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Today was the deadline to deploy a new site for a client. I worked on this alone for the last month or so and finished mid last week. I told the client that their site will be live this Monday morning.

As of last Friday my boss created a new workflow for better deployment and announced it via email. Although the methods he introduced are great and easy to implement in future projects, I developed my site not with these methods in mind. I used to deploy my site on a stage server first, and after the ok by the client I would just migrate to the live server.

The new method by my boss automatically deploys sites from git with the click of a button. This is great, but it didn't work for my site. I worked the whole day today, together with a coworker who implements this method in old projects, to try to fix my site.

Today morning, after lunch, and just now I suggested to my boss to deploy the site my way, just so that the client doesn't get too upset, because their site didn't launch. He didn't see my point all three times I talked to him about this. I'm not sure if he really doesn't understand that missing a deadline is bad, or if he just doesn't care.

As I'm the one holding contact with the client, I'm the one who has to explain why the site didn't launch. Because the issues with the deployment aren't solved yet, I can't estimate if we will be able to launch tomorrow. I don't want to lie to my client, but I don't want to tell them the whole story either.

I'm not sure on how to approach this situation tomorrow. Should I try to reason about the deployment process again or should I just go with it, do as he says and don't mind if we miss the deadline by another day? Should I tell my client straight up what's the cause of this delay or should I lie?

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    What authority does your boss have? Is he a manager or boss of the company. Is there anyone above him? Who is responsible for agreeing deadlines with the client in your company?
    – flexi
    Nov 23 '20 at 17:27
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Who is responsible for setting and agreeing to deadlines and go live dates in your company?

It's often a project manager. Lets assume it's Project Manager.

Essentially, you can't be expected to promise a client a go live date if you don't have the power to ensure it's met, so stop doing it and start putting this responsibility back to a project manager or whoever does have the power. - Then if things change, you tell the project manager to handle the client.

I've been in your current situation, and this is the approach I would take if you can't do the upload your way.

Apologise to the client, and tell them your boss has made an unexpected change to the procedures which is going to prevent you doing the upload on time. Don't promise a new time, you can say you'll do it as soon as you can, but refer them to your manager if they want a set date/time.

I understand you don't want to share all the details with a client and make your company look bad, but you don't have to. You can still be honest and keep detail to a minimum referring them to your manager if they want further details. You could also put a positive swing on it, that the changes are going to make future uploads less time consuming.

Either way, you should never lie to clients, even if your boss asks you to.

Also, have a word with your manager / boss or whoever's in charge, and suggest any changes in procedure should go though a process, instead of changes being sprung on you last minute, that way you can plan for it and avoid this type of situation in the future.

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    Thanks for the answer! I recently got promoted to technical project manager. Due to the virus many of our developers aren't available. Because of that I had to work on this project alone, without a PM. Also I dated the deadline myself, after I estimated on how long the production takes. I apologized to my client and explained the situation. Luckily this client worked with me a lot and I know them quite well, so they knew I was doing my best and pushed the deadline back by a week. I will to talk to my boss after this ordeal is over!
    – Niqql
    Nov 24 '20 at 11:38
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He didn't see my point all three times I talked to him about this.

It easy to see why. Did you care to ask what his motives are? You weren't able to recall a single reason for his part of the story. Imagine any one but you throwing their hands in the air and saying I repeated my opinion three times and he still wasn't convinced.

That's a disscussion 'style' that only works when you are the boss, not vice versa (and even then it usually goes badly.)

He could have different priorities than making good on your estimate, for example:

  • Not granting any exceptions to the workflow in order to avoid discussions about it.
  • Testing you and especially how you handle pressure or communicate bad news. Or your maturity and professionality when confronted with something that upsets you.
  • Enforcing the new process despite obstacles. There will always be a first time for everyone with this, even at a less unfortunate time.
  • Maybe this client is being test-run on purpose, because it's a smaller project (one man-month.)
  • Maybe the client didn't pay yet and is being delayed on purpose.

It seems to be the case that you do not understand either your company nor your boss and it seems you didn't put a lot of work into that so far. You have not mentioned, in your question, who's responsible for deadlines or your bosses side in this story. Your priorities should lie there, and your real problem is with your organization.

As for your client, simply be honest about the situation:

The site itself is finished and that's what you correctly estimated. However, the deployment process was improved on short notice, effective immediately, without exceptions. Your client will benefit from much faster and safer updates, plus you're sorry about the delay this causes.

Your boss seems to have no problem with this project being delayed and you handling the communcication, so go with that. It seems unconceivable that he didn't understand you three times.

If any higher-ups ever ask you about this situation, however unlikely that is, you'll hopefully have gotten around to understanding the change and the suddenness of it by active listening.

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