you’re dealing with a real mismatch between ambition and readiness, which is tricky at any age but particularly acute with early-career employees who haven’t yet internalized how long it actually takes to build senior-level capability.

The key here is consistent, specific feedback about what “ready” looks like. When she brings up next steps, make sure you don’t just say she needs more experience (which sounds vague and dismissive). Instead, be concrete: “You handled XYZ really well, and that’s exactly the kind of work you need to keep doing consistently before you’re ready for a more senior role.”

This is crucial: Demonstrating a skill successfully doesn’t mean someone is ready for a job that requires that skill at a higher level, under more pressure, all the time. A great quarterly presentation doesn’t make someone ready to lead client relationships. Nailing one analysis doesn’t mean they can own strategic planning. Help her see the difference between showing promise and consistently delivering at the next level.

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When you talk about a timeline to promotion, I would also rely on social proof and reference others in the organization: “Most people who are successful at the next level have been in their current role for 2-3 years. That’s not arbitrary—it’s what it takes to build the depth and consistency we need.” This depersonalizes the feedback and shows her it’s not about her specifically, but about normal, healthy career progression.

Often, people create their own narratives about advancement that were never actually part of the deal. So it’s useful (and fair) to turn some of this back on her and ask: “When you interviewed for this role, what timeline did you have in mind when you accepted the position?” Let her articulate her expectations and see if they’re rooted in what was actually discussed. If she can’t point to specific commitments that were made, that’s clarifying for both of you.

There’s also a structural issue worth calling out. While it’s possible this employee may have created her own unrealistic expectations, your company may have set you up to struggle with this conversation. Ideally, career mapping happens at the organizational level—in job descriptions, during onboarding, in formal development programs. In my experience, most organizations don’t do enough here, leaving individual managers to deliver tough messages that feel personal when they’re really structural. If your organization doesn’t do this well, consider flagging it to leadership or HR. You shouldn’t be out there alone navigating these conversations without institutional support.

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I had two recent questions from friends in the midst of job interviews…

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Reader: I’m applying for an internal promotion at my company. I’ve been there for six years and in the same role, and I’ve made up my mind that I need to be more ambitious. If I don’t get this position, I’m fully committed to looking elsewhere. My question is: should I tell my superiors that I plan to look externally if I don’t get this job? I don’t want to come across as arrogant or threatening, but I also don’t want them to overlook me because they assume that I am comfortable. I’m very qualified for the position, but I imagine that in this job market there are other decent candidates.

Fancying a bit of brinkmanship, eh? Pushing in all your chips is a high-risk, high-reward negotiation strategy. If done well, telegraphing your ambition could give you an edge over similarly-qualified candidates. If done well. If done poorly, it could sink your chances at the promotion and make your current job more complicated.

Consider this very plausible scenario: What if you put your foot down and then don’t get the position? As you mentioned, the job market is not great, which means you might be stuck in a position that your boss knows you don’t want. That’s challenging.

Like so much of communication, what matters is not just the message we communicate but the messaging that accompanies it. If you want to take the more aggressive approach, I think there’s a simple way to signal your intentions without the downside of an ultimatum.

Don’t threaten to leave if you don’t get the promotion. Instead, say you’ve outgrown your current role and are watching for the right opportunity—and that you think this might be it. This signals ambition and a hunger for new challenges, without putting your leaders on the defensive. Any perceptive leader will recognize that passing you over could mean losing you. They may still decide to take that risk! That’s their call. But this is the strategic move—assertive, not aggressive.

Reader: I’ve been interviewing for a great job and done well so far, but from my end the interview process has been less than stellar. It’s felt haphazard with very unstructured interviews and two conversations (with different people) that had to be rescheduled last minute. Is this a red flag about the company’s culture or just disfunction with recruiting that wouldn’t impact me if I were hired?

A dysfunctional hiring process may very well be an artifact of a dysfunctional culture. After all, it’s unlikely that an organization which truly has their shit together would also have a horrible recruiting experience. But you’re also wise to consider the possibility that you’re dealing with unique circumstances (especially if this is a newly-created position, or an atypically hectic time for this department). Even more concretely, what if the process is just being managed by someone inexperienced or overwhelmed?

What you’re curious about is the likelihood that the hiring experience will spill over into the job itself. That’s hard to say without more context, but there are two evergreen considerations that I’d offer: First, how much is this process being run by the recruiting department vs. the hiring manager?

If a recruiter has been heavily involved in coordinating everything so far, it’s a decent bet that your sub-optimal experience is the result of recruiting dysfunction that won’t impact your job (unless you are applying for a job in recruiting… in which case, run!).

Second, company size. Small startups tend to lack formality and procedure; this can result in a disorganized candidate experience that often reflects a messy culture. That’s fine—if you thrive in ambiguity! But if you’re craving a job with structure and predictability, it’s likely that a haphazard hiring process is indicative of what you’ll experience on the job. On the other hand, if a small company already has an organized and efficient recruitment process it’s a great sign.

A mid-size or large company with a distinct recruiting function should be expected to execute a smooth hiring experience. While you might expect a slower, belabored process, a chaotic process at a large company can be a red flag. Back in my 20s, I applied for a job at a large company which was still growing exponentially. The recruitment process was such a disaster that I withdrew after my second interview! (In hindsight, that was a great decision despite the company’s current status as one of the Magnificent Seven…).

That said, at a large company it’s also more likely that your role would be completely disconnected from recruiting (dys)function. This is where the hiring manager's involvement in the process really matters. So try to get more clarity on how much of your poor experience is a product of your future team or recruiting.

Trust your gut here: Especially because this seems like a job that you want! If your intuition tells you this is a red flag, you’re probably right.

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