Backstory: I just moved from a very large MNC to a small company for primarily personal reasons. This is my 3rd job since graduating 5 years ago.

I started at a small (~30 person) company a little over two months ago now. My role would be called Senior Director or CTO in another world, but here I’m the lead technical manager. I report directly to the current president, founder, etc.

Things have been going well, and I’m really starting to get a handle on things and drive business improvements. I am having one major problem: my boss doesn’t seem to want to grow out of the company he started many years ago in his basement. My biggest gripe: we have a standing meeting for all the managers at 10:30 twice a week. Often, my boss isn’t even in the building. Sometime around 1:30 or 2:00, normally, he will appear and ask if it’s a good time to meet. Sometimes it is, sometimes it’s not. If I say no, he will hold the meeting until I (or whoever else) shows up. This makes me feel rushed and often leave things half-done for an hour. I have suggested moving the meeting to a later time so it place approximately when the notice is on the calendar, or taking notes. I was basically told “that’s not how it goes.”

How can I make my boss see value in respecting meeting times?

TL;DR: my boss will put meetings on people’s calendars, then ask them to the meeting several hours later. What is the best way to deal with this?

  • 1
    Your question seems very specifically focused on meeting times and how your boss interprets them, yet your question title mentions "not respecting culture." You might want to edit either the question or the title to get them a little more aligned.
    – dwizum
    Jan 28, 2019 at 16:08
  • 1
    You said you report directly to the president, so is he your boss that isn't respecting meeting times?
    – sf02
    Jan 28, 2019 at 16:21
  • @sf02 yes. Sorry for not being more clear Jan 28, 2019 at 16:31
  • 3
    @Dragonel agree, but my role has more management in it than technical doing-of-things right now. If I’m scheduling a call with a vendor or planning a service outage, being pulled away for 30 minutes can be really disruptive. Jan 29, 2019 at 0:10

10 Answers 10


His circus, his monkeys.

Things in small companies are run very VERY differently than in large MNCs

Far less structure, far more room for growth and are often led by "Idea men" like Bill Gates or Steve Jobs. Structure is secondary (if that) to them.

So, if he doesn't respect meeting times, that is unfortunately something you need to negotiate with him. You can pushback to an extent, but it's ultimately his call as to when where and why meetings will be called and how they will function.

Things you can do for gentle pushback:

  • Tell him that they leave you ill-prepared
  • Schedule meetings and have them whether he shows or not.
  • Have separate meetings for staff and prepare notes/minutes/videos/whatever for him.
  • Have two sets of meetings(not optimal) but it might point out the lack of efficiency

If you want to get him to budge at all, and try to stick to the schedule, you need to QUANTIFY things for him and show him WHY it would be in his interests to do as you wish.

Simply saying "we need to do it this way because that is the way it is done" will fall on deaf ears, as you've already learned.

You need to say "if we do 'A', the benefit will be 'B'". If it doesn't help him, and you can't make it clear to him that it will, he won't do it.

  • 10
    I'd add one more of "would you like to call in" if they aren't in the office Jan 29, 2019 at 0:21
  • 3
    I would point out that, especially in the beginning, both Bill Gates and Steve Jobs were far more than "Idea men" and did significant work on the design and implementation and Bill Gates in particular displayed a remarkable, if somewhat ruthless, business savvy. Other than that note, this completely answers the questions. Jan 29, 2019 at 18:34

This is called leading up the chain of command. You must push situational awareness up the chain.

It sounds like you give a straight "yes" or "no" when he asks to meet. That may work against you because it lacks context.

As the owner he wants the company to succeed. If his interruptions have no real impact then there's no problem. It's an annoyance, nothing more. Your task is to make peace with it. But if there is real impact it's your job to communicate that.

It's example time. I once worked for a small company where the owner was known to ask for things on short notice. I'd generally drop what I was doing and give these priority. One day he asked for something by the end of the day, but I was working on a deliverable with real impact for another department.

So I said, "I'm working on the shipping tool for the production line. Should I hold off on that, or can your request wait until tomorrow?"

He stopped and said matter-of-factly, "No, that's more important. Tomorrow is fine."

I was shocked. The whole time I'd been dropping work to catch what the owner tossed my way, all the while thinking he was unreasonable. Yet on reflection it was the first time I'd tried to communicate the impact, and the owner easily agreed that his task was the less urgent of the two.

  • 7
    This should be the top comment, together with the first lines from Richard's answer. It's his show, so you need to let him make the decision on how to hold meetings - but you can do better communicating the impact of his decision.
    – Tom
    Jan 29, 2019 at 7:16
  • 1
    100%. This is how to manage upwards without overstepping boundaries. Jan 29, 2019 at 12:55

Have the meetings without him and then send him the minutes/updates, and/or email him any follow-up questions.

If he can't/won't be there for meetings that he's arranged, then just carry on without him until he decides to either attend or reschedule.

  • 26
    The problem with "just hold the meeting" is that in a small company, the boss / president / founder is the guy who makes the decisions, so he is critical. There's probably no point in holding the meeting w/o him.
    – DaveG
    Jan 28, 2019 at 16:29
  • 4
    @agentroadkill Try it once to see how it goes. I understand how you feel. It's not really a coup, it's just going on as if meeting times were to be respected, which is the explicit understanding when you arrange a meeting. Interestingly many a junta has fallen because people started acting as if they had the freedom the regime claimed they had, but that's another story :)
    – rath
    Jan 28, 2019 at 17:23
  • 3
    @Joe I think it depends on how you present it. If you tell the president, "We (the management) rely on these daily meetings to occur at this time to plan for the day (or whatever) so if you can't make it, that's fine. We'll send out meeting minutes and you can provide feedback as you have time later in the day." That way it doesn't look like a coup, it just looks like we're trying to get work done efficiently. If the president doesn't like this, maybe it will be some motivation for him to show up on time.
    – JeffC
    Jan 28, 2019 at 20:21
  • 2
    @JeffC Someone who's so callous of everyone else's time is not necessarily going to be amenable to that, though. Sure, many owners would be fine with that - but they'd also be courteous enough to attend the meetings and/or get a better schedule that works for them. The ones who are that callous with everyone else's time are a lot more likely to see any sort of move like this negatively, I'd worry. At minimum the answer should include this sort of context.
    – Joe
    Jan 28, 2019 at 20:29
  • 2
    @Joe I don't disagree... I guess my first thought in situations like this is not so much the person is callous towards everyone's time but more likely to be oblivious. A gently reminder might make them aware that everyone else is being inconvenienced by my lack of attention/attendance... but you may very well be right that the owner just doesn't care. That will be a hard one to fix, I think, unless you do arrange a coup with the other managers.
    – JeffC
    Jan 28, 2019 at 20:32

The way I see it. These are different styles of running a company. Convincing your boss to follow strict meeting times will be like trying to convince someone who likes green that blue is better.

Strict meeting times works well in large companies. Dynamic meeting times would cause a chaos there. Small companies on the other hand do not really need that. There is a chance that they are intentionally avoiding that type of system or work culture.

I'd try to cope with the situation and get the best out of it. This seems like a relaxed environment and not super strict. So try to enjoy and manage your time around that. It doesn't sound like they will rush you into a meeting if you are busy with something super urgent at the time. If you are not putting out a fire, join the meeting and figure out a way to manage how to resume work from where you left off. You can also ask your boss for advice on how to cope with it.

EDIT: To clarify few things. I didn't say that I like this boss's approach. I, personally prefer strict meeting times.

Why I think that this is deliberate culture binding? I don't. I simple said it could. That should be a question from OP to colleagues or to the boss on whether this is seen in that company as a better/cooler/flex approach. There could still be a chance that this boss is just inconsiderate of his employees and just wants to do whatever he wants whenever he wants.

I have worked in a large company and a small company. The small one was run as a family business down to the letter and I have seen things like that. Everyone seems to like how relaxed the environment is and sometimes they don't bother sending meeting invites, it's usually done in a way like "Hey, do you have a few minutes to chat about xyz". I didn't see it as disrespectful, they were nice and things were not rushed.

  • Regardless of the size of the company, not being able to plan your day or week is going to be bad for your ability to get things done.
    – Erik
    Jan 28, 2019 at 21:06
  • 3
    @Erik. The difference between Talk to the Boss for 30 mins at 10:30" and "Talk to the Boss for 30 mins sometime today" has little or no effect on my daily plan or effectiveness unless I have to try and fit other things into specific times around it.
    – Dragonel
    Jan 28, 2019 at 22:26
  • 1
    Sorry, but I have to downvote this. This is not a subjective matter of taste. It's not even a matter of politeness, even though what the boss is doing is incredibly rude. It's a matter of productivity. Being randomly pulled off task is terrible for being able to get things done.
    – Kevin
    Jan 29, 2019 at 13:39
  • "There could still be a chance that this boss is just inconsiderate of his employees" is it somehow less inconsiderate if his motivation is "i'd rather work in a 'cool' and 'chill' environment regardless of the impact on my workers"?
    – user371366
    Jan 29, 2019 at 19:28

Seeing as how the boss is the president of the company and required to attend these meetings for any decision making, all you can do is cancel the meeting if he does not show up re-schedule when it is convenient for him. Yes it may be an inconvenience two days of the week but he is your boss and the president of the company so you either have to become accustomed to how he works or seek employment elsewhere.

  • 4
    ...or you can guide him to do things the "right way"... which is the point of this question.
    – JeffC
    Jan 28, 2019 at 20:21

If you know the one person who seems to be essential for the meeting just will not make the time scheduled for the meeting (for whatever reason), then move the time. Then you'll at least have a fixed time that you can plan around. In this case, the meeting is scheduled for 10:30 and normally happens at 1:30 or 2, which is a slide of 3+ hours and messes up everyone's day. So schedule it for 1:30 and then you may slide half an hour, which will have a much smaller impact. Or schedule for 2 and try to get your boss to slide half an hour on the days when he's in at 1:30, which is maybe doable (more so than trying to get him in the office 3 hours earlier).


It sounds as if you're having growing pains. Been there, done that, got the t-shirts (literally).

This is, indeed, a matter of company culture -- a culture that is changing as the company grows. The problem I think I'm hearing is that your boss writes a schedule for one culture, operates with an incompatible culture, and the discrepancies detract from your ability to do your job.

That last phrase is the critical one: his inconsistency is spending company resources to no direct advantage. There may be an indirect advantage: it's possible that having all of you as resources he can interrupt and draw on as befits his intellectual whim, actually makes the company as a whole more effective (I've had both a boss and a peer in that class).

There are many other possibilities. Question #1 for you: how can you determine a more effective operating mode for your group?

I suggest that you hold a 1:1 with your boss to discuss the problem. Prepare by reading up on "effective meetings", and by documenting the cost of interrupting your work flow in the current situation. I suggest that you come to him with this as an idea for improvement: "Boss, I'm having trouble with paying twice for each meeting: once when it's scheduled, and then an interruption when it actually happens. I think I've found some stuff that can help me and my team. Can we try some of these things? How would these fit into your work day? I think it would make my team my effective -- and we need to watch these changes as the company grows."

I could list at least three conditional tracks, including the passive-aggressive things in other answers. I've used some of those as a fall-back position: politely decline to attend an unscheduled mission meeting (a contradiction in terms); starting a meeting on time, and gently telling the late-appearing boss to keep quiet until the end of the round-the-table, when we get back to him. These things meet with mixed success, depending on how the boss balances ego with process formality.

The important goal is to enlist all interested parties -- especially your superior -- as partners in forming a solution to a common problem. Make this "us against the anti-productivity demons" rather than "you're screwing up my schedule".


His company, his rules, his time, his money.

I'm sure you have other things to do, so do those while you wait for him to have time.

If things are urgent or important, relay that information right away.

Other than that, as annoying it may be, as long as it doesn't negatively impact the company or your work, you'll just have to live with it.


Its very Difficult to Convenience your Boss because he is your Boss, But there are Many Ways to Convince your Boss.

  • Request Him to Be on Time for the Meeting
  • Tell Him his Company going to Shut Down if he is Not going to take care of his Company because there are Some Problems which Needs Immediate attention of your Boss.
  • Ask Him about the Purpose of Running this Company if he is not interested in Carrying out this Business.

The Boss has always to respect time.

A boss must be like Bill Gates and Steve Jobs both never wasted time, and they always respected other people's time.

  • 2
    The question is what the employee is supposed to do? It's all very well saying that the boss should respect his employees' time but he isn't. Now what? Jan 30, 2019 at 14:40

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