Theses are challenging times for business. I work for software development company that has developed mainly desktop software (Embarcadero C++ Builder) for years (for sales domain). We have had endeavours in the web development, but these were mainly other projects, not the main business line. These days we are having discussions how to proceed. Management proposes idea to find some tools that can automatically convert our code base of (Embarcadero C++ desktop software) into full featured web sales solutions, aka webshop+web based backoffice solution.

Well, I have always been open to the new ideas and challenges, I am committed to work hard and smart, but this is beyond my comprehension. I have proposed integration between existing webshops (open source and closed source) and our system and gradual development of web interface for our desktop system. But management asks for the immediate development of complete web shop solution without any integration of our current existing system. Current code base can only be used for the more or less automatic generation of complete web solution, without any desktop remains.

This seems to be incomprehensible to me, because:

  • I can't imagine automatic conversion from Embarcadero C++ to PHP/JavaScript (I am exploring options, in no case I am not asking options here), besides, how it will give web frontoffice operations if they have not been here.

  • If we are developing new web sales solutions, then we should have clear picture, what features we can deliver that are not already in the existing web sales solutions or that can not be implemented as the plugins to existing web sales solutions.

My thinking is that integration approach is the only rational option. What makes me uneasy is - how irrational is the approach proposed by management. But I am ready to cool down and change myself and try to see some rationality in it. I don't know what attitude should I take? I don't know whether the management is complete nonsense or maybe the idea from the management is so smart that I can not comprehend it yet?

I am really, really open to new ideas. I acknowledge that Apple is Apple now because there were people who were not afraid of the most impossible ideas. So, I am having some deadlock and rethinking the whole things that I have known so far.

  • 10
    So in short management wants to do something that they don't realise is impossible or at least infeasible and you want to know how to push back? Have you seen these questions? How do you explain to your boss they're wrong without making them feel threatened? and How can I manage an impossible request?
    – Lilienthal
    Commented Apr 17, 2020 at 9:39
  • Well - I am not sure whether I should try to change management. Maybe I am the one who must change? That is the main question. Always there have been people who reached further and always have been people who tried to keep them back. I don't want to be the one that keep others back.
    – TomR
    Commented Apr 17, 2020 at 9:44
  • So, management proposes that the company solve computer science? Visionary!
    – jcm
    Commented Apr 17, 2020 at 9:52
  • 3
    @TomR What do your colleagues think about this proposal? If they all think it's impossible, it likely is (and vice-versa). Commented Apr 17, 2020 at 9:54
  • 2
    @TomR Well there's a difference between cynicism and realism of course, but on the face of it you may be approaching this wrong. Business and IT just don't run on the kind of magical thinking that's often ascribed to companies / "visionaries" like Apple or Microsoft. It still comes down to making plans, analysing them and implementing. Going to the moon seemed fantastical as well but we go there by doing the work and figuring out a way. In your case I guess you should look at what they asked, try to figure it out and then communicate whether it's possible. Is that what you're after here?
    – Lilienthal
    Commented Apr 17, 2020 at 10:04

4 Answers 4


What has been asked of you? Have you been asked to investigate this idea? or implement it?

Request some time to perform an investigation of the implications of this approach, or if that's not your role, suggest that an investigation is performed before any more resources are committed to the task.

My CTO once proposed a ridiculous idea for a project I was leading, and asked me to investigate it. I drafted a small document outlining what I perceived to be the pros and cons of several approaches to the problem. I paid equal attention to his idea as other more-realistic ideas, but the document explained why we would not pursue the crazy idea further. I then talked through these conclusions in a meeting with many of the stakeholders present, and we decided as a group which ideas warranted further investigation.

In these situations, you need to not dismiss an idea immediately because it's stupid (even if it is). Your goal should be to fairly present the advantages and disadvantages of the options, to help your manager make an informed decision.


How irrational is the approach proposed by management?

It depends. You need to look at the costs and benefits of both approaches.

If the management is planning to permanently throw away the knowledge, expertise and flexibility of your current systems in favour of a new, untried approach that no-one is familiar with and won't give you any speed/quality/efficiency advantages, then the approach is very irrational

If the management has a very small budget to produce something that won't be extended and doesn't need to be maintained or scaled-up in the medium/long term, then it would be sensible to use a quick-and-dirty solution

Most projects are somewhere in between and we need to work out what makes commercial sense

In the end, we develop software because someone is paying us for it. If they pay a lot they can have a Rolls Royce. If, for perfectly sound, commercial reasons, they pay peanuts, then they get an old banger


or maybe the idea from the management is so smart that I can not comprehend it yet?

No, you are the subject expert not them. If you judge it unfeasible within the parameters set, then you should be listened to.

I'm not a developer, but converting in such a way seems unlikely at best and if such tools do exist they're probably more trouble than they're worth. However you're in the industry of providing solutions not whining, so investigate feasibility, then change the parameters until you find something that's workable and then take that with you when you explain what will not work.


I actually see two questions here: 1) is the company right doing what it's doing? and 2) how you should tackle that.

On 1):

I come from the business side of the software industry. In business it's important to have a strategy, to know the big picture. It's not to say the strategy should stay the same and not change under changing circumstances, but it should be clear and not changed in a haphazard way, without a solid analysis.

Entering a new market can bring a company huge benefits: diversification of the product portfolio, less dependence on the existing products/ technology, a better adjustment to the changing market environment, synergy effects in production and marketing/sales, economies of scale.

However, it's important to analyze whether it will really be beneficial by scrutinizing e.g. the competitors on the new market (e.g. it's much more difficult to find clients if the two biggest companies dominate 90% of the market than in a fragmented market), the possible customer base, our value chain - to what extent will synergy effects be produced in the process of creating the pipeline for the new product line.

These are just some of the aspects; the list is not complete by any means.

If your employer hasn't analyzed these and other factors, the risk is it will end up with high sunk costs investing in an unsuccessful product line.

But, going to 2): What can you do?

You can ask your boss/ business side for a conversation and ask questions about the overall vision for the new endeavor.

During this conversation you can make it clear that (if I understood you correctly) the synergy effects in the code base will be negligible and the effort involved huge.

This, if others agree with you, should be taken into consideration by the management. It doesn't necessarily mean the company shouldn't go this way. The transparency on the effort/ cost is important even if they decide to do it anyway.

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