Important work event clashing with long-arranged personal plans. How to approach with new boss?

[RobotandPenguin]

What would your workplace do in this situation? Just trying to assess likely reactions before I make a proposal to my boss.

I have recently started a new job, still in the same organisation I have worked for a while but it’s a completely new team/building etc. There is an annual conference later this year which is very specific to my work and it would be very beneficial for me to attend. The conference is literally at the other end of the UK and we’re talking an 8 hour journey by train to get there. The conference lasts two days – Tuesday and Wednesday. My new boss is keen for me to go. Due to the travel distance Monday and Thursday would be travel days.

Here’s the problem. I’m going to a concert in my home city on the Monday evening. This is a real bucket list moment for seeing my absolutely favourite band live and I’m unlikely to get another chance to see them. Tickets were very expensive and booked over a year ago). Both DH and I have been beside ourselves with excitement for this event and splashed out on this in lieu of birthday and Christmas present for each other last year.

I have a few questions: Firstly, can my employers refuse to allow me to spend my Monday evening (non-working time) in the way I please, so that I can attend a work event the following day? Can I refuse to go to the conference on the grounds of already having a personal commitment which wouldn’t allow me to travel in advance?

I have already taken the Monday as leave so that DH and I could make a day of it, and my new boss has accepted and honoured the leave as approved by my previous line manager before switching jobs. He doesn’t seem to have yet realised the dates and conflict with his proposal to have me travel on that day. Technically though, I don’t really need the day’s leave. I could work until 5 as usual and still get to the gig so this is less about having leave booked and more about the evening plans.

The organisation has a no-fly policy. We have to travel by train unless there are very special circumstances. These circumstances are not outlined anywhere and I’m unsure if I can make a case for flying, based on my plans to go to a concert the night before. Again, I’d be keen to know how this would land (no pun intended) in other organisations? I have looked into options and could fly at 6am on the Tuesday morning and get a cab straight to the conference venue, arriving just as the keynote kicks off. I could then either fly home on the Wednesday night or stay overnight and get the train for the return journey. Flying would also be significantly cheaper (£100s) than the train, including saving at least one night’s accommodation although I realise that company policy is focused on the environmental effects rather than cost.

Obviously a late night followed by early flight isn't ideal but I'm willing to do this in order to compromise on the situation.

I know that my previous manager in the same company would likely accept this proposal and allow me to fly (it was a very flexible department with rules being fudged) but the new team seems a lot more rigid and “corporate” (can’t think of a better word) and I don’t want to rock the boat when I’m just in. Ideally I would attend the conference; it’s not just my boss’s desire to have me there, I’d actually like to go – but not at the expense of this concert, nor losing the money we’ve spent on tickets.

Right now, my boss keeps referring to me going to the conference but we haven’t properly discussed arrangements. I’d like to sit down with him and put cards on the table that I want to go but can’t travel on the Monday and offer him the flying solution but, as I say, am keen to hear others opinions before I decide on an approach for this. I absolutely do not want to start lying but I do wonder if I should invent a more sympathetic excuse (family commitments etc) than a concert?

Also for info, so that I don’t drip feed later. The conference is useful for my organisation in general and I have attended it in the past in my old job. It is however, even more directly related to my new job. The conference used to take place in a completely different month of the year so I’ve been caught off guard by the dates being announced and this didn’t and couldn’t have registered with me when organising the concert at that time. I also had no idea, almost 14 months ago when booking the tickets, that I’d be changing jobs and my attendance would be more important than it previously was.

I haven’t had a 1:1 conversation with my boss about this yet. I’m literally three days into the job and the interactions so far have been at team meetings where he’s said things like “of course we’re expecting that Robot will attend the conference and report back on these issues” so there has been nothing concrete and no opportunity to bring up the Monday issue yet. An email went out when the conference dates were announced, saying that due to distance, the arrangement would be travel Monday & Thursday with accommodation for three nights so I know that is the organisational view on things. The conference was announced around 2 weeks ago when I was in my notice period for my old job. My pre-arranged annual leave dates had already been sent over and accepted by him prior to this. I sent an email when the dates were announced asking if I’d be expected to go and could we meet to discuss arrangements as I have concerns about the timings but he hasn’t replied – just keeps referencing in meetings that I will be going to it.

I would just say that you already have commitments on Monday evening and happy to travel up first thing Tuesday but will miss the start.

If they say no to flying, I would pay for the flight myself if it means not cancelling the concert. Uk based flights aren't generally that expensive

Surely you can arrange and pay for flights yourself to get you there for Tuesday and then travel back on the train with the company paying? If it matters that much to you?

Rather than focusing on policies, ‘can they make me’ etc etc. - do you want to make this work? Would you pay for your own flight for example? I suppose it depends on your job etc.

I'd just point out to him that you have AL booked on the Monday and so won't be able to travel until the Tuesday and see what he suggests re flying vs train. I wouldn't even mention the Monday evening concert if you have leave booked that day.

I would tell your manager you have AL on the Monday so won't be able to travel that day. I would offer the solution of the early flight on Tuesday, with costings, to return by train on Thursday. Leave the ball in his court.

Eight hours by train is ludicrous if flying is an alternative.

I work for an organisation which has a similar approach but they're more flexible as they realise that long hours travelling is not an effective use of anyone's time.

Flying first thing Tuesday morning seems sensible, presumably you are in Scotland or Cornwall and need to get to London or vice versa?

Exactly this, you are not available on the Monday. You want to attend the conference. Offer the solution of flying on Tuesday morning.

You need to tell them straight away that you have a long standing commitment on Monday that you have already taken leave for it and so you can't travel on the Monday but you are prepared to go on the Tuesday. Either by plane so you don't miss anything or by train but then you will miss most of tuesday.
Tell them now so they know as soon as possible. The longer you leave it the worse it will seem.

@RobotandPenguin approach this as a business case. Problem, solution, comparison of costs of each option.

Fly first thing Tuesday, can you pay for it is necessary? If they were one of my employees and they'd offered to pay I'd tell them not to worry about it, IK flights aren't that expensive, but at least you've offered (and be prepared to follow through if necessary)

Typos! In a rush!

Yes this. Your annual leave is for the whole day. If they want you to attend the conference on the Tuesday, you need to either arrive late, or fly.

I understand the non-flying policy is probably eco-driven rather than cost driven, but I would be surprised if an 8 hour train journey was cheaper than a flight. If you can find a flight that's significantly cheaper this might be a good way to sell the idea to your boss.

Don't suggest flying you'll end up being exhausted by it all and potentially missing the concert etc. If you can delegate it to someone else in the team, sell it as a development opportunity for them, if you can't do that just be straight with manager about having another commitment but dont say anything about the concert, it will just come across as flakey

They’ve already said in the OP that the flight is a lot cheaper

Don't offer to pay for flights - it's business travel, you're on leave on the Monday, if they want you down there on the Tuesday they can just pay.
The fact the concert is local and its a new job and you are keen to do well is confusing your thinking on this - if you had the Monday booked off because you were flying back from another country then you wouldn't be worrying about this - just remind him you have leave booked. You've done everything right here, don't worry. I know you are keen to make a good impression but your boss will probably just say 'whoops, didn't twig you were on leave, let's get you there tuesday'
And if he doesn't, he's a massive dick tbh.

I wouldn't mention the concert as some people would been dismissive of what they consider an optional activity.

I would simple say "given I am annual leave on Monday due to a long standing personal commitment, I will have to fly on Tuesday morning in order to attend.

I'm looking forward to the conference and don't want to miss it so I'm hoping you can help me find a way to make it possible".

Are you happy to sign off on that? I've costed it and it's actually £X cheaper than the train in any case. I've looked at all options and this seems to be the only way for me to attend.

Of course, I'm happy to take the train back on Thursday"

I'm a senior manager in an organisation where we are encouraged to attend the conference for our professional and regulatory body. However, it is always optional rather than mandatory. I never attend as it always falls on my birthday and there is no way that I am spending my birthday at a bloody work related conference 250 miles away from home. And my career has never been harmed by me not attending.

And from speaking to colleagues who have attended, they have not gained any particular insights or learned anything new. It's just endless presentations and slides from people who say nothing new but think they sound clever and innovative.

I wouldn't bat an eyelid about this and I absolutely wouldn't expect you to change your long booked plans. So please don't. Just tell your Manager that you can't make the sessions on Tuesday morning as you have previous plans.

Many conferences these days have online attendance options. Ours certainly does. Might that be an option? You can join all the sessions and speeches remotely. And it's a lot cheaper than attending in person. I would check if that might be possible.

Don't mention the concert, I don't think that's relevant. You have approved annual leave booked for the Monday so are not available to travel that day. So you'll have to travel on the Tuesday. I'd speak to them about it sooner rather than later though.

What TTPD said.

This.

And definitely don't mention the concert.

Just say that you are away and you will not be returning until very late Monday evening. And for goodness sake, don't worry about lying, it's none of their business what you're doing on your annual leave.

Agree with others.

Tell your boss you have a long standing commitment you already have AL booked for which means you can't travel at all on the Monday.

Ask them to sign off on flights or get the earliest train on the Tuesday morning and join the conference slightly late.

Thank you all. I've definitely been overthinking this due to starting the new job and wanting to create a good impression. I was in my last post for 16 years so this has been a huge change which is as daunting as it is exciting. I know that in my last job, I would have just sat down with my manager and said "urgh, have you seen they've moved the conference this year and I've already got that leave booked which means I can't get there for the Tuesday morning start unless I fly" and we'd have a good conversation from there. She also knows about the concert though, and how excited I have been.

I have already got all the costs, times etc presented as a business plan ready to give the new boss but I got cold feet yesterday about doing this which is why I posted here. Part of the problem is that the boss is pretty unavailable - I haven't had a meeting with him since starting and have only seen him at two whole team meetings which very much had the format of he talks and we listen and then leave. I haven't really guaged his personality yet. I have already emailed to say I'd like to talk to him about my attendance at the conference as I have concerns about arrangements but he hasn't replied - that was two weeks ago, on the day the dates were announced.

I'll follow-up on Monday with another email, actually reminding him that I have AL booked but have a proposal to discuss with him about how to make it work. (Neither he nor I work Fridays). Your replies have definitely given me more confidence in doing this now and I won't mention the concert and will just focus on having AL and not being able at any point on the Monday.

I hadn't thought about offering to pay for the outbound flight. It's not ideal as an extra cost in our lives right now but could be do-able. I actually do want to attend the conference and have always found this particular event useful in the past (other conferences less so). I'm just cursing the organisers for brining it forward by three months! I'll maybe guage his initial reaction to the flight and then offer to pay if I feel that will make the proposal more palatable. The last two years have been hybrid but this year they are doing everything in person - of course!