I'm in a situation where my Boss only wants very simple answers. The problem is that in the information security and software business, this doesn't really exist. Here is the situation.

My Boss is in the process of drawing up contracts for clients where they pay us for services rendered, simple. My Boss brings me in, says "hey, based on our current stack (how everything is set up), could we support 20,000 clients?". My first answer consists of lots of questions. What client is it? How many hosts per client? What operating system? What services? What processes? How is their network set up? Etc. There is not a straight forward answer.

My Boss than says, "I just need a yes or no answer so I can relay this to the client". I basically refuse to give him a answer and try to explain. He wants to say "x=2 and y=3 and so x*y=6. But it is never that simple in the software business because there are many other externalities.

He gets frustrated because he wants a yes or no answer but we do not have the available information from the client to say so. I have expressed that we should tell the client "let's start out with 1000 hosts and we can build our way up as both of us are happy" but this gets refused.

How do I deal with a Boss that does not understand the complexities and wants a clear cut answer I don't feel comfortable giving?

  • What is your boss's background? Did he ever worked in Software Development?
    – Isaiah3015
    May 3, 2018 at 23:11
  • Not a programmer or developer, more of a CISSP person, or in other words, a mile wide and inch deep
    – pm1391
    May 3, 2018 at 23:14
  • Do you have direct contact with the clients or does everything have to go through your boss? May 3, 2018 at 23:18
  • No, my boss interfaces with the clients boss basically.
    – pm1391
    May 3, 2018 at 23:29

6 Answers 6


How do I deal with a Boss that does not understand the complexities and wants a clear cut answer I don't feel comfortable giving?

You could say "Sure boss, if you give me a moment I can evaluate the situation and prepare you a clear answer". Then proceed to evaluate the situation more calmly so you can reach a yes/no answer with more certainty.

Now, sometimes bosses want an answer right there. In that case things get a bit more complicated for you. If such thing happens, and your boss can't wait for you to lay down a plan to answer with certainty, I suggest you give a conditioned yes/no answer.

After a quick evaluation from your part, you can say something like "If we do X, Y, Z, then yes it is possible", or whatever your conclusion is. This way, you are giving him a clear and direct answer, but at the same time politely implying all the requirements necessary for that to be achievable (and also covering your back in the process).

On a further note, seems to me that your boss should start to realize that in the IT world straightforward yes/no answers require at least a bit of input to be able to give them with certainty. However, this is a whole 'nother story.

  • That's a good perspective. It was more of a "right now answer", but I probably should have said "if we do X,Y,Z" as you mention
    – pm1391
    May 4, 2018 at 0:20
  • 3
    I think the conditional yes/no is very dangerous: the boss is going to omit the condition and then you'll be screwed. Aug 7, 2018 at 8:42
  • 1
    @reinerpost we don't know that, you are assuming we know what boss will do
    – DarkCygnus
    Aug 7, 2018 at 14:44
  • 1
    @DarkCygnus: Exactly: I don't know that, and I'm saying, based on what I've read in the question, there is a high risk of that happening. Aug 7, 2018 at 16:29

These sorts of questions are about perspective. Your boss is asking from a business perspective can we handle more customers. Your perspective is if your current capabilities are adequate and without knowing all the details you can't answer that question. However you could reply with a

If the customers have the following OS, network, number of hosts etc then yes. If not we would have to do B, or they would have to do C.

Or you might have a flat out no. If you can't pin your boss down on what the exact potential customer's needs are, but you feel as if he wants you to say yes, I would approach this differently.

Instead I would rephrase this that this is actually as a decision for the business in that what risk they are willing to take on. It is your job to explain this clearly the risks for the various different customers you anticipate to the best of your abilities will be using the service. It's also your job to facilitate the business taking on more customers, if there are ways you can find to enable this that would be ideal.

Instead of being the bearer of bad news imagine if you are responsible for enabling your business to come up with new ways of accomodating more customers and mitigating risk. If you do this in a way which is very visible on the work and solutions you have come up with that would surely lead to reward and or promotion.


Non technical people, even smart people, are hard to figure out the technical details and in IT details are all it matters. You must to be clear and short. Example:

"It's not and yes/no question. You are asking me to make a lot of assumptions about stuff I'm not aware. It's like you asking if can we ship 20.000 boxes using a truck? If it's a big truck and small boxes yes, if it's a small truck and big boxes so no.

So me must first define those boxes size (clients needs) and know the truck (the clients infra)."

and finally you can add

"We sure can handle that amount of clients if they are not demanding ones and all of them got a pretty good network."

and if he insistis on a yes/no:

"Yes! But plan ahead how to mitigate when I was proven wrong."

  • 1
    +1 Great analogy. Its tough putting complicated things into such a short statement for someone
    – pm1391
    May 4, 2018 at 13:08
  • In my experience giving this sort of reply just winds up a boss as they see it as you being awkward especially if the boss is non tecnical
    – Stormy
    May 7, 2018 at 9:46
  • @Stormy In my experience even non technical boss don't care if technical dudes are awkward or not since you proven you are assertive, knows your stuff and can do the job. Of course if you care about politics and have ambitions ont he management job I can advise the contrary, play plain guy and forgget about my last paragraph (but I pity you =))
    – jean
    May 7, 2018 at 10:52

You should really talk to your boss and explain what data you need to make a calculation. Tell him the explanation will take, say, 20 mins, and is good so you can get his thoughts on if you can support it or not.

I'm not from the information security & etc business, so here is how I look at it - and quite probably how your boss does too.

You have, um, a current stack. The total power of your stack or whatever is X. The average client currently uses Y. Is 20,000 * Y > X or not?

If it is, then no. If it is not, then yes. As such, I'd assume I could ask this question and get a pretty yes/no answer.

This is, I assume, not the right way to look at it - you need instead to manage upwards and explain that to make a reasonable guess you need such-and-such data.


Henry Ford once said, "You can have a car of any color, as long as, it's black."

To an engineer such as yourself, this is utter-nonsense, but to your boss and probably the client, what you're saying is gibberish regardless of the technology behind it. Of course there will be constraints. They assume and ignore those more than you do. We all know that you ultimately can't because you're the person who actually has to make it work.

You're going to have to learn how to play the game. Your answer should always be as quick "Yes" unless you're being asked to do something illegal. As you start to get into the details (You know, where the devil hides.), the client has the right to object to the price, timeline, or suggested technology recommendations.

Don't always take these kinds of questions literally especially when you know you're talking to someone who isn't technical. If you ask Elon Musk if he could move a mountain, he'd say 'yes' because he's going to ignore the reality of an astronomical cost (which no one will pay) and the chance it will take so long that no one living today will still be alive when it is finished.


To me it looks like the problem is on your side. It seems you are trying to avoid responsibility, by avoiding to pin down an answer. Possible answers to your boss are:

  • Yes its possible, with customer B we are currently supporting 200.000 clients.
  • No, currently its impossible, our current largest customer has only 20 clients and the servers are on full load; we would need to build a second and third building for a new server farm
  • Yes, if he uses similiar resources as customer C it would fit, but if he uses more we would need to stack up a few server
  • Yes, but if he uses similiar resources as customer D and with a safety margin we would need to double our infrastructure

Which answer is right only you have the expertise and knowledge.

You are the expert, and you have to make an educated guess on the current stack and the current customers, possible to qualify with one or two main assumptions. And then you have the responsibility and you have to make it happen (if the order comes). This is your job.

  • Downvoter, could you please explain?
    – lalala
    Aug 7, 2018 at 9:06
  • "Yes, if he uses similiar resources as customer C it would fit" What is his boss going to do with the information if he does not know how much ressources the new customer will need.
    – FooTheBar
    Aug 7, 2018 at 10:21
  • @FooBar I think this info is valuable for the boss. So the boss knows there is good chance on.current info. There could also be a risk. So he can choose to further inquire if he wants to mitigate the risk, or he can choose to take the risk. I assume here the boss is familiar with the customers. Bosses have to make decisions without all parameters to be known. Also the info helps that if the contract gets signed IT suddenly doesnt say of course 20000 clients is impossible, our id numbering concept stops at 5000.
    – lalala
    Aug 7, 2018 at 10:29

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