Run When You See These 7 Red Flags On The First Day Of Your New Job

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Red Flags. Hard-to-see patterns that emerge from a mismatch in “what should be” vs. “what is”.

Your new job may look scintillating. The offices are nice, the people are nice, everyone’s nodding in approval.

But it all comes crashing soon.

Maybe you see this on day 1 and you don’t pay attention to it. Maybe these anti-patterns reveal themselves in the next 30–60 days.

Many more red flags have been written about. But I always thought that they were too basic.

Without further ado — the 7 red flags for the new job that you should watch out for…


#1 — They have a giant backlog. It needs your urgent input. It’s a mess.

Not to mix product management and product ownership on purpose, but often companies will use these interchangeably. You can even spot issues at this juncture. Product owners deal with the backlog more. So what role are they hiring for?

In any case, backlogs are often “wishing wells”.

Based on what must one prioritize a backlog?

Why do you have such a giant backlog?

Why are all these features weird, without standard structure to them? Some look like month-long projects. Some would take 30 minutes to do.

Let me guess…

#2 — They don’t do due dates.

Nobody cares if you ship that feature in June instead of April. Or June 2020 instead of June 2018.

They put that feature request 3 years ago. What do you want to do? Park it? Do it?

Ok, why not. Easy, because…

#3 — They don’t know why they do what they do and why anyone needs these features.

What strategic objectives would a carousel slider on the homepage achieve? Why does this part of the flow need a sudden redesign? Who benefits from that thing someone saw on another site and it was cute and now we need it too?

Will the business achieve its goals because of these changes, or in spite of them?

Good questions…

#4 — They hired you to be the bad guy.

Because that’s what PM’s do, right? They say No.

So, start by saying No to this [bad department], because their features look dumb. Did they even do any research?

They want us to build it by April and it is March now and we have tons of work. Who said that the users would buy it?

Can you prove that what they want is bogus, with real research?

#5 — They badmouth other departments.

Yeah, this should be red flag #1.

I mean, you want to work there — but do you need to be in the middle of endless petty feuds? Do you want someone outside the team to try to court you so you could help fight their battles from the inside?

Where are the parents? This feels eerily like high school.

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#6 — They don’t do buy vs. build. They always build.

Because it’s cheaper. We’ve got all these engineers. For a generalist dabbler like you, writing code is like speaking to aliens. But to these developers, it’s a piece of cake. It’s what they do. D-E-V-E-L-O-P.

Look, no more third-party widgets. It’ll slow the site down. $15 per month? What are you, crazy? We can build it in like zero time. And it’s ours forever.

You know where this is going…

Build the CRM and the A/B testing system and the marketing automation tools and the CMS, etc. etc. etc.

They would probably try to build Google if it didn’t already exist.

#7 — They are so agile, so they scrapped all that agile nonsense.

There’s a difference between (a) testing and keeping the stuff that works and (b) reading about it and then throwing it out completely.

“It wouldn’t work here”.

Yes, collaboration wouldn’t work here, because we’d be arguing about what matters the most forever (See red flag #3). So of course we have to decide by sheer brute force of will and who’s got the biggest 🍆 now!

And who would want to deal with the fact that if we did research, those brilliant ideas wouldn’t stack up? And we would have to rethink, and probably re-do a lot. We’d face the music and the fact that we’re not super heroes. Scary, I know.

And who knew that test & learn was more than just a buzz word and took a lot of work and instrumentation and money and time and alignment?


After all, you might be stuck in that job right now. What can you do about it?

I wish I had a straightforward answer. But that would be incredibly presumptuous.

Frankly, I don’t know a single place that doesn’t have some red flags (I did 7, but that’s just so you would read this piece).

It’s important to remember that no job is perfect, no company is perfect, and no human is perfect. Organisations have complex histories & tend to amplify weird things that don’t represent all individuals in it correctly.