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Comment by ljw1001 | Hacker News Reader

This is not going to be like the other advice you get, but I've managed many projects in different organizations and I think it is sound. First and foremost, don't sound any alarms.

Many organizations have common characteristics in this regard. First, they don't expect you to be on time. Sales may think you're going to launch on time, but it's in their financial interest to think so. The rest of the org probably made a schedule they know you can't meet because they think it motivates you to work harder.

Second, unless you're in a startup where everyone's inexperienced, most people probably already know you'll be late, but aren't saying it out loud. They likely have discussed it (up the chain) in meetings you're not in.

Third, people do shoot the bearer of bad news. You can earn a rep as a negative person if you make _true_ predictions out-loud that don't fit the common desire. This is especially true if some of the senior people who know (like your boss) haven't been forthcoming with their bosses.

Have a quiet conversation with your boss over lunch or beers - not a meeting - and tell him/her what you think. Be prepared with details, but if he/she doesn't ask for them, don't provide any. There's a good chance he/she already knows as you suspect.

Even more casually (lunch/beers), express your concerns to the project owner. It's probably not new news to him/her either. Being "positive" is a huge part of the corporate game.: Again, if no details are asked for, don't provide any. Shift the conversation to the weather or the world cup.

You're now down. Go back to work.

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Disagree. Just be real. When I joined my current company, they had a project kicking off with a ridiculously short timeline. I asked the product manager to think about how many stories were in the backlog, how many might be added as we went, how many stories they could get through per sprint given the team capacity and then you can put a rough date on it and continue adjusting every sprint as the backlog shrinks and you get a clear picture of velocity. Our first pass put us about 400% over the allotted time (an estimate that has held up pretty well since then).

Next step, is to spell this out to your project team leadership completely unvarnished. Tell them your conclusion and how you got there. Don't let them bargain over your reasoning unless they actually have better evidence. The key is to never say "this is too hard" or "we don't have enough people" or make any other excuses. Not should you be overly emotional. Just give the facts. It's a fait accompli.

Then just ask how they want to deal with it. There is absolutely nothing to be gained from beating around the bush. I've done this more than once and was always taken seriously. One time we had even already signed a fixed-bid contract before I was able to give them an estimate. What you've committed too doesn't change the course of what's actually going to happen.

Oh, hey. You had a fully fleshed out backlog, some initial tracking, with a PO who actually wanted to know rather than just tell the business "everything is okay" and block his ears (knowing that failure to deliver will reflect dev, not him).

You had leaders who were willing to listen to facts rather than prioritize consensus (which brings with it the belief that because you were the dissenting voice in the room demonstrates you're divisive and a problem).

You landed in a really good culture, just one that hadn't faced reality yet. You've yet to plumb the depths of corporate America. :P

> You landed in a really good culture

Here's the crux of the matter. Your approach needs to be tailored to the culture you're in. The higher up in the leadership chain you go, the more important your understanding of the political machinations of your company is.

All corporations have politics, even the smallest startups. Some are just more cutthroat/feudal/kafkaesque than others.

Once you realize you are at a company where telling the truth leads to a negative consequence (an incompetent manager hired after the truth told. Their first time managing a department. The department did not previously exist in the enterprise. The department is specifically to roll out a technology they have never worked with before throughout a large company.

Lets say you were in charge of the project, are intimately familiar with the technology, and had a clear plan that would lead to success but upper management wasn't happy with the timeline. Their goal seems to be to quickly complete this project to display it as a "win".

Now the new manager was brought in, does not understand or care to understand the complexity of the project, and just keeps asking "when will it be done". Then got tired of that and changed to have it done in 2 weeks which is unreasonable, and then gave you an entirely false, negative performance review based on information they apparently forgot to actually verify or they would have known it was already complete and the people who were on the receiving end of the product are incredibly happy.

HR is asking for a meeting to discuss, what do you do? Tell HR about the depth of the incompetence Tell HR you weren't getting support from upper management Tell HR to look into what on earth was the reason this specific manager was selected.

GTFO?

This is a real life circumstance I am dealing with. I believe in the technology but unless changes are made it will be a guaranteed failure. Upper management likes the technology and really wants success here, but I know it wont happen unless then changes are made, and the people between the senior executives and me are making it impossible to be a success.

If its gone to HR its already gone pear-shaped. Lay down the facts as you see them, let them know exactly what happened, tell the truth.

If they take it out on you, you know its time to go, but maybe this guy has been pissing other people off and you have no idea about it. Maybe its HR doing due diligence to fire.

Don't make accusations or shit on anyone, you don't know the whole story. Play to your strengths, which is knowing the tech and what it takes to get it to where it needs to be. Make sure you point out your attempts to communicate this fact. Provide any evidence of this- emails, etc. where you're communicating the state of the project and your projections for it. Let them know you've been frustrated with the miscommunication, but make sure that the miscommunication has started with you.

Again, don't shit on anyone. Stick the facts, so that if it blows up in your face it says more about them than it did about you. Its also the kind of resolution I'd I want to see on the interviewer side of "How did you resolve a difficult situation".

Thanks, it is progressing as expected. The only shitting on that was done involved providing repeated examples of attempts to get clarity or schedule meetings that were repeatedly ignored or cancelled at the last minute (which the supervisor for some reason told HR I was the one cancelling). Didn't call into question their competence, just provided support for my side from others, and examples of where the review was completely falsified. Spoke with CLO prior to all of this who is a mentor of mine and is incredibly upset with the treatment I received and says company will provide severance and recommendations if they can't find a suitable location in another department internally.

If you're being made into a fall-guy, then GTFO is likely your only solution.

Be careful with the 'depths of incompetence' stuff. It's assigning judgement and value to the people you're working with. That may be valid (or it may not!), but it doesn't help you professionally. Try not to assume you know why they do what they do, just deal with situation as it is. Telling HR about how bad everyone else is simply won't help you at all.

Your strongest arguments would be:

* The well-documented original plan vs. what has actually happened.

* The factual discrepancy between your performance review and reality. Emphasize positive feedback, and get them to advocate on your behalf if possible.

If someone cares enough to sift through all this, they might figure it out and save you, but chances are good that it won't happen. Having a plan B seems quite prudent.

If you're the tech lead, you have to insist on it. I can give a thumb in the air guess based on an ask, but it's pretty subjective. Step 1 before giving a commitment is to ask for a few weeks of analysis. Get that high-level backlog.

I should say that I've learned this over many years, but have applied it at the highest levels of corporate America and it does work. If you present an estimate _with evidence_ it makes it so much harder for even the most grizzled IT exec to argue against you. Most are still used to thumbs in the air so if you give them something tangible, they will actually love it.

This is how things should run if the work culture was logic based but with rare exceptions it isn't.

As a borderline autistic person I have a very direct communication style and lost account of how many times I burned myself for failing to "beat around the bush".

You can't say "the project is doomed" even if it is true. You can't say it will be so over budget and take so long that it would be better to cut the losses now. Don't expect to go unpunished for saying "the king is nude".

According to my experience both parents are absolutely right, but the first is how most organizations work and the second is an ideal seldom found in the real world.

PS: you do get some leeway when you just joined a company, enjoy your honeymoon grace period.

Nope. It will tar you forever amongst anyone you say it to as someone with a bad attitude, divisive, etc. I spent three years at a company where a VP basically viewed me dimly (if, admittedly, necessary) because I delivered bad news early on. It was polite and reasonable, but he was in a difficult place, had people actively whispering "Everything is fine" in his ear, and so when it eventually did blow up (and I was one of the ones who swooped in to fix everything ASAP), it was less "I should have listened" and more "(I) just added to (his) pain".

Attitude is important. Like I said, deliver this news as though it's inescapable objective reality. Akin to saying we can't have a picnic because it's raining. It's nobody's fault and it's not due to anyone's shortcomings. Estimating is hard, building good software takes time. This is how much time this project will take. Let us know evaluate the impact and decide how to cope. It doesn't need to be an argument.

It wasn't an argument. It was a messenger bringing bad news they didn't want to hear. And with other messengers who were actively telling him untruths about reality. And he wasn't sufficiently technical to go evaluate the claims himself; he -had- to decide who to listen to. So, unsurprisingly, he listened to the one that felt better.

You seem to believe that everyone is mature enough to hear bad news, delivered objectively, and accept it without blaming the messenger, and without dismissing it because it doesn't conform to their wishes. I wish I had your luck in bosses.

Depends on the circumstances you joined the company.

In some, you actually have to "earn your place" in the company, and most recommendations I've seen are "keep quiet and listen".

Absolutely.

I'm about 3 months in at a new company and starting to see areas for improvement. I just make a note and keep my mouth shut. In another 3-6 months I'll have earned the right to start diplomatically suggesting some of my ideas. For now i just try to understand the thinking that went into decisions that resulted in our current state.

If you want to go into a new organization and "be disruptive" and you're not a management consultant, be prepared for the likely outcome of failure.

I'm not sure if you are talking about the general leeway most new employees get, or if you are saying you get a period of time as a brand new employee to point out everything you think is wrong in a matter of fact way. If the latter, I disagree.

> Just be real.

This works pretty well in smaller companies or startups, but corporate culture is usually political enough that it would be a disaster for your career.

> Then just ask how they want to deal with it.

Disagree. Anytime you find a problem you should come up with at least two solutions before you bring it to leadership. Managers hate people that only come to them with problems. You're closest to the project and you should be the one to know the situation and possible solutions.

Anytime you find a problem you should come up with at least two solutions before you bring it to leadership.

Yes. I think many people who believe they were punished for delivering bad news were actually punished for not offering ways to solve the problem. It's easy to simply say, "the project is doomed" and leave the problem in management's lap; much harder to come up with creative ways to rescue a bad situation.

Being real can be a massive mistake when management is more concerned with preserving management than revenue. It's pretty common, and experienced managers are way better at getting you out than at fixing problems. (Well, they see it as one and the same)

> One time we had even already signed a fixed-bid contract before I was able to give them an estimate.

Only one time?? Are you hiring? :)

So much this it's painful.

You will never be thanked for telling them uncomfortable truths, even if they -don't- know. Even the private conversation is dangerous; as you say, keep it as low key and minimal as possible ("i have some concerns about the timeline" is literally all you should say unless they ask, and your answers to any followup question should be equally circumspect).

Instead, as others have mentioned, just make sure you document what does get done. Ideally have a decent backlog of things that need to get done, but that presumes a PO who does their job (and it sounds like he/she probably isn't). That's your CYA, and your innocent response if they ask why you didn't raise the alarm.

What's PO?

ProductOwner, may also be ProcessOwner in some companies.

Product Ogre

Product Owner

Project Owner

Well put.

Deadlines often slip. It happens ALL THE TIME, regardless of elaborate and sophisticated project management techniques and skilled contributors. Deadline slippage is also RARELY FATAL, but yeah, leads/PM's can absolutely get themselves metaphorically shot by bearing bad news to the wrong people at the wrong time.

Some orgs hire a ridiculous number of PMP's who pretend like they're making a difference but are really just practicing an elaborate dance of goal-post-moving to appease the deadline-gods. People in such orgs often bullshit about a "track record" of being "always on time and under budget".

Best thing OP can do is learn from the mistakes and speak up next time during planning phases, well before deadlines slip.

I've been in organizations where people know projects slip and are mature about it but I've also been in places where projects absolutely do not miss their go-live dates without a major impact for the relevant managers and teams.

Always wise to know what the corporate culture is around these kinds of things.

Agreed, especially when you're dealing with external clients. I've been in situations where internally we've been fine with a slipped go-live date, only for a CEO at a client to send an email at 4:50pm putting everyone on blast and demanding that all developers stay at the office until it is live, or else (no lie, literally had that email, quote for quote, in my inbox less than a year ago).

Corporate culture includes everyone involved in a project. You can't be calm if you have someone outside of your office going mental over something being a day or a week late.

> practicing an elaborate dance of goal-post-moving to appease the deadline-gods

I've seen this so many times, it's like why even bother attempting to describe what we'll deliver. Just put the date down.

> Best thing OP can do is learn from the mistakes and speak up next time during planning phases, well before deadlines slip.

How do you know deadlines are going to slip when planning the project? Makes no sense.

After you gain experience from previous slipped deadlines, you can see patterns that lead to slippage and, more importantly, get wise to the smell of unrealistic expectations. That's how you know that deadlines are going to slip.

you're assuming that deadlines are set based on the amount of time the work requires. Not often true. Generally deadlines are set before anyone knows how much work is required.

That's one of the patterns.

Take your estimation of the work to do, multiply it by 2.

Surprisingly, it works relatively well to estimate how long the project will actually take.

Those multiply by whatever factor estimates are perhaps defensible if you're talking about a few person-hours for a small no-bid project.

It falls apart if you're talking about 10's to 100's of people working for weeks/months/years, or wherever you need to compete with other vendors for the contract.

For those projects, everybody is over-optimistic in their respective bids (some could say they are basically lying...). But that's part of the game unfortunately.

However sometimes, it can be a calculated risk, for most projects, something is provided by the client, and generally they are also late on their parts. If played correctly it can hide delays on your side.

Also, being over-optimistic in a bid doesn't mean you have to be over-optimistic internally, you could set realistic expectations internally and "manage" properly the delays on the customer front.

Just to be clear, this is a cynic view of things. Every time I see something like that, I cringe inside (and even outside).

However the 2x rule can be quite limited in big projects as it doesn't account for the overhead induced by the size. In a team of hundreds, 30, 40 or 50% of the efforts can be lost due to difficulties in communication, management layers, heterogeneous set of competencies and skills, etc. It's harder to identify what this overhead could be. They can be huge differences between relatively well integrated teams and a complete mess.

My business sponsor claimed to always take my estimate, double it and bump the units.

3 hrs => 6 days

2 days => 4 weeks

So how would he estimate 1 year project?

Hopefully no one is looking at a project and saying "that will take a year". You estimate tasks and that gives you a project timeline. Those tasks get the double and bump.

Or say 2 decades and get all the praise when you come in under time and budget.

"Never"

2 decades

How to do you know? Because they almost always slip. Take the original estimate, which is always optimistic, double it, add another 50% "just in case", and you're a lot closer.

This advice is a good first read on the political elements before you make a real move, but it’s not a plan, and it sounds like a recipe for mediocrity. (Not that there is anything wrong with that)

If you actually want to have some integrity when you talk about deadlines before it eats up your insides and you lose sleep you will need to have these beer / lunch conversations to gauge the level of appetite for change and then start talking about how to get something shipped on time as well as the consequences for not shipping on time.

Sounds like you already have this dialog with your manager. Keep talking about how best to manage expectations up the chain.

You’ll want to get buy-in to reduce scope or make whatever other changes you need, otherwise you’ll have to lie to keep up the facade that things will ship on time. It will burn you out.

If the read in the parent comment is bad for your org and it’s NOT normal to BS deadlines and ship late then no paper trail or written warnings, risks, and issues brings with it some badness as well - judge for your organization. I’m guessing you may already know the answer.

This is probably not the best career ladder advice at some firms, but at all costs make sure you never lie for anybody. Keep your integrity. Be honest. Sleep at night.

Of course sometimes “honest” is an excuse to be pessimistic. Look hard to make sure your dire warnings are not “chicken little” pessimism, then talk it out with your management, but don’t lie for them and be honest about your engineering and your team.

> Third, people do shoot the bearer of bad news. You can earn

> a rep as a negative person if you make _true_ predictions

> out-loud that don't fit the common desire.

I've heard this very often, both as advise, complaint and even in an intimidating manner. And yes, I've seen this, people who stay kind of positive stay in their position even if they screw up a project completely so it has to be "rebooted". In fact I've also observed a super negative person, being a colleague of mine for 2.5 years and staying good with everybody despite one screwed up project.

On the other hand people have put me in various settings under high pressure to keep my mouth shut both internally and externally. (That was only in the startup/co-founding setting though.)

My conclusion: I'd take this advice with a biiiiiiig grain of salt. In my experience people get away with everything as long as they stay confident and keep their shit together.

Disclaimer: I'm not a team lead

"Perception is reality"

You can be a negative/realist as long as your perceived value outweighs your "bad" attitude. The problem with this is that people are really bad at placing value on soft skills and all it takes is one clueless manager to sandbag you.

Everything op said above is spot on

I get the point for an Engineer. There the chances to endless promotions are far higher if you stay nice and calm all the time. Hard earned experience, never got a promotion but always more money and "crazier" jobs over time.

But I mean for anyone with team responsibility: staying silent is bad for you, which is okay if you're in for the career. I totally respect that, people should be ambitious if they want to. But this is the recipe to make workplaces toxic and bad for the whole team.

I'm not saying you have to a Bright Ray of Sunshine all the time. But it might not work out so well of you are the office grouch because it wears people out.

(On the other hand...maybe the place is that bad then)

I can agree to that ;)

This is a good advice and all three points are spot on (on time deliveries are unusual; management likely knows you are late; messengers often get shot).

You do need to figure out for yourself a realistic, pretty safe time when you will be ready: an extra month? three months? never? You say the work is outside your team's comfort zone. This is potentially a much bigger red flag than being late. Will the team learn and deliver, or it just cannot execute at the speed requirements are changing or will soon be? Be brutally honest with yourself.

If you think you can safely deliver the product in, say, three extra months, then keep working but be ready with good estimates when the time comes to redo the schedule. When that discussion comes (usually suddenly), having a clear plan and realistic estimates that you can confidently present will likely give you (most of) what you ask for. IME really bad options are either agreeing to fix everything in a week (if you know it will take three months) or not having an estimate at all "we are burning midnight oil and I cannot tell you when we will be done". Either could lead to quick problems.

IME when "what do we do with this crap" time comes, senior management does not care why you are late (everyone is at least some of the time). They want to know if you have a plan and look ready to execute it. Just my 2c. Good luck!

Strongly disagree. I think this is the cynical view, and I'm sure is valid in many companies, but raising potential issues early is really important - other people can't fix problems if they don't know about them. It sounds like you have visibility into a problem that others may not, tell them! Don't assume people already know.

Like some of the other posts said - be real. If people don't respond well to this then the company has a bigger problem than a slipped schedule.

This is not cynical this just reflects how the world is.

You could be right, but in my experience it is extremely unlikely that the lead is the only person who realizes that the project is going to be late.

One sign this isn't healthy environment, frankly, is that no one has (apparently) asked the lead how he/she thinks the project is going. This also suggests that they already know and/or don't want to know.

This is the only really true, non-theoretical advice in the thread.

OP's description is generally how every project at every company has ever worked, forever.

> "Third, people do shoot the bearer of bad news."

True. But under such circumstances chances are pretty good someone(s) is going to be shot anyway.

I think the answer is solid. But if going this route I would update my resume and reach out to my network.

If this ends badly you want to be prepared.

Always be prepared. At the end of the day you are just a resource to a company. Someone who implements some spec for a bit of dough.

> Third, people do shoot the bearer of bad news.

As someone who has been a bearer of bad news, this is a sound advice. Most of the time you are told - "At least give it a try". And even if you tell them - "I did try but still likely we will miss the deadline". They will ask you to check again.

It is mind-numbing when it happens the first time. And most of the time you get disillusioned and think - "I need to look for another job". Guess what? Every corporate works like this. All about positivity and "You can do this" messages. And most importantly people setting up super-aggressive timelines knowing well that you are going to fail.

> Second, unless you're in a startup where everyone's inexperienced,

Curious about this though. So, as per you startups are run by people who don't know how to run projects?

Caveat, this seems to play out fine if the project slips 10-20%, which is sort of within expectation, and your competitors may be slipping the same amount as we speak.

If however the project is due to slip 200%, or 400%- I guess I don't have specific advice, but that kind of project is the sort of project that can sink a company. Of course, you only really get to that point if vice-bigwigs are lying severely to the bigwigs, in which case there may be nothing a team lead can do about it.

> Be prepared with details, but if he/she doesn't ask for them, don't provide any.

Also be prepared with solutions. Any decent manager or product owner is going to ask things like: "What's a realistic timeline?" or "What could be cut to get closer to the timeline?"

It would worry me more if they didn't ask details. In my experience that means they sent you on a fools errand expecting you to fail and take the heat for it.

I agree with much of your premise but one problem I run into: If you have these off-the-record meetings, where is your documentation if they say, 'I didn't know it would be late'? In my experience, people not only dislike bad news, they ignore it:

First they hear what they want to hear, i.e., what is not threatening to them. 'Project delivery will certainly be late' is heard as 'the next milestone will be late' or 'we're a little behind schedule and will catch up' or 'it's making another project late', etc. It's truly incredible what people will construct in their minds. What's the saying? 'Don't expect people to understand what their salary depends on them not understanding'?

Second, like everyone, they ignore or put off dealing with bad news. (Probably, that's a temptation of the OP.) Then they say, 'I didn't know.'

It depends on the people and the organization, of course, but you do you protect yourself from being thrown under the bus?

Documentation won't save you if the shit truly hits the fan. What will save you, if anything, it's that the leadership considers you one of them.

I agree in general; 'I told you so and it's your fault' doesn't help a relationship in crisis. But ...

It can compel some attention and provide an opportunity for extra thought. An unwanted verbal message over lunch is easily forgotten or misremembered, intentionally or not, weeks or months later. A written one is harder to ignore and provides something the recipient can re-read and ponder later.

Also, there are circumstances where documentation is good to have. For example, it may help in a company with more layers; your email to the guy 2 layers up may help when the guy 4 layers up gets involved.

This advice is spot on. I would add one thing: make sure you don't surprise your manager. Talk to her. You and she should be on the same page about your project's progress.

It's her responsibility to help the rest of your business do the best they can with reality. If sales of your existing product have dried up because prospects are waiting for the modernized one, that's a big problem (been there). But it's a problem belonging to product and sales management, not you. Unless you are a founder.

Renovating software is hard, much harder than greenfield software. All the best to you.

This is the right path if you're a lead on one team of many in a larger org, you don't want to risk needing to find another job, and you don't have a burning desire to make a difference and build a track record of change.

If you're in a smaller company, and you have clout due to being closer to the top of the food chain, and you have a vested interest in the success of the operation, to the point that it's worthwhile cutting your losses and moving elsewhere if the outcome isn't positive, then the higher risk strategy of pushing for change makes more sense.

OP needs to be concerned about the blame game if the project is a big deal. The manager won’t want to take blame, same for everyone else in the chain. The best thing OP can do is raise it quietly with the manager, and not terribly forcefully, note that this was raised. I also think going to anyone other than the direct manager is a bad idea. Then take some actions that can be used in retrospect as evidence that OP was trying to ameliorate the situation. Fundamentally this is a management issue, don’t let it become a game of blaming engineering for management’s flaws.

This isn’t fundamentally a management issue. Lead roles should be able to give them a better idea of how long a project will take. if they expect delays, it should’ve been brought up way before. There’s little to no room for change without a dent in the company’s reputation at this point.

However, these things happen time to time and when you have a stubborn PO like that from the beginning, you should have started looking elsewhere way before as a lead role. I’ve never heard of situations where a manager takes the blame. It always falls to the engineers.

Often, if you 'stay positive' and don't make too many waves no-one will get blamed. Like all cultures groups of managers like to see problems as being with external groups or things outside their control, and become more tight-knit as a result.

If you do too much boat-rocking, though, you may find yourself looked on as "external" to the other responsible people, which is not a good place to be.

I hate to agree with you. This honesty/positivity dilemma is something I'm struggling with.

Occasionally people talk about the "compliment sandwich".

1. Focus on something going well. 2. By the way, could you fix this little thing? 3. Return to positive stuff.

This formula can be applied to delivering honesty amid positivity. Ideally whoever you're communicating is mature enough to just take honest feedback straight, but if they aren't then this can be a safe(r) way to deliver it.

This seemingly simple tactic, WORKS. It works even with mature folks. It is just harder to be angry when someone pads your ego or your mood even just a little bit. The 'compliment' does not even have to be direct or a compliment per se, it can even be something positive like news/results about the initiant or a third party. You are just pulling out some positive endorphin mojo, to slow down the angry mojo.

My old boss had a phrase, "bad news doesn't age well". I have followed this throughout my career and it's served me well. I have not found it to be bad to be the bearer of bad news. I have found that it makes me perceived as transparent and honest about expectations.

Bearers of bad news are frowned upon when the bad news is their fault and not presented when its determined to exist. I think this is a distinction that should be made with your phrase.

This is basically the opposite of what I would advise. Count the number of “probably” and “good chance” in that reply!

1. A small course correction can work wonders early on, but if you wait until the ship is seconds from the iceberg there’s nothing anyone can do. Or use the cancer analogy: early detection can be the difference between life and death.

2. Yes, sometimes deadlines are padded and you’re silently expected to miss a little. Sometimes they are not and you’re not. How do you know which one applies to you and your project?

3. Having private conversations is fine but private conversations can be denied and privately made decisions do not become the broadly understood plan of record, leading to confusion and ambiguity, which are risk multipliers.

4. A positive attitude is good and hiding real problems, evading responsibility, and playing corporate games might work in the short term. However if that becomes what you are known for, it will limit your career long term.

I really agree with this advice. I would add that during those quiet conversations the best leads usually say, "we can make this deadline, but we'll need to do x/y/z", where x is increasing resources by a %, y is decreasing scope by some feature(s), and z is increasing time alotted by some days.

That constructive feedback is actionable and adds value. If your manager (or the business) chooses to ignore it, don't be frustrated, but when it's constructive, finite and actionable, you'll be surprised how often they'll make the changes.

There's no reason you can't have an off-the-books meeting and discuss this (separately) with your boss and the PO. No need to go to the extra step of setting up a lunch or having a drink with them, especially if it's not something you do regularly.

If you've been there for 3 years and never had a drink socially with the PO (who presumably OP doesn't report to other than in this status report context) then you suggest it just so you can talk about how you're not hitting the schedule, it's possible they don't take it well.

I was really upset at this comment at first. After thinking about it some more I like that it questions fundamental assumptions about the original question namely,

“What happens if the deadline slips?”

If the project is late, does the company go out of business? Do people get fired? Is the overall deliverable unusable within the org? Is the deal lost?

If the answer to these is a big “no” then totally agreed with OP to not sound an alarm.

However configuring a skilled team and leading it to do excellent work and constantly improve should be something most people strive for.

Or worse, an executive misses getting some of their bonus...

NB Based on one fairly large project I was involved in for a large company where there was a huge drive to get the system delivered on time then.... nothing. Nobody used it for months.

Eventually we found out about the real reason.

Honestly if this is true in your organization you should probably be looking for another job anyways. Even if this is common that doesn't mean it isn't dysfunctional.

From personal experience, I would endorse the above advice. I'm all for being honest, but organizations are strange beasts, and I once got fired for something just like this.

As long as you are sure you will eventually succeed, ignore the problem and keep going. Being late is no big deal; it's actually a confirmation of how amazing and innovative your product is.

If someone senior brings up the issue, don't flinch, and be ready with an alternative timeline.

There are a LOT of assumptions here.

> The rest of the org probably made a schedule they know you can't meet

> Most people probably already know you'll be late, but aren't saying it out loud

> There's a good chance <your boss> already knows as you suspect.

> It's probably not new news to <the project owner> either.

Doesn't take much for one, if not all of those to be untrue. And by the time it unravels, it's too late.

How should you go about delivering a bad news and solutions for without being termed as a negative influence?

> Have a quiet conversation with your boss over lunch or beers - not a meeting

If you do this, follow it up with an email outlining everything you said so you have a paper trail that you brought it up with your boss.

Agree. Also management above you might have scope-reducing contingency plans which they will slide into place to ensure that something gets released on the schedule.

Is there a better way than this? Or is this just how it has to be?

Sound, practical advice, should be top comment.

I don’t understand why he/she needs to sugercoat things so much and do things over lunch, drinks/beer? Imagine this is a female lead asking her male boss out for drinks so she can be the casual bearer of bad news?

That’s just bull.

If your organization isn’t willing to get real and is blaming people instead of processes, it’s the wrong org to be.

Just say things as they are. I’d just raise this in my 1:1 with boss and boss’s boss. “It’s highly likely that we’ll miss X deadline, because of Y reasons. Here are some options we have. Either cut scope to meet deadline, pull in more resources for Z work, that can be parallelized, or push back the deadline.”.

Either you're working in an unusually healthy environment, or you haven't done this often enough to see it backfire. If it's the first. You're very fortunate.

You're not technically wrong, but most of us don't have the good fortune to work in an organization where we can "be real". Yet, we still have to put food on the table. You, in the organization you work in, might feel comfortable going to your boss and boss's boss, but as you read in the parent comment, I hope you understand that not every organization is that way.

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